ZA200102653B - Thiazole-derivatives. - Google Patents
Thiazole-derivatives. Download PDFInfo
- Publication number
- ZA200102653B ZA200102653B ZA200102653A ZA200102653A ZA200102653B ZA 200102653 B ZA200102653 B ZA 200102653B ZA 200102653 A ZA200102653 A ZA 200102653A ZA 200102653 A ZA200102653 A ZA 200102653A ZA 200102653 B ZA200102653 B ZA 200102653B
- Authority
- ZA
- South Africa
- Prior art keywords
- compounds
- thiazole
- alkyl
- amino
- zero
- Prior art date
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- 150000007979 thiazole derivatives Chemical class 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- 125000000732 arylene group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000005864 Sulphur Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- AMFRMGIAYPGXEC-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-2-(2-ethoxy-2-oxoethoxy)benzoate Chemical compound C1=C(OCC(=O)OCC)C(C(=O)OCC(=O)OCC)=CC(NC(=O)C=2N=C(NC(=O)NCC=3C=CC=CC=3)SC=2)=C1 AMFRMGIAYPGXEC-UHFFFAOYSA-N 0.000 claims description 5
- GRWLSDUFGPHETK-UHFFFAOYSA-N ethyl 2-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-2-methoxyphenoxy]acetate Chemical compound C1=C(OC)C(OCC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 GRWLSDUFGPHETK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- QPHMNVXNTWDNCO-JLHYYAGUSA-N ethyl (e)-3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]prop-2-enoate Chemical compound C1=CC(/C=C/C(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 QPHMNVXNTWDNCO-JLHYYAGUSA-N 0.000 claims description 4
- ZBPSCFWGTVZZPK-UHFFFAOYSA-N ethyl 2-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 ZBPSCFWGTVZZPK-UHFFFAOYSA-N 0.000 claims description 4
- MNLUULFDPCPGMS-UHFFFAOYSA-N 2-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 MNLUULFDPCPGMS-UHFFFAOYSA-N 0.000 claims description 3
- ZYINPTSVIAGRBY-UHFFFAOYSA-N 5-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-2-(carboxymethoxy)benzoic acid Chemical compound C1=C(C(O)=O)C(OCC(=O)O)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 ZYINPTSVIAGRBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- -1 dimethyl-cyclopropyl Chemical group 0.000 description 59
- 230000000875 corresponding effect Effects 0.000 description 47
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 230000004614 tumor growth Effects 0.000 description 7
- GPIQOFWTZXXOOV-UHFFFAOYSA-N 2-chloro-4,6-dimethoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(OC)=N1 GPIQOFWTZXXOOV-UHFFFAOYSA-N 0.000 description 6
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- NNRFRJQMBSBXGO-CIUDSAMLSA-N (3s)-3-[[2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-4-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-oxobutanoic acid Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(O)=O NNRFRJQMBSBXGO-CIUDSAMLSA-N 0.000 description 5
- OCZSTRUXDUIHAL-UHFFFAOYSA-N 2-(benzylcarbamoylamino)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 OCZSTRUXDUIHAL-UHFFFAOYSA-N 0.000 description 5
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
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- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 description 4
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- CTDVHLYFOZQCKK-UHFFFAOYSA-N butyl 2-(3-aminopropoxy)acetate;hydrochloride Chemical compound Cl.CCCCOC(=O)COCCCN CTDVHLYFOZQCKK-UHFFFAOYSA-N 0.000 description 4
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- NZRQKOPSAWBGNV-UHFFFAOYSA-N 2-[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]propoxy]acetic acid;hydrochloride Chemical compound Cl.CC=1N=C(NC(N)=N)SC=1C(=O)NCCCOCC(O)=O NZRQKOPSAWBGNV-UHFFFAOYSA-N 0.000 description 2
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- NRPMBSHHBFFYBF-VMPITWQZSA-N ethyl (e)-3-(4-aminophenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(N)C=C1 NRPMBSHHBFFYBF-VMPITWQZSA-N 0.000 description 1
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98119985 | 1998-10-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200102653B true ZA200102653B (en) | 2002-07-01 |
Family
ID=8232838
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200102653A ZA200102653B (en) | 1998-10-22 | 2001-03-30 | Thiazole-derivatives. |
Country Status (31)
Country | Link |
---|---|
US (1) | US6297266B1 (no) |
EP (1) | EP1123283B1 (no) |
JP (1) | JP3530137B2 (no) |
KR (1) | KR100469219B1 (no) |
CN (1) | CN1211375C (no) |
AR (1) | AR023058A1 (no) |
AT (1) | ATE266012T1 (no) |
AU (1) | AU760219B2 (no) |
BR (1) | BR9914666A (no) |
CA (1) | CA2347741C (no) |
CO (1) | CO5150186A1 (no) |
