GB1214077A - Oximes and their carbamoyl esters and the methods of preparation thereof - Google Patents

Oximes and their carbamoyl esters and the methods of preparation thereof

Info

Publication number
GB1214077A
GB1214077A GB46134/68A GB4613468A GB1214077A GB 1214077 A GB1214077 A GB 1214077A GB 46134/68 A GB46134/68 A GB 46134/68A GB 4613468 A GB4613468 A GB 4613468A GB 1214077 A GB1214077 A GB 1214077A
Authority
GB
United Kingdom
Prior art keywords
alkyl
amino
oxime
formula
alkenyl
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
GB46134/68A
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.)
USV Pharmaceutical Corp
Original Assignee
USV Pharmaceutical Corp
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 USV Pharmaceutical Corp filed Critical USV Pharmaceutical Corp
Publication of GB1214077A publication Critical patent/GB1214077A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Abstract

1,214,077. Oxime carbamoyl esters. USV PHARMACEUTICAL CORP. 27 Sept., 1968 [2 Nov., 1967 (2); 20 March, 1968; 5 Aug., 1968], No. 46134/68. Heading C2C. Novel oxime carbamoyl esters of the formula wherein R 1 is C 1-5 alkyl, C 2-5 alkyl, cycloalkyl, aryl, substituted aryl, heterocyclic or substituted heterocyclic; R 2 is H, C 1-5 alkyl, C 2-5 alkenyl, or phenyl-C 1-5 alkyl; R 3 is C 1-5 alkyl, C 2-5 alkenyl, cycloalkyl, phenyl, substituted phenyl, heterocyclic or substituted heterocyclic; Y is C 1-5 alkylene, and X is di-(C 1-5 alkyl) amino,benzylethylamino,di-(C 2-5 alkenyl) amino, benzylethyl amino, di-(C 2-5 alkenyl) amino, di- (cycloalkyl) amino, N-(C 2-5 alkenyl)-N-(C 1-5 alkyl) amino, pyrrolidino, piperidino, morpholino, thio morpholino, homopiperidino, piperazino or N-methylpiperazino and pharmaceutically acceptable acid addition salts thereof are prepared by reacting ketones of the formula with hydroxylamine derivatives of the formula wherein Z is H or CON(R 2 )R 3 , and, when Z in the resulting products is H, reacting them with either isocyanates of the formula or carbamoyl halides or esters of the formula and, if desired, converting compounds of Formula I wherein R 2 is H to those where R 2 is C 1-5 alkyl or phenyl-C 1-5 alkyl by alkylation. 4 Dimethylaminobutyrophenone oxime N,N- dimethylaminovalerophenone oxime and 3-(N,N- dimethylamnino) - 3<SP>1</SP>- chloropropiophenone oxime are prepared by reacting the appropriate aminoketones with hydroxylamine hydrochloride. 4 - Dimethylaminobutyrophenone oxime hydrochloride is made by treating the free base with ethanolic hydrogen chloride. Pharmaceutical compositions having analgesic activity and suitable for oral, parenteral, rectal or topical administration, contain the above novel compounds or pharmaceutically acceptable acid addition salts thereof and suitable carriers or diluents. In addition to the above mentioned analgesic activity some of the compounds also possess anticonvulsant, hypotensive and topical anaesthetic activities.
GB46134/68A 1967-11-02 1968-09-27 Oximes and their carbamoyl esters and the methods of preparation thereof Expired GB1214077A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US68004767A 1967-11-02 1967-11-02
US68001567A 1967-11-02 1967-11-02
US71445068A 1968-03-20 1968-03-20
US75001168A 1968-08-05 1968-08-05

Publications (1)

Publication Number Publication Date
GB1214077A true GB1214077A (en) 1970-12-02

Family

ID=27505389

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46134/68A Expired GB1214077A (en) 1967-11-02 1968-09-27 Oximes and their carbamoyl esters and the methods of preparation thereof

Country Status (13)

Country Link
AT (1) AT310185B (en)
BE (1) BE722318A (en)
BR (1) BR6803426D0 (en)
CH (1) CH490348A (en)
DE (1) DE1805716C3 (en)
DK (1) DK125129B (en)
FI (1) FI49603C (en)
FR (1) FR8419M (en)
GB (1) GB1214077A (en)
IL (1) IL30810A (en)
NL (1) NL145542B (en)
NO (1) NO127396B (en)
SE (1) SE356509B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2062868B1 (en) * 1969-09-15 1973-08-10 Innothera Lab Sa
BE759128R (en) * 1969-11-18 1971-05-18 Usv Pharma Corp CARBAMOYL OXIMES AND THEIR METHOD OF
US3875232A (en) * 1971-04-08 1975-04-01 Diamond Shamrock Corp AC Ketoxime carbamates
FR2204406A1 (en) * 1972-10-26 1974-05-24 Delalande Sa 1-Phenyl-3-aminocarbonylpropan-1-one oxime carbamates - with analgesic, antiinflammatory, hypotensive and sedative activities etc.

Also Published As

Publication number Publication date
NO127396B (en) 1973-06-18
IL30810A (en) 1974-03-14
NL6814556A (en) 1969-05-06
NL145542B (en) 1975-04-15
FI49603C (en) 1975-08-11
BR6803426D0 (en) 1973-02-22
IL30810A0 (en) 1968-12-26
DE1805716A1 (en) 1969-07-24
SE356509B (en) 1973-05-28
CH490348A (en) 1970-05-15
DK125129B (en) 1973-01-02
BE722318A (en) 1969-04-15
FI49603B (en) 1975-04-30
FR8419M (en) 1971-06-10
AT310185B (en) 1973-09-25
DE1805716C3 (en) 1973-10-18
DE1805716B2 (en) 1973-03-22

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees