CS207799B2 - Method of making the derivatives of the 1,2-dihydrochinoline-2-on - Google Patents
Method of making the derivatives of the 1,2-dihydrochinoline-2-on Download PDFInfo
- Publication number
- CS207799B2 CS207799B2 CS798953A CS895379A CS207799B2 CS 207799 B2 CS207799 B2 CS 207799B2 CS 798953 A CS798953 A CS 798953A CS 895379 A CS895379 A CS 895379A CS 207799 B2 CS207799 B2 CS 207799B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- piperazin
- oxo
- dihydroquinoline
- propoxy
- methyl
- Prior art date
Links
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000004885 piperazines Chemical class 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- -1 4-substituted-piperazin-1-yl Chemical group 0.000 abstract description 5
- 230000003266 anti-allergic effect Effects 0.000 abstract description 3
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 12
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
- 206010002198 Anaphylactic reaction Diseases 0.000 description 9
- 208000003455 anaphylaxis Diseases 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000036783 anaphylactic response Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RCKMWOKWVGPNJF-UHFFFAOYSA-N diethylcarbamazine Chemical compound CCN(CC)C(=O)N1CCN(C)CC1 RCKMWOKWVGPNJF-UHFFFAOYSA-N 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 108010058846 Ovalbumin Proteins 0.000 description 4
- 229960003974 diethylcarbamazine Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 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
- 239000000796 flavoring agent Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- MKHVEEJFCLICLI-UHFFFAOYSA-N 6-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]-1,4-dimethylquinolin-2-one Chemical compound C1=C2C(C)=CC(=O)N(C)C2=CC=C1OCCCN(CC1)CCN1CC1=CC=C(Cl)C=C1 MKHVEEJFCLICLI-UHFFFAOYSA-N 0.000 description 2
- ZPDRWQZDLBFSSQ-UHFFFAOYSA-N 6-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]-1h-quinolin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1CCN(CCCOC=2C=C3C=CC(=O)NC3=CC=2)CC1 ZPDRWQZDLBFSSQ-UHFFFAOYSA-N 0.000 description 2
- HAAQRKWTDMETIA-UHFFFAOYSA-N 7-[3-(4-benzylpiperazin-1-yl)propoxy]-4-methyl-1h-quinolin-2-one Chemical compound C=1C=C2C(C)=CC(=O)NC2=CC=1OCCCN(CC1)CCN1CC1=CC=CC=C1 HAAQRKWTDMETIA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 206010030113 Oedema Diseases 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- RIXNISPGHIFOBF-UHFFFAOYSA-N 4-methyl-6-[3-[4-[(2-propoxyphenyl)methyl]piperazin-1-yl]propoxy]-1h-quinolin-2-one Chemical compound CCCOC1=CC=CC=C1CN1CCN(CCCOC=2C=C3C(C)=CC(=O)NC3=CC=2)CC1 RIXNISPGHIFOBF-UHFFFAOYSA-N 0.000 description 1
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PAACCGXVHPOSKG-UHFFFAOYSA-N 6-[2-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]ethoxy]-4-methyl-1H-quinolin-2-one Chemical compound C1=C2C(C)=CC(=O)NC2=CC=C1OCCN(CC1)CCN1CC1=CC=C(Cl)C=C1 PAACCGXVHPOSKG-UHFFFAOYSA-N 0.000 description 1
- QAJIPUFOYYZWON-UHFFFAOYSA-N 6-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]-4-methyl-1h-quinolin-2-one Chemical compound C1=C2C(C)=CC(=O)NC2=CC=C1OCCCN(CC1)CCN1CC1=CC=C(Cl)C=C1 QAJIPUFOYYZWON-UHFFFAOYSA-N 0.000 description 1
- VZHFISFBRKTVHA-UHFFFAOYSA-N 7-[3-(4-benzhydrylpiperazin-1-yl)propoxy]-4-methyl-1h-quinolin-2-one Chemical compound C=1C=C2C(C)=CC(=O)NC2=CC=1OCCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 VZHFISFBRKTVHA-UHFFFAOYSA-N 0.000 description 1
