GB1364231A - N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides - Google Patents
N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamidesInfo
- 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
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title 1
- 150000003936 benzamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 9
- -1 N - (1 - substituted - 3 - pyrrolidinyl) benzamides Chemical class 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 241000287433 Turdus Species 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 230000003474 anti-emetic effect Effects 0.000 abstract 1
- 239000012050 conventional carrier Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole 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.
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)
| 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)
| 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)
| 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 |
-
1973
- 1973-04-02 GB GB1564573A patent/GB1364231A/en not_active Expired
- 1973-04-03 FR FR7312003A patent/FR2182930B2/fr not_active Expired
- 1973-04-03 FR FR7312002A patent/FR2182929B2/fr not_active Expired
Cited By (5)
| 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 |
|---|---|
| FR2182929A2 (en) | 1973-12-14 |
| FR2182930B2 (en) | 1976-05-14 |
| FR2182929B2 (en) | 1976-04-23 |
| FR2182930A2 (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 |