JPS6352031B2 - - Google Patents
Info
- Publication number
- JPS6352031B2 JPS6352031B2 JP9926583A JP9926583A JPS6352031B2 JP S6352031 B2 JPS6352031 B2 JP S6352031B2 JP 9926583 A JP9926583 A JP 9926583A JP 9926583 A JP9926583 A JP 9926583A JP S6352031 B2 JPS6352031 B2 JP S6352031B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- represented
- carbon atoms
- linear
- 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
Links
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 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 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 4
- 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 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical group OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 claims 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 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 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- -1 chloroalkyl ester Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000013076 target substance Substances 0.000 description 4
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 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
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 3
- 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 3
- 229960001597 nifedipine Drugs 0.000 description 3
- 238000002360 preparation method Methods 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
- 230000001629 suppression Effects 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 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
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000004873 systolic arterial blood pressure Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QAGODYZWUHCJQA-UHFFFAOYSA-N (3-nitrophenyl) pyridine-3-carboxylate Chemical compound [O-][N+](=O)C1=CC=CC(OC(=O)C=2C=NC=CC=2)=C1 QAGODYZWUHCJQA-UHFFFAOYSA-N 0.000 description 1
- XVGORVIYIMNEME-UHFFFAOYSA-N 1-ethoxycarbonyl-4H-pyridine-3-carboxylic acid Chemical compound C(C)OC(=O)N1C=C(CC=C1)C(=O)O XVGORVIYIMNEME-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
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 101000583175 Homo sapiens Prolactin-inducible protein Proteins 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 238000006845 Michael addition reaction Methods 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
- 101000898291 Nicotiana tabacum Catalase isozyme 1 Proteins 0.000 description 1
- 102100030350 Prolactin-inducible protein Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101000979255 Sus scrofa Neurolysin, mitochondrial Proteins 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
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 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
- 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
- 230000000694 effects Effects 0.000 description 1
- BPBPAEMKXQYZMB-UHFFFAOYSA-N ethyl 3-oxo-2-(4-pyrimidin-2-ylpiperazin-1-yl)butanoate Chemical compound C1CN(C(C(=O)OCC)C(C)=O)CCN1C1=NC=CC=N1 BPBPAEMKXQYZMB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process 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
- 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
- 230000002265 prevention Effects 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000010898 silica gel chromatography 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
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21678/82A IT1198377B (it) | 1982-06-03 | 1982-06-03 | Esteri basici ad attivita' calcioanatagonista,procedimenti per la loro preparazione e relative composizioni farmaceutiche |
| IT21678A/82 | 1982-06-03 | ||
| IT21043A/83 | 1983-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5916876A JPS5916876A (ja) | 1984-01-28 |
| JPS6352031B2 true JPS6352031B2 (hu) | 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 (hu) |
| IT (1) | IT1198377B (hu) |
| ZA (1) | ZA833997B (hu) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1198377B (it) * | 1982-06-03 | 1988-12-21 | Pierrel Spa | Esteri basici ad attivita' calcioanatagonista,procedimenti per la loro preparazione e relative composizioni farmaceutiche |
| US4755512A (en) * | 1984-04-11 | 1988-07-05 | Bristol-Myers Company | Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities |
| FI853477L (fi) * | 1984-09-14 | 1986-03-15 | Ciba Geigy Ag | Foerfarande foer framstaellning av karbonylfoereningar. |
| JPH0717645B2 (ja) * | 1985-09-06 | 1995-03-01 | 株式会社三和化学研究所 | 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 |
| CA2048668A1 (en) * | 1989-12-29 | 1991-06-30 | Michio Nakanishi | Ethynylphenyl derivative, process for preparing the same and medicament for circulatory disease containing the same as an effective ingredient |
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 ZA ZA833997A patent/ZA833997B/xx unknown
- 1983-06-02 JP JP9926583A patent/JPS5916876A/ja active Granted
-
1986
- 1986-02-01 JP JP61021084A patent/JPS61210070A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61210070A (ja) | 1986-09-18 |
| IT8221678A0 (it) | 1982-06-03 |
| IT1198377B (it) | 1988-12-21 |
| ZA833997B (en) | 1984-02-29 |
| JPS5916876A (ja) | 1984-01-28 |
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