IL127784A - History of thiazole, their preparation and pharmaceutical preparations containing them - Google Patents

History of thiazole, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL127784A
Authority: IL; Israel
Prior art keywords: compounds; carbonyl; thiazole; guanidino; ylmethoxy
Prior art date: 1998-01-02

Application number

IL12778498A

Other languages

English (en)

Hebrew (he)

Other versions

IL127784A0 (en

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1998-01-02

Filing date

1998-12-29

Publication date

2001-09-13

1998-12-29 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1999-10-28 Publication of IL127784A0 publication Critical patent/IL127784A0/xx

2001-09-13 Publication of IL127784A publication Critical patent/IL127784A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 4
150000007979 thiazole derivatives Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 87
125000000217 alkyl group Chemical group 0.000 claims abstract description 43
150000002148 esters Chemical class 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 24
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 14
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
125000005330 8 membered heterocyclic group Chemical group 0.000 claims abstract description 6
125000003277 amino group Chemical group 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 54
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
238000000034 method Methods 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 18
206010028980 Neoplasm Diseases 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
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238000004519 manufacturing process Methods 0.000 claims description 15
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RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
239000000853 adhesive Substances 0.000 claims description 11
230000001070 adhesive effect Effects 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
230000002792 vascular Effects 0.000 claims description 11
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238000011282 treatment Methods 0.000 claims description 10
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208000001647 Renal Insufficiency Diseases 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 9
206010003246 arthritis Diseases 0.000 claims description 9
201000006370 kidney failure Diseases 0.000 claims description 9
208000002780 macular degeneration Diseases 0.000 claims description 9
208000027202 mammary Paget disease Diseases 0.000 claims description 9
208000037803 restenosis Diseases 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
230000007257 malfunction Effects 0.000 claims description 6
238000002560 therapeutic procedure Methods 0.000 claims description 6
IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
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125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
230000003480 fibrinolytic effect Effects 0.000 claims description 2
239000000106 platelet aggregation inhibitor Substances 0.000 claims description 2
240000005020 Acaciella glauca Species 0.000 claims 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
206010027476 Metastases Diseases 0.000 claims 1
208000017442 Retinal disease Diseases 0.000 claims 1
206010038923 Retinopathy Diseases 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
125000004430 oxygen atom Chemical group O* 0.000 abstract description 4
229910052760 oxygen Inorganic materials 0.000 abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
-1 dimethyl-cyclopropyl Chemical group 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 31
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125000001424 substituent group Chemical group 0.000 description 19
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
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239000002904 solvent Substances 0.000 description 11
125000003545 alkoxy group Chemical group 0.000 description 10
239000000872 buffer Substances 0.000 description 10
229910052736 halogen Inorganic materials 0.000 description 10
150000002367 halogens Chemical class 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
239000000047 product Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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239000002585 base Substances 0.000 description 9
230000008878 coupling Effects 0.000 description 9
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238000005859 coupling reaction Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
206010012689 Diabetic retinopathy Diseases 0.000 description 8
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000006260 foam Substances 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
OJOGDTMEXJQOQA-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=C(NC(N)=N)SC=1C(O)=O OJOGDTMEXJQOQA-UHFFFAOYSA-N 0.000 description 7
108010049003 Fibrinogen Proteins 0.000 description 7
102000008946 Fibrinogen Human genes 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
229940012952 fibrinogen Drugs 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000002671 adjuvant Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
125000004356 hydroxy functional group Chemical group O* 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000012071 phase Substances 0.000 description 6
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
PMTHDFWWLRZBAG-UHFFFAOYSA-N 2-(piperidin-3-ylmethoxy)acetic acid;hydrochloride Chemical compound Cl.OC(=O)COCC1CCCNC1 PMTHDFWWLRZBAG-UHFFFAOYSA-N 0.000 description 5
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
230000000694 effects Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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239000001828 Gelatine Substances 0.000 description 4
101000829980 Homo sapiens Ral guanine nucleotide dissociation stimulator Proteins 0.000 description 4
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
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102100023320 Ral guanine nucleotide dissociation stimulator Human genes 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
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DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical group C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
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AYKYVVQCWGHYET-UHFFFAOYSA-N ethyl 3-(piperidine-3-carbonylamino)propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CCNC(=O)C1CCCNC1 AYKYVVQCWGHYET-UHFFFAOYSA-N 0.000 description 3
KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 3
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238000005984 hydrogenation reaction Methods 0.000 description 3
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Classifications

- 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
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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
- 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

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Oncology (AREA)
Orthopedic Medicine & Surgery (AREA)
Hematology (AREA)
Communicable Diseases (AREA)
Diabetes (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Nutrition Science (AREA)
Obesity (AREA)
Virology (AREA)
Cardiology (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

IL12778498A 1998-01-02 1998-12-29 History of thiazole, their preparation and pharmaceutical preparations containing them IL127784A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98100007		1998-01-02

Publications (2)

Publication Number	Publication Date
IL127784A0 IL127784A0 (en)	1999-10-28
IL127784A true IL127784A (en)	2001-09-13

Family

ID=8231230

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12778498A IL127784A (en)	1998-01-02	1998-12-29	History of thiazole, their preparation and pharmaceutical preparations containing them

Country Status (28)

Country	Link
US (1)	US6001855A (de)
JP (1)	JP3154982B2 (de)
KR (1)	KR100312900B1 (de)
CN (1)	CN1098849C (de)
AR (1)	AR014211A1 (de)
AT (1)	ATE217621T1 (de)
AU (1)	AU718659B2 (de)
BR (1)	BR9805750A (de)
CA (1)	CA2257322C (de)
CO (1)	CO4990935A1 (de)
DE (1)	DE69805392T2 (de)
DK (1)	DK0928793T3 (de)
ES (1)	ES2176895T3 (de)
HR (1)	HRP980644B1 (de)
HU (1)	HUP9803041A3 (de)
ID (1)	ID21878A (de)
IL (1)	IL127784A (de)
MA (1)	MA26590A1 (de)
NO (1)	NO312134B1 (de)
PE (1)	PE20000116A1 (de)
PL (1)	PL330620A1 (de)
PT (1)	PT928793E (de)
RU (1)	RU2166503C2 (de)
SG (1)	SG72911A1 (de)
TR (1)	TR199802766A2 (de)
UY (1)	UY25335A1 (de)
YU (1)	YU60998A (de)
ZA (1)	ZA9811923B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HUP0104202A3 (en)	1998-10-22	2003-12-29	Hoffmann La Roche	Thiazole-derivatives, process for their preparation and pharmaceutical compositions containing them
JP4517454B2 (ja) *	2000-06-01	2010-08-04	宇部興産株式会社	４−（１−フルオロエチル）チアゾール−５−カルボン酸アミド誘導体及び農園芸用の有害生物防除剤
US6420566B2 (en) *	2000-06-09	2002-07-16	Aventis Pharma S.A.	Pharmaceutical compositions containing a 4, 5-dihydro-1, 3-thiazol-2-ylamine derivative, novel derivatives and preparation thereof
US6451821B1 (en) *	2000-06-09	2002-09-17	Aventis Pharma S.A.	Use of 2-aminothiazoline derivatives as inhibitors of inducible no-synthase
WO2017095991A1 (en) *	2015-12-04	2017-06-08	Janssen Biotech, Inc.	Treatment of retinal degeneration using progenitor cells

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2138803B (en) *	1983-04-26	1986-06-18	Shionogi & Co	2-guanidino-4-hydroxymethylthiazole and derivatives thereof
GB8714920D0 (en) *	1987-06-25	1987-07-29	Shell Int Research	Thiazole derivatives
IL95548A0 (en) *	1989-09-15	1991-06-30	Fujisawa Pharmaceutical Co	Thiazole derivatives,processes for the preparation thereof and pharmaceutical composition containing the same
TW201303B (de) *	1990-07-05	1993-03-01	Hoffmann La Roche
JPH0867676A (ja) *	1994-03-30	1996-03-12	Eisai Kagaku Kk	保護アミノチアゾリル酢酸誘導体
IL123164A (en) *	1995-08-30	2001-03-19	Searle & Co	Meta-guanidine urea thiourea or azacyclic amino benzoic acid derivatives and pharmaceutical compositions containing them
AU713676B2 (en) *	1996-01-16	1999-12-09	Merck & Co., Inc.	Integrin receptor antagonists
KR19980071340A (ko) *	1997-02-13	1998-10-26	미우라 유이찌	클로로아세틸아미노티아졸아세트산 유도체의 제조 방법
WO1998054164A1 (en) *	1997-05-30	1998-12-03	Takeda Chemical Industries, Ltd.	Sulfonamide derivatives, their production and use

1998
- 1998-12-22 US US09/218,200 patent/US6001855A/en not_active Expired - Fee Related
- 1998-12-28 NO NO19986160A patent/NO312134B1/no unknown
- 1998-12-29 PE PE1998001292A patent/PE20000116A1/es not_active Application Discontinuation
- 1998-12-29 ZA ZA9811923A patent/ZA9811923B/xx unknown
- 1998-12-29 HR HR980644A patent/HRP980644B1/xx not_active IP Right Cessation
- 1998-12-29 IL IL12778498A patent/IL127784A/en not_active IP Right Cessation
- 1998-12-29 AR ARP980106722A patent/AR014211A1/es not_active Application Discontinuation
- 1998-12-29 YU YU60998A patent/YU60998A/sh unknown
- 1998-12-30 DK DK98124819T patent/DK0928793T3/da active
- 1998-12-30 ES ES98124819T patent/ES2176895T3/es not_active Expired - Lifetime
- 1998-12-30 CA CA002257322A patent/CA2257322C/en not_active Expired - Fee Related
- 1998-12-30 AU AU96145/98A patent/AU718659B2/en not_active Ceased
- 1998-12-30 MA MA25410A patent/MA26590A1/fr unknown
- 1998-12-30 HU HU9803041A patent/HUP9803041A3/hu unknown
- 1998-12-30 PL PL98330620A patent/PL330620A1/xx not_active Application Discontinuation
- 1998-12-30 KR KR1019980061644A patent/KR100312900B1/ko not_active Expired - Fee Related
- 1998-12-30 TR TR1998/02766A patent/TR199802766A2/xx unknown
- 1998-12-30 DE DE69805392T patent/DE69805392T2/de not_active Expired - Fee Related
- 1998-12-30 PT PT98124819T patent/PT928793E/pt unknown
- 1998-12-30 CO CO98077474A patent/CO4990935A1/es unknown
- 1998-12-30 SG SG1998005979A patent/SG72911A1/en unknown
- 1998-12-30 AT AT98124819T patent/ATE217621T1/de not_active IP Right Cessation
- 1998-12-31 UY UY25335A patent/UY25335A1/es not_active IP Right Cessation
- 1998-12-31 BR BR9805750-2A patent/BR9805750A/pt not_active Application Discontinuation
- 1998-12-31 CN CN98125981A patent/CN1098849C/zh not_active Expired - Fee Related
1999
- 1999-01-04 ID IDP990002A patent/ID21878A/id unknown
- 1999-01-04 JP JP00020699A patent/JP3154982B2/ja not_active Expired - Fee Related
- 1999-01-05 RU RU99100205/04A patent/RU2166503C2/ru not_active IP Right Cessation

Also Published As

Publication number	Publication date
TR199802766A3 (tr)	1999-07-21
TR199802766A2 (xx)	1999-07-21
PE20000116A1 (es)	2000-02-11
PT928793E (pt)	2002-10-31
CO4990935A1 (es)	2000-12-26
HUP9803041A3 (en)	2001-04-28
CN1098849C (zh)	2003-01-15
AU718659B2 (en)	2000-04-20
ID21878A (id)	1999-08-05
MA26590A1 (fr)	2004-12-20
NO312134B1 (no)	2002-03-25
PL330620A1 (en)	1999-07-05
JP2000053678A (ja)	2000-02-22
US6001855A (en)	1999-12-14
ZA9811923B (en)	2000-06-29
KR19990066903A (ko)	1999-08-16
RU2166503C2 (ru)	2001-05-10
AR014211A1 (es)	2001-02-07
HU9803041D0 (en)	1999-02-01
NO986160L (no)	1999-07-05
JP3154982B2 (ja)	2001-04-09
YU60998A (sh)	2001-12-26
BR9805750A (pt)	2001-04-24
DE69805392D1 (de)	2002-06-20
HK1021733A1 (en)	2000-06-30
DE69805392T2 (de)	2002-12-19
KR100312900B1 (ko)	2002-01-17
HRP980644A2 (en)	1999-10-31
CA2257322C (en)	2003-11-04
IL127784A0 (en)	1999-10-28
AU9614598A (en)	1999-07-22
NO986160D0 (no)	1998-12-28
CA2257322A1 (en)	1999-07-02
UY25335A1 (es)	2001-01-31
CN1227225A (zh)	1999-09-01
HRP980644B1 (en)	2003-08-31
DK0928793T3 (da)	2002-09-09
ATE217621T1 (de)	2002-06-15
ES2176895T3 (es)	2002-12-01
SG72911A1 (en)	2000-05-23
HUP9803041A2 (hu)	2000-04-28

Legal Events

Date	Code	Title	Description
2005-02-20	KB	Patent renewed
2010-04-08	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0928790B1 (de)	2003-03-05	Thiazole Derivate
RS60998B1 (sr)	2020-11-30	Antitela koja sadrže modifikovane regione teškog lanca
US6320054B1 (en)	2001-11-20	Thiazole derivatives
WO2001004103A1 (en)	2001-01-18	Benzazepinones and quinazolines
EP0928793B1 (de)	2002-05-15	Thiazol-Derivate
CA2257322C (en)	2003-11-04	Thiazole derivatives
US6297266B1 (en)	2001-10-02	Thiazole derivatives
MXPA99000216A (en)	2000-06-01	Derivatives of tia
CZ437198A3 (cs)	2000-01-12	Deriváty thiazolu
CZ437098A3 (cs)	2000-01-12	Deriváty thiazolu
MXPA01004000A (en)	2001-11-21	Thiazole-derivatives