CA1139761A - Tetrazolylalkoxycarbostyril derivatives and process for producing the same - Google Patents
Tetrazolylalkoxycarbostyril derivatives and process for producing the sameInfo
- Publication number
- CA1139761A CA1139761A CA000334272A CA334272A CA1139761A CA 1139761 A CA1139761 A CA 1139761A CA 000334272 A CA000334272 A CA 000334272A CA 334272 A CA334272 A CA 334272A CA 1139761 A CA1139761 A CA 1139761A
- Authority
- CA
- Canada
- Prior art keywords
- group
- propoxy
- carbostyril
- cyclohexyltetrazol
- dihydrocarbostyril
- 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
- 238000000034 method Methods 0.000 title claims description 74
- 230000008569 process Effects 0.000 title claims description 52
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract description 146
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 109
- 150000001875 compounds Chemical class 0.000 claims description 103
- -1 hydroxy carbostyril compound Chemical class 0.000 claims description 60
- 238000002360 preparation method Methods 0.000 claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 10
- AQLYZDRHNHZHIS-UHFFFAOYSA-N quinoline-2,6-diol Chemical compound N1C(=O)C=CC2=CC(O)=CC=C21 AQLYZDRHNHZHIS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- AMUDPKZARIEIJI-UHFFFAOYSA-N 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC1=NN=NN1C1CCCCC1 AMUDPKZARIEIJI-UHFFFAOYSA-N 0.000 claims description 5
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical class C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- NJWWTEPHSKGAPV-UHFFFAOYSA-N 6-[3-(1-benzyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC1=NN=NN1CC1=CC=CC=C1 NJWWTEPHSKGAPV-UHFFFAOYSA-N 0.000 claims description 3
- RHYJHOMHCKNQDA-UHFFFAOYSA-N 6-[3-(1-cyclooctyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC1=NN=NN1C1CCCCCCC1 RHYJHOMHCKNQDA-UHFFFAOYSA-N 0.000 claims description 3
- LTGARHHGFRWZAC-UHFFFAOYSA-N 6-[3-(1-phenyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC1=NN=NN1C1=CC=CC=C1 LTGARHHGFRWZAC-UHFFFAOYSA-N 0.000 claims description 3
- TWUOKZPYAVDUAZ-UHFFFAOYSA-N 1-benzyl-5-(3-iodopropyl)tetrazole Chemical compound ICCCC1=NN=NN1CC1=CC=CC=C1 TWUOKZPYAVDUAZ-UHFFFAOYSA-N 0.000 claims description 2
- BGQRIHKGXFJBFV-UHFFFAOYSA-N 1-cyclohexyl-5-(3-iodopropyl)tetrazole Chemical compound ICCCC1=NN=NN1C1CCCCC1 BGQRIHKGXFJBFV-UHFFFAOYSA-N 0.000 claims description 2
- HIGPYAVJGJPLIW-UHFFFAOYSA-N 5-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCC1=NN=NN1C1CCCCC1 HIGPYAVJGJPLIW-UHFFFAOYSA-N 0.000 claims description 2
- AOHRJONEMRREBC-UHFFFAOYSA-N 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-4-methyl-1h-quinolin-2-one Chemical compound C1=C2C(C)=CC(=O)NC2=CC=C1OCCCC1=NN=NN1C1CCCCC1 AOHRJONEMRREBC-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 22
- DYTAJMIPFFMXLK-UHFFFAOYSA-N 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCC1=NN=NN1C1CCCCC1 DYTAJMIPFFMXLK-UHFFFAOYSA-N 0.000 claims 3
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 3
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 claims 2
- VDVBMNUWWISTIB-UHFFFAOYSA-N 6-[3-(1-cyclopentyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC1=NN=NN1C1CCCC1 VDVBMNUWWISTIB-UHFFFAOYSA-N 0.000 claims 2
- GHALECSGOJQOHW-UHFFFAOYSA-N 6-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 GHALECSGOJQOHW-UHFFFAOYSA-N 0.000 claims 2
- ZBGIMUOPQWPIFT-UHFFFAOYSA-N 7-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCC1=NN=NN1C1CCCCC1 ZBGIMUOPQWPIFT-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims 1
- WAHGBQYMLVOUQO-UHFFFAOYSA-N 4-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C12=CC=CC=C2NC(=O)C=C1OCCCC1=NN=NN1C1CCCCC1 WAHGBQYMLVOUQO-UHFFFAOYSA-N 0.000 claims 1
- UTTJAIFHRUAFED-UHFFFAOYSA-N 5-hydroxy-3,4-dihydro-2(1h)-quinolinone Chemical compound N1C(=O)CCC2=C1C=CC=C2O UTTJAIFHRUAFED-UHFFFAOYSA-N 0.000 claims 1
- XPVYFPWJBHMDAT-UHFFFAOYSA-N 6-[3-[1-(cyclohexylmethyl)tetrazol-5-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCC1=NN=NN1CC1CCCCC1 XPVYFPWJBHMDAT-UHFFFAOYSA-N 0.000 claims 1
- MLWJMEZPVTZSKE-UHFFFAOYSA-N 6-hydroxy-4-methyl-1h-quinolin-2-one Chemical compound C1=C(O)C=C2C(C)=CC(=O)NC2=C1 MLWJMEZPVTZSKE-UHFFFAOYSA-N 0.000 claims 1
- LKLSFDWYIBUGNT-UHFFFAOYSA-N 7-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(O)=CC=C21 LKLSFDWYIBUGNT-UHFFFAOYSA-N 0.000 claims 1
- UVIHXVHULNUSGB-UHFFFAOYSA-N 8-[3-(1-cyclohexyltetrazol-5-yl)propoxy]-1h-quinolin-2-one Chemical compound C=12NC(=O)C=CC2=CC=CC=1OCCCC1=NN=NN1C1CCCCC1 UVIHXVHULNUSGB-UHFFFAOYSA-N 0.000 claims 1
- UDKMDIKMJWOSJP-UHFFFAOYSA-N 8-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=C1C=CC=C2O UDKMDIKMJWOSJP-UHFFFAOYSA-N 0.000 claims 1
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 14
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 14
- 230000002401 inhibitory effect Effects 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 230000000144 pharmacologic effect Effects 0.000 abstract description 8
- 230000003727 cerebral blood flow Effects 0.000 abstract description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 5
- 230000009471 action Effects 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 230000000767 anti-ulcer Effects 0.000 abstract description 4
- 230000000304 vasodilatating effect Effects 0.000 abstract description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 3
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 230000002785 anti-thrombosis Effects 0.000 abstract description 2
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 2
- 239000003699 antiulcer agent Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000013078 crystal Substances 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 54
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000012360 testing method Methods 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 239000007788 liquid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 230000002776 aggregation Effects 0.000 description 14
- 238000004220 aggregation Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 210000001772 blood platelet Anatomy 0.000 description 11
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- 102000008186 Collagen Human genes 0.000 description 9
- 108010035532 Collagen Proteins 0.000 description 9
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 9
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- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 8
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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 8
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- 125000004432 carbon atom Chemical group C* 0.000 description 7
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000012000 urushibara nickel Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000008320 venous blood flow Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP107869/78 | 1978-09-01 | ||
| JP10786978A JPS5535019A (en) | 1978-09-01 | 1978-09-01 | Carbostyryl derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1139761A true CA1139761A (en) | 1983-01-18 |
Family
ID=14470137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000334272A Expired CA1139761A (en) | 1978-09-01 | 1979-08-22 | Tetrazolylalkoxycarbostyril derivatives and process for producing the same |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4277479A (en, 2012) |
| JP (1) | JPS5535019A (en, 2012) |
| AR (1) | AR229342A1 (en, 2012) |
| AT (1) | AT364363B (en, 2012) |
| AU (1) | AU538410B2 (en, 2012) |
| BE (1) | BE878548A (en, 2012) |
| CA (1) | CA1139761A (en, 2012) |
| CH (1) | CH641799A5 (en, 2012) |
| DE (1) | DE2934747A1 (en, 2012) |
| DK (1) | DK158788C (en, 2012) |
| ES (1) | ES483792A1 (en, 2012) |
| FI (1) | FI68398C (en, 2012) |
| FR (1) | FR2434809A1 (en, 2012) |
| GB (1) | GB2033893B (en, 2012) |
| IT (1) | IT1119929B (en, 2012) |
| MX (1) | MX6749E (en, 2012) |
| NL (1) | NL183888C (en, 2012) |
| NO (1) | NO153177C (en, 2012) |
| PH (1) | PH18452A (en, 2012) |
| PT (1) | PT70136A (en, 2012) |
| SE (1) | SE432252B (en, 2012) |
| SU (1) | SU1064868A3 (en, 2012) |
| ZA (1) | ZA794627B (en, 2012) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57156469A (en) * | 1981-03-19 | 1982-09-27 | Otsuka Pharmaceut Co Ltd | Preparation of tetrazole derivative |
| JPS57183761A (en) * | 1981-04-30 | 1982-11-12 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| JPS5859980A (ja) * | 1981-10-05 | 1983-04-09 | Otsuka Pharmaceut Co Ltd | カルボスチリル誘導体 |
| JPS5877880A (ja) * | 1981-11-05 | 1983-05-11 | Otsuka Pharmaceut Co Ltd | テトラゾ−ル誘導体 |
| DE3225169A1 (de) * | 1982-07-06 | 1984-01-12 | Basf Ag, 6700 Ludwigshafen | Chinolinderivate, verfahren zu ihrer herstellung, diese enthaltende mikrobizide und ihre verwendung zur bekaempfung von pilzen |
| US4803162A (en) * | 1984-05-15 | 1989-02-07 | Fluorodiagnostic Limited Partners | Composition, article and process for detecting a microorganism |
| PT80533B (en) * | 1984-05-29 | 1987-04-06 | Pfizer | Process for preparing quinolone inotropic agents |
| GB8529362D0 (en) * | 1985-11-28 | 1986-01-02 | Pfizer Ltd | Quinolone cardiac stimulants |
| KR940000785B1 (ko) * | 1986-04-02 | 1994-01-31 | 오오쓰까세이야꾸 가부시끼가이샤 | 카르보스티릴 유도체 및 그의 염의 제조 방법 |
| DK167187A (da) | 1986-04-02 | 1987-10-03 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, fremgangsmaade til fremstilling af saadanne forbindelser og laegemiddel indeholdende disse |
| JPH0681727B2 (ja) * | 1986-04-02 | 1994-10-19 | 大塚製薬株式会社 | 血小板粘着抑制剤 |
| JPH0681752B2 (ja) * | 1986-04-02 | 1994-10-19 | 大塚製薬株式会社 | カルボスチリル誘導体 |
| JP2753622B2 (ja) | 1988-05-02 | 1998-05-20 | 大塚製薬株式会社 | カルボスチリル誘導体 |
| US5064837A (en) * | 1989-11-13 | 1991-11-12 | Schering Corporation | 3-substituted-1-aryl-2(h)-quinolones and their pharmaceutical compositions |
| DK0463173T3 (da) * | 1990-01-08 | 1995-02-13 | Otsuka Pharma Co Ltd | Hårtonikum og -plejepræparat |
| TW201305B (en, 2012) * | 1991-04-03 | 1993-03-01 | Otsuka Pharma Co Ltd | |
| US5506239A (en) * | 1991-08-23 | 1996-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivative and platelets aggregation inhibitory agent |
| JPH0776521A (ja) * | 1993-09-07 | 1995-03-20 | Otsuka Pharmaceut Co Ltd | 気道炎症抑制剤 |
| US6187790B1 (en) | 1999-03-04 | 2001-02-13 | Neal R. Cutler | Use of cilostazol for treatment of sexual dysfunction |
| JP4060523B2 (ja) * | 1999-11-24 | 2008-03-12 | 大塚製薬株式会社 | カルボスチリル誘導体の製造法 |
| US20030045547A1 (en) | 2001-05-02 | 2003-03-06 | Shinji Aki | Process for producing carbostyril derivatives |
| US6525201B2 (en) | 2000-03-20 | 2003-02-25 | Teva Pharmaceutical Industries, Ltd. | Processes for preparing 6-hydroxy-3,4-dihydroquinolinone, cilostazol and N-(4-methoxyphenyl)-3-chloropropionamide |
| US6515128B2 (en) | 2000-03-20 | 2003-02-04 | Teva Pharmaceutical Industries Ltd. | Processes for preparing cilostazol |
| US6825214B2 (en) | 2000-08-14 | 2004-11-30 | Teva Pharmaceutical Industries, Ltd. | Substantially pure cilostazol and processes for making same |
| IL154458A0 (en) * | 2000-08-14 | 2003-09-17 | Teva Pharma | Processes for preparing cilostazol |
| US6458804B1 (en) | 2001-01-26 | 2002-10-01 | R.T. Alamo Venturesi, Llc | Methods for the treatment of central nervous system disorders in certain patient groups |
| US6451813B1 (en) | 2001-01-26 | 2002-09-17 | R. T. Alamo Ventures I, Llc | Treatment of gastroparesis in certain patient groups |
| US7399864B2 (en) * | 2001-05-02 | 2008-07-15 | Otsuka Pharmaceutical Co., Ltd. | Process for producing carbostyril derivatives |
| US20050101631A1 (en) | 2002-08-01 | 2005-05-12 | Otsuka Pharmaceuticals Company | Process for producing carbostyril derivatives |
| JP2003063965A (ja) * | 2001-06-13 | 2003-03-05 | Otsuka Pharmaceut Factory Inc | 注射用シロスタゾール水性製剤 |
| AU2002322456A1 (en) * | 2001-06-29 | 2003-03-03 | Aaipharma, Inc. | Polymorphic forms of 6-(4-(1-cyclohexyl-1h-tetrazol-5-yl)butoxy)-3, 4-dihydro-2(1h)-quinolinone |
| US6596871B2 (en) * | 2001-06-29 | 2003-07-22 | Grayson Walker Stowell | Polymorphic forms of 6-[4-(1-cyclohexyl-1h-tetraol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone |
| WO2003002121A1 (en) * | 2001-06-29 | 2003-01-09 | Aaipharma, Inc. | Polymorphic forms of 6-[4-(1-cyclohexyl-1h-tetrazol-5-yl)butoxy]-3, 4-dihydro-2(1h)-quinolinone |
| US6573382B2 (en) * | 2001-06-29 | 2003-06-03 | Grayson Walker Stowell | Polymorphic forms of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone |
| US6388080B1 (en) | 2001-06-29 | 2002-05-14 | Grayson Walker Stowell | Polymorphic forms of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone |
| US6531603B1 (en) * | 2001-06-29 | 2003-03-11 | Grayson Walker Stowell | Polymorphic forms of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone |
| US6657061B2 (en) * | 2001-06-29 | 2003-12-02 | Grayson Walker Stowell | Polymorphic forms of 6-[4-1(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone |
| US6660864B2 (en) * | 2001-06-29 | 2003-12-09 | Grayson Walker Stowell | Polymorphic forms of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone |
| ATE496907T1 (de) * | 2002-09-10 | 2011-02-15 | Otsuka Pharma Co Ltd | Verfahren zur herstellung von cilostazol |
| US6743806B2 (en) * | 2002-10-23 | 2004-06-01 | Otsuka Pharmaceutical Company, Limited | Active oxygen scavenger |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| TWI323660B (en) | 2003-02-25 | 2010-04-21 | Otsuka Pharma Co Ltd | Pten inhibitor or maxi-k channels opener |
| ITMI20031670A1 (it) * | 2003-08-26 | 2005-02-27 | Dinamite Dipharma S P A In Forma A Bbreviata Diph | Processo per la preparazione di cilostazolo e di suoi intermedi. |
| US7524960B2 (en) * | 2004-03-16 | 2009-04-28 | Chemagis Ltd. | Highly pure cilostazol and an improved process for obtaining same |
| US20050255155A1 (en) * | 2004-05-11 | 2005-11-17 | Glenmark Pharmaceuticals Limited | Modified release cilostazol compositions |
| WO2006030301A1 (en) * | 2004-09-17 | 2006-03-23 | Ranbaxy Laboratories Limited | Cilostazol- containing pharmaceutical composition based on particles of less than 50 micrometers |
| CN100462360C (zh) * | 2005-08-15 | 2009-02-18 | 上海立科药物化学有限公司 | N-环己基-5-(4-氯丁基)-1h-四氮唑的合成方法 |
| AR057520A1 (es) | 2005-09-15 | 2007-12-05 | Otsuka Pharma Co Ltd | Farmaco combinado |
| US20070105898A1 (en) * | 2005-11-09 | 2007-05-10 | Apotex Pharmachem Inc. | Process for the production of cilostazol |
| AR065588A1 (es) | 2007-03-09 | 2009-06-17 | Otsuka Pharma Co Ltd | Un medicamento para tratar enfermedad pulmonar obstructiva cronica |
| TW200848041A (en) | 2007-03-30 | 2008-12-16 | Otsuka Pharma Co Ltd | A medicament for treating schizophrenia comprising cilostazol |
| US8349817B2 (en) * | 2007-04-25 | 2013-01-08 | Concert Pharmaceuticals, Inc. | Analogues of cilostazol |
| ES2401914T3 (es) | 2007-04-25 | 2013-04-25 | Concert Pharmaceuticals Inc. | Análogos de Cilostazol |
| US20100298375A1 (en) * | 2007-05-22 | 2010-11-25 | Heii Arai | medicament comprising a carbostyril derivative and donepezil for treating alzheimer's disease |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| DK2170930T3 (da) | 2007-06-04 | 2012-11-05 | Synergy Pharmaceuticals Inc | Agonister af guanylatcyclase, anvendelige til behandlingen af gastrointestinale sygdomme, inflammation, cancer og andre sygdomme |
| US8034782B2 (en) | 2008-07-16 | 2011-10-11 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP2328910B1 (en) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP2194048A1 (en) | 2008-12-02 | 2010-06-09 | Dirk Sartor | Nitrate esters for the treatment of vascular and metabolic diseases |
| CN102933205B (zh) | 2010-04-28 | 2014-08-13 | 诺弗米克斯有限公司 | 西洛他唑共晶和组合物 |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CN108676076A (zh) | 2011-03-01 | 2018-10-19 | 辛纳吉制药公司 | 制备鸟苷酸环化酶c激动剂的方法 |
| JP6499591B2 (ja) | 2013-02-25 | 2019-04-10 | シナジー ファーマシューティカルズ インコーポレイテッド | 結腸洗浄において用いるためのグアニル酸シクラーゼ受容体アゴニスト |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| KR102272746B1 (ko) | 2013-06-05 | 2021-07-08 | 보슈 헬스 아일랜드 리미티드 | 구아닐레이트 사이클라제 c의 초순수 작용제, 및 이의 제조 및 사용 방법 |
| US20160184387A1 (en) | 2013-08-09 | 2016-06-30 | Dominique Charmot | Compounds and methods for inhibiting phosphate transport |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2470084A (en) * | 1945-09-25 | 1949-05-17 | Bilhuber Inc E | Substituted alpha-halogen alkyl tetrazoles and process for obtaining the same |
| US2470085A (en) * | 1947-03-07 | 1949-05-17 | Bilhuber Inc E | Substituted amino alkyl tetrazoles |
| AR207554A1 (es) * | 1972-12-02 | 1976-10-15 | Otsuka Pharma Co Ltd | Procedimiento para producir derivados de 3-alquil-5-((3,4-dihidro-5-carbostiril)oximetil)-oxazolidinona-(2) |
| JPS5310986B2 (en, 2012) * | 1974-02-05 | 1978-04-18 | ||
| JPS5310989B2 (en, 2012) * | 1974-04-25 | 1978-04-18 | ||
| FI59246C (fi) * | 1974-06-24 | 1981-07-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av benscykloamidderivat anvaendbara vid trombos- och emboliterapin |
| 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 |
| US4129565A (en) * | 1975-07-11 | 1978-12-12 | Nisshin Flour Milling Co., Ltd. | Isocarbostyril derivatives |
| US4210753A (en) * | 1976-03-17 | 1980-07-01 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds |
| JPS52116482A (en) * | 1976-03-24 | 1977-09-29 | Otsuka Pharmaceut Co Ltd | Carbostyril derivatives and its preparation |
| JPS5430183A (en) * | 1977-08-10 | 1979-03-06 | Otsuka Pharmaceut Co Ltd | 3,4-dihydrocarbostyril derivative |
-
1978
- 1978-09-01 JP JP10786978A patent/JPS5535019A/ja active Granted
-
1979
- 1979-08-22 CA CA000334272A patent/CA1139761A/en not_active Expired
- 1979-08-28 DE DE19792934747 patent/DE2934747A1/de active Granted
- 1979-08-29 US US06/070,710 patent/US4277479A/en not_active Expired - Lifetime
- 1979-08-29 AU AU50397/79A patent/AU538410B2/en not_active Expired
- 1979-08-29 AR AR277883A patent/AR229342A1/es active
- 1979-08-29 PH PH22976A patent/PH18452A/en unknown
- 1979-08-30 NL NLAANVRAGE7906523,A patent/NL183888C/xx not_active IP Right Cessation
- 1979-08-30 DK DK363179A patent/DK158788C/da active
- 1979-08-30 FI FI792699A patent/FI68398C/fi not_active IP Right Cessation
- 1979-08-30 SU SU792804457A patent/SU1064868A3/ru active
- 1979-08-31 SE SE7907236A patent/SE432252B/sv not_active IP Right Cessation
- 1979-08-31 CH CH792079A patent/CH641799A5/de not_active IP Right Cessation
- 1979-08-31 IT IT68748/79A patent/IT1119929B/it active
- 1979-08-31 FR FR7921869A patent/FR2434809A1/fr active Granted
- 1979-08-31 ZA ZA00794627A patent/ZA794627B/xx unknown
- 1979-08-31 NO NO792829A patent/NO153177C/no unknown
- 1979-08-31 MX MX798357U patent/MX6749E/es unknown
- 1979-08-31 BE BE0/196976A patent/BE878548A/xx not_active IP Right Cessation
- 1979-08-31 ES ES483792A patent/ES483792A1/es not_active Expired
- 1979-08-31 PT PT70136A patent/PT70136A/pt unknown
- 1979-09-03 AT AT0584579A patent/AT364363B/de not_active IP Right Cessation
- 1979-09-03 GB GB7930520A patent/GB2033893B/en not_active Expired
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