GB1481465A - Thiazole derivatives and the production thereof - Google Patents
Thiazole derivatives and the production thereofInfo
- Publication number
- GB1481465A GB1481465A GB4504874A GB4504874A GB1481465A GB 1481465 A GB1481465 A GB 1481465A GB 4504874 A GB4504874 A GB 4504874A GB 4504874 A GB4504874 A GB 4504874A GB 1481465 A GB1481465 A GB 1481465A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- hydrolysis
- thiazole
- general formula
- 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
- 150000007979 thiazole derivatives Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 230000007062 hydrolysis Effects 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 150000003557 thiazoles Chemical class 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- 150000007960 acetonitrile Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 238000007333 cyanation reaction Methods 0.000 abstract 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 1
- 125000006843 cycloalkyl-C1-5-alkyl Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 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
- 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
- C07D277/34—Oxygen 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
-
- 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
- C07D277/36—Sulfur 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
- C07D277/42—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
- C07D277/20—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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11958373A JPS565747B2 (enrdf_load_stackoverflow) | 1973-10-24 | 1973-10-24 | |
| JP12153473A JPS5742629B2 (enrdf_load_stackoverflow) | 1973-10-29 | 1973-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1481465A true GB1481465A (en) | 1977-07-27 |
Family
ID=26457278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4504874A Expired GB1481465A (en) | 1973-10-24 | 1974-10-17 | Thiazole derivatives and the production thereof |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1051906A (enrdf_load_stackoverflow) |
| DE (1) | DE2450617C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2248835B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1481465A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088008A1 (en) * | 1982-02-26 | 1983-09-07 | Shionogi & Co., Ltd. | Improved process for the production of 2-(4-(2-thiazolyloxy)phenyl)propionic acid |
| WO2006122011A3 (en) * | 2005-05-09 | 2007-05-03 | Achillion Pharmaceuticals Inc | Thiazole compounds and methods of use |
| EP2166006A1 (en) * | 2008-09-18 | 2010-03-24 | Dompe' S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| US9238026B2 (en) | 2011-04-07 | 2016-01-19 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
| US9493402B2 (en) | 2001-02-27 | 2016-11-15 | Dompé Farmaceutici S.P.A. | Omega-aminoalkylamides of R-2-aryl-propionic acids as inhibitors of the chemotaxis of polymorphonucleate and mononucleate cells |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2500452A1 (fr) * | 1981-02-26 | 1982-08-27 | Roussel Uclaf | Alcools heterocycliques et derives fonctionnels, ainsi que leur procede de preparation |
| AU628485B2 (en) * | 1989-02-23 | 1992-09-17 | Otsuka Pharmaceutical Factory, Inc. | P-aminophenol derivative and production and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1145884A (en) * | 1966-11-18 | 1969-03-19 | Wyeth John & Brother Ltd | Thiazole derivatives |
-
1974
- 1974-10-09 CA CA211,104A patent/CA1051906A/en not_active Expired
- 1974-10-17 GB GB4504874A patent/GB1481465A/en not_active Expired
- 1974-10-23 FR FR7435615A patent/FR2248835B1/fr not_active Expired
- 1974-10-24 DE DE19742450617 patent/DE2450617C2/de not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088008A1 (en) * | 1982-02-26 | 1983-09-07 | Shionogi & Co., Ltd. | Improved process for the production of 2-(4-(2-thiazolyloxy)phenyl)propionic acid |
| US9493402B2 (en) | 2001-02-27 | 2016-11-15 | Dompé Farmaceutici S.P.A. | Omega-aminoalkylamides of R-2-aryl-propionic acids as inhibitors of the chemotaxis of polymorphonucleate and mononucleate cells |
| WO2006122011A3 (en) * | 2005-05-09 | 2007-05-03 | Achillion Pharmaceuticals Inc | Thiazole compounds and methods of use |
| US8088806B2 (en) | 2005-05-09 | 2012-01-03 | Achillion Pharmaceuticals, Inc. | Thiazole compounds and methods of use |
| EP2166006A1 (en) * | 2008-09-18 | 2010-03-24 | Dompe' S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| WO2010031835A3 (en) * | 2008-09-18 | 2010-06-24 | Dompe' S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| US8624036B2 (en) | 2008-09-18 | 2014-01-07 | Dompe S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| RU2520212C2 (ru) * | 2008-09-18 | 2014-06-20 | Домпе С.П.А. | 2-арилпропионовые кислоты и производные, и фармацевтические композиции, содержащие указанные соединения |
| AU2009294558B2 (en) * | 2008-09-18 | 2014-12-18 | Dompe' Farmaceutici S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
| US9238026B2 (en) | 2011-04-07 | 2016-01-19 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2450617A1 (de) | 1975-04-30 |
| DE2450617C2 (de) | 1984-11-22 |
| FR2248835A1 (enrdf_load_stackoverflow) | 1975-05-23 |
| FR2248835B1 (enrdf_load_stackoverflow) | 1977-09-09 |
| AU7454974A (en) | 1976-04-29 |
| CA1051906A (en) | 1979-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |