GB1421063A - Fused-ring indole derivatives - Google Patents

Fused-ring indole derivatives

Info

Publication number
GB1421063A
GB1421063A GB688373A GB688373A GB1421063A GB 1421063 A GB1421063 A GB 1421063A GB 688373 A GB688373 A GB 688373A GB 688373 A GB688373 A GB 688373A GB 1421063 A GB1421063 A GB 1421063A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compounds
formula
amides
acids
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
GB688373A
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.)
Wyeth Canada Inc
Original Assignee
Ayerst Mckenna and Harrison Inc
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 US00226287A external-priority patent/US3833575A/en
Priority claimed from US297130A external-priority patent/US3904617A/en
Application filed by Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc
Publication of GB1421063A publication Critical patent/GB1421063A/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)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1421063 Oxazino- and thiazino[4,3-a]-indoles AYERST McKENNA & HARRISON Ltd 13 Feb 1973 [14 Feb 1972 12 Oct 1972] 6883/73 Heading C2C The invention comprises compounds of formula wherein R<SP>1</SP> is alkyl or C 3-6 cycloalkyl; R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and B<SP>5</SP> are each H or alkyl; R<SP>6</SP> is H, alkyl, OH, C 1-4 alkoxy, C 2-6 alkanoyloxy, NO 2 or halogen; R<SP>7</SP> is alkyl; X is O or S; Alk is alkylene (as defined in the Specification); R<SP>8</SP> and R<SP>9</SP> are each H or alkyl, or NR<SP>8</SP>R<SP>9</SP> is pyrrolidino, piperidino, morpholino or 4-Z-piperazino, where Z is H, alkyl or hydroxyalkyl; and "alkyl" means (C 1-6 ) straight-chain or (up to C 4 ) branched-chain. In examples, these compounds are prepared by reducing the analogous # - nitroalkyl compounds, dimethylimmonium salts, oximes or amides (containing CONR<SP>8</SP>R<SP>9</SP>) or by reacting an iodoalkyl compound with HNR<SP>8</SP>R<SP>9</SP>. The amides are obtained by treating the corresponding acids with ClCO 2 Et/NEt 3 , followed by HNR<SP>8</SP>R<SP>9</SP>. The acids are obtained by hydrolysing the corresponding esters, but amides, acids and esters may also be made by reacting an appropriately substituted 1-(2-hydroxyethyl)indole (but unsubstituted in the 2-position) with an #-R<SP>1</SP>CO-alkanoic acid or its alkyl ester or amide. Starting materials otherwise prepared are those of formula YCHO, YCO 2 H, YCO 2 Et, YCH 2 Br, YS 2 O 3 Na, Y 2 S 2 , YSH (possibly alphasubstituted by SH), where Y is substituted indol-1-ylmethyl; and analogues of the compounds of Formula (I) containing instead of the Alk-NR<SP>8</SP>R<SP>9</SP> group, -CH 2 CH 2 CHO, -(CH 2 ) 2-3 -OH, -(CH 2 ) 3 OCOMe or -(CH 2 ) 3-4 - OTs. Therapeutic compositions having antidepressant and anti-ulcer activity comprise compounds of the above Formula (I), and may be administered orally or parenterally.
GB688373A 1972-02-14 1973-02-13 Fused-ring indole derivatives Expired GB1421063A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US00226287A US3833575A (en) 1972-02-14 1972-02-14 Oxazinoindole-and thiazinoindole derivatives
US297130A US3904617A (en) 1972-10-12 1972-10-12 Process for preparing new heterocyclic derivatives

Publications (1)

Publication Number Publication Date
GB1421063A true GB1421063A (en) 1976-01-14

Family

ID=26920388

Family Applications (1)

Application Number Title Priority Date Filing Date
GB688373A Expired GB1421063A (en) 1972-02-14 1973-02-13 Fused-ring indole derivatives

Country Status (6)

Country Link
JP (1) JPS4886895A (en)
CA (1) CA1036596A (en)
DE (1) DE2306809A1 (en)
FR (1) FR2181727B1 (en)
GB (1) GB1421063A (en)
IE (1) IE37234B1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT387576B (en) * 1983-10-25 1989-02-10 Richter Gedeon Vegyeszet METHOD FOR PRODUCING NEW 1,3-OXAZINO (4,3-A) ISOCHINOLINE DERIVATIVES

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU191301B (en) * 1984-03-23 1987-02-27 Richter Gedeon Vegyeszeti Gyar Rt,Hu Process for preparing 1-/hydroxy-methyl/-1,6,7,11b-tetrahydro-2h,4h-/1,3/-oxazino- or -thiazino/4,3-a/isoquinoline -derivatives
TW270114B (en) * 1993-10-22 1996-02-11 Hoffmann La Roche

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT387576B (en) * 1983-10-25 1989-02-10 Richter Gedeon Vegyeszet METHOD FOR PRODUCING NEW 1,3-OXAZINO (4,3-A) ISOCHINOLINE DERIVATIVES

Also Published As

Publication number Publication date
IE37234L (en) 1973-08-14
IE37234B1 (en) 1977-06-08
DE2306809A1 (en) 1973-08-30
FR2181727B1 (en) 1976-10-22
JPS4886895A (en) 1973-11-15
FR2181727A1 (en) 1973-12-07
CA1036596A (en) 1978-08-15

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee