GB1158532A - 2-Oxoindoline-3-Carboxylic Acids and Esters thereof - Google Patents

2-Oxoindoline-3-Carboxylic Acids and Esters thereof

Info

Publication number
GB1158532A
GB1158532A GB8168A GB8168A GB1158532A GB 1158532 A GB1158532 A GB 1158532A GB 8168 A GB8168 A GB 8168A GB 8168 A GB8168 A GB 8168A GB 1158532 A GB1158532 A GB 1158532A
Authority
GB
United Kingdom
Prior art keywords
diethyl
malonate
prepared
group
alkyl
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
GB8168A
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.)
Centre National de la Recherche Scientifique CNRS
Original Assignee
Centre National de la Recherche Scientifique CNRS
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
Priority claimed from FR90089A external-priority patent/FR1536200A/en
Priority claimed from FR133763A external-priority patent/FR93638E/en
Application filed by Centre National de la Recherche Scientifique CNRS filed Critical Centre National de la Recherche Scientifique CNRS
Publication of GB1158532A publication Critical patent/GB1158532A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,158,532. 2 - oxo - indoline 3 - carboxylic acids. CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE. 1 Jan., 1968 [5 Jan., 1967 (2); 26 Dec., 1967 (2)], No. 81/68. Heading C2C. Novel compounds of the general formula in which each of R and R<SP>1</SP> is a hydrogen atom or an unsubstituted or substituted alkyl alkenyl, alkynyl or aralkyl group, R<SP>2</SP> represents OH or is selected from the same class as R and R<SP>1</SP> and each of X and Y is a hydrogen or halogen atom or an alkyl or alkoxy group having from 1 to 5 carbon atoms, or an aralkoxy, trifluoromethyl, hydroxy, amine or sulphonamide group, are prepared by reducing a 2-(2-nitrophenylmalonic compound of the formula wherein R and R<SP>1</SP> are defined as above and each of X<SP>1</SP> and Y<SP>1</SP> is selected from the same group as X and Y or is NO 2 , this becoming an NH 2 group in the reduction process, preferably by means of hydrogen in the presence of an hydrogenation catalyst or by a reducing compound in a neutral, acid or alkaline medium, or where it is desired that R<SP>2</SP> be an alkyl, aralkyl, alkenyl or alkynyl subjecting the product to alkylation, aralkylation, alkenylation or alkynylation. Preferred substituents on the alkyl or aralkyl groups represented by R, R<SP>1</SP> or R<SP>2</SP> include halogen atoms, free, etherified and esterified hydroxy groups, carboxy and carboxyester groups, amide, nitrile, nitro and amine groups which may be substituted or quaternized. The compounds may be obtained in the form of acid addition salts. They possess therapeutic properties. Diethyl - 2 - methyl (or ethyl) - 2 - (2 - nitro - 4- trifluoromethyl-phenyl)-malonate is prepared by reacting the diethyl ester of methyl (or ethyl)- malonic acid with 2-nitro-4-trifluoromethylchlorobenzene. Diethyl 2 - (6- (or 5-)methoxy - 2 - nitrophenyl)- malonate is prepared by reacting diethyl malonate with 6- (or 5-)methoxy-2-nitrochlorobenzene. Diethyl 2 - (4 - N,N - dimethylsulohonamide- 2-nitrophenyl)-malonate is prepared by reacting diethyl malonate with 4-N,N-dimethylsulphonamido-2-nitrochlorobenzene. Diethyl (or dimethyl)-2-nitrophenylmalonate are prepared from 2-nitrochlorobenzene and diethyl (or dimethyl) malonate. Diethyl 2 - (4 - methyl - 2 - nitrophenyl)- malonate, diethyl 2-(2,6-dinitrophenyl)-malonate and diethyl 2-(2,4-dinitrophenyl)-malonate are prepared from diethyl malonate and the correspondingly substituted chloronitrobenzene.
GB8168A 1967-01-05 1968-01-01 2-Oxoindoline-3-Carboxylic Acids and Esters thereof Expired GB1158532A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR90090 1967-01-05
FR90089A FR1536200A (en) 1967-01-05 1967-01-05 Carboxylic derivatives of indolinone-2 and their preparation
FR133763A FR93638E (en) 1967-01-05 1967-12-26 Carboxylic derivatives of indolinone-2 and their preparation.
FR133762 1967-12-26

Publications (1)

Publication Number Publication Date
GB1158532A true GB1158532A (en) 1969-07-16

Family

ID=27444753

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8168A Expired GB1158532A (en) 1967-01-05 1968-01-01 2-Oxoindoline-3-Carboxylic Acids and Esters thereof

Country Status (3)

Country Link
CH (1) CH495981A (en)
DE (1) DE1670496A1 (en)
GB (1) GB1158532A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089875A (en) * 1976-08-02 1978-05-16 Hoffmann-La Roche Inc. Process and intermediates for isoindole derivatives
EP0161632A2 (en) * 1984-05-12 1985-11-21 Roche Diagnostics GmbH Pyrrolo-benzimidazoles, process for their preparation, medicaments containing them and intermediates
US4556672A (en) * 1984-03-19 1985-12-03 Pfizer Inc. 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents
US4569942A (en) * 1984-05-04 1986-02-11 Pfizer Inc. N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents
US4658037A (en) * 1984-02-07 1987-04-14 Pfizer Inc. Intermediates for 1,3-disubstituted 2-oxindoles as analgesic and antiinflammatory agents
US4690943A (en) * 1984-09-19 1987-09-01 Pfizer Inc. Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US4694017A (en) * 1983-05-19 1987-09-15 Otsuka Pharmaceutical Co., Ltd. 2-amido 3(oxindol-3-yl)propionic acids having antiulcer activity
US4721712A (en) * 1984-06-12 1988-01-26 Pfizer Inc. 1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
US4752609A (en) * 1985-06-20 1988-06-21 Pfizer Inc. Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US4808601A (en) * 1984-09-19 1989-02-28 Pfizer Inc. Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US5310935A (en) * 1992-06-30 1994-05-10 Pharmagroup International Optically active 5-oxygenated (3S)-1,3-dimethyloxindole-3-acetic acids
WO1996023770A1 (en) * 1995-01-30 1996-08-08 Catalytica, Inc. Process for preparing 2-oxindoles and n-hydroxy-2-oxindoles

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089875A (en) * 1976-08-02 1978-05-16 Hoffmann-La Roche Inc. Process and intermediates for isoindole derivatives
US4694017A (en) * 1983-05-19 1987-09-15 Otsuka Pharmaceutical Co., Ltd. 2-amido 3(oxindol-3-yl)propionic acids having antiulcer activity
US4658037A (en) * 1984-02-07 1987-04-14 Pfizer Inc. Intermediates for 1,3-disubstituted 2-oxindoles as analgesic and antiinflammatory agents
US4556672A (en) * 1984-03-19 1985-12-03 Pfizer Inc. 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents
US4569942A (en) * 1984-05-04 1986-02-11 Pfizer Inc. N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents
EP0161632A2 (en) * 1984-05-12 1985-11-21 Roche Diagnostics GmbH Pyrrolo-benzimidazoles, process for their preparation, medicaments containing them and intermediates
EP0161632A3 (en) * 1984-05-12 1986-06-11 Boehringer Mannheim Gmbh Pyrrolo-benzimidazoles, process for their preparation, medicaments containing them and intermediates
US4963686A (en) * 1984-05-12 1990-10-16 Boehringer Mannheim Gmbh Certain pyridinoylamino-indolin-2-one derivatives
US4721712A (en) * 1984-06-12 1988-01-26 Pfizer Inc. 1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
US4808601A (en) * 1984-09-19 1989-02-28 Pfizer Inc. Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US4690943A (en) * 1984-09-19 1987-09-01 Pfizer Inc. Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US4752609A (en) * 1985-06-20 1988-06-21 Pfizer Inc. Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US5310935A (en) * 1992-06-30 1994-05-10 Pharmagroup International Optically active 5-oxygenated (3S)-1,3-dimethyloxindole-3-acetic acids
WO1996023770A1 (en) * 1995-01-30 1996-08-08 Catalytica, Inc. Process for preparing 2-oxindoles and n-hydroxy-2-oxindoles
CN1078590C (en) * 1995-01-30 2002-01-30 卡塔鲁逖克公司 Process for preparing 2 -oxindoles and N -hydroxy -2 -oxindoles
US6469181B1 (en) * 1995-01-30 2002-10-22 Catalytica, Inc. Process for preparing 2-oxindoles and N-hydroxy-2-oxindoles

Also Published As

Publication number Publication date
CH495981A (en) 1970-09-15
DE1670496A1 (en) 1972-04-06

Similar Documents

Publication Publication Date Title
GB1158532A (en) 2-Oxoindoline-3-Carboxylic Acids and Esters thereof
GB1147336A (en) Quinoline-3-carboxylic acid derivatives
GB1064531A (en) Substituted 5-carboxyimidazole derivatives and preparation thereof
GB1450250A (en) Process for the manufacture of 2-arylamino-2-imidazoline derivatives and their salts
ES343692A1 (en) N-(1-alkyl-2-pyrrolidylmethyl)-3-alkoxy-(or hydroxy)-indoles-2-carboxamides
GB1221237A (en) Malonitriles and their use as pesticides
YU45810B (en) PROCESS FOR THE PREPARATION OF QUINOLINE CARBOXYLIC ACIDS
GB1201090A (en) New derivatives of 1,4-bis-[benzoxazolyl-(2&#39;)]-naphthalene, processes for their manufacture and their use as optical brighteners
GB1132318A (en) New substituted phenylacetic esters, their production and compositions containing them
GB1221600A (en) Phenylamino-trifluoromethylquinolines and pharmaceutical compositions containing them
Hullar et al. Pyridoxal phosphate. II. Benzene analogs. 2-Formylphenoxyacetic acids as potential antimetabolites of pyridoxal phosphate
GB1325828A (en) Process for the preparation of 3-anilino-pyrazolones-5
KR970010758A (en) Substituted 4H-pyran
GB1201759A (en) Triazolyl-coumarins
GB1342807A (en) Process for the preparation of alphaanilinocarboxylic acids and or derivatives thereof
GB1147832A (en) Fluorene xanthene and thioxanthene derivatives
ES2038260T3 (en) PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF PHENOXIALKYLCARBOXYLIC ACID.
GB1506913A (en) Process for the preparation of 2-phenylamino-2-imidazoline derivatives
US3493602A (en) Process for preparing phenyl alanines
GB1180208A (en) 5-Nitrofuran Derivatives
KR870008849A (en) Pyrazoles having germ killing effect
IE33494L (en) Cycloalkano-quinolones
GB1219848A (en) NOVEL N-SUBSTITUTED-o-PHENYLENE AMINES, AND PROCESSES FOR THEIR PREPARATION
GB1262078A (en) Preparation of phenoxy fumaric acid compounds and chromone-2-carboxylic acid compounds therefrom
GB1129358A (en) 5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine derivatives, and processes for the preparation thereof

Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees