DK141603B - Analogifremgangsmåde til fremstilling af 3,4-dihydrocarbostyril-derivater. - Google Patents
Analogifremgangsmåde til fremstilling af 3,4-dihydrocarbostyril-derivater. Download PDFInfo
- Publication number
- DK141603B DK141603B DK2773AA DK2773A DK141603B DK 141603 B DK141603 B DK 141603B DK 2773A A DK2773A A DK 2773AA DK 2773 A DK2773 A DK 2773A DK 141603 B DK141603 B DK 141603B
- Authority
- DK
- Denmark
- Prior art keywords
- dihydrocarbostyril
- propoxy
- hydroxy
- formula
- added
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 11
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 title claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- -1 piperazino Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 50
- 239000013078 crystal Substances 0.000 description 41
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- 238000006243 chemical reaction Methods 0.000 description 36
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- 238000004458 analytical method Methods 0.000 description 7
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- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 5
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- 238000002844 melting Methods 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KNRFNTVMEIIKEB-UHFFFAOYSA-N 1,3,4,6,7,8-hexahydroquinoline-2,5-dione Chemical compound N1C(=O)CCC2=C1CCCC2=O KNRFNTVMEIIKEB-UHFFFAOYSA-N 0.000 description 4
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 101150066742 TRI1 gene Proteins 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GTVRLHPVICIJFQ-UHFFFAOYSA-N hexane;tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl.CCCCCC GTVRLHPVICIJFQ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 101150009274 nhr-1 gene Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK137976A DK137976A (da) | 1972-04-13 | 1976-03-29 | Fremgangsmade til fremstilling af 2,4-dihydrocarbostyril-derivater |
| DK138076A DK152492C (da) | 1972-04-13 | 1976-03-29 | 3,4-dihydrocarbostyril-derivater til anvendelse som mellemprodukter til fremstilling af biologisk aktive 3,4-dihydrocarbostyril-derivater |
Applications Claiming Priority (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3718272 | 1972-04-13 | ||
| JP3718172 | 1972-04-13 | ||
| JP47037182A JPS48103590A (en:Method) | 1972-04-13 | 1972-04-13 | |
| JP47037181A JPS517672B2 (en:Method) | 1972-04-13 | 1972-04-13 | |
| JP47092558A JPS5241268B2 (en:Method) | 1972-09-14 | 1972-09-14 | |
| JP9255772 | 1972-09-14 | ||
| JP9256072 | 1972-09-14 | ||
| JP9255772A JPS5324431B2 (en:Method) | 1972-09-14 | 1972-09-14 | |
| JP9255872 | 1972-09-14 | ||
| JP47092560A JPS5246231B2 (en:Method) | 1972-09-14 | 1972-09-14 | |
| JP12095372 | 1972-12-02 | ||
| JP47120953A JPS5229745B2 (en:Method) | 1972-04-13 | 1972-12-02 | |
| JP47125858A JPS5239036B2 (en:Method) | 1972-04-13 | 1972-12-14 | |
| JP12585872 | 1972-12-14 | ||
| JP47128972A JPS5241269B2 (en:Method) | 1972-04-13 | 1972-12-21 | |
| JP12897272 | 1972-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141603B true DK141603B (da) | 1980-05-05 |
| DK141603C DK141603C (en:Method) | 1980-10-06 |
Family
ID=27572212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK2773AA DK141603B (da) | 1972-04-13 | 1973-01-03 | Analogifremgangsmåde til fremstilling af 3,4-dihydrocarbostyril-derivater. |
Country Status (17)
| Country | Link |
|---|---|
| JP (5) | JPS48103590A (en:Method) |
| AR (1) | AR209575A1 (en:Method) |
| AU (1) | AU475964B2 (en:Method) |
| BE (1) | BE794669A (en:Method) |
| CA (1) | CA1025447A (en:Method) |
| CH (1) | CH575929A5 (en:Method) |
| DD (2) | DD112446A5 (en:Method) |
| DE (1) | DE2302027C2 (en:Method) |
| DK (1) | DK141603B (en:Method) |
| FI (1) | FI53703C (en:Method) |
| FR (1) | FR2179715B1 (en:Method) |
| GB (2) | GB1424571A (en:Method) |
| HK (1) | HK19481A (en:Method) |
| NL (1) | NL158176B (en:Method) |
| NO (1) | NO140589C (en:Method) |
| SE (1) | SE380018B (en:Method) |
| YU (1) | YU41187B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154970B (da) * | 1976-03-17 | 1989-01-16 | Otsuka Pharma Co Ltd | Analogifremgangsmaade til fremstilling af carbosty rilderivater |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5082218A (en:Method) * | 1973-11-10 | 1975-07-03 | ||
| US4022784A (en) * | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-substituted-carbostyril and -3,4-dihydrocarbostyril derivatives |
| US4137331A (en) | 1974-06-19 | 1979-01-30 | Sandoz Ltd. | 3-Piperidino-2-hydroxypropoxy substituted-2-indolinones |
| JPS516971A (en) * | 1974-07-08 | 1976-01-20 | Otsuka Pharma Co Ltd | Nitoro 3*44 jihidorokarubosuchirirujudotaino seizoho |
| JPS5129486A (en) * | 1974-09-02 | 1976-03-12 | Otsuka Pharma Co Ltd | * 33 arukiruamino 22 hidorokishi * purohokishi 3 44 jihidorokarubosuchirirujudotai no seizoho |
| JPS5148674A (en) * | 1974-10-17 | 1976-04-26 | Otsuka Pharma Co Ltd | 3 44 jihidorokarubosuchirirujudotaino seizoho |
| JPS5152178A (ja) * | 1974-10-31 | 1976-05-08 | Otsuka Pharma Co Ltd | Karubosuchirirujudotaino seizoho |
| JPS5152180A (ja) * | 1974-10-31 | 1976-05-08 | Otsuka Pharma Co Ltd | Karubosuchirirujudotaino seizoho |
| JPS5152179A (ja) * | 1974-10-31 | 1976-05-08 | Otsuka Pharma Co Ltd | Karubosuchirirujudotaino seizoho |
| FI58329C (fi) * | 1974-11-08 | 1981-01-12 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av i 8-staellning substituerade 5-(3'-alkylamino-2'-hydroxi)propoxi-3,4-dihydrokarbostyrilderivat |
| US4081447A (en) * | 1975-04-09 | 1978-03-28 | Abbott Laboratories | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof |
| DE2719562C2 (de) * | 1976-05-08 | 1986-05-07 | Otsuka Pharmaceutical Co. Ltd., Tokio/Tokyo | 3, 4-Dihydrocarbostyrilderivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
| US4146630A (en) * | 1976-11-12 | 1979-03-27 | Boehringer Mannheim Gmbh | Blood pressure lowering and adrenergic β-receptor inhibiting 3-(4-phenoxymethylpiperidino)-propyl-phenyl ethers |
| JPS54130587A (en) * | 1978-03-30 | 1979-10-09 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivative |
| DE2960178D1 (en) * | 1978-06-06 | 1981-04-09 | Hoechst Ag | New substituted phenylpiperazine derivatives, pharmaceutical compositions containing them and process for their preparation |
| DE2827566A1 (de) * | 1978-06-23 | 1980-01-10 | Boehringer Mannheim Gmbh | 1,2-dihydro-chinolin-2-on-derivate und verfahren zu ihrer herstellung |
| AU518814B2 (en) * | 1979-01-30 | 1981-10-22 | Otsuka Pharamaceutical Co. | Glaucoma treatment |
| DE3034237A1 (de) * | 1979-09-18 | 1981-04-16 | Otsuka Pharmaceutical Co. Ltd., Tokyo | Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel |
| JPS56122356A (en) * | 1980-02-29 | 1981-09-25 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| JPS58103343A (ja) * | 1981-12-15 | 1983-06-20 | Ota Seiyaku Kk | プロパノ−ルアミン化合物の製造法 |
| JPS597186A (ja) * | 1982-07-02 | 1984-01-14 | Ota Seiyaku Kk | １，３，２−ジオキサチオラン２−オキシド誘導体 |
| JPS63193086U (en:Method) * | 1987-05-30 | 1988-12-13 | ||
| DE3808136A1 (de) * | 1988-03-11 | 1989-09-21 | Thomae Gmbh Dr K | Arzneimittel, enthaltend chinolin-2,5-dione, neue chinolin-2,5-dione und verfahren zu ihrer herstellung |
| ES2070151T3 (es) * | 1988-08-10 | 1995-06-01 | Otsuka Pharma Co Ltd | Agentes cardiotonicos. |
| US5266577A (en) * | 1988-08-10 | 1993-11-30 | Otsuka Pharmaceutical Company Ltd. | Method of treating congestive heart failure using carbostyril derivatives |
| US5506239A (en) * | 1991-08-23 | 1996-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivative and platelets aggregation inhibitory agent |
| ES2048108B1 (es) * | 1992-07-17 | 1994-10-01 | Lusochimica Spa | Procedimiento para la preparacion de 5-(3-terc-butilamino-2-hidroxipropoxi)-3,4-dihidrocarboestirilo. |
| IT1264816B1 (it) * | 1993-07-28 | 1996-10-10 | Pergam Srl | Procedimento per la preparazione di derivati del procedimento per la preparazione di derivati del 3,4-diidrocarbostirile 3,4-diidrocarbostirile |
| CZ300351B6 (cs) * | 2005-05-26 | 2009-04-29 | Zentiva, A. S. | Zpusob prípravy 7-hydroxy-3,4-dihydrokarbostyrilu |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| CH523899A (de) * | 1968-07-05 | 1972-06-15 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydro-chinolins |
-
1972
- 1972-04-13 JP JP47037182A patent/JPS48103590A/ja active Pending
- 1972-04-13 JP JP47037181A patent/JPS517672B2/ja not_active Expired
- 1972-12-02 JP JP47120953A patent/JPS5229745B2/ja not_active Expired
- 1972-12-14 JP JP47125858A patent/JPS5239036B2/ja not_active Expired
- 1972-12-21 JP JP47128972A patent/JPS5241269B2/ja not_active Expired
-
1973
- 1973-01-03 DK DK2773AA patent/DK141603B/da active Protection Beyond IP Right Term
- 1973-01-10 NO NO73105A patent/NO140589C/no unknown
- 1973-01-10 FR FR7300739A patent/FR2179715B1/fr not_active Expired
- 1973-01-11 CA CA161,000A patent/CA1025447A/en not_active Expired
- 1973-01-16 DE DE2302027A patent/DE2302027C2/de not_active Expired
- 1973-01-22 GB GB325173A patent/GB1424571A/en not_active Expired
- 1973-01-22 GB GB3417075A patent/GB1424572A/en not_active Expired
- 1973-01-29 BE BE794669D patent/BE794669A/xx active Protection Beyond IP Right Term
- 1973-01-31 FI FI279/73A patent/FI53703C/fi active
- 1973-02-02 DD DD178082*A patent/DD112446A5/xx unknown
- 1973-02-02 DD DD168643A patent/DD108293A5/xx unknown
- 1973-02-09 SE SE7301863A patent/SE380018B/xx unknown
- 1973-02-12 AR AR246548A patent/AR209575A1/es active
- 1973-02-20 NL NL7302353.A patent/NL158176B/xx not_active IP Right Cessation
- 1973-03-19 CH CH393973A patent/CH575929A5/xx not_active IP Right Cessation
- 1973-04-11 AU AU54386/73A patent/AU475964B2/en not_active Expired
-
1979
- 1979-10-19 YU YU2549/79A patent/YU41187B/xx unknown
-
1981
- 1981-05-14 HK HK194/81A patent/HK19481A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154970B (da) * | 1976-03-17 | 1989-01-16 | Otsuka Pharma Co Ltd | Analogifremgangsmaade til fremstilling af carbosty rilderivater |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired | ||
| CTFF | Application for supplementary protection certificate (spc) filed |
Spc suppl protection certif: CA 1993 00001 Filing date: 19930102 |
|
| CTFF | Application for supplementary protection certificate (spc) filed |
Spc suppl protection certif: CA 1993 00001 Filing date: 19930102 |