JPS5916876A - カルシウムに拮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 - Google Patents
カルシウムに拮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Info
- Publication number
- JPS5916876A JPS5916876A JP9926583A JP9926583A JPS5916876A JP S5916876 A JPS5916876 A JP S5916876A JP 9926583 A JP9926583 A JP 9926583A JP 9926583 A JP9926583 A JP 9926583A JP S5916876 A JPS5916876 A JP S5916876A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- formula
- unsubstituted
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims description 4
- 239000011575 calcium Substances 0.000 title claims description 4
- 229910052791 calcium Inorganic materials 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 7
- 230000003042 antagnostic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- -1 chenyl Chemical group 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 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 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 1
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 claims 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims 1
- NGWKGSCSHDHHAJ-YPFQVHCOSA-N Liquoric acid Chemical compound C1C[C@H](O)C(C)(C)C2CC[C@@]3(C)[C@]4(C)C[C@H]5O[C@@H]([C@](C6)(C)C(O)=O)C[C@@]5(C)[C@@H]6C4=CC(=O)C3[C@]21C NGWKGSCSHDHHAJ-YPFQVHCOSA-N 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000011505 plaster Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000013076 target substance Substances 0.000 description 5
- 230000001077 hypotensive effect Effects 0.000 description 4
- 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 4
- 229960001597 nifedipine Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 230000002213 calciumantagonistic effect Effects 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- GQJVIHJCIFNCCB-UHFFFAOYSA-N 2,6-dimethyl-5-(2-methylpropoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound CC(C)COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 GQJVIHJCIFNCCB-UHFFFAOYSA-N 0.000 description 1
- GTMIXYICYSFTRJ-UHFFFAOYSA-N 2-(4-phenylpiperazin-1-yl)ethanol Chemical compound C1CN(CCO)CCN1C1=CC=CC=C1 GTMIXYICYSFTRJ-UHFFFAOYSA-N 0.000 description 1
- PZYZNVGUXXOFHD-UHFFFAOYSA-N 2-(4-phenylpiperazin-1-yl)ethyl 3-oxobutanoate Chemical compound C1CN(CCOC(=O)CC(=O)C)CCN1C1=CC=CC=C1 PZYZNVGUXXOFHD-UHFFFAOYSA-N 0.000 description 1
- JAEUQHNZRROYID-UHFFFAOYSA-N 2-chloroethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCl JAEUQHNZRROYID-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- YPOLXKVVRKLRKR-UHFFFAOYSA-N 3-o-(2-chloroethyl) 5-o-(2-methylpropyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCl)C1C1=CC=CC([N+]([O-])=O)=C1 YPOLXKVVRKLRKR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YJTOAPUZSSOZSE-UHFFFAOYSA-N 5-o-(2-chloroethyl) 3-o-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCl)C1C1=CC=CC([N+]([O-])=O)=C1 YJTOAPUZSSOZSE-UHFFFAOYSA-N 0.000 description 1
- PYAZZLMSTSUOEG-UHFFFAOYSA-N 5-o-(2-chloroethyl) 3-o-ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCl)C1C1=CC=CC([N+]([O-])=O)=C1 PYAZZLMSTSUOEG-UHFFFAOYSA-N 0.000 description 1
- HFLGCPOPFWAWDG-UHFFFAOYSA-N 5-o-(2-chloroethyl) 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)OCCCl)C1C1=CC=CC([N+]([O-])=O)=C1 HFLGCPOPFWAWDG-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 1
- 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 1
- 241000700159 Rattus Species 0.000 description 1
- 241000244155 Taenia Species 0.000 description 1
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- XYIBRDXRRQCHLP-XMUWKQMQSA-N ethyl 3-oxobutanoate Chemical compound CCO[13C](=O)[13CH2][13C]([13CH3])=O XYIBRDXRRQCHLP-XMUWKQMQSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 231100001231 less toxic Toxicity 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
- 238000002156 mixing Methods 0.000 description 1
- 229960001783 nicardipine Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000004873 systolic arterial blood pressure Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21678A/82 | 1982-06-03 | ||
| IT21678/82A IT1198377B (it) | 1982-06-03 | 1982-06-03 | Esteri basici ad attivita' calcioanatagonista,procedimenti per la loro preparazione e relative composizioni farmaceutiche |
| IT21043A/83 | 1983-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5916876A true JPS5916876A (ja) | 1984-01-28 |
| JPS6352031B2 JPS6352031B2 (enrdf_load_stackoverflow) | 1988-10-17 |
Family
ID=11185263
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9926583A Granted JPS5916876A (ja) | 1982-06-03 | 1983-06-02 | カルシウムに拮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 |
| JP61021084A Pending JPS61210070A (ja) | 1982-06-03 | 1986-02-01 | 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61021084A Pending JPS61210070A (ja) | 1982-06-03 | 1986-02-01 | 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 |
Country Status (3)
| Country | Link |
|---|---|
| JP (2) | JPS5916876A (enrdf_load_stackoverflow) |
| IT (1) | IT1198377B (enrdf_load_stackoverflow) |
| ZA (1) | ZA833997B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6117562A (ja) * | 1984-04-11 | 1986-01-25 | ブリストル−マイア−ズ コムパニ− | 薬剤に有用なジヒドロピリジニルジカルボン酸アミド及びエステル |
| JPS6172751A (ja) * | 1984-09-14 | 1986-04-14 | チバ・ガイギー・アクチエンゲゼルシヤフト | カルボニル化合物、その製造方法及び該化合物を含む医薬製剤 |
| JPS61210070A (ja) * | 1982-06-03 | 1986-09-18 | ピエルレル・エツセ・ピ・ア | 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 |
| JPS6256473A (ja) * | 1985-09-06 | 1987-03-12 | Sanwa Kagaku Kenkyusho:Kk | 新規な１，４―ジヒドロピリジン誘導体及びその塩並びにこれらの化合物を有効成分とする循環器系作用剤 |
| WO1991009847A1 (fr) * | 1989-12-29 | 1991-07-11 | Kaken Pharmaceutical Co., Ltd. | Derive d'ethynylphenyle, production de ce derive et medicament de traitement des maladies des organes du systeme circulatoire contenant ce derive comme ingredient actif |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58201765A (ja) * | 1982-05-10 | 1983-11-24 | Takeda Chem Ind Ltd | ジヒドロピリジン誘導体，その製造法および用途 |
| IT1198377B (it) * | 1982-06-03 | 1988-12-21 | Pierrel Spa | Esteri basici ad attivita' calcioanatagonista,procedimenti per la loro preparazione e relative composizioni farmaceutiche |
-
1982
- 1982-06-03 IT IT21678/82A patent/IT1198377B/it active
-
1983
- 1983-06-02 JP JP9926583A patent/JPS5916876A/ja active Granted
- 1983-06-02 ZA ZA833997A patent/ZA833997B/xx unknown
-
1986
- 1986-02-01 JP JP61021084A patent/JPS61210070A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61210070A (ja) * | 1982-06-03 | 1986-09-18 | ピエルレル・エツセ・ピ・ア | 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 |
| JPS6117562A (ja) * | 1984-04-11 | 1986-01-25 | ブリストル−マイア−ズ コムパニ− | 薬剤に有用なジヒドロピリジニルジカルボン酸アミド及びエステル |
| JPS6172751A (ja) * | 1984-09-14 | 1986-04-14 | チバ・ガイギー・アクチエンゲゼルシヤフト | カルボニル化合物、その製造方法及び該化合物を含む医薬製剤 |
| JPS6256473A (ja) * | 1985-09-06 | 1987-03-12 | Sanwa Kagaku Kenkyusho:Kk | 新規な１，４―ジヒドロピリジン誘導体及びその塩並びにこれらの化合物を有効成分とする循環器系作用剤 |
| WO1991009847A1 (fr) * | 1989-12-29 | 1991-07-11 | Kaken Pharmaceutical Co., Ltd. | Derive d'ethynylphenyle, production de ce derive et medicament de traitement des maladies des organes du systeme circulatoire contenant ce derive comme ingredient actif |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1198377B (it) | 1988-12-21 |
| JPS61210070A (ja) | 1986-09-18 |
| ZA833997B (en) | 1984-02-29 |
| IT8221678A0 (it) | 1982-06-03 |
| JPS6352031B2 (enrdf_load_stackoverflow) | 1988-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4656181A (en) | Esters of 1,4-dihydropyridines, processes for the preparation of the new esters, and medicaments containing the same | |
| Meguro et al. | New 1, 4-dihydropyridine derivatives with potent and long-lasting hypotensive effect | |
| EP0094159B1 (en) | Dihydropyridine derivatives, their production and use | |
| KR870000809B1 (ko) | 1,4-디하이드로피리딘의 제조방법 | |
| EP0097821B1 (en) | Dihydropyridines with an antagonistic activity to calcium, process for their preparation, and pharmaceutical compositions containing them | |
| KR880000180B1 (ko) | 디하이드로 피리딘의 제조방법 | |
| CA1320204C (en) | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters | |
| JPH0588226B2 (enrdf_load_stackoverflow) | ||
| EP1641765A1 (fr) | Produits aryl-heteroaromatiques, compositions les contenant et utilisation | |
| JPS63297365A (ja) | ジヒドロピリジン類 | |
| KR960009427B1 (ko) | 1,4-디히드로피리딘 유도체, 그의 약학적 조성물 및 그 제조방법 | |
| JPS5916876A (ja) | カルシウムに拮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 | |
| JPS61257983A (ja) | 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 | |
| EP1191022A1 (en) | Novel dihydropyridine derivative | |
| JPH0379359B2 (enrdf_load_stackoverflow) | ||
| JP2640245B2 (ja) | １，４−ジヒドロピリジン誘導体 | |
| JPS6289662A (ja) | １，４−ジヒドロピリジン誘導体 | |
| JP2664941B2 (ja) | １，４―ジヒドロピリジン化合物 | |
| EP0264232A1 (en) | 2-Azetidinone derivatives | |
| EP0220917B1 (en) | 1,4-dihydropyridine pharmaceutical derivatives and their salts, and the preparation thereof | |
| JPS5976083A (ja) | ジヒドロピリジン類 | |
| JPS62501972A (ja) | 新規ピペラジン誘導体 | |
| JP4163260B2 (ja) | １，４−ジヒドロピリジン誘導体および治療におけるその使用 | |
| JPS5885884A (ja) | ４−（２，１，３−ベンゾキサジアゾル−４−イル）−１，４−ジヒドロピリダジン類およびそれを含む薬学的組成物 | |
| EP0370821A2 (en) | 1,4-dihydropyridine derivatives |