GB1150397A - New Indole-4-Acetic Acid Compounds and Methods for Their Production - Google Patents

New Indole-4-Acetic Acid Compounds and Methods for Their Production

Info

Publication number
GB1150397A
GB1150397A GB784368A GB784368A GB1150397A GB 1150397 A GB1150397 A GB 1150397A GB 784368 A GB784368 A GB 784368A GB 784368 A GB784368 A GB 784368A GB 1150397 A GB1150397 A GB 1150397A
Authority
GB
United Kingdom
Prior art keywords
formula
acetic acid
acid
phenyl
compound
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
GB784368A
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB1150397A publication Critical patent/GB1150397A/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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

1,150,397. lndole-4-acetic acid compounds. PARKE DAVIS & CO. 16 Feb., 1968 [23 Feb., 1967], No. 7843/68. Heading C2C. Novel 1-substituted.indole-4-acetic acid compounds of the general formula and pharmaceutically-acceptable salts thereof; where R 1 is phenyl, mono(halo)phenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, mono (lower alkyl) phenyl, methoxy phenyl, or cyclohexyl; R 2 is hydrogen, lower alkyl or phenyl, R 4 is hydrogen or lower alkyl; each of R 3 , R 5 and R 6 is hydrogen or methyl, with the further proviso that not more than one of R 3 , R 5 and R 6 is methyl; and A is a single bond or a double bond, are prepared by hydrolysing an ester compound having the general formula where R 1 , R 2 , R 3 , R 4 , R 6 , R 6 and A are as defined above and R<SP>1</SP> represents lower alkyl, preferably methyl or ethyl. The hydrolysis is carried out by heating a solution or suspension of the starting material in a solvent containing an acid or a base at a temperature between 0‹ and 120‹ C., or at the reflux temperature of the solvent, for 1-60 hours. The ester starting materials in the foregoing process may be prepared by reacting 4,5,6,7- tetrahydro - 4 - oxo - 3 - benzofurancarboxylic acid, 4,5,6,7 - tetrahydro - 3 - methyl - 4 - oxo - 2-benzofurancarboxylic acid, or 4,5,6,7-tetrahydro - 4 - oxo - 6 - methyl - 3 - benzofurancarboxylic acid with an amine having the formula R 1 -NH 2 followed by treatment of the resulting 4,5,6,7 - tetrahydro - 4 - iminoindole compound having the formula with acid to give a 6,7-dihydroindol-4(5H)-one compound having the formula or alternatively, by reaction of a 1,3-cycle hexanedione compound having the formula with an amine having the formula R 1 -NH 2 in acetic acid to give a 6,7-dihydroindol-4(5H)-one compound having the formula The 6,7-dihydroindol-4(5H)-one compounds are reacted with an α-haloacetic acid ester having the formula in the presence of zinc, followed by treatment of the reaction product with a strong acid to produce a 6,7-dihydroindole-4-acetic acid ester compound or a 6,7-dihydroindole-#<SP>4(5H)α</SP>-acetic acid ester compound or a mixture of both that can be represented by the formula which ester or mixture of esters is heated at an elevated temperature in a high-boiling point unreactive solvent in the presence of a dehydrogenating agent such as palladium on carbon, chloranil or sulphur, to produce an indole-4- acetic acid ester compound having the formula In the foregoing formulµ R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R<SP>1</SP> have the same meaning as above, R 7 is lower alkyl or phenyl and X represents chlorine, bromine or iodine. Pharmacological compositions containing the above free acid or salt forms possess antiinflammatory activity, and are administered orally or parenterally.
GB784368A 1967-02-23 1968-02-16 New Indole-4-Acetic Acid Compounds and Methods for Their Production Expired GB1150397A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US61786467A 1967-02-23 1967-02-23

Publications (1)

Publication Number Publication Date
GB1150397A true GB1150397A (en) 1969-04-30

Family

ID=24475362

Family Applications (1)

Application Number Title Priority Date Filing Date
GB784368A Expired GB1150397A (en) 1967-02-23 1968-02-16 New Indole-4-Acetic Acid Compounds and Methods for Their Production

Country Status (1)

Country Link
GB (1) GB1150397A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5599774A (en) * 1992-01-22 1997-02-04 Imperial Chemical Industries Plc N-arylindoles and their use as herbicides
WO1999062899A1 (en) * 1998-06-04 1999-12-09 Merck Sharp & Dohme Limited Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition
WO2002070477A1 (en) * 2001-03-01 2002-09-12 Ono Pharmaceutical Co., Ltd. 2-methylindole-4-acetic acid, process for producing the same, and process for producing intermediate therefor

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5599774A (en) * 1992-01-22 1997-02-04 Imperial Chemical Industries Plc N-arylindoles and their use as herbicides
US5739353A (en) * 1992-01-22 1998-04-14 Zeneca Limited N-arylindoles and their use as herbicides
WO1999062899A1 (en) * 1998-06-04 1999-12-09 Merck Sharp & Dohme Limited Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition
US6395766B1 (en) 1998-06-04 2002-05-28 Merck Sharp & Dohme Limited Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition
WO2002070477A1 (en) * 2001-03-01 2002-09-12 Ono Pharmaceutical Co., Ltd. 2-methylindole-4-acetic acid, process for producing the same, and process for producing intermediate therefor

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Legal Events

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