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GB1232836A - - Google Patents

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Publication number
GB1232836A
GB1232836A GB1232836DA GB1232836A GB 1232836 A GB1232836 A GB 1232836A GB 1232836D A GB1232836D A GB 1232836DA GB 1232836 A GB1232836 A GB 1232836A
Authority
GB
United Kingdom
Prior art keywords
ethyl
methoxy
acetamido
substituted
alkyl
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
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 filed Critical
Publication of GB1232836A publication Critical patent/GB1232836A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,232,836. 2 - Alkoxy (or alkenoxy) - 4,5- azimidobenzamides. SOC. D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILEDE-FRANCE. 16 Aug., 1968 [17 Aug., 1967; 6 Nov., 1967], No. 39270/68. Heading C2C. The novel title compounds of the Formula I wherein A is either -N(R 1 )R 2 in which R 1 and R 2 , which may be the same or different are H or C 1-5 alkyl, or R 1 and R 2 together with the N atom form a heterocyclic ring, optionally containing an additional N atom, which may be substituted by C 1-5 alkyl or a further O or S atom, or a heterocyclic radical of the formula in which R is C 1-5 alkyl and m is 1 to 3; and n is 1 or 2, the dextro- and levorotatory isomers of those compounds of the above Formula I which contain 1 or more asymmetric carbon atoms, and the acid addition and quaternary ammonium salts thereof, are prepared by treating the appropriate N-substituted-2-alkoxy (or alkenoxy)-4,5-diamino-benzamide with a metallic nitrite in an acid medium. Methyl - 2 - methoxy - 4 - acetamido - 5 - nitrobenzoate is obtained by nitrating methyl 2- methoxy-4-acetamido-benzoate. N - (Diethylaminoethyl) -, N - (1 - ethyl - 2- pyrrolidylmethyl) -, dextrorotatory N - (1 - ethyl- 2 - pyrrolidylmethyl) -, and N - (N<SP>1</SP> - ethyl - N<SP>1</SP>- propylaminoethyl) - 2 - methoxy - 4,5 - diaminobenzamides are prepared by reducing the corresponding N - substituted 2 - methoxy - 4 - amino- 5-nitrobenzamides resulting from the reaction of methyl 2-methoxy-4-acetamido-5-nitrobenzoate with diethylaminoethylamine, 1-ethyl-2- aminomethylpyrrolidine, dextrorotatory 1- ethyl - 2 - aminoethylpyrrolidine and N - ethyl- N-propylethylenediamine respectively. Pharmaceutical compositions, having antiemetic activity and suitable for oral, parenteral or rectal administration contain the above novel compounds or their acid addition or quaternary ammonium salts as the active ingredient and pharmaceutically acceptable carriers or diluents.
GB1232836D 1967-08-17 1968-08-16 Expired GB1232836A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR118161A FR6787M (en) 1967-08-17 1967-08-17
FR127131 1967-11-06
US75173768A 1968-08-12 1968-08-12
US00117836A US3839330A (en) 1967-08-17 1971-02-22 2-alkoxy-4,5-azimidobenzamides

Publications (1)

Publication Number Publication Date
GB1232836A true GB1232836A (en) 1971-05-19

Family

ID=27444886

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1232836D Expired GB1232836A (en) 1967-08-17 1968-08-16

Country Status (7)

Country Link
US (1) US3839330A (en)
BE (1) BE719048A (en)
CH (1) CH496007A (en)
DE (1) DE1795653C3 (en)
FR (2) FR6787M (en)
GB (1) GB1232836A (en)
OA (1) OA03879A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039672A (en) * 1975-01-11 1977-08-02 Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France N-(1'-allypyrrolidinyl 2'-methyl) 2-methoxy 4,5-azimido benzamide and its pharmaceutically acceptable salts
FR2297041A1 (en) * 1975-01-11 1976-08-06 Ile De France N- (1'-ALLYLPYRROLIDINYL 2'METHYL) 2-METHOXY 4,5-AZIMIDO BENZAMIDE, ITS DERIVATIVES AND PROCESSES FOR PREPARATION
US4255580A (en) * 1976-08-04 1981-03-10 Siociete D'etudes Scientifiques Et Industrielles De L'ile-De-France Substituted 2,3-alkylene bis (oxy) benzamides and derivatives
US4186135A (en) * 1976-08-04 1980-01-29 Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France Substituted 2,3-alkylene bis (oxy) benzamides and derivatives and method of preparation
FR2440946A2 (en) * 1978-01-20 1980-06-06 Ile De France NOVEL SUBSTITUTED HETEROCYCLIC BENZAMIDES, PROCESSES FOR THEIR PREPARATION AND THEIR APPLICATION AS BEHAVIOR MODIFIERS
FR2574795B1 (en) * 1984-12-18 1987-11-20 Ile De France NEW INDUSTRIAL PROCESS FOR SYNTHESIS OF N - ((1'-ALLYL 2'-PYRROLIDINYL) METHYL) 2-METHOXY 4,5-AZIMIDO BENZAMIDE
FR2699533A1 (en) * 1992-12-21 1994-06-24 Mouhtaram Mohamed N-2-piperazinyl 4-amino:benzamide derivs. having antiemetic and antipsychotic activity
US5610265A (en) * 1996-02-02 1997-03-11 The United States Of America As Represented By The Secretary Of The Air Force Armomatic polyimides derived from 2-(N-benzoylimino)-4,4-diaminobiphenyl

Also Published As

Publication number Publication date
FR1572168A (en) 1969-06-27
OA03879A (en) 1975-08-14
DE1795110B2 (en) 1973-01-18
DE1795653A1 (en) 1973-02-08
FR6787M (en) 1969-03-17
DE1795653B2 (en) 1974-10-24
US3839330A (en) 1974-10-01
BE719048A (en) 1969-02-05
DE1795653C3 (en) 1975-06-05
CH496007A (en) 1970-09-15
DE1795110A1 (en) 1972-03-30

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee