GB1464259A - Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents - Google Patents
Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agentsInfo
- Publication number
- GB1464259A GB1464259A GB4430374A GB4430374A GB1464259A GB 1464259 A GB1464259 A GB 1464259A GB 4430374 A GB4430374 A GB 4430374A GB 4430374 A GB4430374 A GB 4430374A GB 1464259 A GB1464259 A GB 1464259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- compounds
- alkyl
- thiadiazole
- 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
- UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical compound C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title abstract 2
- 229940124597 therapeutic agent Drugs 0.000 title 1
- -1 acetoxy, hydroxy Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000002541 furyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052740 iodine Chemical group 0.000 abstract 2
- 239000011630 iodine Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- LBLZPOGZQOBQKC-UHFFFAOYSA-N thiadiazole-4-sulfonamide Chemical class NS(=O)(=O)C1=CSN=N1 LBLZPOGZQOBQKC-UHFFFAOYSA-N 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- WKXVETMYCFRGET-UHFFFAOYSA-N 1,3-thiazole-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CS1 WKXVETMYCFRGET-UHFFFAOYSA-N 0.000 abstract 1
- 101100188552 Arabidopsis thaliana OCT3 gene Proteins 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1464259 Imidazo-thiazole and thiadiazole sulphonamides PFIZER Ltd 3 Oct 1975 [12 Oct 1974] 44303/74 Heading C2C The invention comprises compounds of the general Formula I wherein X represents N or CH; and R and R<SP>1</SP>, which may be the same or different, each represent a hydrogen atom; a C 1 -C 10 alkyl group; a C 1 to C 4 alkyl group substituted by an aryl, heteroaryl or C 3 -C 10 cycloalkyl group; a phenyl group; a pyridyl group; a thienyl group; a furyl group; a phenyl, pyridyl, thienyl or furyl group substituted by one or more groups selected from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, acetoxy, hydroxy, halogen, nitro, amino, C 2 -C 5 acylamino, C 1 -C 4 alkylsulphonylamino and sulphamoyl; a carbethoxy group; an adamantyl group; or a C 3 -C 10 cycloalkyl group; or R and R<SP>1</SP> taken together represent an alkylene group of the formula -(OH 2 ) n - wherein n is 3, 4 or 5, said alkylene group being optionally substituted by one or more C 1 -C 4 alkyl groups; and the pharmaceutically acceptable acid addition or alkali metal salts of the compounds of the Formula (I) which form such salts. The compounds of Formula I may be prepared by reacting a thiazole sulphonamide or thiadiazole sulphonamide of formula with either (a) an α-halo carbonyl compound of the formula R<SP>1</SP>.COCH(R)(Y) where R and R<SP>1</SP> are as above and Y is bromine, chlorine or iodine with the proviso that when R and R<SP>1</SP> are both hydrogen Y is chlorine or (b) an acetal of formula R<SP>1</SP>.C(OR<SP>2</SP>) 2 .CH(R)(Y) where R and R<SP>1</SP> are as defined above, R<SP>2</SP> is a C 1 to C 4 alkyl group and Y is bromine, chlorine or iodine. The compounds of Formula I are used as pharmaceuticals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4430374A GB1464259A (en) | 1975-10-03 | 1975-10-03 | Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4430374A GB1464259A (en) | 1975-10-03 | 1975-10-03 | Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1464259A true GB1464259A (en) | 1977-02-09 |