CZ (1) | CZ20011395A3 (no) |
DE (1) | DE69917058T2 (no) |
DK (1) | DK1123283T3 (no) |
ES (1) | ES2221482T3 (no) |
HK (1) | HK1047281A1 (no) |
HR (1) | HRP20010275A2 (no) |
HU (1) | HUP0104202A3 (no) |
ID (1) | ID28356A (no) |
IL (1) | IL142090A0 (no) |
MA (1) | MA26756A1 (no) |
NO (1) | NO20011908L (no) |
NZ (1) | NZ510676A (no) |
PE (1) | PE20001116A1 (no) |
PL (1) | PL347427A1 (no) |
PT (1) | PT1123283E (no) |
RU (1) | RU2214404C2 (no) |
TR (1) | TR200101115T2 (no) |
WO (1) | WO2000024724A1 (no) |
YU (1) | YU29201A (no) |
ZA (1) | ZA200102653B (no) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2391550T3 (es) | 1999-04-15 | 2012-11-27 | Bristol-Myers Squibb Company | Inhibidores cíclicos de la proteína tirosina quinasa |
US7125875B2 (en) | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
NZ520143A (en) * | 2000-01-19 | 2005-01-28 | Alteon Inc | Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging |
ATE357444T1 (de) | 2000-08-17 | 2007-04-15 | Lumera Corp | Design und synthese von nlo-materialien für electro-optische anwendungen, die von thiophen abgeleitet sind |
EP1347971B1 (en) | 2000-12-21 | 2006-03-01 | Bristol-Myers Squibb Company | Thiazolyl inhibitors of tec family tyrosine kinases |
EA012607B1 (ru) * | 2004-09-20 | 2009-10-30 | 4Сц Аг | НОВЫЕ ГЕТЕРОЦИКЛИЧЕСКИЕ ИНГИБИТОРЫ NF-κB |
UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
WO2010012793A1 (en) * | 2008-08-01 | 2010-02-04 | Bayer Cropscience Sa | Fungicide aminothiazole derivatives |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL95548A0 (en) * | 1989-09-15 | 1991-06-30 | Fujisawa Pharmaceutical Co | Thiazole derivatives,processes for the preparation thereof and pharmaceutical composition containing the same |
CA2037153A1 (en) * | 1990-03-09 | 1991-09-10 | Leo Alig | Acetic acid derivatives |
US5273982A (en) | 1990-03-09 | 1993-12-28 | Hoffmann-La Roche Inc. | Acetic acid derivatives |
US6306840B1 (en) * | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
JPH0987237A (ja) * | 1995-09-21 | 1997-03-31 | Kyowa Hakko Kogyo Co Ltd | 芳香族誘導体 |
EP0928793B1 (en) * | 1998-01-02 | 2002-05-15 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
EP0928790B1 (en) * | 1998-01-02 | 2003-03-05 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
-
1999
- 1999-10-15 CZ CZ20011395A patent/CZ20011395A3/cs unknown
- 1999-10-15 AT AT99970988T patent/ATE266012T1/de not_active IP Right Cessation
- 1999-10-15 DE DE69917058T patent/DE69917058T2/de not_active Expired - Fee Related
- 1999-10-15 TR TR2001/01115T patent/TR200101115T2/xx unknown
- 1999-10-15 DK DK99970988T patent/DK1123283T3/da active
- 1999-10-15 AU AU11519/00A patent/AU760219B2/en not_active Ceased
- 1999-10-15 NZ NZ510676A patent/NZ510676A/xx unknown
- 1999-10-15 PT PT99970988T patent/PT1123283E/pt unknown
- 1999-10-15 ID IDW20010863A patent/ID28356A/id unknown
- 1999-10-15 ES ES99970988T patent/ES2221482T3/es not_active Expired - Lifetime
- 1999-10-15 KR KR10-2001-7004899A patent/KR100469219B1/ko not_active IP Right Cessation
- 1999-10-15 PL PL99347427A patent/PL347427A1/xx not_active Application Discontinuation
- 1999-10-15 CN CNB998124265A patent/CN1211375C/zh not_active Expired - Fee Related
- 1999-10-15 RU RU2001113285/04A patent/RU2214404C2/ru not_active IP Right Cessation
- 1999-10-15 IL IL14209099A patent/IL142090A0/xx unknown
- 1999-10-15 JP JP2000578294A patent/JP3530137B2/ja not_active Expired - Fee Related
- 1999-10-15 EP EP99970988A patent/EP1123283B1/en not_active Expired - Lifetime
- 1999-10-15 HU HU0104202A patent/HUP0104202A3/hu unknown
- 1999-10-15 BR BR9914666-5A patent/BR9914666A/pt not_active IP Right Cessation
- 1999-10-15 WO PCT/EP1999/007824 patent/WO2000024724A1/en active IP Right Grant
- 1999-10-15 CA CA002347741A patent/CA2347741C/en not_active Expired - Fee Related
- 1999-10-15 YU YU29201A patent/YU29201A/sh unknown
- 1999-10-18 PE PE1999001048A patent/PE20001116A1/es not_active Application Discontinuation
- 1999-10-19 US US09/420,387 patent/US6297266B1/en not_active Expired - Fee Related
- 1999-10-20 CO CO99066263A patent/CO5150186A1/es unknown
- 1999-10-20 AR ARP990105306A patent/AR023058A1/es not_active Application Discontinuation
-
2001
- 2001-03-30 ZA ZA200102653A patent/ZA200102653B/en unknown
- 2001-04-12 HR HR20010275A patent/HRP20010275A2/hr not_active Application Discontinuation
- 2001-04-18 NO NO20011908A patent/NO20011908L/no not_active Application Discontinuation
- 2001-04-20 MA MA26171A patent/MA26756A1/fr unknown
-
2002
- 2002-12-09 HK HK02108922.4A patent/HK1047281A1/zh unknown
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