GB1364231A - N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides - Google Patents

N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides

Info

Publication number
GB1364231A
GB1364231A GB1564573A GB1564573A GB1364231A GB 1364231 A GB1364231 A GB 1364231A GB 1564573 A GB1564573 A GB 1564573A GB 1564573 A GB1564573 A GB 1564573A GB 1364231 A GB1364231 A GB 1364231A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
compounds
amino
acetamido
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
GB1564573A
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.)
AH Robins Co Inc
Original Assignee
AH Robins Co 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
Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc
Publication of GB1364231A publication Critical patent/GB1364231A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D207/10—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 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1364231 N - (1 - substituted - 3 - pyrrolidinyl) benzamides and thiobenzamides A H ROBINS CO Inc 2 April 1973 [3 April 1972 12 March 1973] 15645/73 Addition to 1281188 Heading C2C The invention comprises compounds having the general formula wherein R is cycloalkyl, phenyl or phenylalkyl, R<SP>1</SP> is hydrogen, C 1 -C 8 alkyl or phenyl, R<SP>2</SP> is halogen, alkyl, alkoxy, amino, nitro, mono- or di - alkylamino, mercaptomethyl, acetamido, sulphamoyl, cyano, hydroxy, benzloxy or trifluoromethyl, and n is 0 or an integer from 1 to 3; and wherein R is cycloalkyl, R<SP>1</SP> is hydrogen or alkyl, R<SP>2</SP> is nitro, amino, halogen, sulphamoyl or alkoxy, and n is 0 or an integer of 1 to 3. The compounds of Formula I may be prepared by reacting a compound of the formula with a compound of the formula when R<SP>2</SP> is not primary amino or acetamido, and optionally hydrogenating the product when R<SP>2</SP> is nitro to form the corresponding amino compound which may be acylated to form the acetamido compound. The compounds of Formula II may be prepared by reacting a compound of Formula I with P 2 S 5 and K 2 S or by reacting a compound of formula with sulphur and a compound of Formula III. The compounds of the invention exhibit antiemetic activity and may be administered alone or in admixture with conventional carriers or diluents orally or parenterally.
GB1564573A 1968-12-23 1973-04-02 N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides Expired GB1364231A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US78642068A 1968-12-23 1968-12-23
US87498669A 1969-11-07 1969-11-07
US24084072A 1972-04-03 1972-04-03
US34041773A 1973-03-12 1973-03-12

Publications (1)

Publication Number Publication Date
GB1364231A true GB1364231A (en) 1974-08-21

Family

ID=27500024

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1564573A Expired GB1364231A (en) 1968-12-23 1973-04-02 N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides

Country Status (2)

Country Link
FR (2) FR2182930B2 (en)
GB (1) GB1364231A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4405636A (en) 1980-08-28 1983-09-20 Societe D'etudes Scientifiques Et Industrielles De L'ile-De France N-(1-Allyl-2-pyrrolidinyl-methyl)2-methoxy-4-amino-5-methylsufamoyl benzamide, its method of preparation and its use as a medicament
US4816471A (en) * 1978-01-20 1989-03-28 Societe D'etudes Scientifiques Et Industrielles De L'ille-De France Substituted heterocyclic benzamides, methods of preparing them and their application as anti-emetics
US6673829B2 (en) 2001-09-14 2004-01-06 Novo Nordisk A/S Aminoazetidine,-pyrrolidine and -piperidine derivatives
WO2003024928A3 (en) * 2001-09-14 2004-03-04 Novo Nordisk As Novel aminoazetidine, -pyrrolidine and -piperidine derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4002757A (en) * 1974-12-26 1977-01-11 A. H. Robins Company, Incorporated N-(1-substituted-3-pyrrolidinyl)-4-quinolinecarboxamides
US4049821A (en) * 1976-05-12 1977-09-20 A. H. Robins Company, Inc. Method of treating allergy

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3577440A (en) * 1968-12-23 1971-05-04 Robins Co Inc A H 1-substituted-3-amido-pyrrolidines

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4816471A (en) * 1978-01-20 1989-03-28 Societe D'etudes Scientifiques Et Industrielles De L'ille-De France Substituted heterocyclic benzamides, methods of preparing them and their application as anti-emetics
US4405636A (en) 1980-08-28 1983-09-20 Societe D'etudes Scientifiques Et Industrielles De L'ile-De France N-(1-Allyl-2-pyrrolidinyl-methyl)2-methoxy-4-amino-5-methylsufamoyl benzamide, its method of preparation and its use as a medicament
US4550179A (en) * 1980-08-28 1985-10-29 Societe D'etudes Scientifiques Et Industrielles De L'ile-De France N-(1-Allyl-2-pyrrolidinyl-methyl) 2-methoxy-4-amino-5-methylsulfamoyl benzamide
US6673829B2 (en) 2001-09-14 2004-01-06 Novo Nordisk A/S Aminoazetidine,-pyrrolidine and -piperidine derivatives
WO2003024928A3 (en) * 2001-09-14 2004-03-04 Novo Nordisk As Novel aminoazetidine, -pyrrolidine and -piperidine derivatives

Also Published As

Publication number Publication date
FR2182930B2 (en) 1976-05-14
FR2182930A2 (en) 1973-12-14
FR2182929B2 (en) 1976-04-23
FR2182929A2 (en) 1973-12-14

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Legal Events

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