SK174399A3 - 3-substituted pyrido [3',4':4,5] thieno [2,3-d] pyrimidine derivatives, and production and use of the same - Google Patents

3-substituted pyrido [3',4':4,5] thieno [2,3-d] pyrimidine derivatives, and production and use of the same Download PDF

Info

Publication number: SK174399A3
Authority: SK; Slovakia
Prior art keywords: group; alkyl; ethyl; thieno; substituted
Prior art date: 1997-06-13

Application number

SK1743-99A

Other languages

English (en)

Slovak (sk)

Inventor

Gerd Steiner

Uta Dullweber

Dorothea Starck

Alfred Bach

Karsten Wicke

Hans-Jurgen Teschendorf

Francisco Javier Garcia-Ladona

Franz Emling

Original Assignee

Basf Ag

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.)

1997-06-13

Filing date

1998-05-29

Publication date

2000-05-16

1998-05-29 Application filed by Basf Ag filed Critical Basf Ag

2000-05-16 Publication of SK174399A3 publication Critical patent/SK174399A3/sk

Links

-1 3-substituted pyrido [3',4':4,5] thieno [2,3-d] pyrimidine Chemical class 0.000 title claims abstract description 39
238000004519 manufacturing process Methods 0.000 title claims description 3
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 23
125000005843 halogen group Chemical group 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 4
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 56
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
229940076279 serotonin Drugs 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000005557 antagonist Substances 0.000 claims description 4
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
230000009103 reabsorption Effects 0.000 claims description 3
208000020401 Depressive disease Diseases 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
230000005764 inhibitory process Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
BKIIZRGYTNRNQH-UHFFFAOYSA-N 1,4,5,6,7,8-hexahydropyrido[2,3]thieno[2,4-b]pyrimidine Chemical class N1=CNCC2=C1SC1=C2CNCC1 BKIIZRGYTNRNQH-UHFFFAOYSA-N 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
230000008485 antagonism Effects 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
102000005962 receptors Human genes 0.000 abstract description 9
108020003175 receptors Proteins 0.000 abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 5
239000000935 antidepressant agent Substances 0.000 abstract description 4
229940005513 antidepressants Drugs 0.000 abstract description 4
230000002401 inhibitory effect Effects 0.000 abstract description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract 1
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract 1
101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 abstract 1
102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 abstract 1
101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 abstract 1
102100027493 5-hydroxytryptamine receptor 1D Human genes 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
230000000697 serotonin reuptake Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
JEDVKUHCDPPWNR-UHFFFAOYSA-N 3h-thieno[2,3-d]pyrimidin-4-one Chemical compound O=C1NC=NC2=C1C=CS2 JEDVKUHCDPPWNR-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
102000007527 Autoreceptors Human genes 0.000 description 6
108010071131 Autoreceptors Proteins 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000000903 blocking effect Effects 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000003518 presynaptic effect Effects 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
208000000044 Amnesia Diseases 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
208000026139 Memory disease Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
208000028017 Psychotic disease Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
UXBDIUBADZDARJ-UHFFFAOYSA-N ethyl 2-(ethoxymethylideneamino)-5-ethyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-3-carboxylate Chemical compound C1CN(CC)CC2=C1SC(N=COCC)=C2C(=O)OCC UXBDIUBADZDARJ-UHFFFAOYSA-N 0.000 description 2
LVFGODMUVKPRMQ-UHFFFAOYSA-N ethyl 2-amino-5-ethyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-3-carboxylate Chemical compound C1CN(CC)CC2=C1SC(N)=C2C(=O)OCC LVFGODMUVKPRMQ-UHFFFAOYSA-N 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
230000000862 serotonergic effect Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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RWHGRWSDPVNGMH-UHFFFAOYSA-N 1-acetylpiperidin-3-one Chemical compound CC(=O)N1CCCC(=O)C1 RWHGRWSDPVNGMH-UHFFFAOYSA-N 0.000 description 1
DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
UDMMJJYIAHHNQA-UHFFFAOYSA-N 1-ethylpiperidin-3-one Chemical compound CCN1CCCC(=O)C1 UDMMJJYIAHHNQA-UHFFFAOYSA-N 0.000 description 1
FJYZKZJLHXJMPA-UHFFFAOYSA-N 1h-pyrido[3,4-d]pyrimidin-2-one Chemical compound C1=NC=C2NC(=O)N=CC2=C1 FJYZKZJLHXJMPA-UHFFFAOYSA-N 0.000 description 1
NDVVQPVEUGLAPX-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethanamine Chemical compound COC1=CC=CC=C1N1CCN(CCN)CC1 NDVVQPVEUGLAPX-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
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JMBLSGAXSMOKPN-UHFFFAOYSA-N 2-methylnaphthalen-1-amine Chemical compound C1=CC=CC2=C(N)C(C)=CC=C21 JMBLSGAXSMOKPN-UHFFFAOYSA-N 0.000 description 1
FOAVELKIOCPPDJ-UHFFFAOYSA-N 3-[2-[4-(2,3-dimethylphenyl)piperazin-1-yl]ethyl]-6-ethyl-7,8-dihydro-5h-pyrido[2,3]thieno[2,4-d]pyrimidin-4-one Chemical compound O=C1C=2C=3CN(CC)CCC=3SC=2N=CN1CCN(CC1)CCN1C1=CC=CC(C)=C1C FOAVELKIOCPPDJ-UHFFFAOYSA-N 0.000 description 1
OSFSHRADFTYVRU-UHFFFAOYSA-N 3-[2-[4-(2-chlorophenyl)piperazin-1-yl]ethyl]-6-ethyl-7,8-dihydro-5h-pyrido[2,3]thieno[2,4-d]pyrimidin-4-one Chemical compound O=C1C=2C=3CN(CC)CCC=3SC=2N=CN1CCN(CC1)CCN1C1=CC=CC=C1Cl OSFSHRADFTYVRU-UHFFFAOYSA-N 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000000586 desensitisation Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
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235000014632 disordered eating Nutrition 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
208000024732 dysthymic disease Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
208000031424 hyperprolactinemia Diseases 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
230000006984 memory degeneration Effects 0.000 description 1
208000023060 memory loss Diseases 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
KFOPKOFKGJJEBW-ZSSYTAEJSA-N methyl 2-[(1s,7r,8s,9s,10r,13r,14s,17r)-1,7-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]acetate Chemical compound C([C@H]1O)C2=CC(=O)C[C@H](O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC(=O)OC)[C@@]1(C)CC2 KFOPKOFKGJJEBW-ZSSYTAEJSA-N 0.000 description 1
230000004899 motility Effects 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960002296 paroxetine Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
210000000063 presynaptic terminal Anatomy 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
230000001107 psychogenic effect Effects 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
208000012672 seasonal affective disease Diseases 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000003727 serotonin 1A antagonist Substances 0.000 description 1
239000004000 serotonin 1B antagonist Substances 0.000 description 1
208000012201 sexual and gender identity disease Diseases 0.000 description 1
208000015891 sexual disease Diseases 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- 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
- A61P25/24—Antidepressants
- 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

Landscapes

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

SK1743-99A 1997-06-13 1998-05-29 3-substituted pyrido [3',4':4,5] thieno [2,3-d] pyrimidine derivatives, and production and use of the same SK174399A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19724979A DE19724979A1 (de)	1997-06-13	1997-06-13	3-substituierte Pyrido [3,4,5]thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung
PCT/EP1998/003231 WO1998056793A1 (fr)	1997-06-13	1998-05-29	Derives de pyrido[3',4':4,5]thieno[2,3-d]pyrimidine 3-substitues, leur preparation et leur utilisation

Publications (1)

Publication Number	Publication Date
SK174399A3 true SK174399A3 (en)	2000-05-16

Family

ID=7832351

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1743-99A SK174399A3 (en)	1997-06-13	1998-05-29	3-substituted pyrido [3',4':4,5] thieno [2,3-d] pyrimidine derivatives, and production and use of the same

Country Status (27)

Country	Link
US (1)	US6159981A (fr)
EP (1)	EP1023296B1 (fr)
JP (1)	JP2002504104A (fr)
KR (1)	KR20010013698A (fr)
CN (1)	CN1259954A (fr)
AR (1)	AR014354A1 (fr)
AT (1)	ATE256686T1 (fr)
AU (1)	AU748697B2 (fr)
BG (1)	BG103921A (fr)
BR (1)	BR9810008A (fr)
CA (1)	CA2293440A1 (fr)
CO (1)	CO4940481A1 (fr)
DE (2)	DE19724979A1 (fr)
ES (1)	ES2215312T3 (fr)
HR (1)	HRP980318A2 (fr)
HU (1)	HUP0002736A3 (fr)
ID (1)	ID24045A (fr)
IL (1)	IL132985A0 (fr)
MY (1)	MY132993A (fr)
NO (1)	NO996045L (fr)
NZ (1)	NZ502237A (fr)
PL (1)	PL337454A1 (fr)
SK (1)	SK174399A3 (fr)
TR (1)	TR199903061T2 (fr)
TW (1)	TW479059B (fr)
WO (1)	WO1998056793A1 (fr)
ZA (1)	ZA985120B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19900673A1 (de)	1999-01-11	2000-07-13	Basf Ag	Verwendung von Bindungspartnern für 5-HT5-Rezeptoren zur Behandlung neurodegenerativer und neuropsychiatrischer Störungen
DE19900545A1 (de)	1999-01-11	2000-07-13	Basf Ag	Verwendung von Pyrimidinderivaten zur Prophylaxe und Therapie der zerebralen Ischämie
DE10031389A1 (de) *	2000-07-03	2002-01-17	Knoll Ag	Pyrimidinderivate und ihre Verwendung zur Prophylaxe und Therapie der zerebralen Ischämie
DE10259382A1 (de) *	2002-12-18	2004-07-01	Abbott Gmbh & Co. Kg	3-Substituierte 3,4-Dihydro-thieno[2,3-d]pyrimidin-4-on-Derivate, ihre Herstellung und Verwendung
US8877316B2 (en) *	2002-12-20	2014-11-04	The Procter & Gamble Company	Cloth-like personal care articles
MX2009008507A (es)	2007-02-07	2009-08-20	Astellas Pharma Inc	Derivado de acilguanidina.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5001130A (en) *	1988-02-18	1991-03-19	Bristol-Myers Company	Psychotropic heterobicycloalkylpiperazine derivatives
US4835157A (en) *	1988-03-15	1989-05-30	Ortho Pharmaceutical Corporation	Thieno- and furopyrimidine-2,4-dione piperidine derivatives as serotonin antagonists and alpha adrenergic blocking agents
DE19636769A1 (de) *	1996-09-10	1998-03-12	Basf Ag	3-Substituierte Pyrido [4',3':4,5]thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung

1997
- 1997-06-13 DE DE19724979A patent/DE19724979A1/de not_active Withdrawn
1998
- 1998-05-29 SK SK1743-99A patent/SK174399A3/sk unknown
- 1998-05-29 TR TR1999/03061T patent/TR199903061T2/xx unknown
- 1998-05-29 EP EP98936299A patent/EP1023296B1/fr not_active Expired - Lifetime
- 1998-05-29 IL IL13298598A patent/IL132985A0/xx unknown
- 1998-05-29 KR KR1019997011713A patent/KR20010013698A/ko not_active Withdrawn
- 1998-05-29 ES ES98936299T patent/ES2215312T3/es not_active Expired - Lifetime
- 1998-05-29 AT AT98936299T patent/ATE256686T1/de not_active IP Right Cessation
- 1998-05-29 CA CA002293440A patent/CA2293440A1/fr not_active Abandoned
- 1998-05-29 US US09/445,178 patent/US6159981A/en not_active Expired - Lifetime
- 1998-05-29 BR BR9810008-4A patent/BR9810008A/pt not_active IP Right Cessation
- 1998-05-29 AU AU85357/98A patent/AU748697B2/en not_active Ceased
- 1998-05-29 ID IDW991495A patent/ID24045A/id unknown
- 1998-05-29 PL PL98337454A patent/PL337454A1/xx not_active Application Discontinuation
- 1998-05-29 WO PCT/EP1998/003231 patent/WO1998056793A1/fr not_active Ceased
- 1998-05-29 JP JP50145999A patent/JP2002504104A/ja active Pending
- 1998-05-29 CN CN98806104A patent/CN1259954A/zh active Pending
- 1998-05-29 HU HU0002736A patent/HUP0002736A3/hu unknown
- 1998-05-29 DE DE59810485T patent/DE59810485D1/de not_active Expired - Fee Related
- 1998-05-29 NZ NZ502237A patent/NZ502237A/en unknown
- 1998-06-03 TW TW087108721A patent/TW479059B/zh not_active IP Right Cessation
- 1998-06-11 CO CO98033543A patent/CO4940481A1/es unknown
- 1998-06-11 AR ARP980102768A patent/AR014354A1/es not_active Application Discontinuation
- 1998-06-12 HR HR19724979.5A patent/HRP980318A2/hr not_active Application Discontinuation
- 1998-06-12 ZA ZA9805120A patent/ZA985120B/xx unknown
- 1998-06-13 MY MYPI98002644A patent/MY132993A/en unknown
1999
- 1999-11-24 BG BG103921A patent/BG103921A/xx unknown
- 1999-12-08 NO NO996045A patent/NO996045L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP1023296A1 (fr)	2000-08-02
CN1259954A (zh)	2000-07-12
AU8535798A (en)	1998-12-30
WO1998056793A1 (fr)	1998-12-17
AR014354A1 (es)	2001-02-28
KR20010013698A (ko)	2001-02-26
NO996045D0 (no)	1999-12-08
AU748697B2 (en)	2002-06-13
HUP0002736A2 (hu)	2001-02-28
TR199903061T2 (xx)	2000-07-21
PL337454A1 (en)	2000-08-14
ID24045A (id)	2000-07-06
DE59810485D1 (de)	2004-01-29
DE19724979A1 (de)	1998-12-17
MY132993A (en)	2007-10-31
HUP0002736A3 (en)	2001-04-28
IL132985A0 (en)	2001-03-19
HRP980318A2 (en)	1999-04-30
ATE256686T1 (de)	2004-01-15
BR9810008A (pt)	2000-09-19
TW479059B (en)	2002-03-11
ZA985120B (en)	1999-12-13
ES2215312T3 (es)	2004-10-01
CO4940481A1 (es)	2000-07-24
JP2002504104A (ja)	2002-02-05
NO996045L (no)	1999-12-08
EP1023296B1 (fr)	2003-12-17
BG103921A (en)	2000-07-31
CA2293440A1 (fr)	1998-12-17
NZ502237A (en)	2001-08-31
US6159981A (en)	2000-12-12

Publication	Publication Date	Title
US6159962A (en)	2000-12-12	3-substituted 3,4-dihydro-thieno[2,3-D]pyrimidine derivatives and production and use of the same
SK283039B6 (sk)	2003-02-04	3-Substituované 3,4,5,6,7,8-hexahydropyrido [4',3':4,5] tieno [2,3-d]-pyrimidínové deriváty a ich použitie
US6414157B1 (en)	2002-07-02	3-Substituted tetrahydropyridopyrimidinone derivatives, method for producing the same, and their use
US6355647B1 (en)	2002-03-12	3-substituted 3,4,5,7-tetrahedropyrrolo[3′,4′:4,5]thieno-[2,3-d]pyrimidine derivatives, their preparation and use
SK174399A3 (en)	2000-05-16	3-substituted pyrido [3',4':4,5] thieno [2,3-d] pyrimidine derivatives, and production and use of the same
CZ448399A3 (cs)	2000-04-12	3-substituované deriváty pyrido[3',4':4,5] thieno[2,3-d] pyrimidinu, jejich výroba a použití
MXPA99010621A (en)	2000-09-04	3-substituted pyrido [3',4':4,5]thieno [2,3-d]pyrimidine derivatives, and production and use of the same
MXPA99010622A (en)	2000-09-04	3-substituted 3,4 dihydro-thieno[2, 3-d]pyrimidine derivatives and production and use of the same
MXPA00001119A (en)	2001-05-07	3-substituted 3,4,5,7-tetrahydro-pyrrolo3',4':4,5 thieno2,3-dpyrimidine derivatives, their preparation and use as 5ht antagonists