- LCCTZXMYVQICSZ-UHFFFAOYSA-N 7-[3-[4-[(2-methoxyphenyl)methyl]piperazin-1-yl]propoxy]-4-methyl-1h-quinolin-2-one Chemical compound COC1=CC=CC=C1CN1CCN(CCCOC=2C=C3NC(=O)C=C(C)C3=CC=2)CC1 LCCTZXMYVQICSZ-UHFFFAOYSA-N 0.000 description 1
- UUIBZEVSXTXQFL-UHFFFAOYSA-N 7-[3-[4-[(3-methoxyphenyl)methyl]piperazin-1-yl]propoxy]-4-methyl-1h-quinolin-2-one Chemical compound COC1=CC=CC(CN2CCN(CCCOC=3C=C4NC(=O)C=C(C)C4=CC=3)CC2)=C1 UUIBZEVSXTXQFL-UHFFFAOYSA-N 0.000 description 1
- SIAJZNTXEPLBER-UHFFFAOYSA-N 7-[3-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]propoxy]-4-methyl-1h-quinolin-2-one Chemical compound C1=CC(OC)=CC=C1CN1CCN(CCCOC=2C=C3NC(=O)C=C(C)C3=CC=2)CC1 SIAJZNTXEPLBER-UHFFFAOYSA-N 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (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)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782827566 DE2827566A1 (de) | 1978-06-23 | 1978-06-23 | 1,2-dihydro-chinolin-2-on-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207799B2 true CS207799B2 (en) | 1981-08-31 |
Family
ID=6042551
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS798953A CS207799B2 (en) | 1978-06-23 | 1979-06-21 | Method of making the derivatives of the 1,2-dihydrochinoline-2-on |
| CS794286A CS207798B2 (en) | 1978-06-23 | 1979-06-21 | Method of making the derivatives of the 1,2-dihydrochinoline-2-on |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS794286A CS207798B2 (en) | 1978-06-23 | 1979-06-21 | Method of making the derivatives of the 1,2-dihydrochinoline-2-on |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4234585A (en]) |
| EP (1) | EP0006506B1 (en]) |
| JP (1) | JPS552693A (en]) |
| AT (1) | ATE224T1 (en]) |
| CA (1) | CA1122218A (en]) |
| CS (2) | CS207799B2 (en]) |
| DE (2) | DE2827566A1 (en]) |
| ES (1) | ES481729A1 (en]) |
| HU (1) | HU177959B (en]) |
| IL (1) | IL57577A (en]) |
| PL (1) | PL115260B1 (en]) |
| SU (1) | SU831077A3 (en]) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54130587A (en) | 1978-03-30 | 1979-10-09 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivative |
| JPS55162774A (en) * | 1979-06-06 | 1980-12-18 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| 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 |
| PH17194A (en) * | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| DE3033112A1 (de) * | 1980-09-03 | 1982-04-01 | Hochtemperatur-Reaktorbau GmbH, 5000 Köln | Atomkernreaktor |
| JPS57130210A (en) * | 1981-02-06 | 1982-08-12 | Kinseishiya Kk | Power switch noise remover for audio appliance |
| US4442111A (en) * | 1981-07-25 | 1984-04-10 | Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung | Antithrombotic sulfimino and sulfoximino indolinones-2 |
| 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 |
| DE3434271A1 (de) * | 1984-09-19 | 1986-03-20 | Beiersdorf Ag, 2000 Hamburg | Substituierte 3,4-dihydro-chinolin-2(1h)-one verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| DE3442570A1 (de) * | 1984-11-22 | 1986-05-22 | Hoechst Ag, 6230 Frankfurt | Neue substituierte phenylpiperazinderivate, verfahren zu deren herstellung und die verwendung substituierter phenylpiperazinderivate als aggressionshemmer fuer tiere |
| GB8502267D0 (en) * | 1985-01-30 | 1985-02-27 | Pfizer Ltd | Quinolone inotropic agents |
| JPS63119467A (ja) * | 1987-10-21 | 1988-05-24 | Otsuka Pharmaceut Co Ltd | カルボスチリル誘導体 |
| US5006528A (en) * | 1988-10-31 | 1991-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| JP2608788B2 (ja) * | 1988-10-31 | 1997-05-14 | 大塚製薬 株式会社 | 精神分裂病治療剤 |
| US5457099A (en) * | 1992-07-02 | 1995-10-10 | Sawai Pharmaceutical Co., Ltd. | Carbostyril derivatives and antiallergic agent |
| DE4410822A1 (de) * | 1994-03-24 | 1995-09-28 | Schering Ag | Neue Piperidin-Derivate |
| CA2180190A1 (en) * | 1995-07-10 | 1997-01-11 | Kazumi Ogata | Benzylpiperazine derivatives |
| GB0203778D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| CN100497325C (zh) * | 2004-04-21 | 2009-06-10 | 齐鲁制药有限公司 | 哌嗪衍生物及其在制备喹啉酮衍生物中的用途 |
| TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
| CN101538252B (zh) * | 2008-03-20 | 2011-04-20 | 成都康弘药业集团股份有限公司 | 阿立哌唑的制备方法及其中间体 |
| NZ603076A (en) | 2010-08-24 | 2014-12-24 | Otsuka Pharma Co Ltd | Suspension and cake composition containing carbostyril derivative and silicone oil and/or silicone oil derivative |
| CA2872883A1 (en) * | 2012-05-09 | 2013-11-14 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| CN109180577B (zh) * | 2018-10-15 | 2021-11-16 | 迪嘉药业集团有限公司 | 一种阿立哌唑的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH523899A (de) * | 1968-07-05 | 1972-06-15 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydro-chinolins |
| JPS517672B2 (en]) * | 1972-04-13 | 1976-03-10 | ||
| DE2337461A1 (de) * | 1973-07-24 | 1975-02-06 | Boehringer Mannheim Gmbh | Neue indolderivate und verfahren zu deren herstellung |
| GB1501149A (en) * | 1975-07-11 | 1978-02-15 | Nisshin Flour Milling Co | Isocarbostyril derivatives |
| JPS54130587A (en) * | 1978-03-30 | 1979-10-09 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivative |
| JPS55124766A (en) * | 1979-03-20 | 1980-09-26 | Otsuka Pharmaceut Co Ltd | Antihistaminic |
-
1978
- 1978-06-23 DE DE19782827566 patent/DE2827566A1/de not_active Withdrawn
-
1979
- 1979-06-04 US US06/045,472 patent/US4234585A/en not_active Expired - Lifetime
- 1979-06-08 DE DE7979101827T patent/DE2960820D1/de not_active Expired
- 1979-06-08 AT AT79101827T patent/ATE224T1/de not_active IP Right Cessation
- 1979-06-08 EP EP79101827A patent/EP0006506B1/de not_active Expired
- 1979-06-13 CA CA000329712A patent/CA1122218A/en not_active Expired
- 1979-06-17 IL IL57577A patent/IL57577A/xx unknown
- 1979-06-18 PL PL1979216409A patent/PL115260B1/pl unknown
- 1979-06-20 ES ES481729A patent/ES481729A1/es not_active Expired
- 1979-06-21 CS CS798953A patent/CS207799B2/cs unknown
- 1979-06-21 CS CS794286A patent/CS207798B2/cs unknown
- 1979-06-22 SU SU792782353A patent/SU831077A3/ru active
- 1979-06-22 JP JP7823079A patent/JPS552693A/ja active Granted
- 1979-06-22 HU HU79BO1793A patent/HU177959B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SU831077A3 (ru) | 1981-05-15 |
| CS207798B2 (en) | 1981-08-31 |
| IL57577A (en) | 1982-03-31 |
| PL115260B1 (en) | 1981-03-31 |
| JPS6331465B2 (en]) | 1988-06-23 |
| HU177959B (en) | 1982-02-28 |
| EP0006506A1 (de) | 1980-01-09 |
| JPS552693A (en) | 1980-01-10 |
| DE2960820D1 (en) | 1981-12-03 |
| IL57577A0 (en) | 1979-10-31 |
| EP0006506B1 (de) | 1981-09-16 |
| CA1122218A (en) | 1982-04-20 |
| US4234585A (en) | 1980-11-18 |
| ATE224T1 (de) | 1981-10-15 |
| PL216409A1 (en]) | 1980-03-24 |
| DE2827566A1 (de) | 1980-01-10 |
| ES481729A1 (es) | 1980-03-01 |
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