GB1456257A - 2-aminothiazole derivatives - Google Patents
2-aminothiazole derivativesInfo
- Publication number
- GB1456257A GB1456257A GB2161474A GB2161474A GB1456257A GB 1456257 A GB1456257 A GB 1456257A GB 2161474 A GB2161474 A GB 2161474A GB 2161474 A GB2161474 A GB 2161474A GB 1456257 A GB1456257 A GB 1456257A
- Authority
- GB
- United Kingdom
- Prior art keywords
- atom
- general formula
- linked
- optionally
- nitrogen
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1456257 2 - Aminothiazole derivatives CENTRE D'ETUDES POUR L'INDUSTRIE PHARMACEUTIQUE 15 May 1974 [16 May 1973] 21614/74 Heading C2C Novel 2-aminothiazole derivatives of the general formula wherein R is a group of formula or linked with the sulphur atom by its central carbon atom: R 1 and R 2 , which may be the same or different, are hydrogen atoms or alkenyl, alkyl, cycloalkyl, aryl or aralkyl groups (which groups may optionally be substituted by halogen atoms or hydroxy groups), or form, together with the nitrogen atom to which they are linked, a saturated heterocyclic ring having 4 to 8 ring members and optionally containing a nitrogen, oxygen, or sulphur atom as a second heteroatom and being optionally substituted by an alkyl group; and R 3 and R 4 , which may be the same or different, are hydrogen atoms or alkyl or cycloalkyl groups, or form, together with the nitrogen atom to which they are linked, a saturated heterocyclic ring having 5 or 6 ring members and optionally containing oxygen, nitrogen, or sulphur as a second hetero-atom which (in the case of nitrogen) is optionally substituted by an aryl, haloaryl, alkoxyaryl, alkyl, hydroxyalkyl, haloalkyl, alkoxy, trifluoromethyl or halohydroxyalkyl group; and the mineral and organic acid addition and quaternary ammonium salts thereof are prepared by reacting AH with BNCS. (A being -NR 1 R 2 when B is -CH 2 -R 0 -CH 2 -NR 3 R 4 and, when R 2 is H, being when B is R 1 , R 0 being -CH = CH- or -C # C-) and cyclizing the resulting thiourea of the general formula by heating in an acid medium to form a thiazoline of the general formula wherein R is (b) above, when R 0 is -CH = CH-, or (a) above linked to the N atom by the C atom which is not adjacent to its double bond, when R 0 is -C # C-, and optionally isomerizing the thiazoline obtained in which R is (a) above by heating in solution at above 100 C. or treating with concentrated acid to form a thiazole of the first general formula above wherein R is linked to the N atom by the C atom adjacent to its double bond; followed optionally by salification. Isothiocyanates of the general formula are prepared by treating with CS 2 in the presence of cyclohexylcarbodiimide at a low temperature in a solvent. Pharmaceutical compositions having antiinflammatory and hypocholesterolemic activity comprise, as active ingredient, a 2-aminothiazole derivative of the first general formula above a mineral or organic acid addition or quaternary ammonium salt thereof, together with a physiologically acceptable carrier or excipient.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7317698A FR2247234B1 (en) | 1973-05-16 | 1973-05-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1456257A true GB1456257A (en) | 1976-11-24 |
Family
ID=9119403
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2161474A Expired GB1456257A (en) | 1973-05-16 | 1974-05-15 | 2-aminothiazole derivatives |
Country Status (19)
Country | Link |
---|---|
JP (1) | JPS5030888A (en) |
AT (1) | AT334894B (en) |
BE (1) | BE814579A (en) |
CA (1) | CA1057292A (en) |
CH (1) | CH595364A5 (en) |
DD (1) | DD112268A5 (en) |
DE (1) | DE2423403A1 (en) |
ES (1) | ES426206A1 (en) |
FR (1) | FR2247234B1 (en) |
GB (1) | GB1456257A (en) |
HU (1) | HU169176B (en) |
IL (1) | IL44845A (en) |
NL (1) | NL7406490A (en) |
PL (1) | PL91265B1 (en) |
RO (1) | RO66055A (en) |
SE (1) | SE429653B (en) |
SU (1) | SU535906A3 (en) |
YU (1) | YU36712B (en) |
ZA (1) | ZA743048B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4018786A (en) * | 1974-08-06 | 1977-04-19 | Centre D'etudes Pour L'industrie Pharmaceutique | 2-Aminothiazolines and a process for preparation thereof |
GB2550950B (en) * | 2016-06-02 | 2021-03-10 | Dixon Barnaby | Puppet |
-
1973
- 1973-05-16 FR FR7317698A patent/FR2247234B1/fr not_active Expired
- 1973-05-16 RO RO7378803A patent/RO66055A/en unknown
-
1974
- 1974-05-05 SU SU742027407A patent/SU535906A3/en active
- 1974-05-06 BE BE143945A patent/BE814579A/en not_active IP Right Cessation
- 1974-05-11 ES ES426206A patent/ES426206A1/en not_active Expired
- 1974-05-13 ZA ZA00743048A patent/ZA743048B/en unknown
- 1974-05-14 DD DD178502A patent/DD112268A5/xx unknown
- 1974-05-14 DE DE2423403A patent/DE2423403A1/en not_active Withdrawn
- 1974-05-15 CA CA199,994A patent/CA1057292A/en not_active Expired
- 1974-05-15 SE SE7406478A patent/SE429653B/en unknown
- 1974-05-15 CH CH665274A patent/CH595364A5/xx not_active IP Right Cessation
- 1974-05-15 GB GB2161474A patent/GB1456257A/en not_active Expired
- 1974-05-15 HU HUCE999A patent/HU169176B/hu unknown
- 1974-05-15 NL NL7406490A patent/NL7406490A/xx not_active Application Discontinuation
- 1974-05-15 YU YU1332/74A patent/YU36712B/en unknown
- 1974-05-15 AT AT403574A patent/AT334894B/en not_active IP Right Cessation
- 1974-05-16 JP JP49053961A patent/JPS5030888A/ja active Pending
- 1974-05-16 IL IL44845A patent/IL44845A/en unknown
- 1974-05-16 PL PL1974171105A patent/PL91265B1/pl unknown
Also Published As
Publication number | Publication date |
---|---|
ES426206A1 (en) | 1976-07-01 |
CA1057292A (en) | 1979-06-26 |
ATA403574A (en) | 1976-06-15 |
FR2247234A1 (en) | 1975-05-09 |
SU535906A3 (en) | 1976-11-15 |
YU133274A (en) | 1982-06-18 |
PL91265B1 (en) | 1977-02-28 |
IL44845A (en) | 1977-06-30 |
YU36712B (en) | 1984-08-31 |
AT334894B (en) | 1977-02-10 |
BE814579A (en) | 1974-09-02 |
RO66055A (en) | 1981-07-30 |
FR2247234B1 (en) | 1977-01-21 |
NL7406490A (en) | 1974-11-19 |
IL44845A0 (en) | 1974-07-31 |
DD112268A5 (en) | 1975-04-05 |
SE429653B (en) | 1983-09-19 |
AU6889574A (en) | 1975-11-20 |
ZA743048B (en) | 1975-05-28 |
DE2423403A1 (en) | 1974-12-05 |
HU169176B (en) | 1976-10-28 |
CH595364A5 (en) | 1978-02-15 |
JPS5030888A (en) | 1975-03-27 |
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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 |