GB1385652A - Glyceryl 5-aroyl-pyrrole-acetates and propionates and pharmaceutical compositions containing them - Google Patents
Glyceryl 5-aroyl-pyrrole-acetates and propionates and pharmaceutical compositions containing themInfo
- Publication number
- GB1385652A GB1385652A GB281673A GB281673A GB1385652A GB 1385652 A GB1385652 A GB 1385652A GB 281673 A GB281673 A GB 281673A GB 281673 A GB281673 A GB 281673A GB 1385652 A GB1385652 A GB 1385652A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- pyrrole
- alkyl
- toluoyl
- methyl
- 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
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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1385652 Glyceryl - 5 - aroyl - pyrrole - acetates and propionates and pharmaceutical compositions containing them McNEIL LABORATORIES Inc 19 Jan 1973 [21 Jan 1972] 2816/73 Heading C2C The invention comprises compounds of formula wherein Gly represents -CH 2 CH(OH)CH 2 OH; Ar represents a phenyl, thienyl, 5-methylthienyl, mono-, di- or tri-substituted phenyl group, each substituent of said substituted phenyl being a halo, C 1-6 alkyl, -CF 3 , C 1-6 alkoxy, nitro, -NH 2 , -CN or -SCH 3 group; Ar represents a phenyl, mono-, di- or trisubstituted phenyl group, each substituent of said phenyl group being a halo, C 1-6 alkyl, or C 1-6 alkoxy group; R represents H or a C 1-6 alkyl group; R 1 represents a H, C 1-6 alkyl or benzyl group; and R 2 represents H or a C 1-6 alkyl group, provided that: (i) when Ar is a nitro-substituted phenyl or amino-substituted phenyl group, then, with regard to Formula (I-a), R is H and R 1 is a C 1-6 alkyl group; and with regard to Formula (I-e), said R 2 is H; (ii) when Ar is a cyanophenyl group, then R 1 is a C 1-6 alkyl group; and (iii) when R 1 is H, then R is also a hydrogen atom. These compounds may be obtained by heating a compound of formula wherein X is the residual portion of Formulµ I-a, I-b, I-c, I-d or I-e defined above which is attached to the carboxylic function, with an aqueous solution of acetic acid. The following intermediates are referred to: cyanomethyl- 1 - methyl - 5 - (p - toluoyl) - pyrrole - 2 - acetate obtained by the reaction of sodium-1-methyl-5- (p - toluoyl) - pyrrole - 2 - acetate with chloroacetonitrile, in Example I. For similar intermediates see also Example II. 2,2-Dimethyl-1,3- dioxolanylmethyl - 1 - methyl - 5 - (p - toluoyl)- pyrrole-2-acetate is obtained by treating cyanomethyl - 1 - methyl - 5 - (p - toluoyl) - pyrrole- 2-acetate with acetone ketal of glycerine in Example III. For similar intermediates see also Example IV. The invention also comprises a pharmaceutical composition which contains as an active ingredient a compound according to the invention together with a pharmaceutically acceptable inert diluent or carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21986572A | 1972-01-21 | 1972-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1385652A true GB1385652A (en) | 1975-02-26 |
Family
ID=22821084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB281673A Expired GB1385652A (en) | 1972-01-21 | 1973-01-19 | Glyceryl 5-aroyl-pyrrole-acetates and propionates and pharmaceutical compositions containing them |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5825671B2 (en) |
| AT (1) | AT323149B (en) |
| AU (1) | AU476415B2 (en) |
| BE (1) | BE794163A (en) |
| CA (1) | CA1016949A (en) |
| CH (1) | CH577965A5 (en) |
| DE (1) | DE2302670A1 (en) |
| FR (1) | FR2183661B1 (en) |
| GB (1) | GB1385652A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62289493A (en) * | 1986-06-09 | 1987-12-16 | ヤマハ発動機株式会社 | Mounting structure of starting motor for motorcycle |
-
0
- BE BE794163D patent/BE794163A/en not_active IP Right Cessation
-
1973
- 1973-01-15 AU AU51094/73A patent/AU476415B2/en not_active Expired
- 1973-01-17 CH CH64973A patent/CH577965A5/xx not_active IP Right Cessation
- 1973-01-18 FR FR7301767A patent/FR2183661B1/fr not_active Expired
- 1973-01-19 AT AT47173A patent/AT323149B/en not_active IP Right Cessation
- 1973-01-19 DE DE2302670A patent/DE2302670A1/en active Pending
- 1973-01-19 CA CA161,628A patent/CA1016949A/en not_active Expired
- 1973-01-19 GB GB281673A patent/GB1385652A/en not_active Expired
- 1973-01-22 JP JP48009396A patent/JPS5825671B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU5109473A (en) | 1974-07-18 |
| DE2302670A1 (en) | 1973-07-26 |
| JPS4880554A (en) | 1973-10-29 |
| FR2183661B1 (en) | 1975-11-21 |
| JPS5825671B2 (en) | 1983-05-28 |
| CH577965A5 (en) | 1976-07-30 |
| AU476415B2 (en) | 1976-09-23 |
| BE794163A (en) | 1973-07-17 |
| FR2183661A1 (en) | 1973-12-21 |
| CA1016949A (en) | 1977-09-06 |
| AT323149B (en) | 1975-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |