CA1337865C - Derives de la 1,4-dihydropyridine; methode de preparation; compositions pharmaceutiques a base de ces derives - Google Patents

Derives de la 1,4-dihydropyridine; methode de preparation; compositions pharmaceutiques a base de ces derives

Info

Publication number: CA1337865C
Authority: CA; Canada
Prior art keywords: ester; ethyl; dimethyl; dicarboxylic acid; methyl
Prior art date: 1984-12-14
Legal status (The legal status 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 status listed.): Expired - Fee Related

Application number

CA 497635

Other languages

English (en)

Inventor

Koichiro Hagihara

Hiroyasu Koyama

Yoshikuni Suzuki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nisshin Seifun Group Inc

Original Assignee

Nisshin Seifun Group Inc

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.)

1984-12-14

Filing date

1985-12-13

Publication date

1996-01-02

1985-12-02 Priority claimed from JP60269302A external-priority patent/JPH0631223B2/ja

1985-12-13 Application filed by Nisshin Seifun Group Inc filed Critical Nisshin Seifun Group Inc

1986-06-13 Priority claimed from JP61136152A external-priority patent/JPH0676405B2/ja

1996-01-02 Application granted granted Critical

1996-01-02 Publication of CA1337865C publication Critical patent/CA1337865C/fr

2013-01-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 17
239000008194 pharmaceutical composition Substances 0.000 title claims 6
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title abstract description 6
238000002360 preparation method Methods 0.000 title description 11
-1 benzoquinolyl Chemical group 0.000 claims abstract description 155
150000001875 compounds Chemical class 0.000 claims abstract description 90
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 60
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 8
229910052736 halogen Inorganic materials 0.000 claims abstract 8
150000002367 halogens Chemical group 0.000 claims abstract 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims abstract 5
125000002541 furyl group Chemical group 0.000 claims abstract 4
125000003373 pyrazinyl group Chemical group 0.000 claims abstract 4
125000004076 pyridyl group Chemical group 0.000 claims abstract 4
125000005493 quinolyl group Chemical group 0.000 claims abstract 4
125000001544 thienyl group Chemical group 0.000 claims abstract 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 93
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
RMZQSAMHIQBMLW-UHFFFAOYSA-N 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1[N+]([O-])=O RMZQSAMHIQBMLW-UHFFFAOYSA-N 0.000 claims description 43
ZGDIGQLFOVNBBC-UHFFFAOYSA-N 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1C(F)(F)F ZGDIGQLFOVNBBC-UHFFFAOYSA-N 0.000 claims description 36
239000004480 active ingredient Substances 0.000 claims description 20
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 19
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
TZDPJNSHSWMCPN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 TZDPJNSHSWMCPN-UHFFFAOYSA-N 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 3
SCPXABNYELAPNT-UHFFFAOYSA-N 3-o-methyl 5-o-[2-(pyridine-3-carbonyloxy)ethyl] 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC=CC=2)C1C1=CC=CC(Cl)=C1Cl SCPXABNYELAPNT-UHFFFAOYSA-N 0.000 claims description 2
IVAXNUKOXRLCIP-UHFFFAOYSA-N 5-o-(2-methylpropyl) 3-o-[2-(pyridine-3-carbonyloxy)ethyl] 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC=CC=2)C1C1=CC=CC=C1[N+]([O-])=O IVAXNUKOXRLCIP-UHFFFAOYSA-N 0.000 claims description 2
CKYHCCCOXZRIJT-UHFFFAOYSA-N 5-o-[2-(6-chloropyridine-3-carbonyl)oxyethyl] 3-o-methyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC(Cl)=CC=2)C1C1=CC=CC=C1C(F)(F)F CKYHCCCOXZRIJT-UHFFFAOYSA-N 0.000 claims description 2
PJYBOOZVINNWIT-UHFFFAOYSA-N 5-o-[2-(6-methoxypyridine-3-carbonyl)oxyethyl] 3-o-methyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC(OC)=CC=2)C1C1=CC=CC=C1C(F)(F)F PJYBOOZVINNWIT-UHFFFAOYSA-N 0.000 claims description 2
QUXYDXXSVYTJNY-UHFFFAOYSA-N 5-o-propan-2-yl 3-o-[2-(pyridine-3-carbonyloxy)ethyl] 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC=CC=2)C1C1=CC=CC=C1[N+]([O-])=O QUXYDXXSVYTJNY-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
WZJYKHNJTSNBHV-UHFFFAOYSA-N benzoquinoline Natural products C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000005905 mesyloxy group Chemical group 0.000 claims description 2
230000036772 blood pressure Effects 0.000 claims 4
239000003937 drug carrier Substances 0.000 claims 4
230000024883 vasodilation Effects 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
SMFUATLXJMVXCN-UHFFFAOYSA-N 3-o-(2-methoxyethyl) 5-o-[2-(pyridine-3-carbonyloxy)ethyl] 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC=CC=2)C1C1=CC=CC=C1[N+]([O-])=O SMFUATLXJMVXCN-UHFFFAOYSA-N 0.000 claims 1
SGGHNFOAAREHNI-UHFFFAOYSA-N 3-o-ethyl 5-o-[2-(pyridine-3-carbonyloxy)ethyl] 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC=CC=2)C1C1=CC=CC=C1[N+]([O-])=O SGGHNFOAAREHNI-UHFFFAOYSA-N 0.000 claims 1
OCCVIAWIOXCECO-UHFFFAOYSA-N 3-o-methyl 5-o-[2-(6-methylpyridine-3-carbonyl)oxyethyl] 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC(=O)C=2C=NC(C)=CC=2)C1C1=CC=CC=C1C(F)(F)F OCCVIAWIOXCECO-UHFFFAOYSA-N 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
206010020772 Hypertension Diseases 0.000 abstract description 3
208000026106 cerebrovascular disease Diseases 0.000 abstract description 3
230000000304 vasodilatating effect Effects 0.000 abstract description 3
230000004531 blood pressure lowering effect Effects 0.000 abstract description 2
208000019622 heart disease Diseases 0.000 abstract description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
239000000843 powder Substances 0.000 description 37
238000005160 1H NMR spectroscopy Methods 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
238000005481 NMR spectroscopy Methods 0.000 description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
239000000203 mixture Substances 0.000 description 14
239000000243 solution Substances 0.000 description 12
125000000623 heterocyclic group Chemical group 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
239000001828 Gelatine Substances 0.000 description 8
229920000159 gelatin Polymers 0.000 description 8
235000019322 gelatine Nutrition 0.000 description 8
230000000704 physical effect Effects 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 6
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229940093499 ethyl acetate Drugs 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 6
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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125000000217 alkyl group Chemical group 0.000 description 3
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YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229960001866 silicon dioxide Drugs 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
HZJCAUPKLDBZPN-UHFFFAOYSA-M sodium;thiophene-3-carboxylate Chemical compound [Na+].[O-]C(=O)C=1C=CSC=1 HZJCAUPKLDBZPN-UHFFFAOYSA-M 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
FDCJOQNCHBIAOV-WAYWQWQTSA-N tert-butyl (z)-3-aminobut-2-enoate Chemical compound C\C(N)=C\C(=O)OC(C)(C)C FDCJOQNCHBIAOV-WAYWQWQTSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000001993 wax Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 497635 1984-12-14 1985-12-13 Derives de la 1,4-dihydropyridine; methode de preparation; compositions pharmaceutiques a base de ces derives Expired - Fee Related CA1337865C (fr)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
JP262942/1984		1984-12-14
JP26294284		1984-12-14
JP233350/1985		1985-10-21
JP233349/1985		1985-10-21
JP23335085		1985-10-21
JP23334985		1985-10-21
JP269302/1985		1985-12-02
JP60269302A JPH0631223B2 (ja)	1984-12-14	1985-12-02	１，４−ジヒドロピリジン誘導体およびその製造法
JP61136152A JPH0676405B2 (ja)	1986-06-13	1986-06-13	１，４―ジヒドロピリジン誘導体およびそれを含有する医薬組成物
JPS.D.136152/86		1986-06-13

Publications (1)

Publication Number	Publication Date
CA1337865C true CA1337865C (fr)	1996-01-02

Family

ID=27527447

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 497635 Expired - Fee Related CA1337865C (fr)	1984-12-14	1985-12-13	Derives de la 1,4-dihydropyridine; methode de preparation; compositions pharmaceutiques a base de ces derives

Country Status (1)

Country	Link
CA (1)	CA1337865C (fr)

1985
- 1985-12-13 CA CA 497635 patent/CA1337865C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2001-01-02	MKLA	Lapsed

Publication	Publication Date	Title
CA1239401A (fr)	1988-07-19	Derives de dihydropyridine-3,5-dicarboxylate et de pyran-3,5-dicarboxylate
EP0094159A1 (fr)	1983-11-16	Dérivés de la dihydropyridine, leur préparation et leur application
KR920005742B1 (ko)	1992-07-18	약제학상 유용한 디하이드로피리디닐디카르복실레이트 아마이드 및 에스테르의 제조방법
US4994461A (en)	1991-02-19	1,4-dihydropyridine enantiomers
KR860001921B1 (ko)	1986-10-25	1,4-디하이드로피리딘의 제조방법
US5068337A (en)	1991-11-26	1,4-dihydropyridines and their ability to inhibit blood platelet aggregation, inhibit thromboxane synthetase and phospholipase
EP0097821B1 (fr)	1988-07-13	Dihydropyridines douées d'une activité antagoniste pour le calcium, leur procédé de préparation et leur application dans des compositions pharmaceutiques
AU610130B2 (en)	1991-05-16	1,4-dihydropyridine derivatives and pharmaceutical composition thereof
US4757071A (en)	1988-07-12	1,4-dihydropyridine derivatives, and pharmaceutical compositions containing same, useful for treating cardiovascular diseases
WO2002022588A1 (fr)	2002-03-21	Nouveau derive de pyrimidine et nouveau derive de pyridine
NO860471L (no)	1986-08-12	Fremgangsmaate for fremstilling av nye heterocykliske derivater.
JPS61257983A (ja)	1986-11-15	１，４−ジヒドロピリジン及びこれを有効成分とする医薬組成物
JPH0641464B2 (ja)	1994-06-01	ジヒドロピリジン類
CA1337865C (fr)	1996-01-02	Derives de la 1,4-dihydropyridine; methode de preparation; compositions pharmaceutiques a base de ces derives
US5064839A (en)	1991-11-12	1,4-dihydropyridines with a 2-amino group or with an ether group in a side chain
EP0177965B1 (fr)	1990-03-21	Dérivés d'oxa et de thiadiazole et leur utilisation
US5045550A (en)	1991-09-03	Substituted tetrahydropyridines as central nervous system agents
US4877797A (en)	1989-10-31	1,4-Dihydropyridine derivatives and pharmaceutical compositions containing same
US4639522A (en)	1987-01-27	1-benzyl-3,5-dimethyl-4-piperdyl ester of a Hantzsch dihydropyridine
US5364860A (en)	1994-11-15	Naphthyridine compounds which inhibit tyrosine kinase and their pharmaceutical compositions
US4900750A (en)	1990-02-13	1.4-Dihydropyridines
EP0194752A1 (fr)	1986-09-17	Dihydropyridine alkanolamines, leur procédé de préparation et les compositions pharmaceutiques les contenant
US5187280A (en)	1993-02-16	Substituted tetrahydropyridines and their use as central nervous system agents
JP2678786B2 (ja)	1997-11-17	１，４―ジヒドロピリジン誘導体
JPS61210070A (ja)	1986-09-18	カルシウムにきつ抗する塩基性エステル、その製造法およびそれを有効成分とする医薬