GB1121411A - Carbostyril derivatives and their preparation - Google Patents

Carbostyril derivatives and their preparation

Info

Publication number
GB1121411A
GB1121411A GB395567A GB395567A GB1121411A GB 1121411 A GB1121411 A GB 1121411A GB 395567 A GB395567 A GB 395567A GB 395567 A GB395567 A GB 395567A GB 1121411 A GB1121411 A GB 1121411A
Authority
GB
United Kingdom
Prior art keywords
group
alkyl
amino
substituted
carbostyrils
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
Application number
GB395567A
Inventor
Ulrich Horlein
Karl Meng
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB1121411A publication Critical patent/GB1121411A/en
Expired legal-status Critical Current

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Novel carbostyril derivatives useful for reinforcing or potentiating diurectics and of the general formula <FORM:1121411/C2/1> wherein R1 represents from 1 to 4 monovalent substituent atoms or groups which may be the same or different and which may be a halogen atom or atoms, an alkyl group or groups having up to 4 carbons, or a nitro, amino, acylamino, nitrile, alkoxy, hydroxy, acyloxy, acyl or alkylmercapto group or groups; R2 is a ring substituted or unsubstituted cycloalkyl, aralkyl or aryl group, or an unsubstituted or amino - substituted alkyl, alkoxyalkyl or alkylmercapto-alkyl group; R3 is a carboxyalkyl, carbalkoxyalkyl, cyanoalkyl or cyano group; R4 is hydrogen or an alkyl or acyl group, are prepared (a) by the condensation of an acid derivative of the formula X.COCH2R3 (X is halogen, alkoxy or hydroxyl) and the appropriate R1 substituted anthranilic acid alkyl or phenyl ester (one of the hydrogen atoms of the amino group being replaced by the R2 group) with subsequent cyclization of the amide intermediate, (b) by interaction of the appropriate aniline derivative and a substituted malonic acid, R3.CH(CO2H)2 in the presence of phosphorus oxychloride, (c) by the interaction of a 3-halo - 4 - oxo - carbostyril compound and a metal cyanide, and (d) by the conversion of amino-carbostyrils (R1 is -NH2 in formula above) of the invention to the corresponding halo- or cyano-carbostyrils using a Sandmeyer reaction. The products of (a), (b) and (c) may be optionally alkylated or acylated to yield carbostyrils wherein R4 is an alkyl or acyl group, or dealkylated. 2 - Methylamino - chlorobenzoic acid methyl ester is prepared by the esterification of the free acid.
GB395567A 1966-01-26 1967-01-26 Carbostyril derivatives and their preparation Expired GB1121411A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0048267 1966-01-26

Publications (1)

Publication Number Publication Date
GB1121411A true GB1121411A (en) 1968-07-24

Family

ID=7102138

Family Applications (1)

Application Number Title Priority Date Filing Date
GB395567A Expired GB1121411A (en) 1966-01-26 1967-01-26 Carbostyril derivatives and their preparation

Country Status (6)

Country Link
AT (1) AT267538B (en)
CH (1) CH471784A (en)
ES (1) ES336046A1 (en)
FR (2) FR1509468A (en)
GB (1) GB1121411A (en)
SE (1) SE318877B (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4128649A (en) 1977-06-29 1978-12-05 Sandoz, Inc. 4-Hydroxy-pyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acids and esters
US4187309A (en) 1977-06-20 1980-02-05 Sandoz, Inc. 4-Hydroxy-2-quinolinone-3-carboxylic acids and salts thereof
US4192876A (en) * 1975-07-23 1980-03-11 Sandoz, Inc. 4-Hydroxy-3-nitro-quinoline-2(1H)-ones
US4221797A (en) 1978-08-14 1980-09-09 Sandoz, Inc. Dihydroquinoline-one derivatives
US4232027A (en) * 1979-01-29 1980-11-04 E. R. Squibb & Sons, Inc. 1,2-Dihydro-2-oxo-4-phenyl-3-quinolinecarbonitrile derivatives
US4273930A (en) * 1977-06-20 1981-06-16 Sandoz, Inc. 4-Hydroxy-2-quinolinone-3-carboxylic acid esters
US4281131A (en) 1977-06-20 1981-07-28 Sandoz, Inc. 4-Hydroxy-2-quinolinone-3-carboxylic acids and salts thereof
US4738971A (en) * 1981-03-03 1988-04-19 Aktiebolaset Leo N-aryl-1,2-dihydro-4-substituted-1-alkyl-2-oxo-quinoline-3-carboxamides
EP0382185A2 (en) * 1989-02-10 1990-08-16 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivatives
US5244898A (en) * 1991-04-19 1993-09-14 Otsuka Pharmaceutical Co., Ltd. Benzoheterocyclic compounds
US5436254A (en) * 1989-02-10 1995-07-25 Otsuka Pharmaceutical Company, Ltd. Carbostyril derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1770480B2 (en) * 1968-05-22 1977-09-29 Basf Ag, 6700 Ludwigshafen PROCESS FOR THE PRODUCTION OF 2,4-DIHYDROXYCHINOLIN
DE2651581A1 (en) * 1976-11-12 1978-05-18 Merck Patent Gmbh CHINOLONE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4192876A (en) * 1975-07-23 1980-03-11 Sandoz, Inc. 4-Hydroxy-3-nitro-quinoline-2(1H)-ones
US4187309A (en) 1977-06-20 1980-02-05 Sandoz, Inc. 4-Hydroxy-2-quinolinone-3-carboxylic acids and salts thereof
US4273930A (en) * 1977-06-20 1981-06-16 Sandoz, Inc. 4-Hydroxy-2-quinolinone-3-carboxylic acid esters
US4281131A (en) 1977-06-20 1981-07-28 Sandoz, Inc. 4-Hydroxy-2-quinolinone-3-carboxylic acids and salts thereof
US4128649A (en) 1977-06-29 1978-12-05 Sandoz, Inc. 4-Hydroxy-pyrido[2,3-b]pyridine-2(1H)-one-3-carboxylic acids and esters
US4221797A (en) 1978-08-14 1980-09-09 Sandoz, Inc. Dihydroquinoline-one derivatives
US4232027A (en) * 1979-01-29 1980-11-04 E. R. Squibb & Sons, Inc. 1,2-Dihydro-2-oxo-4-phenyl-3-quinolinecarbonitrile derivatives
US4738971A (en) * 1981-03-03 1988-04-19 Aktiebolaset Leo N-aryl-1,2-dihydro-4-substituted-1-alkyl-2-oxo-quinoline-3-carboxamides
EP0382185A2 (en) * 1989-02-10 1990-08-16 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivatives
EP0382185A3 (en) * 1989-02-10 1991-09-18 Otsuka Pharmaceutical Co., Ltd. Carbostyril derivatives
US5436254A (en) * 1989-02-10 1995-07-25 Otsuka Pharmaceutical Company, Ltd. Carbostyril derivatives
US5244898A (en) * 1991-04-19 1993-09-14 Otsuka Pharmaceutical Co., Ltd. Benzoheterocyclic compounds

Also Published As

Publication number Publication date
FR1509468A (en) 1968-01-12
CH471784A (en) 1969-04-30
ES336046A1 (en) 1967-12-16
SE318877B (en) 1969-12-22
AT267538B (en) 1969-01-10
FR6213M (en) 1968-07-29

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