IE35956L - Fused ring indole derivatives - Google Patents

Fused ring indole derivatives

Info

Publication number
IE35956L
IE35956L IE720014A IE1472A IE35956L IE 35956 L IE35956 L IE 35956L IE 720014 A IE720014 A IE 720014A IE 1472 A IE1472 A IE 1472A IE 35956 L IE35956 L IE 35956L
Authority
IE
Ireland
Prior art keywords
alkyl
aryl
ketones
prepared
possibly
Prior art date
Application number
IE720014A
Other versions
IE35956B1 (en
Original Assignee
Wyeth John & Brother 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
Application filed by Wyeth John & Brother Ltd filed Critical Wyeth John & Brother Ltd
Publication of IE35956L publication Critical patent/IE35956L/en
Publication of IE35956B1 publication Critical patent/IE35956B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Rheumatology (AREA)
  • Nutrition Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)

Abstract

1366133 Fused-ring indolines JOHN WYETH & BRO Ltd 14 Dec 1971 [11 Jan 1971 2 Sept 1971 6 Dec 1971] 1250/71 40959/71 and 56467/71 Heading C2C The invention comprises compounds of formula and their acid addition or quaternary ammonium salts, wherein R is OH (or its C 1-6 alkyl, aryl- C 1-6 -alkyl or tetrahydropyracyl ether, or ester derivative); R<SP>1</SP> is aryl (mono- or bicyclic), C 1-6 alkyl (possibly aryl- or amino-substituted), or up to C 6 alkenyl or alkynyl; or RR<SP>1</SP> is O=, or (when n is 1) its alkylene or di-(C 1-6 alkyl) ketal; R<SP>2</SP>, R<SP>5</SP> are each H, OH, halogen, NH 2 (possibly mono- or di-C 1-6 -alkyl substituted), or C 1-6 alkyl, haloalkyl or alkoxy, or (when RR<SP>1</SP> is O = or a ketal thereof) NO 2 ; R<SP>3</SP>, R<SP>4</SP> are each H or C 1-6 alkyl, or R<SP>3</SP> is H and R<SP>4</SP> is OH; n is 0-2; and R<SP>6</SP> (present only when the optional bond represented by the broken line is absent) is H, acyl, C 1-6 alkyl (possibly substituted by aryl, or up to C 6 alkenyl or alkynyl. In Examples, (1) the compounds containing the optional bond are prepared thus: (a) the ethylene ketals (A) by reductive ring-closure of corresponding 1-cyanoalkylizatin-3-ethyleneketals; (b) the ketones (B) by either hydrolysing ketals (A), or ring-closing corresponding 2-halophenyl/heterocyclyl ketones (C); (c) the alcohols by reacting ketones (B) with R<SP>1</SP>Mg-halide or R<SP>1</SP>-Li; (d) halogenation, nitration or esterification; ... (2) the compounds not containing the optional bond are prepared by reducing those containing it, possibly in the form of a quaternary ammonium salt. Ketones (C) are prepared by oxidizing the corresponding alcohols. 1 - (2 - Cyanoethyl) - 5 - methoxyizatin, bromo-tert-butyl cyanide and isatin-3-ethyleneketal are also prepared. Therapeutic compositions for oral or parenteral administration comprise compounds of the above formula (other than those where RR<SP>1</SP> is O= or a ketal thereof), which have antidepressant, antiinflammatory, antihistaminic, cardiovascular, diuretic and/or hypoglycaemic activity. [GB1366133A]
IE14/72A 1971-01-11 1972-01-08 Fused ring indole derivatives IE35956B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB125071*[A GB1366133A (en) 1971-01-11 1971-01-11 Fused ring indole derivatives
GB4095971 1971-09-02
GB5646771 1971-12-06

Publications (2)

Publication Number Publication Date
IE35956L true IE35956L (en) 1972-07-11
IE35956B1 IE35956B1 (en) 1976-07-07

Family

ID=27253859

Family Applications (1)

Application Number Title Priority Date Filing Date
IE14/72A IE35956B1 (en) 1971-01-11 1972-01-08 Fused ring indole derivatives

Country Status (20)

Country Link
JP (1) JPS5531156B2 (en)
AR (1) AR192734A1 (en)
AT (1) AT312595B (en)
AU (1) AU464388B2 (en)
BE (1) BE777911A (en)
CA (1) CA1012150A (en)
CH (1) CH573938A5 (en)
CY (1) CY926A (en)
DK (1) DK150143C (en)
EG (1) EG10888A (en)
ES (2) ES398678A1 (en)
FI (1) FI54120C (en)
FR (1) FR2121699B1 (en)
GB (1) GB1366133A (en)
HK (1) HK52877A (en)
IE (1) IE35956B1 (en)
KE (1) KE2777A (en)
MY (1) MY7800048A (en)
NL (1) NL174251C (en)
SE (1) SE398645B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1520611A (en) * 1976-06-11 1978-08-09 Wyeth John & Brother Ltd Fused ring indole derivatives
JPS5845741B2 (en) * 1977-06-06 1983-10-12 株式会社日立製作所 information retrieval device
ZA824382B (en) * 1981-07-07 1984-02-29 Wyeth John & Brother Ltd Anti-obesity agents
JPS60204057A (en) * 1984-03-28 1985-10-15 Casio Comput Co Ltd Small-sized electronic apparatus with data storage function
GB8606253D0 (en) * 1986-03-13 1986-04-16 Wyeth John & Brother Ltd Pyrimidoindoles
GB8606254D0 (en) * 1986-03-13 1986-04-16 Wyeth John & Brother Ltd Substituted pyrimidoindoles
GB8614246D0 (en) * 1986-06-11 1986-07-16 Wyeth John & Brother Ltd Substituted pyrimidoindoles
WO2010090680A1 (en) * 2008-12-15 2010-08-12 Wyeth Llc Substituted oxindole cb2 agonists

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3888846A (en) * 1967-03-30 1975-06-10 Hoffmann La Roche Process for 2(2-(1,3-diazacycloalk-2-enyl))benzophenone derivatives and 1,3-diazacycloalkenyl(2,1-a)isoindole derivatives
US3586693A (en) * 1969-07-07 1971-06-22 American Home Prod Imidazo(1,2-a)indolin-9-ols

Also Published As

Publication number Publication date
IE35956B1 (en) 1976-07-07
DK150143B (en) 1986-12-15
DK150143C (en) 1987-06-01
JPS4839500A (en) 1973-06-09
FI54120C (en) 1978-10-10
CA1012150A (en) 1977-06-14
FI54120B (en) 1978-06-30
AR192734A1 (en) 1973-03-14
EG10888A (en) 1978-06-30
JPS5531156B2 (en) 1980-08-15
GB1366133A (en) 1974-09-11
HK52877A (en) 1977-10-20
FR2121699A1 (en) 1972-08-25
NL174251B (en) 1983-12-16
FR2121699B1 (en) 1975-08-01
SE398645B (en) 1978-01-09
ES409296A1 (en) 1976-03-16
CY926A (en) 1977-12-23
NL7200415A (en) 1972-07-13
KE2777A (en) 1977-10-21
MY7800048A (en) 1978-12-31
CH573938A5 (en) 1976-03-31
BE777911A (en) 1972-07-11
ES398678A1 (en) 1975-05-16
NL174251C (en) 1984-05-16
AT312595B (en) 1974-01-10
AU464388B2 (en) 1975-08-28
AU3755872A (en) 1973-07-05

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