NO873650L - Dihydropyridinderivater. - Google Patents

Dihydropyridinderivater.

Info

Publication number: NO873650L
Authority: NO; Norway
Prior art keywords: alkyl; compounds; methyl; starting; substituted
Prior art date: 1986-08-29

Application number

NO873650A

Other languages

English (en)

Norwegian (no)

Other versions

NO873650D0 (no

Inventor

Kelvin Cooper

Michael John Parry

Peter Edward Cross

Kenneth Richardson

Original Assignee

Pfizer Ltd

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.)

1986-08-29

Filing date

1987-08-28

Publication date

1988-03-01

1987-08-28 Application filed by Pfizer Ltd filed Critical Pfizer Ltd

1987-08-28 Publication of NO873650D0 publication Critical patent/NO873650D0/no

1988-03-01 Publication of NO873650L publication Critical patent/NO873650L/no

Links

YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 54
-1 piperidino, morpholino, piperazinyl Chemical group 0.000 claims abstract description 28
125000001424 substituent group Chemical group 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 12
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
125000001589 carboacyl group Chemical group 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
239000007858 starting material Substances 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 10
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000007854 aminals Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000013638 trimer Substances 0.000 claims description 4
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 3
HXZWVKSYFIZLAE-UHFFFAOYSA-N ethyl 4-(2-chlorophenyl)-6-methyl-5-[(6-methylpyridin-2-yl)carbamoyl]-2-[2-(2,4,5-trimethylimidazol-1-yl)ethoxymethyl]-1,4-dihydropyridine-3-carboxylate Chemical compound N1C(C)=C(C(=O)NC=2N=C(C)C=CC=2)C(C=2C(=CC=CC=2)Cl)C(C(=O)OCC)=C1COCCN1C(C)=NC(C)=C1C HXZWVKSYFIZLAE-UHFFFAOYSA-N 0.000 claims description 3
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
DFCDELKRBYJIFS-UHFFFAOYSA-N 3-oxo-4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]butanoic acid Chemical compound CC=1N=C(C)N(CCOCC(=O)CC(O)=O)C=1C DFCDELKRBYJIFS-UHFFFAOYSA-N 0.000 claims 2
238000010438 heat treatment Methods 0.000 claims 2
KQMNASUFBNGUJZ-SREVYHEPSA-N (z)-3-amino-n-(6-methylpyridin-2-yl)but-2-enamide Chemical compound C\C(N)=C\C(=O)NC1=CC=CC(C)=N1 KQMNASUFBNGUJZ-SREVYHEPSA-N 0.000 claims 1
CGJGMHQUYSLYDT-WAYWQWQTSA-N (z)-3-amino-n-tert-butylbut-2-enamide Chemical compound C\C(N)=C\C(=O)NC(C)(C)C CGJGMHQUYSLYDT-WAYWQWQTSA-N 0.000 claims 1
FFPIXHCJPIBFRX-UHFFFAOYSA-N ethyl 5-(tert-butylcarbamoyl)-4-(2-chlorophenyl)-6-methyl-2-[2-(2,4,5-trimethylimidazol-1-yl)ethoxymethyl]-1,4-dihydropyridine-3-carboxylate Chemical compound N1C(C)=C(C(=O)NC(C)(C)C)C(C=2C(=CC=CC=2)Cl)C(C(=O)OCC)=C1COCCN1C(C)=NC(C)=C1C FFPIXHCJPIBFRX-UHFFFAOYSA-N 0.000 claims 1
230000000172 allergic effect Effects 0.000 abstract description 7
208000010668 atopic eczema Diseases 0.000 abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 6
230000002757 inflammatory effect Effects 0.000 abstract description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
239000005557 antagonist Substances 0.000 abstract description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 31
108010003541 Platelet Activating Factor Proteins 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
GUKKGBSNKJVHDK-IHWYPQMZSA-N (z)-2-aminobut-2-enamide Chemical compound C\C=C(/N)C(N)=O GUKKGBSNKJVHDK-IHWYPQMZSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000007787 solid Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
206010003246 arthritis Diseases 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
230000007885 bronchoconstriction Effects 0.000 description 3
239000007853 buffer solution Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
230000004968 inflammatory condition Effects 0.000 description 3
238000001802 infusion Methods 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
XMXLBDNVSIHRRA-UHFFFAOYSA-N 4,5-dimethyl-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1C XMXLBDNVSIHRRA-UHFFFAOYSA-N 0.000 description 2
CBNXGQUIJRGZRX-UHFFFAOYSA-N 5-[4-fluoro-3-(trifluoromethyl)phenyl]furan-2-carbaldehyde Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1=CC=C(C=O)O1 CBNXGQUIJRGZRX-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
238000003445 Hantzsch reaction Methods 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000013566 allergen Substances 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 2
VTPVMAXVWBYDDL-UHFFFAOYSA-N ethyl 3-oxo-4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]butanoate Chemical compound CCOC(=O)CC(=O)COCCN1C(C)=NC(C)=C1C VTPVMAXVWBYDDL-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
229940090044 injection Drugs 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
LRFWGTBYNKYYOH-UHFFFAOYSA-N n-(4-methylpiperazin-1-yl)-3-oxobutanamide Chemical compound CN1CCN(NC(=O)CC(C)=O)CC1 LRFWGTBYNKYYOH-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000000770 proinflammatory effect Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000000527 sonication Methods 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
230000001960 triggered effect Effects 0.000 description 2
230000008728 vascular permeability Effects 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
YWTRXACYCWOQMR-FPLPWBNLSA-N (z)-3-amino-n-phenylbut-2-enamide Chemical compound C\C(N)=C\C(=O)NC1=CC=CC=C1 YWTRXACYCWOQMR-FPLPWBNLSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PTBPTNCGZUOCBK-UHFFFAOYSA-N 2,4,5-trimethyl-1h-imidazole Chemical compound CC1=NC(C)=C(C)N1 PTBPTNCGZUOCBK-UHFFFAOYSA-N 0.000 description 1
FCCASFKLQWALKT-UHFFFAOYSA-N 2-(2,4,5-trimethylimidazol-1-yl)ethanol Chemical compound CC=1N=C(C)N(CCO)C=1C FCCASFKLQWALKT-UHFFFAOYSA-N 0.000 description 1
LZQPHIILIDBHCR-UHFFFAOYSA-N 2-(2,4,5-trimethylimidazol-1-yl)propan-1-ol Chemical compound OCC(C)N1C(C)=NC(C)=C1C LZQPHIILIDBHCR-UHFFFAOYSA-N 0.000 description 1
CNAFLPCTUWEEHP-UHFFFAOYSA-N 2-(2-azidoethoxymethyl)-1,4-dihydropyridine Chemical compound [N-]=[N+]=NCCOCC1=CCC=CN1 CNAFLPCTUWEEHP-UHFFFAOYSA-N 0.000 description 1
OEBGHTCVVRCZKC-UHFFFAOYSA-N 2-(2-methyl-4,5,6,7-tetrahydrobenzimidazol-1-yl)ethanol Chemical compound C1CCCC2=C1N=C(C)N2CCO OEBGHTCVVRCZKC-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
SWJVFAOGXDGTCX-UHFFFAOYSA-N 2-cyanoethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCC#N SWJVFAOGXDGTCX-UHFFFAOYSA-N 0.000 description 1
ZICZOGXPFDQCKE-UHFFFAOYSA-N 2-methyl-3-(2-methylimidazol-1-yl)propan-1-ol Chemical compound OCC(C)CN1C=CN=C1C ZICZOGXPFDQCKE-UHFFFAOYSA-N 0.000 description 1
XMLUAPAWXDNVTM-UHFFFAOYSA-N 2-methyl-4,5,6,7-tetrahydro-1h-benzimidazole Chemical compound C1CCCC2=C1N=C(C)N2 XMLUAPAWXDNVTM-UHFFFAOYSA-N 0.000 description 1
IWMDVLIESVGDLX-UHFFFAOYSA-N 3-oxo-n-(1,3-thiazol-2-yl)butanamide Chemical compound CC(=O)CC(=O)NC1=NC=CS1 IWMDVLIESVGDLX-UHFFFAOYSA-N 0.000 description 1
UVXCXLOTBZOCHF-UHFFFAOYSA-N 3-oxo-n-(pyridin-2-ylmethyl)butanamide Chemical compound CC(=O)CC(=O)NCC1=CC=CC=N1 UVXCXLOTBZOCHF-UHFFFAOYSA-N 0.000 description 1
JSYFBSLKZLDZOC-UHFFFAOYSA-N 3-oxo-n-pyridin-2-ylbutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=N1 JSYFBSLKZLDZOC-UHFFFAOYSA-N 0.000 description 1
ZWRYWVBALYOSPQ-UHFFFAOYSA-N 4,5-dichloro-2-methyl-1h-imidazole Chemical compound CC1=NC(Cl)=C(Cl)N1 ZWRYWVBALYOSPQ-UHFFFAOYSA-N 0.000 description 1
RJMAISNHEGOYGT-UHFFFAOYSA-N 5-o-(2-cyanoethyl) 3-o-ethyl 2-(2-azidoethoxy)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(OCCN=[N+]=[N-])NC(C)=C(C(=O)OCCC#N)C1C1=CC=CC=C1Cl RJMAISNHEGOYGT-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010006429 Bronchial conditions Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
206010012434 Dermatitis allergic Diseases 0.000 description 1
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 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
241001465754 Metazoa Species 0.000 description 1
FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000282887 Suidae Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
230000002253 anti-ischaemic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
229940098773 bovine serum albumin Drugs 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
206010006451 bronchitis Diseases 0.000 description 1
239000004044 bronchoconstricting agent Substances 0.000 description 1
230000003435 bronchoconstrictive effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000005796 circulatory shock Effects 0.000 description 1
238000004040 coloring Methods 0.000 description 1
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
VAIWPFHNWZPCFG-UHFFFAOYSA-N ethyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-5-(4-methylpiperazine-1-carbonyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)N2CCN(C)CC2)C1C1=CC=CC=C1Cl VAIWPFHNWZPCFG-UHFFFAOYSA-N 0.000 description 1
SPONXKRNIUIQHG-UHFFFAOYSA-N ethyl 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-5-(propan-2-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)NC(C)C)C1C1=CC=CC=C1Cl SPONXKRNIUIQHG-UHFFFAOYSA-N 0.000 description 1
XUBVTDPFZKSXOP-UHFFFAOYSA-N ethyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-5-(propan-2-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(COCCN=[N+]=[N-])NC(C)=C(C(=O)NC(C)C)C1C1=CC=CC=C1Cl XUBVTDPFZKSXOP-UHFFFAOYSA-N 0.000 description 1
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
DXLCZEHLKSXDON-UHFFFAOYSA-N ethyl 2-methyl-3-(2-methylimidazol-1-yl)propanoate Chemical compound CCOC(=O)C(C)CN1C=CN=C1C DXLCZEHLKSXDON-UHFFFAOYSA-N 0.000 description 1
KTVPZBURNBMJNW-UHFFFAOYSA-N ethyl 4-(2-azidoethoxy)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCCN=[N+]=[N-] KTVPZBURNBMJNW-UHFFFAOYSA-N 0.000 description 1
UHSFMPSYQQRDQV-UHFFFAOYSA-N ethyl 4-[2-(2-methyl-4,5,6,7-tetrahydrobenzimidazol-1-yl)ethoxy]-3-oxobutanoate Chemical compound C1CCCC2=C1N=C(C)N2CCOCC(=O)CC(=O)OCC UHSFMPSYQQRDQV-UHFFFAOYSA-N 0.000 description 1
QGLCPEUDGIYPHW-UHFFFAOYSA-N ethyl 4-[2-(4,5-dichloro-2-methylimidazol-1-yl)ethoxy]-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCCN1C(C)=NC(Cl)=C1Cl QGLCPEUDGIYPHW-UHFFFAOYSA-N 0.000 description 1
DFVOSDHLAHVVTJ-UHFFFAOYSA-N ethyl 4-[2-methyl-2-(2-methylimidazol-1-yl)propoxy]-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCC(C)(C)N1C=CN=C1C DFVOSDHLAHVVTJ-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
210000004072 lung Anatomy 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
VGNKBNUUULVJMA-UHFFFAOYSA-N methyl 3-oxo-4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]butanoate Chemical compound COC(=O)CC(=O)COCCN1C(C)=NC(C)=C1C VGNKBNUUULVJMA-UHFFFAOYSA-N 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
DAVFIHSAWGXCGF-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-thiazol-2-yl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=NC(C)=C(C)S1 DAVFIHSAWGXCGF-UHFFFAOYSA-N 0.000 description 1
BTJZBEVIGBVBHP-UHFFFAOYSA-N n-(5-methyl-1,3,4-thiadiazol-2-yl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=NN=C(C)S1 BTJZBEVIGBVBHP-UHFFFAOYSA-N 0.000 description 1
RCUFPCZPNROCFP-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(C)=N1 RCUFPCZPNROCFP-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229950004354 phosphorylcholine Drugs 0.000 description 1
238000000053 physical method Methods 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
QGXXYENLFXEUND-UHFFFAOYSA-N propan-2-yl 3-oxo-4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]butanoate Chemical compound CC(C)OC(=O)CC(=O)COCCN1C(C)=NC(C)=C1C QGXXYENLFXEUND-UHFFFAOYSA-N 0.000 description 1
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
229940100817 propranolol injection Drugs 0.000 description 1
230000001185 psoriatic effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
230000035939 shock Effects 0.000 description 1
231100000444 skin lesion Toxicity 0.000 description 1
206010040882 skin lesion Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000002123 temporal effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000036269 ulceration Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Pulmonology (AREA)
Animal Behavior & Ethology (AREA)
Immunology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Dental Preparations (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

