DE2302027C2 - In 5- oder 8-Stellung substituierte 3,4-Dihydrocarbostyril-Derivate und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel - Google Patents
In 5- oder 8-Stellung substituierte 3,4-Dihydrocarbostyril-Derivate und ihre Salze, Verfahren zu ihrer Herstellung und ArzneimittelInfo
- Publication number
- DE2302027C2 DE2302027C2 DE2302027A DE2302027A DE2302027C2 DE 2302027 C2 DE2302027 C2 DE 2302027C2 DE 2302027 A DE2302027 A DE 2302027A DE 2302027 A DE2302027 A DE 2302027A DE 2302027 C2 DE2302027 C2 DE 2302027C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- dihydrocarbostyril
- propoxy
- hydroxy
- compounds
- 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
- 238000002360 preparation method Methods 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 title claims description 8
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical group C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 20
- -1 alkyl radical Chemical class 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 229960001317 isoprenaline Drugs 0.000 claims description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 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 description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229960003712 propranolol Drugs 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
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- 150000003254 radicals Chemical class 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-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
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 claims 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 claims 1
- 239000000219 Sympatholytic Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
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- 239000000969 carrier Substances 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 229960002275 pentobarbital sodium Drugs 0.000 claims 1
- 239000003087 receptor blocking agent Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 20
- 239000013078 crystal Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- FVXYRXMYPXVHNY-UHFFFAOYSA-N 3-propoxy-3,4-dihydro-1H-quinolin-2-one Chemical compound C(CC)OC1C(NC2=CC=CC=C2C1)=O FVXYRXMYPXVHNY-UHFFFAOYSA-N 0.000 description 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000008282 halocarbons Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- HBNKDRKDIGEFQB-UHFFFAOYSA-N 3-propoxy-3,4-dihydro-1H-quinolin-2-one hydrochloride Chemical compound Cl.CCCOC1Cc2ccccc2NC1=O HBNKDRKDIGEFQB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 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
- 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
- 239000000376 reactant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47037181A JPS517672B2 (en, 2012) | 1972-04-13 | 1972-04-13 | |
| JP47037182A JPS48103590A (en, 2012) | 1972-04-13 | 1972-04-13 | |
| JP47092558A JPS5241268B2 (en, 2012) | 1972-09-14 | 1972-09-14 | |
| JP9255772A JPS5324431B2 (en, 2012) | 1972-09-14 | 1972-09-14 | |
| JP47092560A JPS5246231B2 (en, 2012) | 1972-09-14 | 1972-09-14 | |
| JP47120953A JPS5229745B2 (en, 2012) | 1972-04-13 | 1972-12-02 | |
| JP47125858A JPS5239036B2 (en, 2012) | 1972-04-13 | 1972-12-14 | |
| JP47128972A JPS5241269B2 (en, 2012) | 1972-04-13 | 1972-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2302027A1 DE2302027A1 (de) | 1973-12-06 |
| DE2302027C2 true DE2302027C2 (de) | 1983-03-17 |
Family
ID=27572212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2302027A Expired DE2302027C2 (de) | 1972-04-13 | 1973-01-16 | In 5- oder 8-Stellung substituierte 3,4-Dihydrocarbostyril-Derivate und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel |
Country Status (17)
| Country | Link |
|---|---|
| JP (5) | JPS48103590A (en, 2012) |
| AR (1) | AR209575A1 (en, 2012) |
| AU (1) | AU475964B2 (en, 2012) |
| BE (1) | BE794669A (en, 2012) |
| CA (1) | CA1025447A (en, 2012) |
| CH (1) | CH575929A5 (en, 2012) |
| DD (2) | DD112446A5 (en, 2012) |
| DE (1) | DE2302027C2 (en, 2012) |
| DK (1) | DK141603B (en, 2012) |
| FI (1) | FI53703C (en, 2012) |
| FR (1) | FR2179715B1 (en, 2012) |
| GB (2) | GB1424571A (en, 2012) |
| HK (1) | HK19481A (en, 2012) |
| NL (1) | NL158176B (en, 2012) |
| NO (1) | NO140589C (en, 2012) |
| SE (1) | SE380018B (en, 2012) |
| YU (1) | YU41187B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5082218A (en, 2012) * | 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 |
| CH619453A5 (en, 2012) * | 1976-03-17 | 1980-09-30 | Otsuka Pharma Co Ltd | |
| 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, 2012) * | 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
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |