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WO1999043650A3 - Process(es) for the preparation of 6-trifluoromethyl-indoline derivatives - Google Patents

Process(es) for the preparation of 6-trifluoromethyl-indoline derivatives Download PDF

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Publication number
WO1999043650A3
WO1999043650A3 PCT/EP1999/001273 EP9901273W WO9943650A3 WO 1999043650 A3 WO1999043650 A3 WO 1999043650A3 EP 9901273 W EP9901273 W EP 9901273W WO 9943650 A3 WO9943650 A3 WO 9943650A3
Authority
WO
WIPO (PCT)
Prior art keywords
trifluoromethyl
indoline
preparation
benzyl
nitro
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.)
Ceased
Application number
PCT/EP1999/001273
Other languages
French (fr)
Other versions
WO1999043650A2 (en
Inventor
Ian Philip Andrews
Erol Ali Faruk
Matthew Gray
Frank Hossner
John Kitteringham
Sandra Jane Paknoham
Martyn Voyle
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.)
SmithKline Beecham Ltd
Original Assignee
SmithKline Beecham Ltd
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 GBGB9803802.9A external-priority patent/GB9803802D0/en
Priority claimed from GBGB9805196.4A external-priority patent/GB9805196D0/en
Priority claimed from GBGB9805195.6A external-priority patent/GB9805195D0/en
Priority claimed from GBGB9809046.7A external-priority patent/GB9809046D0/en
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Priority to AU30308/99A priority Critical patent/AU3030899A/en
Publication of WO1999043650A2 publication Critical patent/WO1999043650A2/en
Publication of WO1999043650A3 publication Critical patent/WO1999043650A3/en
Anticipated expiration legal-status Critical
Ceased 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

The present invention relates to a process for the preparation of 5-methyl-6-trifluoromethyl-indoline which is a key intermediate in the preparation of compounds having 5-HT2C receptor antagonist activity. The reaction sequence starts from 1-chloro-2-nitro-4-trifluoromethyl-benzene (VII) via cyano-(2-nitro-trifluoromethylphenyl)acetic acid benzyl ester (VI), 6-trifluoromethyl-indole (V), 6-trifluoromethyl-indoline (IV), 1-benzyl-6-trifluoromethyl-indoline (III), 1-benzyl-5-bromo-6-trifluoromethyl-indoline (II) and 1-benzyl-5-methyl-6-trifluoromethyl-indoline (I). In a further aspect the present invention also relates to the compounds of formulae (I), (II), (III), (IV) and (VI).
PCT/EP1999/001273 1998-02-25 1999-02-22 Process(es) for the preparation of 6-trifluoromethyl-indoline derivatives Ceased WO1999043650A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU30308/99A AU3030899A (en) 1998-02-25 1999-02-22 Process(es) for the preparation of 6-trifluoromethyl-indoline derivatives

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GBGB9803802.9A GB9803802D0 (en) 1998-02-25 1998-02-25 Novel compounds
GB9803802.9 1998-02-25
GB9805196.4 1998-03-11
GB9805195.6 1998-03-11
GBGB9805196.4A GB9805196D0 (en) 1998-03-11 1998-03-11 Process
GBGB9805195.6A GB9805195D0 (en) 1998-03-11 1998-03-11 Process
GB9809046.7 1998-04-29
GBGB9809046.7A GB9809046D0 (en) 1998-04-29 1998-04-29 Process

Publications (2)

Publication Number Publication Date
WO1999043650A2 WO1999043650A2 (en) 1999-09-02
WO1999043650A3 true WO1999043650A3 (en) 1999-12-09

Family

ID=27451756

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/001273 Ceased WO1999043650A2 (en) 1998-02-25 1999-02-22 Process(es) for the preparation of 6-trifluoromethyl-indoline derivatives

Country Status (2)

Country Link
AU (1) AU3030899A (en)
WO (1) WO1999043650A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006038113A1 (en) 2006-08-14 2008-02-21 Qiagen Gmbh A method of synthesizing a cDNA in a sample in an enzymatic reaction and simultaneously providing a first enzyme having polyadenylation activity and a second enzyme having reverse transcriptase activity

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996023783A1 (en) * 1995-02-02 1996-08-08 Smithkline Beecham Plc Indole derivatives as 5-ht receptor antagonist
WO1997048700A1 (en) * 1996-06-20 1997-12-24 Smithkline Beecham Plc Indoline derivatives useful as 5-ht-2c receptor antagonists
WO1997048699A1 (en) * 1996-06-20 1997-12-24 Smithkline Beecham Plc Indoline derivatives useful as 5-ht-2c receptor antagonists

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996023783A1 (en) * 1995-02-02 1996-08-08 Smithkline Beecham Plc Indole derivatives as 5-ht receptor antagonist
WO1997048700A1 (en) * 1996-06-20 1997-12-24 Smithkline Beecham Plc Indoline derivatives useful as 5-ht-2c receptor antagonists
WO1997048699A1 (en) * 1996-06-20 1997-12-24 Smithkline Beecham Plc Indoline derivatives useful as 5-ht-2c receptor antagonists

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BROMIDGE S.M. ET AL.: "Novel and selective 5-HT2C/2B receptor antagonists as potential anxiolytic agents: Synthesis, quantitative structure-activity relationships, and molecular modeling of substituted 1-(3-pyridylcarbamoyl)indolines", JOURNAL OF MEDICINAL CHEMISTRY, vol. 41, no. 10, 7 May 1998 (1998-05-07), pages 1598 - 1612, XP002110144 *

Also Published As

Publication number Publication date
WO1999043650A2 (en) 1999-09-02
AU3030899A (en) 1999-09-15

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