JPH0314307B2 - - Google Patents
Info
- Publication number
- JPH0314307B2 JPH0314307B2 JP59088411A JP8841184A JPH0314307B2 JP H0314307 B2 JPH0314307 B2 JP H0314307B2 JP 59088411 A JP59088411 A JP 59088411A JP 8841184 A JP8841184 A JP 8841184A JP H0314307 B2 JPH0314307 B2 JP H0314307B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dihydropyridine
- dimethyl
- ester
- substituted
- Prior art date
- 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 - Lifetime
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- -1 nitro-substituted phenyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 32
- 238000000921 elemental analysis Methods 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 description 6
- 230000004531 blood pressure lowering effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 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 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000001077 hypotensive effect Effects 0.000 description 4
- 229960001597 nifedipine Drugs 0.000 description 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960001783 nicardipine Drugs 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KJEBULYHNRNJTE-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid O3-(2-methoxyethyl) ester O5-(3-phenylprop-2-enyl) ester Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC=CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 KJEBULYHNRNJTE-UHFFFAOYSA-N 0.000 description 1
- QQEOWRHUXVDVJC-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-5-propan-2-yloxycarbonyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 QQEOWRHUXVDVJC-UHFFFAOYSA-N 0.000 description 1
- SGNOPIMYWCJCTF-UHFFFAOYSA-N 3-o-ethyl 5-o-(4-phenylbut-3-en-2-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C=CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 SGNOPIMYWCJCTF-UHFFFAOYSA-N 0.000 description 1
- YFKXWATZEKNNNE-UHFFFAOYSA-N 3-o-methyl 5-o-(1-phenylhex-1-en-3-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C=1C=CC=CC=1C=CC(CCC)OC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 YFKXWATZEKNNNE-UHFFFAOYSA-N 0.000 description 1
- UQYBBLVCMHECAA-UHFFFAOYSA-N 3-o-methyl 5-o-(2-methyl-4-phenylbut-3-en-2-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)C=CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 UQYBBLVCMHECAA-UHFFFAOYSA-N 0.000 description 1
- VTGYIDGNWJLDOT-UHFFFAOYSA-N 3-o-methyl 5-o-(3-phenylprop-2-enyl) 2,6-dimethyl-4-(4-methylsulfanylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC=CC=2C=CC=CC=2)C1C1=CC=C(SC)C=C1 VTGYIDGNWJLDOT-UHFFFAOYSA-N 0.000 description 1
- XIHYNBMVKDUNED-UHFFFAOYSA-N 3-o-methyl 5-o-(3-phenylprop-2-enyl) 4-(2-cyanophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC=CC=2C=CC=CC=2)C1C1=CC=CC=C1C#N XIHYNBMVKDUNED-UHFFFAOYSA-N 0.000 description 1
- JAKXGEPKVUIGER-UHFFFAOYSA-N 3-o-methyl 5-o-(4-methyl-1-phenylpent-1-en-3-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C=CC=2C=CC=CC=2)C(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 JAKXGEPKVUIGER-UHFFFAOYSA-N 0.000 description 1
- FTVJQPPBOIJVEH-UHFFFAOYSA-N 3-o-methyl 5-o-(4-naphthalen-2-ylbut-3-enyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC=CC=2C=C3C=CC=CC3=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 FTVJQPPBOIJVEH-UHFFFAOYSA-N 0.000 description 1
- YEDDVNQGOLMSDK-UHFFFAOYSA-N 3-o-methyl 5-o-(4-phenylbut-3-en-2-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C=CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 YEDDVNQGOLMSDK-UHFFFAOYSA-N 0.000 description 1
- WVJCYCCJJIJHDC-UHFFFAOYSA-N 3-o-methyl 5-o-[2-(2-phenylethylamino)ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCNCCC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WVJCYCCJJIJHDC-UHFFFAOYSA-N 0.000 description 1
- MTLIBDLYSVXMIM-UHFFFAOYSA-N 5-(2-methoxyethoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 MTLIBDLYSVXMIM-UHFFFAOYSA-N 0.000 description 1
- KZLKFNFSRYRTAP-UHFFFAOYSA-N 5-o-(1,3-diphenylprop-2-enyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C=CC=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 KZLKFNFSRYRTAP-UHFFFAOYSA-N 0.000 description 1
- UFEICAJTEROYST-UHFFFAOYSA-N 5-o-(2,3-diphenylprop-2-enyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(=CC=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 UFEICAJTEROYST-UHFFFAOYSA-N 0.000 description 1
- IFUSNPKNWGFLHX-UHFFFAOYSA-N 5-o-(4,4-dimethyl-1-phenylpent-1-en-3-yl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C=CC=2C=CC=CC=2)C(C)(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 IFUSNPKNWGFLHX-UHFFFAOYSA-N 0.000 description 1
- KSSXFTLQNZRCJY-UHFFFAOYSA-N 5-o-(4,4-diphenylbut-3-enyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC=C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 KSSXFTLQNZRCJY-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LMFHGFATTGOQNO-UHFFFAOYSA-O CC(NC(C)=C(C1C2=CC([N+]([O-])=O)=CC=C2)C(OCC=CC2=C[S+](C)C=C2)=O)=C1C(OC)=O Chemical compound CC(NC(C)=C(C1C2=CC([N+]([O-])=O)=CC=C2)C(OCC=CC2=C[S+](C)C=C2)=O)=C1C(OC)=O LMFHGFATTGOQNO-UHFFFAOYSA-O 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- XTFPDGZNWTZCMF-UHFFFAOYSA-N pranidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC=CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 XTFPDGZNWTZCMF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59088411A JPS60233058A (ja) | 1984-05-04 | 1984-05-04 | １，４−ジヒドロピリジン誘導体 |
| US06/727,692 US4672068A (en) | 1984-05-04 | 1985-04-26 | Antihypertensive 1,4-dihydropyridines having a conjugated ester |
| EP85303141A EP0161877B1 (en) | 1984-05-04 | 1985-05-02 | 1,4-dihydropyridine derivatives, methods for their production and pharmaceutical compositions comprising the same |
| DE8585303141T DE3582952D1 (de) | 1984-05-04 | 1985-05-02 | Dihydropyridin-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59088411A JPS60233058A (ja) | 1984-05-04 | 1984-05-04 | １，４−ジヒドロピリジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60233058A JPS60233058A (ja) | 1985-11-19 |
| JPH0314307B2 true JPH0314307B2 (no) | 1991-02-26 |
Family
ID=13942053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59088411A Granted JPS60233058A (ja) | 1984-05-04 | 1984-05-04 | １，４−ジヒドロピリジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60233058A (no) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350766B1 (en) | 1997-04-25 | 2002-02-26 | Ajinomoto Co., Inc. | Dihydropyridine derivative |
| AU5568300A (en) | 1999-06-23 | 2001-01-09 | Ajinomoto Co., Inc. | Novel dihydropyridine derivative |
| WO2000078719A1 (fr) | 1999-06-23 | 2000-12-28 | Ajinomoto Co., Inc. | Derive de la dihydropyridine |
| CN114206441B (zh) * | 2019-05-31 | 2024-07-02 | R发现有限责任公司 | Drp1-细丝蛋白复合物形成抑制剂 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60120861A (ja) * | 1983-12-02 | 1985-06-28 | Otsuka Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
-
1984
- 1984-05-04 JP JP59088411A patent/JPS60233058A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60120861A (ja) * | 1983-12-02 | 1985-06-28 | Otsuka Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60233058A (ja) | 1985-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080226 Year of fee payment: 17 |