NO312297B1 - Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament - Google Patents

Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament Download PDF

Info

Publication number: NO312297B1
Authority: NO; Norway
Prior art keywords: benzenesulfonyl; pyrazolo; methyl; methylsulfanyl; pyrimidine
Prior art date: 1998-03-11

Application number

NO19991150A

Other languages

English (en)

Norwegian (no)

Other versions

NO991150D0 (no

NO991150L (no

Inventor

Michael Boes

Claus Riemer

Heinz Stadler

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-03-11

Filing date

1999-03-10

Publication date

2002-04-22

1999-03-10 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1999-03-10 Publication of NO991150D0 publication Critical patent/NO991150D0/no

1999-09-13 Publication of NO991150L publication Critical patent/NO991150L/no

2002-04-22 Publication of NO312297B1 publication Critical patent/NO312297B1/no

Links

239000003814 drug Substances 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 10
229940079593 drug Drugs 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 8
APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
PEYVWBGHBCDXRT-UHFFFAOYSA-N N1=NNC2=CN=NC2=C1 Chemical class N1=NNC2=CN=NC2=C1 PEYVWBGHBCDXRT-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 64
-1 di-lower-alkyl-amino Chemical group 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 23
208000024827 Alzheimer disease Diseases 0.000 claims description 7
208000023105 Huntington disease Diseases 0.000 claims description 7
208000026139 Memory disease Diseases 0.000 claims description 7
208000012902 Nervous system disease Diseases 0.000 claims description 7
208000025966 Neurological disease Diseases 0.000 claims description 7
208000018737 Parkinson disease Diseases 0.000 claims description 7
208000028017 Psychotic disease Diseases 0.000 claims description 7
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
201000000980 schizophrenia Diseases 0.000 claims description 7
MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 6
208000020925 Bipolar disease Diseases 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
208000020401 Depressive disease Diseases 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
VFCWRGUKFKHOAB-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C VFCWRGUKFKHOAB-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
CCEJDZJFMKQICA-UHFFFAOYSA-N 10-(benzenesulfonyl)-11-ethyl-2-piperazin-1-yl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(CC)=NN2C=1N1CCNCC1 CCEJDZJFMKQICA-UHFFFAOYSA-N 0.000 claims description 3
UDOLYSWYIJXJRX-UHFFFAOYSA-N 10-(benzenesulfonyl)-2-(4-methylpiperazin-1-yl)-11-methylsulfanyl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 UDOLYSWYIJXJRX-UHFFFAOYSA-N 0.000 claims description 3
WEUOAFDJWUMTLR-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-5-yl]oxyethanol Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(OCCO)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WEUOAFDJWUMTLR-UHFFFAOYSA-N 0.000 claims description 3
LVVLVQQEHHNMTM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 LVVLVQQEHHNMTM-UHFFFAOYSA-N 0.000 claims description 3
IOMUIPHNKVJREA-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 IOMUIPHNKVJREA-UHFFFAOYSA-N 0.000 claims description 3
LCERYWUKXGPGNQ-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 LCERYWUKXGPGNQ-UHFFFAOYSA-N 0.000 claims description 3
KDPDMXQMBHTUHG-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-7-piperazin-1-yl-5-propylpyrazolo[1,5-a]pyrimidine Chemical compound N12N=C(SC)C(S(=O)(=O)C=3C=CC=CC=3)=C2N=C(CCC)C=C1N1CCNCC1 KDPDMXQMBHTUHG-UHFFFAOYSA-N 0.000 claims description 3
WRCGHUOBWDSGJY-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-[(dimethylamino)methyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(CN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WRCGHUOBWDSGJY-UHFFFAOYSA-N 0.000 claims description 3
NBTJXYKEPGRADD-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NBTJXYKEPGRADD-UHFFFAOYSA-N 0.000 claims description 3
SRMFGSKGKUHKCH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 SRMFGSKGKUHKCH-UHFFFAOYSA-N 0.000 claims description 3
ACAVEAGQNALEAY-UHFFFAOYSA-N 3-benzenesulphonyl-2-methylsulphanyl-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-8-ylamine Chemical compound CSC1=NN2C(N)=C3CCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 ACAVEAGQNALEAY-UHFFFAOYSA-N 0.000 claims description 3
WTLHPKQGVWVPFJ-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(N)N4N=C3SC)=CC=C21 WTLHPKQGVWVPFJ-UHFFFAOYSA-N 0.000 claims description 3
HCYCQIRHCHFSLZ-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-7-piperazin-1-yl-3-thiophen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CS1 HCYCQIRHCHFSLZ-UHFFFAOYSA-N 0.000 claims description 3
PNYWTBNVJKJDDI-UHFFFAOYSA-N 8-(benzenesulfonyl)-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound CSC1=NN2C(N)=NC=NC2=C1S(=O)(=O)C1=CC=CC=C1 PNYWTBNVJKJDDI-UHFFFAOYSA-N 0.000 claims description 3
UJZYDAYPPURDES-UHFFFAOYSA-N C=12CSCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 Chemical compound C=12CSCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 UJZYDAYPPURDES-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
PPPVADQGCXVIIG-UHFFFAOYSA-N chembl1642114 Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 PPPVADQGCXVIIG-UHFFFAOYSA-N 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
MZHLYLPLUQNPRH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,6-dimethyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CC=1C(C)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 MZHLYLPLUQNPRH-UHFFFAOYSA-N 0.000 claims description 2
CJYVLEUNNDIHSZ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(methoxymethyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-6-amine Chemical compound CSC1=NN2C=C(N)C(COC)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CJYVLEUNNDIHSZ-UHFFFAOYSA-N 0.000 claims description 2
KHHFVHLOIOOBGE-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KHHFVHLOIOOBGE-UHFFFAOYSA-N 0.000 claims description 2
GQNCJZJRMRMGDJ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-n,5-n-dimethyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CSC1=NN2C(N)=CC(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 GQNCJZJRMRMGDJ-UHFFFAOYSA-N 0.000 claims description 2
RPYDLZZCQDDXIB-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-3-(4-propan-2-ylphenyl)sulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)C)C=C1 RPYDLZZCQDDXIB-UHFFFAOYSA-N 0.000 claims description 2
FBXQGDKVKMTEAF-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C FBXQGDKVKMTEAF-UHFFFAOYSA-N 0.000 claims description 2
OWSYFTNTDMXBFQ-UHFFFAOYSA-N 5-methyl-3-(3-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC(C)=C1 OWSYFTNTDMXBFQ-UHFFFAOYSA-N 0.000 claims description 2
MYJPFAZGUCRKJF-UHFFFAOYSA-N 8-(benzenesulfonyl)-2-methyl-4-(4-methylpiperazin-1-yl)-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=NC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 MYJPFAZGUCRKJF-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
JXXCBUALBBAQPF-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-n-[2-(dimethylamino)ethyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CSC1=NN2C(N)=CC(NCCN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 JXXCBUALBBAQPF-UHFFFAOYSA-N 0.000 claims 1
239000012876 carrier material Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 261
239000000243 solution Substances 0.000 description 190
239000000460 chlorine Substances 0.000 description 181
239000013078 crystal Substances 0.000 description 149
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 114
238000004587 chromatography analysis Methods 0.000 description 76
239000012074 organic phase Substances 0.000 description 72
238000006243 chemical reaction Methods 0.000 description 69
239000008346 aqueous phase Substances 0.000 description 63
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 60
229910004298 SiO 2 Inorganic materials 0.000 description 60
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 40
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
238000002425 crystallisation Methods 0.000 description 35
230000008025 crystallization Effects 0.000 description 35
239000006260 foam Substances 0.000 description 30
238000010992 reflux Methods 0.000 description 29
239000000725 suspension Substances 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
239000005457 ice water Substances 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 16
YPAKCUFDMDPCIC-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 YPAKCUFDMDPCIC-UHFFFAOYSA-N 0.000 description 15
GKLYGEGLNUHNLL-UHFFFAOYSA-N 4-(benzenesulfonyl)-3-methylsulfanyl-1h-pyrazol-5-amine Chemical compound CSC1=NNC(N)=C1S(=O)(=O)C1=CC=CC=C1 GKLYGEGLNUHNLL-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
238000001816 cooling Methods 0.000 description 14
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
239000000843 powder Substances 0.000 description 11
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
229910019213 POCl3 Inorganic materials 0.000 description 8
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 7
108091005435 5-HT6 receptors Proteins 0.000 description 7
239000000969 carrier Substances 0.000 description 7
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 7
IGCRGHDZSHBTDW-UHFFFAOYSA-N 8-(benzenesulfonyl)-2-methyl-7-methylsulfanyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one Chemical compound CSc1nn2c(nc(C)[nH]c2=O)c1S(=O)(=O)c1ccccc1 IGCRGHDZSHBTDW-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
QRDJOPPWGSQVOM-UHFFFAOYSA-N 3-benzenesulphonyl-8-chloro-2-ethyl-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(Cl)=C3CCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 QRDJOPPWGSQVOM-UHFFFAOYSA-N 0.000 description 5
DZYUVRHAYHLENB-UHFFFAOYSA-N 7-chloro-5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C DZYUVRHAYHLENB-UHFFFAOYSA-N 0.000 description 5
PYVQMTMOQHNLMH-UHFFFAOYSA-N 7-chloro-5-methyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 PYVQMTMOQHNLMH-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 description 4
QDXCKTWVCDZHRQ-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-7-chloro-2-ethyl-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 QDXCKTWVCDZHRQ-UHFFFAOYSA-N 0.000 description 4
FTZKOANCFYYPIB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-7-chloro-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 FTZKOANCFYYPIB-UHFFFAOYSA-N 0.000 description 4
IWOSYEFGLRMIRJ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-chloro-2-ethyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(Cl)=NC2=C1S(=O)(=O)C1=CC=CC=C1 IWOSYEFGLRMIRJ-UHFFFAOYSA-N 0.000 description 4
IMQJGMJCTIKWBE-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-2-ethyl-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 IMQJGMJCTIKWBE-UHFFFAOYSA-N 0.000 description 4
JAUCHTAOSJANQT-UHFFFAOYSA-N 4-(benzenesulfonyl)-5-ethyl-1h-pyrazol-3-amine Chemical compound CCC1=NNC(N)=C1S(=O)(=O)C1=CC=CC=C1 JAUCHTAOSJANQT-UHFFFAOYSA-N 0.000 description 4
WRKVACOFBHIWBF-UHFFFAOYSA-N 7-chloro-2-ethyl-3-(4-methoxyphenyl)sulfonyl-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC)C=C1 WRKVACOFBHIWBF-UHFFFAOYSA-N 0.000 description 4
VKDRQCBLABJLGJ-UHFFFAOYSA-N 7-chloro-3-(4-chlorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1 VKDRQCBLABJLGJ-UHFFFAOYSA-N 0.000 description 4
OVVNZESVHFXDCO-UHFFFAOYSA-N 7-chloro-5-methyl-2-methylsulfanyl-3-(4-propan-2-ylphenyl)sulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)C)C=C1 OVVNZESVHFXDCO-UHFFFAOYSA-N 0.000 description 4
FYCKCTMUJQEGRA-UHFFFAOYSA-N 7-chloro-5-methyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(Cl)N4N=C3SC)=CC=C21 FYCKCTMUJQEGRA-UHFFFAOYSA-N 0.000 description 4
ATVDUCNTYOUCTK-UHFFFAOYSA-N 7-chloro-5-methyl-2-methylsulfanyl-3-pyridin-3-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CN=C1 ATVDUCNTYOUCTK-UHFFFAOYSA-N 0.000 description 4
AXPKJVKSWHUAAU-UHFFFAOYSA-N CSc1nn2c(O)cc(CCl)nc2c1S(=O)(=O)c1ccccc1 Chemical compound CSc1nn2c(O)cc(CCl)nc2c1S(=O)(=O)c1ccccc1 AXPKJVKSWHUAAU-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RMPSNHPHGIGSOZ-UHFFFAOYSA-N 10-(benzenesulfonyl)-2-chloro-11-methylsulfanyl-5-thia-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound CSC1=NN2C(Cl)=C3CSCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 RMPSNHPHGIGSOZ-UHFFFAOYSA-N 0.000 description 3
REESBMRYLNMERW-UHFFFAOYSA-N 2-(3-methylphenyl)sulfonylacetonitrile Chemical compound CC1=CC=CC(S(=O)(=O)CC#N)=C1 REESBMRYLNMERW-UHFFFAOYSA-N 0.000 description 3
ZFCFFNGBCVAUDE-UHFFFAOYSA-N 2-(benzenesulfonyl)acetonitrile Chemical compound N#CCS(=O)(=O)C1=CC=CC=C1 ZFCFFNGBCVAUDE-UHFFFAOYSA-N 0.000 description 3
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
UXHXCOFSTMIBKC-UHFFFAOYSA-N 2-pyridin-3-ylsulfonylacetonitrile Chemical compound N#CCS(=O)(=O)C1=CC=CN=C1 UXHXCOFSTMIBKC-UHFFFAOYSA-N 0.000 description 3
BRRHWLGFUNZJQK-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-ethyl-7-hydroxy-4H-pyrazolo[1,5-a]pyrimidin-5-one Chemical compound CCc1nn2c(O)cc(O)nc2c1S(=O)(=O)c1ccccc1 BRRHWLGFUNZJQK-UHFFFAOYSA-N 0.000 description 3
CVQZKRQWQKIANB-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,7-dichloro-2-ethylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(Cl)=CC(Cl)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CVQZKRQWQKIANB-UHFFFAOYSA-N 0.000 description 3
NRMJUSDLZMFVPN-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-chloro-2-ethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CCC1=NN2C(N)=CC(Cl)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NRMJUSDLZMFVPN-UHFFFAOYSA-N 0.000 description 3
JXBHIZIFPAHYFC-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-2-methylsulfanyl-5-propylpyrazolo[1,5-a]pyrimidine Chemical compound C=12N=C(CCC)C=C(Cl)N2N=C(SC)C=1S(=O)(=O)C1=CC=CC=C1 JXBHIZIFPAHYFC-UHFFFAOYSA-N 0.000 description 3
FDIQCMRTVKGMAH-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-5,6-dimethyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=C(C)C(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 FDIQCMRTVKGMAH-UHFFFAOYSA-N 0.000 description 3
OCXUMBPDUBIEPU-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-5-cyclopropyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 OCXUMBPDUBIEPU-UHFFFAOYSA-N 0.000 description 3
JAADPEFHUZULOK-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound C=12N=C(C)C=C(Cl)N2N=CC=1S(=O)(=O)C1=CC=CC=C1 JAADPEFHUZULOK-UHFFFAOYSA-N 0.000 description 3
RZWNMHXIONNJFQ-UHFFFAOYSA-N 4-[[3-(benzenesulfonyl)-7-chloro-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-5-yl]methyl]morpholine Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C(Cl)=CC=1CN1CCOCC1 RZWNMHXIONNJFQ-UHFFFAOYSA-N 0.000 description 3
DNHDSNXQPNDJMQ-UHFFFAOYSA-N 7-chloro-3-(2,4-dichlorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1Cl DNHDSNXQPNDJMQ-UHFFFAOYSA-N 0.000 description 3
RBOGFYWPOJTELW-UHFFFAOYSA-N 7-chloro-3-(4-fluorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 RBOGFYWPOJTELW-UHFFFAOYSA-N 0.000 description 3
WJZHWSPOCNYEMZ-UHFFFAOYSA-N 7-chloro-3-(4-methoxyphenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=C2N=C(C)C=C(Cl)N2N=C1SC WJZHWSPOCNYEMZ-UHFFFAOYSA-N 0.000 description 3
HQJXODIYIZXNMX-UHFFFAOYSA-N 7-chloro-5-methyl-2-methylsulfanyl-3-[4-(trifluoromethoxy)phenyl]sulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 HQJXODIYIZXNMX-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
TYYOJHWYTSYYNK-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)C(F)(F)F)SC Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)C(F)(F)F)SC TYYOJHWYTSYYNK-UHFFFAOYSA-N 0.000 description 3
VTGJRJFWBWWKQC-UHFFFAOYSA-N CSc1nn2c(O)cc(C)nc2c1S(=O)(=O)c1ccc(cc1)C(C)C Chemical compound CSc1nn2c(O)cc(C)nc2c1S(=O)(=O)c1ccc(cc1)C(C)C VTGJRJFWBWWKQC-UHFFFAOYSA-N 0.000 description 3
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
229910052681 coesite Inorganic materials 0.000 description 3
229910052906 cristobalite Inorganic materials 0.000 description 3
QUBIPGOCOCXBEM-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonyl)-5-methyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-2-yl]oxyacetate Chemical compound CCOC(=O)COC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 QUBIPGOCOCXBEM-UHFFFAOYSA-N 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000003446 ligand Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229910052682 stishovite Inorganic materials 0.000 description 3
229910052905 tridymite Inorganic materials 0.000 description 3
RILZJLQVGRBIAW-SEYXRHQNSA-N (z)-2-(benzenesulfonyl)-3-ethoxypent-2-enenitrile Chemical compound CCO\C(CC)=C(\C#N)S(=O)(=O)C1=CC=CC=C1 RILZJLQVGRBIAW-SEYXRHQNSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UWTJOSKHTDTQCT-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)-7-chloro-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-5-yl]-n,n-dimethylmethanamine Chemical compound CSC1=NN2C(Cl)=CC(CN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 UWTJOSKHTDTQCT-UHFFFAOYSA-N 0.000 description 2
NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
ZMAUEMGCCPSKEV-UHFFFAOYSA-N 2-(2-methylphenyl)sulfonylacetonitrile Chemical compound CC1=CC=CC=C1S(=O)(=O)CC#N ZMAUEMGCCPSKEV-UHFFFAOYSA-N 0.000 description 2
KSKSEVVFIOHIAT-UHFFFAOYSA-N 2-(4-bromophenyl)sulfonylacetonitrile Chemical compound BrC1=CC=C(S(=O)(=O)CC#N)C=C1 KSKSEVVFIOHIAT-UHFFFAOYSA-N 0.000 description 2
WSKDIKKGBGYFLB-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonylacetonitrile Chemical compound COC1=CC=C(S(=O)(=O)CC#N)C=C1 WSKDIKKGBGYFLB-UHFFFAOYSA-N 0.000 description 2
VLYADXJGWWPTGA-UHFFFAOYSA-N 2-[[5-amino-4-(benzenesulfonyl)-1h-pyrazol-3-yl]oxy]ethanol Chemical compound N1N=C(OCCO)C(S(=O)(=O)C=2C=CC=CC=2)=C1N VLYADXJGWWPTGA-UHFFFAOYSA-N 0.000 description 2
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 2
RXMWSGXTCHWDNM-UHFFFAOYSA-N 3,3-bis(methylsulfanyl)-2-(4-propan-2-ylphenyl)sulfonylprop-2-enenitrile Chemical compound CSC(SC)=C(C#N)S(=O)(=O)C1=CC=C(C(C)C)C=C1 RXMWSGXTCHWDNM-UHFFFAOYSA-N 0.000 description 2
RXTXAYDQMHKGIZ-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-7-chloro-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 RXTXAYDQMHKGIZ-UHFFFAOYSA-N 0.000 description 2
FCZXUYICWPTIQR-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,7-dichloro-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(Cl)=NC2=C1S(=O)(=O)C1=CC=CC=C1 FCZXUYICWPTIQR-UHFFFAOYSA-N 0.000 description 2
VHIXPTUZNSPQLW-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(2-methoxyethyl)-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound N12N=C(SC)C(S(=O)(=O)C=3C=CC=CC=3)=C2N=C(CCOC)C=C1N1CCNCC1 VHIXPTUZNSPQLW-UHFFFAOYSA-N 0.000 description 2
DBVBXSDDWHHCMA-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-[(4-methylpiperazin-1-yl)methyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C(N)=CC=1CN1CCN(C)CC1 DBVBXSDDWHHCMA-UHFFFAOYSA-N 0.000 description 2
QPWLDIKVRCSPCW-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-chloro-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(Cl)=NC2=C1S(=O)(=O)C1=CC=CC=C1 QPWLDIKVRCSPCW-UHFFFAOYSA-N 0.000 description 2
PKCYEDLEDNIFPU-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-chloro-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(Cl)=NC2=C1S(=O)(=O)C1=CC=CC=C1 PKCYEDLEDNIFPU-UHFFFAOYSA-N 0.000 description 2
ZHGXZFLDLCMRHP-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 ZHGXZFLDLCMRHP-UHFFFAOYSA-N 0.000 description 2
CMBXHYQYCNBQAR-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-2-methylsulfanyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CMBXHYQYCNBQAR-UHFFFAOYSA-N 0.000 description 2
WTNUCOIJLCGPKL-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-2-methylsulfanyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WTNUCOIJLCGPKL-UHFFFAOYSA-N 0.000 description 2
ICBHTCWDCFTTBU-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-5-(2-methoxyethyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound C=12N=C(CCOC)C=C(Cl)N2N=C(SC)C=1S(=O)(=O)C1=CC=CC=C1 ICBHTCWDCFTTBU-UHFFFAOYSA-N 0.000 description 2
ZOKOAUKKUGBULX-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-hydroxy-2-methylsulfanyl-4H-pyrazolo[1,5-a]pyrimidin-5-one Chemical compound CSc1nn2c(O)cc(O)nc2c1S(=O)(=O)c1ccccc1 ZOKOAUKKUGBULX-UHFFFAOYSA-N 0.000 description 2
IJZIAGRBCMJQCQ-UHFFFAOYSA-N 3-benzenesulphonyl-8-chloro-2-methylsulphanyl-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=C3CCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 IJZIAGRBCMJQCQ-UHFFFAOYSA-N 0.000 description 2
PWCMYVJXHPBJNZ-UHFFFAOYSA-N 4-(benzenesulfonyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(S(=O)(=O)C=2C=CC=CC=2)=C1N PWCMYVJXHPBJNZ-UHFFFAOYSA-N 0.000 description 2
DQNHZOVLUDLGAK-UHFFFAOYSA-N 5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanyl-3-(4-propan-2-ylphenyl)sulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)C)C=C1 DQNHZOVLUDLGAK-UHFFFAOYSA-N 0.000 description 2
PIVOBWIEGXPEQB-UHFFFAOYSA-N 7-chloro-5-methyl-2-methylsulfanyl-3-thiophen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CS1 PIVOBWIEGXPEQB-UHFFFAOYSA-N 0.000 description 2
WFPSVNDXPCGZOD-UHFFFAOYSA-N 7-chloro-5-methyl-3-(3-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC(C)=C1 WFPSVNDXPCGZOD-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
FYTSOLLZBOHCMF-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)CN2CCN(CC2)C)SC Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)CN2CCN(CC2)C)SC FYTSOLLZBOHCMF-UHFFFAOYSA-N 0.000 description 2
HOBRLKYWDMSTEE-UHFFFAOYSA-N CCOC(=O)COc1nn2c(O)cc(C)nc2c1S(=O)(=O)c1ccccc1 Chemical compound CCOC(=O)COc1nn2c(O)cc(C)nc2c1S(=O)(=O)c1ccccc1 HOBRLKYWDMSTEE-UHFFFAOYSA-N 0.000 description 2
OGGGTHGEQCVGFN-UHFFFAOYSA-N CCOC(=O)Cc1c(C)nc2c(c(SC)nn2c1O)S(=O)(=O)c1ccccc1 Chemical compound CCOC(=O)Cc1c(C)nc2c(c(SC)nn2c1O)S(=O)(=O)c1ccccc1 OGGGTHGEQCVGFN-UHFFFAOYSA-N 0.000 description 2
YUAKIVZOCRGQGT-UHFFFAOYSA-N CCc1nn2c(O)cc(C)nc2c1S(=O)(=O)c1ccccc1 Chemical compound CCc1nn2c(O)cc(C)nc2c1S(=O)(=O)c1ccccc1 YUAKIVZOCRGQGT-UHFFFAOYSA-N 0.000 description 2
HLRXDIVIIDNSTM-UHFFFAOYSA-N CSc1nn2c(O)cc(CN(C)C)nc2c1S(=O)(=O)c1ccccc1 Chemical compound CSc1nn2c(O)cc(CN(C)C)nc2c1S(=O)(=O)c1ccccc1 HLRXDIVIIDNSTM-UHFFFAOYSA-N 0.000 description 2
FLTXKLORTSCBAB-UHFFFAOYSA-N CSc1nn2c(O)cc(CN3CCOCC3)nc2c1S(=O)(=O)c1ccccc1 Chemical compound CSc1nn2c(O)cc(CN3CCOCC3)nc2c1S(=O)(=O)c1ccccc1 FLTXKLORTSCBAB-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
229910017852 NH2NH2 Inorganic materials 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
238000009739 binding Methods 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000003925 fat Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000012528 membrane Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000001993 wax Substances 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
CJQUCTSQALRPGK-UHFFFAOYSA-N 1-[8-(benzenesulfonyl)-2-methyl-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CSC1=NN2C(C(N)CCN(C)C)=NC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CJQUCTSQALRPGK-UHFFFAOYSA-N 0.000 description 1
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
ZCSBENFHYLOLIP-UHFFFAOYSA-N 10-(benzenesulfonyl)-11-ethyl-2-(4-methylpiperazin-1-yl)-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(CC)=NN2C=1N1CCN(C)CC1 ZCSBENFHYLOLIP-UHFFFAOYSA-N 0.000 description 1
MXDRXNIGGKXEQC-UHFFFAOYSA-N 10-(benzenesulfonyl)-11-methyl-2-(4-methylpiperazin-1-yl)-5-thia-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene-6-thiol Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C1C(=C2N2CCN(CC2)C)CSC1S)C MXDRXNIGGKXEQC-UHFFFAOYSA-N 0.000 description 1
HHVXXRIZJCXXQH-IYBDPMFKSA-N 10-(benzenesulfonyl)-2-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-11-ethyl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(CC)=NN2C=1N1C[C@H](C)N[C@H](C)C1 HHVXXRIZJCXXQH-IYBDPMFKSA-N 0.000 description 1
RIJAUKHQIOCSTA-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)sulfonylacetonitrile Chemical compound ClC1=CC=C(S(=O)(=O)CC#N)C(Cl)=C1 RIJAUKHQIOCSTA-UHFFFAOYSA-N 0.000 description 1
HAQGVGPNKGGSMK-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfonylacetonitrile Chemical compound ClC1=CC=C(S(=O)(=O)CC#N)C=C1 HAQGVGPNKGGSMK-UHFFFAOYSA-N 0.000 description 1
WBXJZTLPEMITJL-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfonylacetonitrile Chemical compound FC1=CC=C(S(=O)(=O)CC#N)C=C1 WBXJZTLPEMITJL-UHFFFAOYSA-N 0.000 description 1
DDSYWTCBKZSLED-UHFFFAOYSA-N 2-(4-iodophenyl)sulfonylacetonitrile Chemical compound IC1=CC=C(S(=O)(=O)CC#N)C=C1 DDSYWTCBKZSLED-UHFFFAOYSA-N 0.000 description 1
SIIXKRNTWBNFPO-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)sulfonylacetonitrile Chemical compound CC(C)C1=CC=C(S(=O)(=O)CC#N)C=C1 SIIXKRNTWBNFPO-UHFFFAOYSA-N 0.000 description 1
UKRHKLHRSIUATR-UHFFFAOYSA-N 2-(4-tert-butylphenyl)sulfonylacetonitrile Chemical compound CC(C)(C)C1=CC=C(S(=O)(=O)CC#N)C=C1 UKRHKLHRSIUATR-UHFFFAOYSA-N 0.000 description 1
WGGILLZYBNAKKM-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-(dimethylamino)prop-2-enenitrile Chemical compound CN(C)C=C(C#N)S(=O)(=O)C1=CC=CC=C1 WGGILLZYBNAKKM-UHFFFAOYSA-N 0.000 description 1
KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
SNHNAXYBMJUCGH-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-6-yl]ethanol Chemical compound OCCC=1C(C)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 SNHNAXYBMJUCGH-UHFFFAOYSA-N 0.000 description 1
AWXPHHFMCOJVSU-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]sulfonylacetonitrile Chemical compound FC(F)(F)OC1=CC=C(S(=O)(=O)CC#N)C=C1 AWXPHHFMCOJVSU-UHFFFAOYSA-N 0.000 description 1
NZWYXVYRISVGKR-UHFFFAOYSA-N 2-[4-[3-(benzenesulfonyl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-yl]piperazin-1-yl]ethanol Chemical compound CSC1=NN2C(N3CCN(CCO)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NZWYXVYRISVGKR-UHFFFAOYSA-N 0.000 description 1
SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
BCDQPGOYBNLFRB-UHFFFAOYSA-N 2-ethyl-3-(4-methoxyphenyl)sulfonyl-5-methyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC)C=C1 BCDQPGOYBNLFRB-UHFFFAOYSA-N 0.000 description 1
OXNOEGHEJRBNBW-UHFFFAOYSA-N 2-ethyl-3-(4-methoxyphenyl)sulfonyl-5-methyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC)C=C1 OXNOEGHEJRBNBW-UHFFFAOYSA-N 0.000 description 1
IMIXSCIWNBXXKC-UHFFFAOYSA-N 2-ethyl-3-(4-methoxyphenyl)sulfonyl-5-methylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CCC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC)C=C1 IMIXSCIWNBXXKC-UHFFFAOYSA-N 0.000 description 1
SVBMTLDXBDCGBQ-UHFFFAOYSA-N 2-naphthalen-2-ylsulfonylacetonitrile Chemical compound C1=CC=CC2=CC(S(=O)(CC#N)=O)=CC=C21 SVBMTLDXBDCGBQ-UHFFFAOYSA-N 0.000 description 1
JWLFPYPXODBUFB-UHFFFAOYSA-N 2-thiophen-2-ylsulfonylacetonitrile Chemical compound N#CCS(=O)(=O)C1=CC=CS1 JWLFPYPXODBUFB-UHFFFAOYSA-N 0.000 description 1
PZEOTHCNQMHVAI-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1Cl PZEOTHCNQMHVAI-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
ODHGOZBTDKEAHW-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-2-ethyl-5-methyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 ODHGOZBTDKEAHW-UHFFFAOYSA-N 0.000 description 1
BPPSTFSPLCHLER-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 BPPSTFSPLCHLER-UHFFFAOYSA-N 0.000 description 1
HQQJTRVUALOFMG-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 HQQJTRVUALOFMG-UHFFFAOYSA-N 0.000 description 1
PTWVIIFRAPJRRE-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 PTWVIIFRAPJRRE-UHFFFAOYSA-N 0.000 description 1
ZSDXQWFIJBXIOF-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1 ZSDXQWFIJBXIOF-UHFFFAOYSA-N 0.000 description 1
VPQPDAWPGQFLFR-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1 VPQPDAWPGQFLFR-UHFFFAOYSA-N 0.000 description 1
GYAMFRKIACRVKX-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GYAMFRKIACRVKX-UHFFFAOYSA-N 0.000 description 1
FGQDXQMEBMCUSG-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 FGQDXQMEBMCUSG-UHFFFAOYSA-N 0.000 description 1
ITYGVGGVSMLMIT-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 ITYGVGGVSMLMIT-UHFFFAOYSA-N 0.000 description 1
SFDOQRHWEVCXCJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=C2N=C(C)C=C(N3CCNCC3)N2N=C1SC SFDOQRHWEVCXCJ-UHFFFAOYSA-N 0.000 description 1
MSYZKHJLOLSEDY-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=C2N=C(C)C=C(N)N2N=C1SC MSYZKHJLOLSEDY-UHFFFAOYSA-N 0.000 description 1
UQGKABPBLRFPAK-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=C2N=C(C)C=C(N3CCN(C)CC3)N2N=C1SC UQGKABPBLRFPAK-UHFFFAOYSA-N 0.000 description 1
ZQNWXCQMJBYYDQ-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ZQNWXCQMJBYYDQ-UHFFFAOYSA-N 0.000 description 1
TVVWYTNWTTWYIT-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 TVVWYTNWTTWYIT-UHFFFAOYSA-N 0.000 description 1
JHVBYEAIBLRRFC-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-ethyl-5,7-bis(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(N3CCN(C)CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 JHVBYEAIBLRRFC-UHFFFAOYSA-N 0.000 description 1
WJHBTHVULRNEBW-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-ethyl-5-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CCC1=NN2C(N)=CC(N3CCN(C)CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WJHBTHVULRNEBW-UHFFFAOYSA-N 0.000 description 1
NJZTZFZNQYMSDG-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-ethyl-5-methyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NJZTZFZNQYMSDG-UHFFFAOYSA-N 0.000 description 1
PKQDMKIPXPWXTM-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-ethyl-5-n,5-n-dimethylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CCC1=NN2C(N)=CC(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 PKQDMKIPXPWXTM-UHFFFAOYSA-N 0.000 description 1
KQXNWTGTSMAOKL-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-ethyl-n,n-dimethyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KQXNWTGTSMAOKL-UHFFFAOYSA-N 0.000 description 1
CROTWENMHNVRDG-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-7-piperazin-1-yl-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C(F)(F)F)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CROTWENMHNVRDG-UHFFFAOYSA-N 0.000 description 1
NJGRYIAQIRQZSV-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-9-piperazin-1-yl-5,6,7,8-tetrahydropyrazolo[5,1-b]quinazoline Chemical compound C=12CCCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 NJGRYIAQIRQZSV-UHFFFAOYSA-N 0.000 description 1
OAIVKIJOMGRLPW-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,6-dimethyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CC=1C(C)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 OAIVKIJOMGRLPW-UHFFFAOYSA-N 0.000 description 1
XUGXZHUOKLZSTM-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(2-methoxyethyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=12N=C(CCOC)C=C(N)N2N=C(SC)C=1S(=O)(=O)C1=CC=CC=C1 XUGXZHUOKLZSTM-UHFFFAOYSA-N 0.000 description 1
FLUZNTSTLIXDPR-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(N3CCN(C)CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 FLUZNTSTLIXDPR-UHFFFAOYSA-N 0.000 description 1
NZQXSEVUWFGRDG-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(methoxymethyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=12N=C(COC)C=C(N)N2N=C(SC)C=1S(=O)(=O)C1=CC=CC=C1 NZQXSEVUWFGRDG-UHFFFAOYSA-N 0.000 description 1
HGDVWXRTIXBISN-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methoxy-6-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CC=1C(OC)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 HGDVWXRTIXBISN-UHFFFAOYSA-N 0.000 description 1
RJOTXUULUZLADR-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methyl-2-methylsulfanyl-7-(4-phenylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(CC3)C=3C=CC=CC=3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 RJOTXUULUZLADR-UHFFFAOYSA-N 0.000 description 1
SRAGNJUJWHGGEZ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 SRAGNJUJWHGGEZ-UHFFFAOYSA-N 0.000 description 1
NHQBTXANAWDWJD-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NHQBTXANAWDWJD-UHFFFAOYSA-N 0.000 description 1
KJAZKOUWQSSPBS-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound N12N=CC(S(=O)(=O)C=3C=CC=CC=3)=C2N=C(C)C=C1N1CCNCC1 KJAZKOUWQSSPBS-UHFFFAOYSA-N 0.000 description 1
QBIDANPXEWLGCP-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound C=12N=C(C)C=CN2N=CC=1S(=O)(=O)C1=CC=CC=C1 QBIDANPXEWLGCP-UHFFFAOYSA-N 0.000 description 1
PTWWKUVCUFNCPK-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-n-[2-(dimethylamino)ethyl]-2-ethylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CCC1=NN2C(N)=CC(NCCN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 PTWWKUVCUFNCPK-UHFFFAOYSA-N 0.000 description 1
ZPDXVLTUHQCNFH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-tert-butyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C(C)(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 ZPDXVLTUHQCNFH-UHFFFAOYSA-N 0.000 description 1
XDXWVASZINMBMX-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-tert-butyl-7-chloro-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C(C)(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 XDXWVASZINMBMX-UHFFFAOYSA-N 0.000 description 1
NVTCKVRVUNFQNJ-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-(4-benzylpiperazin-1-yl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(CC=4C=CC=CC=4)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NVTCKVRVUNFQNJ-UHFFFAOYSA-N 0.000 description 1
WBNRTADBLPZTOB-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC=NC2=C1S(=O)(=O)C1=CC=CC=C1 WBNRTADBLPZTOB-UHFFFAOYSA-N 0.000 description 1
MJMRDEAMUWHQTO-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-5-[(4-methylpiperazin-1-yl)methyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C(N2CCN(C)CC2)=CC=1CN1CCN(C)CC1 MJMRDEAMUWHQTO-UHFFFAOYSA-N 0.000 description 1
AEIUTXIWFVFUQX-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-chloro-5-[(4-methylpiperazin-1-yl)methyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C(Cl)=CC=1CN1CCN(C)CC1 AEIUTXIWFVFUQX-UHFFFAOYSA-N 0.000 description 1
LPINVXNOMRXJPC-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-imidazol-1-yl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3C=NC=C3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 LPINVXNOMRXJPC-UHFFFAOYSA-N 0.000 description 1
SRYQDHNEGQWCQD-UHFFFAOYSA-N 3-(benzenesulfonyl)-9-chloro-2-methylsulfanyl-5,6,7,8-tetrahydropyrazolo[5,1-b]quinazoline Chemical compound CSC1=NN2C(Cl)=C3CCCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 SRYQDHNEGQWCQD-UHFFFAOYSA-N 0.000 description 1
OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
BCJLUYOZTPLLPL-UHFFFAOYSA-N 3-benzenesulphonyl-2-ethyl-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-8-ylamine Chemical compound CCC1=NN2C(N)=C3CCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 BCJLUYOZTPLLPL-UHFFFAOYSA-N 0.000 description 1
STGSMBZBKCRWIQ-UHFFFAOYSA-N 4-(4-methylphenyl)sulfonyl-3-methylsulfanyl-1h-pyrazol-5-amine Chemical compound CSC1=NNC(N)=C1S(=O)(=O)C1=CC=C(C)C=C1 STGSMBZBKCRWIQ-UHFFFAOYSA-N 0.000 description 1
HLJNLELGTSBCBB-UHFFFAOYSA-N 4-(benzenesulfonyl)-5-methylsulfonyl-1H-pyrazol-3-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NN=C1S(=O)(=O)C)N HLJNLELGTSBCBB-UHFFFAOYSA-N 0.000 description 1
HUQXJHAGAVLFAQ-UHFFFAOYSA-N 4-[2-[3-(benzenesulfonyl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-yl]oxyethyl]morpholine Chemical compound C=1C(C)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1OCCN1CCOCC1 HUQXJHAGAVLFAQ-UHFFFAOYSA-N 0.000 description 1
ZQVKJCVQABICID-UHFFFAOYSA-N 4-[[3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-5-yl]methyl]morpholine Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C(N2CCN(C)CC2)=CC=1CN1CCOCC1 ZQVKJCVQABICID-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
OAYJWCLIEKOYGT-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-7-piperazin-1-yl-3-(4-propan-2-ylphenyl)sulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)C)C=C1 OAYJWCLIEKOYGT-UHFFFAOYSA-N 0.000 description 1
FZKMMQRNNCRFFT-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-7-piperazin-1-yl-3-[4-(trifluoromethoxy)phenyl]sulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 FZKMMQRNNCRFFT-UHFFFAOYSA-N 0.000 description 1
ROOQSCCLMPGCRS-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-7-piperazin-1-yl-3-pyridin-3-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CN=C1 ROOQSCCLMPGCRS-UHFFFAOYSA-N 0.000 description 1
RUFFPXDYUAOQDB-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C RUFFPXDYUAOQDB-UHFFFAOYSA-N 0.000 description 1
XHCURFXTMSFGPU-UHFFFAOYSA-N 5-methyl-3-(3-methylphenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC(C)=C1 XHCURFXTMSFGPU-UHFFFAOYSA-N 0.000 description 1
BBHRGHLRVSPOTB-UHFFFAOYSA-N 5-methyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 BBHRGHLRVSPOTB-UHFFFAOYSA-N 0.000 description 1
KFYRLOUBTRUMEH-UHFFFAOYSA-N 5-methyl-3-(4-methylphenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 KFYRLOUBTRUMEH-UHFFFAOYSA-N 0.000 description 1
ALYHVJVYHFSVDN-UHFFFAOYSA-N 5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanyl-3-[4-(trifluoromethoxy)phenyl]sulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 ALYHVJVYHFSVDN-UHFFFAOYSA-N 0.000 description 1
SKGMLPKBYQDKRP-UHFFFAOYSA-N 5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C(C)=NC2=C(S(=O)(=O)C=3C=C4C=CC=CC4=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 SKGMLPKBYQDKRP-UHFFFAOYSA-N 0.000 description 1
AFWNTPQGTFPHHV-UHFFFAOYSA-N 5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanyl-3-pyridin-3-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CN=C1 AFWNTPQGTFPHHV-UHFFFAOYSA-N 0.000 description 1
ZSDJULMKCSBPMM-UHFFFAOYSA-N 5-methyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanyl-3-thiophen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CS1 ZSDJULMKCSBPMM-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
IFAPBJGVENXFAY-IYBDPMFKSA-N 7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-2-ethyl-3-(4-methoxyphenyl)sulfonyl-5-methylpyrazolo[1,5-a]pyrimidine Chemical compound CCC1=NN2C(N3C[C@@H](C)N[C@@H](C)C3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(OC)C=C1 IFAPBJGVENXFAY-IYBDPMFKSA-N 0.000 description 1
VQHTXWCXICJZPK-UHFFFAOYSA-N 7-chloro-3-(4-iodophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(Cl)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(I)C=C1 VQHTXWCXICJZPK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
QODIJPMYXVHZSV-UHFFFAOYSA-N 8-(benzenesulfonyl)-n,2-dimethyl-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound CSC1=NN2C(NC)=NC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 QODIJPMYXVHZSV-UHFFFAOYSA-N 0.000 description 1
ISNGLOZSLPLVPV-UHFFFAOYSA-N 8-(benzenesulfonyl)-n,n,2-trimethyl-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound CSC1=NN2C(N(C)C)=NC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 ISNGLOZSLPLVPV-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
238000006418 Brown reaction Methods 0.000 description 1
UVEKLTYDIZKEKJ-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C(=C2O)S)C)C Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C(=C2O)S)C)C UVEKLTYDIZKEKJ-UHFFFAOYSA-N 0.000 description 1
WZVCNOLKZYKNRJ-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)C)SC Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)C)SC WZVCNOLKZYKNRJ-UHFFFAOYSA-N 0.000 description 1
GBFQPJDQMKWPNI-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)CCOC)SC Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)CCOC)SC GBFQPJDQMKWPNI-UHFFFAOYSA-N 0.000 description 1
FDZRPLDQIQLRAK-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)COC)SC Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C(=NN2C1N=C(C=C2O)COC)SC FDZRPLDQIQLRAK-UHFFFAOYSA-N 0.000 description 1
MOFOCUXQBPUDOS-UHFFFAOYSA-N CC1=NC=2N(C(=C1)O)N=C(C2S(=O)(=O)C2=CC=C(C=C2)C)SC Chemical compound CC1=NC=2N(C(=C1)O)N=C(C2S(=O)(=O)C2=CC=C(C=C2)C)SC MOFOCUXQBPUDOS-UHFFFAOYSA-N 0.000 description 1
UUVJNYKIGKQYCX-UHFFFAOYSA-N CSc1nn2c(O)cc(nc2c1S(=O)(=O)c1ccccc1)C(C)(C)C Chemical compound CSc1nn2c(O)cc(nc2c1S(=O)(=O)c1ccccc1)C(C)(C)C UUVJNYKIGKQYCX-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229910017976 MgO 4 Inorganic materials 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CIZBDTQOZXVEAM-UHFFFAOYSA-N ethyl 2-[3-(benzenesulfonyl)-7-chloro-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-6-yl]acetate Chemical compound CSC1=NN2C(Cl)=C(CC(=O)OCC)C(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CIZBDTQOZXVEAM-UHFFFAOYSA-N 0.000 description 1
FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 1
FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 1
JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
LFSVADABIDBSBV-UHFFFAOYSA-N ethyl 3-cyclopropyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1CC1 LFSVADABIDBSBV-UHFFFAOYSA-N 0.000 description 1
KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
VUYNTIDSHCJIKF-UHFFFAOYSA-N ethyl 4,4-dimethyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)(C)C VUYNTIDSHCJIKF-UHFFFAOYSA-N 0.000 description 1
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
CMKOJBYFNYDATH-UHFFFAOYSA-N ethyl 4-methoxy-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COC CMKOJBYFNYDATH-UHFFFAOYSA-N 0.000 description 1
XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
KYCDKCMASTUOPK-UHFFFAOYSA-N ethyl n-ethoxycarbonylethanimidate Chemical compound CCOC(C)=NC(=O)OCC KYCDKCMASTUOPK-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
LEAKUJFYXNILRB-UHFFFAOYSA-N methyl 4-oxothiolane-3-carboxylate Chemical compound COC(=O)C1CSCC1=O LEAKUJFYXNILRB-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
SVYCFYNZKMXSEU-UHFFFAOYSA-N n,5-dimethyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(NC)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 SVYCFYNZKMXSEU-UHFFFAOYSA-N 0.000 description 1
MCVKRCNWTSRZKG-UHFFFAOYSA-N n,n,5-trimethyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(N4N=C3SC)N(C)C)=CC=C21 MCVKRCNWTSRZKG-UHFFFAOYSA-N 0.000 description 1
XONFMUICYNIBEQ-UHFFFAOYSA-N n,n,5-trimethyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 XONFMUICYNIBEQ-UHFFFAOYSA-N 0.000 description 1
SGTHBUSRDBXVCQ-UHFFFAOYSA-N n-[3-(4-bromophenyl)sulfonyl-2-ethyl-5-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=NN2C(NCCN(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 SGTHBUSRDBXVCQ-UHFFFAOYSA-N 0.000 description 1
NNKXIULLHBGRTD-UHFFFAOYSA-N n-[3-(benzenesulfonyl)-2-ethyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(NCCN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NNKXIULLHBGRTD-UHFFFAOYSA-N 0.000 description 1
KGSMVKIWXJCCQV-UHFFFAOYSA-N n-[3-(benzenesulfonyl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CSC1=NN2C(NCCN(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KGSMVKIWXJCCQV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229960001779 pargyline Drugs 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
KCVNFNZJAATRIK-UHFFFAOYSA-M sodium;pyridine-3-sulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CN=C1 KCVNFNZJAATRIK-UHFFFAOYSA-M 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
KQWHKLZRDFJOCN-UHFFFAOYSA-N thieno[3,4-d]pyrimidine Chemical compound N1=CN=CC2=CSC=C21 KQWHKLZRDFJOCN-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Psychology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO19991150A 1998-03-11 1999-03-10 Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament NO312297B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98104346		1998-03-11

Publications (3)

Publication Number	Publication Date
NO991150D0 NO991150D0 (no)	1999-03-10
NO991150L NO991150L (no)	1999-09-13
NO312297B1 true NO312297B1 (no)	2002-04-22

Family

ID=8231568

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19991150A NO312297B1 (no)	1998-03-11	1999-03-10	Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament

Country Status (33)

Country	Link
US (1)	US6194410B1 (es)
EP (1)	EP0941994B1 (es)
JP (1)	JP3231288B2 (es)
KR (1)	KR100313181B1 (es)
CN (1)	CN1118468C (es)
AR (1)	AR016453A1 (es)
AT (1)	ATE240332T1 (es)
AU (1)	AU752408B2 (es)
BR (1)	BR9901095A (es)
CA (1)	CA2265095C (es)
CZ (1)	CZ291514B6 (es)
DE (1)	DE69907784T2 (es)
DK (1)	DK0941994T3 (es)
ES (1)	ES2198095T3 (es)
HR (1)	HRP990077B1 (es)
HU (1)	HUP9900589A1 (es)
ID (1)	ID23575A (es)
IL (1)	IL128869A (es)
MA (1)	MA26612A1 (es)
MY (1)	MY119536A (es)
NO (1)	NO312297B1 (es)
NZ (1)	NZ334526A (es)
PE (1)	PE20000337A1 (es)
PL (1)	PL331875A1 (es)
PT (1)	PT941994E (es)
RU (1)	RU2218340C2 (es)
SG (1)	SG78336A1 (es)
SI (1)	SI0941994T1 (es)
TR (1)	TR199900531A3 (es)
TW (1)	TW585865B (es)
UY (1)	UY25419A1 (es)
YU (1)	YU12099A (es)
ZA (1)	ZA991946B (es)

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2000059907A2 (en) *	1999-04-06	2000-10-12	Du Pont Pharmaceuticals Company	Pyrazolotriazines as crf antagonists
DE19956791A1 (de) *	1999-11-25	2001-05-31	Merck Patent Gmbh	Neue Sulfonyloxazolamine
PE20020394A1 (es)	2000-08-18	2002-06-21	Agouron Pharma	Compuestos de pirazol y composiciones farmaceuticas que los contienen, que modulan y/o inhiben la actividad de erab/hadh2
IL157615A0 (en) *	2001-03-13	2004-03-28	Bristol Myers Squibb Co	4-(2-butylamino)-2,7-dimethyl-8-(2-methyl-6-methoxypyrid-3-yl) pyrazolo-[1,5-a]-1,3,5-triazine, its enantiomers and pharmaceutically acceptable salts as corticotropin releasing factor receptor ligands
YU96103A (sh)	2001-06-07	2006-08-17	F.Hoffmann-La Roche Ag.	Novi derivati indola sa afinitetom za 5-ht6 receptor
ATE331707T1 (de)	2001-06-15	2006-07-15	Hoffmann La Roche	4 piperazinylindolderivate mit affinität zum 5- ht6-rezeptor
WO2003013510A1 (en) *	2001-08-07	2003-02-20	Smithkline Beecham P.L.C.	3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders
IL162243A0 (en) *	2001-12-20	2005-11-20	Wyeth Corp	Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands
US6642381B2 (en) *	2001-12-27	2003-11-04	Hoffman-La Roche Inc.	Pyrimido[5,4-e][1,2,4]triazine-5,7-diamine compounds as protein tyrosine phosphatase inhibitors
GB0202679D0 (en) *	2002-02-05	2002-03-20	Glaxo Group Ltd	Novel compounds
UA78999C2 (en) *	2002-06-04	2007-05-10	Wyeth Corp	1-(aminoalkyl)-3-sulfonylazaindoles as ligands of 5-hydroxytryptamine-6
US6875771B2 (en)	2002-07-26	2005-04-05	Bristol-Myers Squibb Company	Pyridopyrimidine derivatives as 5-HT6 antagonists
US7196078B2 (en) *	2002-09-04	2007-03-27	Schering Corpoartion	Trisubstituted and tetrasubstituted pyrazolopyrimidines as cyclin dependent kinase inhibitors
EP2194058B1 (en) *	2002-09-04	2013-11-27	Merck Sharp & Dohme Corp.	Pyrazolopyrimidines suitable for the treatment of cancer diseases
US7329658B2 (en) *	2003-02-06	2008-02-12	Pfizer Inc	Cannabinoid receptor ligands and uses thereof
JP2006517966A (ja) *	2003-02-14	2006-08-03	ワイス	５−ヒドロキシトリプタミン−６リガンドとしてのヘテロサイクリル−３−スルホニルアザインドールまたは−アザインダゾール誘導体
MXPA05008955A (es)	2003-02-28	2006-02-22	Teijin Pharma Ltd	Derivados de pirazolo [1,5-a] pirimidina.
GB0305559D0 (en) *	2003-03-11	2003-04-16	Teijin Ltd	Compounds
US7585881B2 (en) *	2004-02-18	2009-09-08	Astrazeneca Ab	Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
WO2005112936A1 (en) *	2004-05-14	2005-12-01	The Regents Of The University Of Michigan	Compositions and methods relating to protein kinase inhibitors
KR20070090172A (ko) *	2004-11-04	2007-09-05	버텍스 파마슈티칼스 인코포레이티드	단백질 키나아제의 억제제로서 유용한피라졸로[1,5-ａ]피리미딘
RU2390523C2 (ru) *	2005-10-21	2010-05-27	Мицубиси Танабе Фарма Корпорейшн	ПРОИЗВОДНОЕ ПИРАЗОЛ[1,5-a]ПИРИМИДИНА
RU2330854C2 (ru) *	2006-03-15	2008-08-10	Государственное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия Федерального агентства по здравоохранению и социальному развитию" (ГОУВПО "ПГФА Росздрава")	Способ получения конденсированных гем-диметилзамещенных амино-1,3,5-триазинов
RU2369600C1 (ru) *	2008-01-24	2009-10-10	Андрей Александрович Иващенко	ЗАМЕЩЕННЫЕ 4-СУЛЬФОНИЛ-ПИРАЗОЛЫ И 3-СУЛЬФОНИЛ-ПИРАЗОЛО[1,5-a]ПИРИМИДИНЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ5-HT6 РЕЦЕПТОРОВ, АКТИВНЫЙ КОМПОНЕНТ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, ЛЕКАРСТВЕННОЕ СРЕДСТВО И СПОСОБЫ ИХ ПОЛУЧЕНИЯ
WO2009093210A2 (ru)	2008-01-24	2009-07-30	Alla Chem, Llc	ЗАМЕЩЕННЫЕ ЦИKЛOAЛKAHO[e ИЛИ d]ПИPAЗOЛO[l,5-a]ПИPИMИДИHЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ
EA017805B1 (ru) *	2008-01-24	2013-03-29	Андрей Александрович ИВАЩЕНКО	2-АЛКИЛАМИНО-3-АРИЛСУЛЬФОНИЛЦИКЛОАЛКАНО[e ИЛИ d]ПИРАЗОЛО[1,5-a]ПИРИМИДИНЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-НТРЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ
EA017968B1 (ru)	2008-01-24	2013-04-30	Андрей Александрович ИВАЩЕНКО	ЗАМЕЩЕННЫЕ 2-АМИНО-3-СУЛЬФОНИЛПИРАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-НТРЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ
RU2384581C2 (ru)	2008-05-07	2010-03-20	Андрей Александрович Иващенко	ЗАМЕЩЕННЫЕ 2-АМИНО-3-СУЛЬФОНИЛ-ТЕТРАГИДРО-ПИРАЗОЛО[1,5-a]ПИРИДО-ПИРИМИДИНЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ
CA2755968C (en) *	2008-10-06	2019-03-19	Andrey Alexandrovich Ivashchenko	Substituted 3-arylsulfonyl-pyrazolo[1,5-a]pyrimidines, serotonin 5-ht6 receptor antagonists and methods for the production and use thereof
AR074231A1 (es)	2008-11-27	2010-12-29	Boehringer Ingelheim Int	Derivados de 6, 7, 8, 9-tetrahidro-5h-1, 4, 7, 10a-tetraaza-ciclohept[f]indeno, composiciones farmacéuticas que contienen estos compuestos, su uso en el agonismo del receptor 5-ht2c y procesos para prepararlos.
GB0908394D0 (en)	2009-05-15	2009-06-24	Univ Leuven Kath	Novel viral replication inhibitors
GB0913636D0 (en)	2009-08-05	2009-09-16	Univ Leuven Kath	Novel viral replication inhibitors
BR112013011737A2 (pt)	2010-11-15	2016-08-09	Univ Leuven Kath	composto, uso de um composto composição farmacêutica, e, método de tratamento ou prevenção de uma infecção por hiv
RU2443697C1 (ru)	2010-12-21	2012-02-27	Александр Васильевич Иващенко	Замещенные метил-амины, антагонисты серотониновых 5-ht6 рецепторов, способы получения и применения
MX342177B (es)	2011-09-30	2016-09-20	Ipsen Pharma Sas	Inhibidores de cinasa 2 de repeticion rica en leucina (lrrk2) macrociclica.
MX381849B (es) *	2012-03-09	2025-03-13	Lexicon Pharmaceuticals Inc	Compuestos a base de pirazol[1,5-a]pirimidina, composiciones que los comprenden, y métodos para su uso.
TW201542550A (zh) *	2013-09-06	2015-11-16	Lexicon Pharmaceuticals Inc	吡唑并［１，５－ａ］嘧啶基化合物、包含彼之組合物以及使用彼之方法
TW201620911A (zh) *	2014-03-17	2016-06-16	雷西肯製藥股份有限公司	銜接子關聯激酶１之抑制劑、包含其之組成物、及其使用方法
CA2960777A1 (en)	2014-09-17	2016-03-24	Oncodesign S.A.	Macrocyclic lrrk2 kinase inhibitors
CA2978170C (en)	2015-03-09	2024-02-27	Aurigene Discovery Technologies Limited	Pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives as cdk inhibitors
WO2017052394A1 (en) *	2015-09-23	2017-03-30	Uniwersytet Jagielloński	Imidazopyridine compounds and their use as 5-ht6 receptor ligands
HK1256751A1 (zh)	2015-11-02	2019-10-04	Janssen Pharmaceutica Nv	[1，2，4]三唑并[1，5-a]嘧啶-7-基化合物
TWI764950B (zh)	2016-11-02	2022-05-21	比利時商健生藥品公司	Ｐｄｅ２抑制劑
EA039102B1 (ru)	2016-11-02	2021-12-03	Янссен Фармацевтика Нв	Соединения [1,2,4]триазоло[1,5-a]пиримидина в качестве ингибиторов pde2
ES2912264T3 (es)	2016-11-02	2022-05-25	Janssen Pharmaceutica Nv	Compuestos de [1,2,4]triazolo[1,5-a]pirimidina como inhibidores de PDE2
US20220296595A1 (en)	2019-05-05	2022-09-22	Qilu Regor Therapeutics Inc.	Cdk inhibitors
CN112142744A (zh) *	2019-06-28	2020-12-29	上海瑛派药业有限公司	取代的稠合杂芳双环化合物作为激酶抑制剂及其应用
CN115209952B (zh)	2020-01-13	2025-05-30	维基分析有限公司	经取代的吡唑并嘧啶及其用途

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3907799A (en) *	1971-08-16	1975-09-23	Icn Pharmaceuticals	Xanthine oxidase inhibitors
WO1989000994A2 (en)	1987-07-31	1989-02-09	E.I. Du Pont De Nemours And Company	Herbicidal sulfonamides
US4921527A (en) *	1987-07-31	1990-05-01	E. I. Du Pont De Nemours And Company	Herbicidal sulfonamides
DE3825043A1 (de)	1988-07-20	1990-02-15	Schering Ag	3-methylsulfonyl-pyrazolo(1,5-a)pyrimidin-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, pflanzenwuchsregulierender und fungizider wirkung
US5571813A (en) *	1993-06-10	1996-11-05	Beiersdorf-Lilly Gmbh	Fused pyrimidine compounds and their use as pharmaceuticals
WO1997011075A1 (en)	1995-09-22	1997-03-27	Takeda Chemical Industries, Ltd.	Triazole compounds, their production and use
CA2274055A1 (en)	1996-12-19	1998-06-25	Smithkline Beecham P.L.C.	N-piperazin-1-ylphenyl-benzamide derivatives
DZ2376A1 (fr)	1996-12-19	2002-12-28	Smithkline Beecham Plc	Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant.
WO1999002502A2 (en)	1997-07-11	1999-01-21	Smithkline Beecham Plc	Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation

1999
- 1999-02-24 US US09/256,927 patent/US6194410B1/en not_active Expired - Fee Related
- 1999-03-03 EP EP99102872A patent/EP0941994B1/en not_active Expired - Lifetime
- 1999-03-03 PT PT99102872T patent/PT941994E/pt unknown
- 1999-03-03 DK DK99102872T patent/DK0941994T3/da active
- 1999-03-03 AT AT99102872T patent/ATE240332T1/de not_active IP Right Cessation
- 1999-03-03 DE DE69907784T patent/DE69907784T2/de not_active Expired - Fee Related
- 1999-03-03 ES ES99102872T patent/ES2198095T3/es not_active Expired - Lifetime
- 1999-03-03 SI SI9930320T patent/SI0941994T1/xx unknown
- 1999-03-08 IL IL12886999A patent/IL128869A/xx not_active IP Right Cessation
- 1999-03-08 PE PE1999000183A patent/PE20000337A1/es not_active Application Discontinuation
- 1999-03-08 NZ NZ334526A patent/NZ334526A/xx unknown
- 1999-03-08 YU YU12099A patent/YU12099A/sh unknown
- 1999-03-08 CA CA002265095A patent/CA2265095C/en not_active Expired - Fee Related
- 1999-03-08 MA MA25485A patent/MA26612A1/fr unknown
- 1999-03-09 JP JP06114999A patent/JP3231288B2/ja not_active Expired - Fee Related
- 1999-03-09 UY UY25419A patent/UY25419A1/es unknown
- 1999-03-09 SG SG1999001080A patent/SG78336A1/en unknown
- 1999-03-09 AR ARP990100990A patent/AR016453A1/es unknown
- 1999-03-09 MY MYPI99000853A patent/MY119536A/en unknown
- 1999-03-10 ID IDP990198D patent/ID23575A/id unknown
- 1999-03-10 ZA ZA9901946A patent/ZA991946B/xx unknown
- 1999-03-10 HU HU9900589A patent/HUP9900589A1/hu not_active Application Discontinuation
- 1999-03-10 RU RU99105137/04A patent/RU2218340C2/ru active
- 1999-03-10 KR KR1019990007881A patent/KR100313181B1/ko not_active Expired - Fee Related
- 1999-03-10 PL PL99331875A patent/PL331875A1/xx unknown
- 1999-03-10 CZ CZ1999825A patent/CZ291514B6/cs not_active IP Right Cessation
- 1999-03-10 NO NO19991150A patent/NO312297B1/no unknown
- 1999-03-10 TW TW088103692A patent/TW585865B/zh not_active IP Right Cessation
- 1999-03-10 BR BR9901095-0A patent/BR9901095A/pt not_active Application Discontinuation
- 1999-03-11 CN CN99105964A patent/CN1118468C/zh not_active Expired - Fee Related
- 1999-03-11 TR TR1999/00531A patent/TR199900531A3/tr unknown
- 1999-03-11 AU AU20383/99A patent/AU752408B2/en not_active Ceased
- 1999-03-11 HR HR990077A patent/HRP990077B1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
HRP990077A2 (en)	2000-02-29
AU2038399A (en)	1999-09-23
CN1236780A (zh)	1999-12-01
BR9901095A (pt)	2000-05-02
PL331875A1 (en)	1999-09-13
DK0941994T3 (da)	2003-09-08
HU9900589D0 (en)	1999-05-28
MA26612A1 (fr)	2004-12-20
IL128869A (en)	2003-09-17
DE69907784T2 (de)	2004-03-25
SG78336A1 (en)	2001-02-20
TR199900531A2 (xx)	1999-10-21
YU12099A (sh)	2000-10-30
KR100313181B1 (ko)	2001-11-05
ES2198095T3 (es)	2004-01-16
ID23575A (id)	2000-05-04
EP0941994A1 (en)	1999-09-15
PT941994E (pt)	2003-09-30
NO991150D0 (no)	1999-03-10
CZ82599A3 (cs)	1999-09-15
NO991150L (no)	1999-09-13
CA2265095C (en)	2008-07-22
CN1118468C (zh)	2003-08-20
DE69907784D1 (de)	2003-06-18
TR199900531A3 (tr)	1999-10-21
CA2265095A1 (en)	1999-09-11
RU2218340C2 (ru)	2003-12-10
IL128869A0 (en)	2000-01-31
KR19990077741A (ko)	1999-10-25
CZ291514B6 (cs)	2003-03-12
AU752408B2 (en)	2002-09-19
PE20000337A1 (es)	2000-05-13
UY25419A1 (es)	2001-11-30
ZA991946B (en)	1999-09-13
US6194410B1 (en)	2001-02-27
NZ334526A (en)	2000-07-28
HK1023343A1 (en)	2000-09-08
AR016453A1 (es)	2001-07-04
TW585865B (en)	2004-05-01
JP3231288B2 (ja)	2001-11-19
EP0941994B1 (en)	2003-05-14
HRP990077B1 (en)	2003-08-31
SI0941994T1 (en)	2003-10-31
HUP9900589A1 (hu)	2000-03-28
JP2000186090A (ja)	2000-07-04
ATE240332T1 (de)	2003-05-15
MY119536A (en)	2005-06-30

Publication	Publication Date	Title
NO312297B1 (no)	2002-04-22	Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament
Francis et al.	1988	Structure-activity profile of a series of novel triazoloquinazoline adenosine antagonists
Abu‐Hashem et al.	2011	Synthesis, antioxidant, antituomer activities of some new thiazolopyrimidines, pyrrolothiazolopyrimidines and triazolopyrrolothiazolopyrimidines derivatives
CN105209463B (zh)	2017-10-13	2‑氨基吡啶并[4,3‑d]嘧啶‑5‑酮衍生物及其作为Wee‑1抑制剂的用途
Tišler	1973	Some aspects of azido-tetrazolo isomerization
CA2251453C (en)	2002-03-19	5-arylalkyl-substituted pyrazolo(4,3-d)pyrimidine-7-ones
Shamroukh et al.	2007	Synthesis, isomerization, and antimicrobial evaluation of some pyrazolopyranotriazolopyrimidine derivatives
BRPI0714908A2 (pt)	2013-05-28	derivado de pirimidina como inibidor de pi3k e uso do mesmo
HRP20000799A2 (en)	2001-06-30	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
Mamedov et al.	2021	The Dimroth rearrangement in the synthesis of condensed pyrimidines–structural analogs of antiviral compounds
MX2011001667A (es)	2011-03-24	Derivados de 2-alquil-6-cicloamino-3-(piridin-4-il)imidazo[1,2-b]- piridazina, su preparacion y su aplicacion en terapeutica.
SK23099A3 (en)	1999-08-06	3-substituted pyrido[4',3':4,5]thieno[2,3-d]pyrimidine derivatives, their preparation and their use
NZ214663A (en)	1988-02-12	Imidazo derivatives and pharmaceutical compositions
Modica et al.	2000	High affinity and selectivity of [[(arylpiperazinyl) alkyl] thio] thieno [2, 3-d] pyrimidinone derivatives for the 5-HT1A receptor. Synthesis and structure–affinity relationships
Zaki et al.	2018	A facile synthesis, reactions, and spectral characterization of some novel thieno [3, 2‐e] pyrazolo [3, 4‐b] pyrazine compounds
Kelley et al.	1995	Synthesis and anticonvulsant activity of N-Benzylpyrrolo [2, 3-d]-,-pyrazolo [3, 4-d]-, and-triazolo [4, 5-d] pyrimidines: imidazole ring-modified analogs of 9-(2-Fluorobenzyl)-6-(methylamino)-9H-purine
US4528288A (en)	1985-07-09	Substituted triazolo[1,5-c]pyrimidines
HU208693B (en)	1993-12-28	Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them
WO2005111040A1 (en)	2005-11-24	Pyrrolobenzimidazolones and their use as antiproliferative agents
Meyer Jr et al.	1979	Synthesis of fused [1, 2, 6] thiadiazine 1, 1-dioxides as potential transition-state analog inhibitors of xanthine oxidase and guanase
MXPA99002273A (es)	2000-08-01	Pirazolopirimidinas y pirazolotriazinas
El-Gazzar et al.	2002	Synthesis of some new thiazolo [3, 2-a] pyrido [2, 3-d] pyrimidinones and Isoxazolo [5′, 4′: 4, 5] thiazolo [3, 2-a] pyrido [2, 3-d] pyrimidinone
Brukstus et al.	2000	A facile synthesis of benzo [4, 5] imidazo [2, 1-b]-pyrimido [5, 4-f][1, 3, 4] thiadiazepines
Ali et al.	2018	6-(2-Morpholinoethyl)-thiazolo [3, 2-a] pyrimidin-5-one: A novel scaffold for the synthesis of potential PI3kα inhibitors
EP0121341B1 (en)	1988-11-17	Triazolo(4,3-c)pyrimidines and triazolo(1,5-c)pyrimidines substituted by nitrogen-containing heterocyclic rings