Family
ID=10432666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4430374A Expired GB1464259A (en) | 1975-10-03 | 1975-10-03 | Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1464259A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4265898A (en) * | 1978-05-31 | 1981-05-05 | Bayer Aktiengesellschaft | Imidazo[2,1-b]-[1,3,4]-thiadiazole compounds, composition and their medicinal use |
| FR2646159A1 (en) * | 1989-04-19 | 1990-10-26 | Roussel Uclaf | PROCESS FOR THE PREPARATION OF IMIDAZO (2,1-B) BENZOTHIAZOLES AND THEIR SALTS, THE NEW PRODUCTS THUS OBTAINED, THE MEDICINAL APPLICATION OF THESE NEW PRODUCTS AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THEM |
| WO2003051890A1 (en) * | 2001-12-14 | 2003-06-26 | Aegera Therapeutics Inc. | Imidazo [2,1-b]-1,3,4-thiadiazole suflonamides |
| WO2004111061A1 (en) * | 2003-06-13 | 2004-12-23 | Aegera Therapeutics Inc. | ACYLATED AND NON-ACYLATED IMIDAZO[2,1-b]-1,3,4,-THIADIAZOLE-2-SULFONAMIDES, AND USES THEREOF |
| WO2009040552A2 (en) * | 2007-09-27 | 2009-04-02 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Substituted imidazo (2, 1-b) -1, 3, 4-thiazole compounds, their pharmaceutical compositions and uses thereof |
| JP2014511883A (en) * | 2011-04-18 | 2014-05-19 | ユセベ ファルマ ソシエテ アノニム | 2-Oxo-1-imidazolidinyl imidazoliadiazole derivatives |
| US8815918B2 (en) | 2009-04-02 | 2014-08-26 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Imidazo [2, 1-B] [1, 3, 4] thiadiazole derivatives |
| WO2020045638A1 (en) | 2018-08-30 | 2020-03-05 | 日本メジフィジックス株式会社 | Radioactive imidazothiadiazole derivative compound |
-
1975
- 1975-10-03 GB GB4430374A patent/GB1464259A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4265898A (en) * | 1978-05-31 | 1981-05-05 | Bayer Aktiengesellschaft | Imidazo[2,1-b]-[1,3,4]-thiadiazole compounds, composition and their medicinal use |
| FR2646159A1 (en) * | 1989-04-19 | 1990-10-26 | Roussel Uclaf | PROCESS FOR THE PREPARATION OF IMIDAZO (2,1-B) BENZOTHIAZOLES AND THEIR SALTS, THE NEW PRODUCTS THUS OBTAINED, THE MEDICINAL APPLICATION OF THESE NEW PRODUCTS AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THEM |
| US7741349B2 (en) | 2001-12-14 | 2010-06-22 | Aegera Therapeutics Inc. | Imidazo[2, 1-b]-1,3,4-thiadiazole sulfonamides |
| WO2003051890A1 (en) * | 2001-12-14 | 2003-06-26 | Aegera Therapeutics Inc. | Imidazo [2,1-b]-1,3,4-thiadiazole suflonamides |
| US7230019B2 (en) * | 2001-12-14 | 2007-06-12 | Aegera Therapeutics, Inc. | Imidazo [2,1-b]-1,3,4-thiadiazole sulfonamides |
| AU2002350333B2 (en) * | 2001-12-14 | 2008-08-21 | Pharmascience Inc. | Imidazo [2,1-b]-1,3,4-thiadiazole suflonamides |
| US20090042953A1 (en) * | 2001-12-14 | 2009-02-12 | Aegera Therapeutics, Inc. | IMIDAZO [2,1,-b]-1,3,4-THIADIAZOLE SULFONAMIDES |
| US7772260B2 (en) | 2001-12-14 | 2010-08-10 | Aegera Therapeutics Inc. | Imidazo[2,1-b]-1,3,4-thiadiazole sulfonamides |
| US7700635B2 (en) | 2001-12-14 | 2010-04-20 | Aegera Therapeutics Inc. | Imidazo[2,1-b]-1,3,4-thiadiazole sulfonamides |
| US7714003B2 (en) | 2001-12-14 | 2010-05-11 | Aegera Therapeutics Inc. | Imidazo[2,1-b ]-1,3,4-thiadiazole sulfonamides |
| JP2010106030A (en) * | 2001-12-14 | 2010-05-13 | Aegera Therapeutics Inc | Imidazo[2, 1-b]-1, 3, 4-thiadiazole sulfonamide |
| WO2004111061A1 (en) * | 2003-06-13 | 2004-12-23 | Aegera Therapeutics Inc. | ACYLATED AND NON-ACYLATED IMIDAZO[2,1-b]-1,3,4,-THIADIAZOLE-2-SULFONAMIDES, AND USES THEREOF |
| WO2009040552A2 (en) * | 2007-09-27 | 2009-04-02 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Substituted imidazo (2, 1-b) -1, 3, 4-thiazole compounds, their pharmaceutical compositions and uses thereof |
| WO2009040552A3 (en) * | 2007-09-27 | 2009-05-22 | Ct Nac De Investigaciones Onco | Substituted imidazo (2, 1-b) -1, 3, 4-thiazole compounds, their pharmaceutical compositions and uses thereof |
| US8563550B2 (en) | 2007-09-27 | 2013-10-22 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Imidazolothiadiazoles for use as protein kinase inhibitors |
| CN101878219B (en) * | 2007-09-27 | 2014-04-02 | 西班牙国家癌症研究中心 | Imidazolothiadiazoles for use as protein kinase inhibitors |
| US8815918B2 (en) | 2009-04-02 | 2014-08-26 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Imidazo [2, 1-B] [1, 3, 4] thiadiazole derivatives |
| JP2014511883A (en) * | 2011-04-18 | 2014-05-19 | ユセベ ファルマ ソシエテ アノニム | 2-Oxo-1-imidazolidinyl imidazoliadiazole derivatives |
| WO2020045638A1 (en) | 2018-08-30 | 2020-03-05 | 日本メジフィジックス株式会社 | Radioactive imidazothiadiazole derivative compound |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2243199A1 (en) | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents | |
| IE37538B1 (en) | New 1,4-dihydropyridine carboxylic acid compounds their production and their medicinal use | |
| GB1418822A (en) | Imidazo-and pyrimido-2,1-b-quinazolin-2-ones and a process for the preparation thereof | |
| SE7807811L (en) | 3-HYDROXICROTONIC ACID DERIVATIVES | |
| GB1464259A (en) | Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents | |
| GB1505885A (en) | Substituted cephalosporins | |
| IE42218L (en) | Pyrazinoisoquinoline derivatives | |
| GB1271466A (en) | Thiocarbamic acid derivatives | |
| GB1482099A (en) | Sulphonamido derivatives | |
| GB1169945A (en) | Pharmaceutical Compositions containing Diphenylalkyl-amine Derivatives | |
| GB1496431A (en) | Plant-protective pyrazines | |
| GB1292737A (en) | Haloepoxides | |
| ES446132A1 (en) | A procedure for the preparation of new derivatives of 2-alkyl (bottom) -2 or 3-cefem-4-carboxylic acid. (Machine-translation by Google Translate, not legally binding) | |
| GB1297401A (en) | ||
| GB1421305A (en) | 1,4-dihydroquinoline derivatives their production and their medicinal use | |
| FR2331335B2 (en) | ||
| GB1494757A (en) | Anhydro-2-mercapto-1,3,4-thiadiazolium hydroxides | |
| GB1477996A (en) | Quinolizine derivatives and their preparation | |
| GB1430188A (en) | Diaza-oxa-bicyclodecane derivatives | |
| ES473991A1 (en) | A procedure for the preparation of new derivatives of acids 1-carba-2-penem-3-carboxilicos. (Machine-translation by Google Translate, not legally binding) | |
| GB1500359A (en) | 4-aminopyrimidine derivatives | |
| GB1495680A (en) | 1-(2-benzoylphenoxy)-2-hydroxy-3-aminopropanes | |
| GB1423430A (en) | Thioamides | |
| GB1282405A (en) | Piperidine spiro compounds and pharmaceutical preparations thereof | |
| GB1501588A (en) | 4,5-disubstituted 2-oxazolealkanoic acids esters and alkali metal salts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |