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GB1285025A - Hexahydroazepines - Google Patents

Hexahydroazepines

Info

Publication number
GB1285025A
GB1285025A GB4694/69A GB469469A GB1285025A GB 1285025 A GB1285025 A GB 1285025A GB 4694/69 A GB4694/69 A GB 4694/69A GB 469469 A GB469469 A GB 469469A GB 1285025 A GB1285025 A GB 1285025A
Authority
GB
United Kingdom
Prior art keywords
radical
lower alkyl
hydrogen atom
formula
cooalk
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
GB4694/69A
Inventor
John Frederick Cavalla
Alan Chapman White
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.)
John Wyeth and Brother Ltd
Original Assignee
John Wyeth and 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 John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd
Priority to IE1102/69A priority Critical patent/IE33382B1/en
Priority to IL32801A priority patent/IL32801A/en
Priority to FR6928129A priority patent/FR2015812A1/en
Priority to IT20967/69A priority patent/IT1053698B/en
Priority to ES370497A priority patent/ES370497A1/en
Priority to BE737548D priority patent/BE737548A/xx
Priority to DE1941534A priority patent/DE1941534C3/en
Priority to SU1476793A priority patent/SU460625A3/en
Priority to SU1360508A priority patent/SU425396A3/en
Priority to NL6912483.A priority patent/NL164275C/en
Priority to NO3311/69A priority patent/NO132046C/no
Priority to DK439969AA priority patent/DK141401B/en
Priority to CH1056472A priority patent/CH554864A/en
Priority to HUWI160A priority patent/HU162512B/hu
Priority to YU2102/69A priority patent/YU34124B/en
Priority to CH340773A priority patent/CH554865A/en
Priority to JP44064669A priority patent/JPS505197B1/ja
Priority to FI692393A priority patent/FI51479C/en
Priority to CH1241969A priority patent/CH536843A/en
Priority to SE11395/69A priority patent/SE366043B/xx
Priority to AT809471A priority patent/AT312613B/en
Priority to AT789269A priority patent/AT312611B/en
Priority to DK340571A priority patent/DK150849C/en
Priority to AR239343A priority patent/AR194353A1/en
Publication of GB1285025A publication Critical patent/GB1285025A/en
Priority to NO750442A priority patent/NO142395C/en
Priority to YU02716/75A priority patent/YU39170B/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1285025 Hexahydroazepine derivatives JOHN WYETH & BRO Ltd 12 Aug 1969 [16 Aug 1968 4 Sept 1968 28 Jan 1969] 39201/68 42060/68 and 4694/69 Heading C2C Novel compounds of Formula I: and the acid addition and quaternary ammonium salts thereof, in which R<SP>1</SP> is a hydrogen atom, a lower alkyl radical, a benzyl radical or a lower alkanoyl radical, R<SP>2</SP> is a lower alkyl radical, R<SP>3</SP> is a hydrogen atom, a lower alkyl, lower alkenyl, lower alkynyl, cyclopropylmethyl, lower alkanoyl, lower alkoxycarbonyl, formyl, phenacyl or phenethyl group both of which may be substituted in the benzene ring or a #- benzoylethyl radical which may be substituted in the benzene ring, n is 3 or 4, m is 0 or 1 with the proviso that n+m is always equal to 4, R is a hydrogen atom or a lower alkyl radical when m is 0, or a hydrogen atom only when m is 1, and the term "lower" means that the radical contains up to 6, preferably up to 4 carbon atoms, are generally prepared by (a) cyclizing a compound of Formula II: in which X is -CH 2 .NH 2 when Y is -(CH 2 ) 4 . - Hal, -(CH 2 ) 4 .OH or -(CH 2 ) 3 .COOAlk, or X is -CN when Y is -(CH 2 ) 3 .COOALK, or X is -COOAlk when Y is -(CH 2 ) 4 .NH 2 or -(CH 2 ) 3 .CN; Hal is a halogen atom and Alk is a lower alkyl radical, and, if necessary, reducing and/or alkylating or acylating the product or (b) reducing a compound of the Formula III: wherein X-Y is -N = CR-, R and R<SP>3</SP> being as defined above and Y<SP>1</SP> is -CH 2 -, or X-Y is and Y<SP>1</SP> is C=O, Z is R<SP>2</SP> or COR<SP>4</SP>, R<SP>2</SP> being as defined above and R<SP>4</SP> being hydrogen or lower alkyl, p is 2 or 3 and m is 0 or 1 and m+p is 3. Other methods are also disclosed. Starting materials and intermediates are prepared according to the following reaction schemes: Pharmaceutical compositions having analgesic activity and, in some eases, the ability to antagonise narcotic analgesics, comprise a compound of Formula I together with a pharmaceutical carrier. The compositions may be administered orally or parenterally.
GB4694/69A 1968-08-16 1969-01-28 Hexahydroazepines Expired GB1285025A (en)

Priority Applications (26)

Application Number Priority Date Filing Date Title
IE1102/69A IE33382B1 (en) 1968-08-16 1969-08-06 Hexahydroazepines
IL32801A IL32801A (en) 1968-08-16 1969-08-08 Hexahydroazepines,their preparation and pharmaceutical compositions containing them
FR6928129A FR2015812A1 (en) 1968-08-16 1969-08-14 Analgesic hexahydro 1h azepine derivs
IT20967/69A IT1053698B (en) 1968-08-16 1969-08-14 ESAIDROAZEPINE
ES370497A ES370497A1 (en) 1968-08-16 1969-08-14 A procedure for the preparation of a compound of hexahidro-1-h-azepine. (Machine-translation by Google Translate, not legally binding)
BE737548D BE737548A (en) 1968-08-16 1969-08-14
DE1941534A DE1941534C3 (en) 1968-08-16 1969-08-14 Hexahydroazepine and medicinal products containing these compounds
HUWI160A HU162512B (en) 1968-08-16 1969-08-15
CH1241969A CH536843A (en) 1968-08-16 1969-08-15 Process for the production of new hexahydroazepines
NL6912483.A NL164275C (en) 1968-08-16 1969-08-15 PROCESS FOR THE PREPARATION OF ANALGETICALLY ACTIVE HEXAHYDRO-1H-AZEPINE DERIVATIVES, PROCESS FOR PREPARING PHARMACEUTICAL PREPARATIONS BASED ON HEXAHYDRO-1H-AZEPINE DERIVATIVES AND THEIR DUE-IN-ART.
NO3311/69A NO132046C (en) 1968-08-16 1969-08-15
DK439969AA DK141401B (en) 1968-08-16 1969-08-15 Analogous process for preparing hexahydro-1H-azepine compounds or acid addition or quaternary ammonium salts thereof.
CH1056472A CH554864A (en) 1968-08-16 1969-08-15 METHOD FOR MANUFACTURING NEW HEXAHYDROACEPINES.
SU1476793A SU460625A3 (en) 1968-08-16 1969-08-15 The method of producing hexahydro -1n-azeline derivatives or their salts
YU2102/69A YU34124B (en) 1968-08-16 1969-08-15 Process for preparing hexahydro-1h-azepine derivatives
CH340773A CH554865A (en) 1968-08-16 1969-08-15 METHOD FOR MANUFACTURING NEW HEXAHYDROACEPINES.
JP44064669A JPS505197B1 (en) 1968-08-16 1969-08-15
FI692393A FI51479C (en) 1968-08-16 1969-08-15 A process for preparing a therapeutically useful 3,3-disubstituted hexahydro-1H-azepine compound.
SU1360508A SU425396A3 (en) 1968-08-16 1969-08-15 METHOD FOR PRODUCING HEXAGIDRO-7YA-AZEPIN DERIVATIVES OR THEIR SALTS
SE11395/69A SE366043B (en) 1968-08-16 1969-08-15
AT809471A AT312613B (en) 1968-08-16 1969-08-18 Process for the preparation of new hexahydro-1H-azepine derivatives and their acid addition or quaternary ammonium salts
AT789269A AT312611B (en) 1968-08-16 1969-08-18 Process for the preparation of new hexahydro-1H-azepine compounds, their acid addition salts or quaternary ammonium salts
DK340571A DK150849C (en) 1968-08-16 1971-07-09 HEXAHYDRO-2H-AZEPIN-2-ONES USED AS INTERMEDIATES IN THE PREPARATION OF HEXAHYDRO-1H-AZEPINE DERIVATIVES OR ANY ACID ADDITION SALT OR QUATERNATE AMMONIUM SALT
AR239343A AR194353A1 (en) 1968-08-16 1971-11-30 PROCEDURE FOR THE PREPARATION OF NOVELTY HEXAHYDRO-1H-AZEPINE DERIVATIVES
NO750442A NO142395C (en) 1968-08-16 1975-02-11 ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY ACTIVE Witch Hydro-1H AZEPINES
YU02716/75A YU39170B (en) 1968-08-16 1975-10-27 Process for preparing hexahydro-1h-azepine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3920168 1968-08-16

Publications (1)

Publication Number Publication Date
GB1285025A true GB1285025A (en) 1972-08-09

Family

ID=10408242

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4694/69A Expired GB1285025A (en) 1968-08-16 1969-01-28 Hexahydroazepines

Country Status (4)

Country Link
CS (1) CS187305B2 (en)
GB (1) GB1285025A (en)
MY (1) MY7400045A (en)
ZA (1) ZA695740B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4197241A (en) * 1977-12-22 1980-04-08 John Wyeth & Brother Limited Hexahydroazepine, piperidine and pyrrolidine derivatives
US4296029A (en) * 1979-07-03 1981-10-20 John Wyeth & Brother Limited Process for preparing hexahydroazepine, piperidine and pyrrolidine derivatives
EP0062019A1 (en) * 1981-04-01 1982-10-06 Aktiebolaget Hässle New phenyl-perhydroazepines
EP0082599A1 (en) * 1981-12-02 1983-06-29 JOHN WYETH &amp; BROTHER LIMITED m-Hydroxyphenyl substituted compounds
US4466963A (en) * 1982-07-08 1984-08-21 John Wyeth & Brother Limited Pharmaceutical compositions
CN103467376A (en) * 2013-08-19 2013-12-25 北京万全阳光医学技术有限公司 New method for preparation of meptazinol hydrochloride critical impurity

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4197241A (en) * 1977-12-22 1980-04-08 John Wyeth & Brother Limited Hexahydroazepine, piperidine and pyrrolidine derivatives
US4197239A (en) * 1977-12-22 1980-04-08 John Wyeth & Brother Limited Hexahydroazepine, piperidine and pyrrolidine derivatives
US4296029A (en) * 1979-07-03 1981-10-20 John Wyeth & Brother Limited Process for preparing hexahydroazepine, piperidine and pyrrolidine derivatives
EP0021772B1 (en) * 1979-07-03 1985-01-02 JOHN WYETH &amp; BROTHER LIMITED Method of preparing 2-oxo- and 2-unsubstituted-hexahydroazepine derivatives
EP0062019A1 (en) * 1981-04-01 1982-10-06 Aktiebolaget Hässle New phenyl-perhydroazepines
EP0082599A1 (en) * 1981-12-02 1983-06-29 JOHN WYETH &amp; BROTHER LIMITED m-Hydroxyphenyl substituted compounds
US4463177A (en) * 1981-12-02 1984-07-31 John Wyeth & Brother Limited Process for making m-hydroxyphenyl substituted compounds
US4466963A (en) * 1982-07-08 1984-08-21 John Wyeth & Brother Limited Pharmaceutical compositions
EP0099186A3 (en) * 1982-07-08 1984-11-07 John Wyeth & Brother Limited Pharmaceutical compositions
CN103467376A (en) * 2013-08-19 2013-12-25 北京万全阳光医学技术有限公司 New method for preparation of meptazinol hydrochloride critical impurity

Also Published As

Publication number Publication date
MY7400045A (en) 1974-12-31
CS187305B2 (en) 1979-01-31
ZA695740B (en) 1971-03-31

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years