NO873650A 1986-08-29 1987-08-28 Dihydropyridinderivater. NO873650L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868620880A GB8620880D0 (en)	1986-08-29	1986-08-29	Therapeutic agents

Publications (2)

Publication Number	Publication Date
NO873650D0 NO873650D0 (no)	1987-08-28
NO873650L true NO873650L (no)	1988-03-01

Family

ID=10603368

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO873650A NO873650L (no)	1986-08-29	1987-08-28	Dihydropyridinderivater.

Country Status (18)

Country	Link
US (1)	US4788205A (pt)
EP (1)	EP0258033B1 (pt)
JP (1)	JPS6363661A (pt)
KR (1)	KR880002829A (pt)
CN (1)	CN87106032A (pt)
AT (1)	ATE92486T1 (pt)
AU (1)	AU7767887A (pt)
DD (1)	DD262023A5 (pt)
DK (1)	DK450687A (pt)
FI (1)	FI873725A7 (pt)
GB (1)	GB8620880D0 (pt)
HU (1)	HUT45047A (pt)
IE (1)	IE872317L (pt)
IL (1)	IL83681A0 (pt)
NO (1)	NO873650L (pt)
PL (1)	PL267485A1 (pt)
PT (1)	PT85607B (pt)
ZA (1)	ZA876437B (pt)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8712747D0 (en) *	1987-05-30	1987-07-01	Pfizer Ltd	Therapeutic agents
GB8716971D0 (en) *	1987-07-17	1987-08-26	Pfizer Ltd	Therapeutic agents
US5070205A (en) *	1987-09-30	1991-12-03	Pfizer Inc.	Alkyl 2-benzylidene-4-(benzimidazol-1-yl) benzoylacetate esters as intermediates
MY104933A (en) *	1987-09-30	1994-07-30	Pfizer Ltd	Platelet activating factor antagonists
GB8803963D0 (en) *	1988-02-19	1988-03-23	Pfizer Ltd	Therapeutic agents
GB8804439D0 (en) *	1988-02-25	1988-03-23	Pfizer Ltd	Dihydropyridines
US5030856A (en) *	1989-05-04	1991-07-09	International Business Machines Corporation	Receiver and level converter circuit with dual feedback
US5470851A (en) *	1990-06-27	1995-11-28	Sankyo Company, Limited	Thiazolidinecarboxylic acid amide derivatives and their therapeutic uses
NO912475L (no) *	1990-06-27	1991-12-30	Sankyo Co	Tiazolidinkarboksylsyreamidderivater med antiallergisk aktivitet, og fremgangsmaate til fremstilling derav.
US5478848A (en) *	1994-01-26	1995-12-26	Bayer Corporation	Inhibition of arthritis by L-type calcium channel antagonists nimodipine, nisoldipine and nifedipine
US5496855A (en) *	1995-01-27	1996-03-05	Smithkline Beecham Corp.	Anti-inflammatory compounds
JP4202250B2 (ja)	2001-07-25	2008-12-24	バイオマリンファーマシューティカルインコーポレイテッド	血液脳関門輸送を調節するための組成物および方法
US6566359B1 (en)	2002-05-20	2003-05-20	Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College	2,4,6-trimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid esters as neuroprotective drugs
CA2789262C (en)	2005-04-28	2016-10-04	Proteus Digital Health, Inc.	Pharma-informatics system
US8795627B2 (en)	2007-03-21	2014-08-05	Raptor Pharmaceuticals Inc.	Treatment of liver disorders by administration of RAP conjugates
ES2919563T3 (es)	2009-02-20	2022-07-27	Enhanx Biopharm Inc	Sistema de administración de medicamentos a base de glutatión
CN110075069A (zh)	2009-05-06	2019-08-02	实验室护肤股份有限公司	包含活性剂-磷酸钙颗粒复合物的皮肤递送组合物及其应用
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates
DE102013021933A1 (de)	2013-12-20	2015-06-25	Skw Stickstoffwerke Piesteritz Gmbh	Verwendung von Pyrazol-Derivaten als Mittel zur Verbesserung der Trockenstresstoleranz

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2210674C3 (de) *	1972-03-06	1981-09-24	Bayer Ag, 5090 Leverkusen	2-Amino-6-methyl-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2228377A1 (de) *	1972-06-10	1974-01-03	Bayer Ag	Dihydropyridin-carbonsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0100189B1 (en) *	1982-07-22	1986-05-28	Pfizer Limited	Dihydropyridine anti-ischaemic and antihypertensive agents
EP0111453A1 (de) *	1982-12-10	1984-06-20	Ciba-Geigy Ag	Amid-Verbindungen
US4515799A (en) *	1983-02-02	1985-05-07	Pfizer Inc.	Dihydropyridine anti-ischaemic and antihypertensive agents
EP0174131A3 (en) *	1984-09-01	1989-06-07	FISONS plc	Dihydropyridines, processes and intermediates for their production, and pharmaceutical formulations containing them

1986
- 1986-08-29 GB GB868620880A patent/GB8620880D0/en active Pending
1987
- 1987-07-20 US US07/075,379 patent/US4788205A/en not_active Expired - Fee Related
- 1987-08-25 EP EP87307494A patent/EP0258033B1/en not_active Expired - Lifetime
- 1987-08-25 AT AT87307494T patent/ATE92486T1/de active
- 1987-08-27 DD DD87306414A patent/DD262023A5/de unknown
- 1987-08-27 CN CN198787106032A patent/CN87106032A/zh active Pending
- 1987-08-27 JP JP62214129A patent/JPS6363661A/ja active Pending
- 1987-08-27 FI FI873725A patent/FI873725A7/fi not_active Application Discontinuation
- 1987-08-27 PT PT85607A patent/PT85607B/pt not_active IP Right Cessation
- 1987-08-27 PL PL1987267485A patent/PL267485A1/xx unknown
- 1987-08-28 DK DK450687A patent/DK450687A/da not_active Application Discontinuation
- 1987-08-28 AU AU77678/87A patent/AU7767887A/en not_active Abandoned
- 1987-08-28 HU HU873795A patent/HUT45047A/hu unknown
- 1987-08-28 KR KR870009443A patent/KR880002829A/ko not_active Ceased
- 1987-08-28 NO NO873650A patent/NO873650L/no unknown
- 1987-08-28 IL IL83681A patent/IL83681A0/xx unknown
- 1987-08-28 IE IE872317A patent/IE872317L/xx unknown
- 1987-08-28 ZA ZA876437A patent/ZA876437B/xx unknown

Also Published As

Publication number	Publication date
US4788205A (en)	1988-11-29
ZA876437B (en)	1989-03-29
PT85607A (en)	1987-09-01
FI873725A7 (fi)	1988-03-01
EP0258033B1 (en)	1993-08-04
CN87106032A (zh)	1988-03-23
IE872317L (en)	1988-02-29
FI873725A0 (fi)	1987-08-27
ATE92486T1 (de)	1993-08-15
PT85607B (pt)	1990-05-31
AU7767887A (en)	1988-03-10
JPS6363661A (ja)	1988-03-22
NO873650D0 (no)	1987-08-28
DK450687A (da)	1988-03-01
KR880002829A (ko)	1988-05-11
PL267485A1 (en)	1988-09-01
HUT45047A (en)	1988-05-30
EP0258033A2 (en)	1988-03-02
DK450687D0 (da)	1987-08-28
IL83681A0 (en)	1988-01-31
DD262023A5 (de)	1988-11-16
GB8620880D0 (en)	1986-10-08
EP0258033A3 (en)	1990-11-07

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