DD262023A5 - Verfahren zur herstellung von dihydropyridinen - Google Patents

Verfahren zur herstellung von dihydropyridinen Download PDF

Info

Publication number: DD262023A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; alkyl; formula; chlorophenyl; pyrid
Prior art date: 1986-08-29

Application number

DD87306414A

Other languages

German (de)

English (en)

Inventor

Kelvin Cooper

Michael J Parry

Peter E Cross

Kenneth Richardson

Original Assignee

��@��Kk��

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

1987-08-27

Publication date

1988-11-16

1987-08-27 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1988-11-16 Publication of DD262023A5 publication Critical patent/DD262023A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 33
230000008569 process Effects 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title abstract description 7
150000001412 amines Chemical class 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 12
239000013638 trimer Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 52
-1 cyano, substituted phenyl Chemical group 0.000 claims description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 12
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 11
125000001424 substituent group Chemical group 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
125000003118 aryl group Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
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 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 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
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000008194 pharmaceutical composition 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
238000010438 heat treatment Methods 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 8
230000000172 allergic effect Effects 0.000 abstract description 6
208000010668 atopic eczema Diseases 0.000 abstract description 6
230000004968 inflammatory condition Effects 0.000 abstract description 4
241001465754 Metazoa Species 0.000 abstract description 2
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract description 2
150000007854 aminals Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
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 30
108010003541 Platelet Activating Factor Proteins 0.000 description 30
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 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
229940093499 ethyl acetate Drugs 0.000 description 15
235000019439 ethyl acetate Nutrition 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000000047 product Substances 0.000 description 13
239000000377 silicon dioxide Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000004458 analytical method Methods 0.000 description 9
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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000007858 starting material Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
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
230000000694 effects Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
GUKKGBSNKJVHDK-IHWYPQMZSA-N (z)-2-aminobut-2-enamide Chemical class C\C=C(/N)C(N)=O GUKKGBSNKJVHDK-IHWYPQMZSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000003756 stirring Methods 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
239000006260 foam Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010992 reflux Methods 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
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
208000006673 asthma Diseases 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000003937 drug carrier 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
239000000284 extract Substances 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
238000001802 infusion Methods 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
210000004072 lung Anatomy 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
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 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
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
206010006482 Bronchospasm Diseases 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
241000282412 Homo Species 0.000 description 2
206010061218 Inflammation Diseases 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
241000700159 Rattus Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000013566 allergen Substances 0.000 description 2
239000005557 antagonist 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
206010003246 arthritis Diseases 0.000 description 2
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000007885 bronchoconstriction Effects 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000006185 dispersion 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
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 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
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
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
230000003389 potentiating effect Effects 0.000 description 2
230000004044 response 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
239000012453 solvate Substances 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction 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
210000003462 vein Anatomy 0.000 description 2
125000004169 (C1-C6) alkyl 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
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-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
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
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 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
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 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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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206010002383 Angina Pectoris Diseases 0.000 description 1
206010061430 Arthritis allergic Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 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
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
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
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
206010020751 Hypersensitivity Diseases 0.000 description 1
208000001953 Hypotension Diseases 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
229910018062 Ni-M Inorganic materials 0.000 description 1
FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000007107 Stomach Ulcer Diseases 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
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
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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
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
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
230000003435 bronchoconstrictive effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000012085 chronic inflammatory response Effects 0.000 description 1
230000005796 circulatory shock Effects 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 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
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
JBYRBOVXVKJHCX-UHFFFAOYSA-N ethyl 3-oxo-4-[2-(2,4,5-trimethylimidazol-1-yl)propoxy]butanoate Chemical compound CCOC(=O)CC(=O)COCC(C)N1C(C)=NC(C)=C1C JBYRBOVXVKJHCX-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
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
GSFNONLQOASVIL-UHFFFAOYSA-N ethyl 4-[2-methyl-3-(2-methylimidazol-1-yl)propoxy]-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)COCC(C)CN1C=CN=C1C GSFNONLQOASVIL-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
230000002008 hemorrhagic effect Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 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
230000002401 inhibitory effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000002346 iodo group Chemical group I* 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
230000001665 lethal effect Effects 0.000 description 1
150000002617 leukotrienes Chemical class 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
238000004519 manufacturing process Methods 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000012544 monitoring process Methods 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
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
230000035699 permeability Effects 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
230000002265 prevention Effects 0.000 description 1
230000000770 proinflammatory effect Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
VMVWAHNRTQGXPJ-UHFFFAOYSA-N propan-2-yl 4-(2-chlorophenyl)-5-(pyridin-2-ylcarbamoyl)-2-[2-(2,4,5-trimethylimidazol-1-yl)ethoxymethyl]-1,4-dihydropyridine-3-carboxylate Chemical compound N1C=C(C(=O)NC=2N=CC=CC=2)C(C=2C(=CC=CC=2)Cl)C(C(=O)OC(C)C)=C1COCCN1C(C)=NC(C)=C1C VMVWAHNRTQGXPJ-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
229940100817 propranolol injection Drugs 0.000 description 1
230000001185 psoriatic effect Effects 0.000 description 1
210000001147 pulmonary artery Anatomy 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
230000000241 respiratory effect Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
206010040882 skin lesion Diseases 0.000 description 1
231100000444 skin lesion Toxicity 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000000527 sonication Methods 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
229910021653 sulphate ion Inorganic materials 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
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
230000001960 triggered effect Effects 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
239000003981 vehicle Substances 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)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)

DD87306414A 1986-08-29 1987-08-27 Verfahren zur herstellung von dihydropyridinen DD262023A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD262023A5 true DD262023A5 (de)	1988-11-16

Family

ID=10603368

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87306414A DD262023A5 (de)	1986-08-29	1987-08-27	Verfahren zur herstellung von dihydropyridinen

Country Status (18)

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

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
MY104933A (en) *	1987-09-30	1994-07-30	Pfizer Ltd	Platelet activating factor antagonists
US5070205A (en) *	1987-09-30	1991-12-03	Pfizer Inc.	Alkyl 2-benzylidene-4-(benzimidazol-1-yl) benzoylacetate esters as intermediates
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
NO912475L (no) *	1990-06-27	1991-12-30	Sankyo Co	Tiazolidinkarboksylsyreamidderivater med antiallergisk aktivitet, og fremgangsmaate til fremstilling derav.
US5470851A (en) *	1990-06-27	1995-11-28	Sankyo Company, Limited	Thiazolidinecarboxylic acid amide derivatives and their therapeutic uses
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
AU2002322720B2 (en)	2001-07-25	2008-11-13	Raptor Pharmaceutical Inc.	Compositions and methods for modulating blood-brain barrier transport
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
CN102379684B (zh)	2005-04-28	2014-11-19	普罗透斯数字保健公司	药物信息系统
KR20090071598A (ko)	2006-09-18	2009-07-01	랩터 파마슈티컬 인코포레이티드	수용체 결합 단백질(ｒａｐ)-접합체 투여에 의한 간 질환의 치료
EP2398500B1 (en)	2009-02-20	2019-03-13	2-BBB Medicines B.V.	Glutathione-based drug delivery system
ES2942923T3 (es)	2009-05-06	2023-06-07	Laboratory Skin Care Inc	Composiciones de administración dérmica que comprenden complejos de agente activo-partículas de fosfato de calcio y métodos de uso de las mismas
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
ATE20064T1 (de) *	1982-07-22	1986-06-15	Pfizer	Anti-ischaemische und antihypertensive dihydropyridin-derivate.
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 AT AT87307494T patent/ATE92486T1/de active
- 1987-08-25 EP EP87307494A patent/EP0258033B1/en not_active Expired - Lifetime
- 1987-08-27 PT PT85607A patent/PT85607B/pt not_active IP Right Cessation
- 1987-08-27 FI FI873725A patent/FI873725A7/fi not_active Application Discontinuation
- 1987-08-27 JP JP62214129A patent/JPS6363661A/ja active Pending
- 1987-08-27 PL PL1987267485A patent/PL267485A1/xx unknown
- 1987-08-27 CN CN198787106032A patent/CN87106032A/zh active Pending
- 1987-08-27 DD DD87306414A patent/DD262023A5/de unknown
- 1987-08-28 KR KR870009443A patent/KR880002829A/ko not_active Ceased
- 1987-08-28 ZA ZA876437A patent/ZA876437B/xx unknown
- 1987-08-28 IL IL83681A patent/IL83681A0/xx unknown
- 1987-08-28 HU HU873795A patent/HUT45047A/hu unknown
- 1987-08-28 IE IE872317A patent/IE872317L/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 NO NO873650A patent/NO873650L/no unknown

Also Published As

Publication number	Publication date
FI873725A7 (fi)	1988-03-01
HUT45047A (en)	1988-05-30
DK450687D0 (da)	1987-08-28
PT85607B (pt)	1990-05-31
EP0258033A2 (en)	1988-03-02
GB8620880D0 (en)	1986-10-08
PT85607A (en)	1987-09-01
EP0258033B1 (en)	1993-08-04
CN87106032A (zh)	1988-03-23
JPS6363661A (ja)	1988-03-22
NO873650D0 (no)	1987-08-28
NO873650L (no)	1988-03-01
KR880002829A (ko)	1988-05-11
DK450687A (da)	1988-03-01
US4788205A (en)	1988-11-29
IE872317L (en)	1988-02-29
IL83681A0 (en)	1988-01-31
AU7767887A (en)	1988-03-10
EP0258033A3 (en)	1990-11-07
ZA876437B (en)	1989-03-29
FI873725A0 (fi)	1987-08-27
PL267485A1 (en)	1988-09-01
ATE92486T1 (de)	1993-08-15

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DD261787A5 (de)	1988-11-09	Antiarrhythmisch wirksame phenylpiperazin-mittel
DE4430639A1 (de)	1996-03-07	Verwendung von 5-substituierten Pyridin- und Hexahydrochinolin-3-carbonsäurederivaten
EP0260675A1 (de)	1988-03-23	4-[N-(Substituierte)-amino-phenyl]-substituierte 1,4-Di-(hydro)-pyridinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
CH637130A5 (de)	1983-07-15	Chinazolin-derivate, verfahren zu ihrer herstellung und verwendung dieser derivate in arzneimitteln.
DD213920A5 (de)	1984-09-26	Verfahren zur herstellung von dihydropyridinen
DE19824175A1 (de)	1999-12-02	Amino-azol-Verbindungen
DE2712023A1 (de)	1977-10-06	Sulfonamidoaminobenzoesaeurederivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben
DE4027278A1 (de)	1992-03-05	Heterocyclisch substituierte indolsulfonamide
DE3230209A1 (de)	1983-03-10	Carbostyrilderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten
DD283996A5 (de)	1990-10-31	Verfahren zur herstellung von aminoderivaten
DE2410938A1 (de)	1974-09-19	Chinazolinderivate und diese enthaltende arzneimittel
EP0515940B1 (de)	1996-07-17	Neue 2-Amino-5-cyano-1,4-dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0018360B1 (de)	1981-09-30	N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung
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