NO314455B1 - Karboksamidotiazolderivater, fremgangsmåter for fremstilling derav og farmasöytiske blandinger - Google Patents

Karboksamidotiazolderivater, fremgangsmåter for fremstilling derav og farmasöytiske blandinger Download PDF

Info

Publication number: NO314455B1
Authority: NO; Norway
Prior art keywords: chloro; dimethoxyphenyl; cyclohexylethyl; thiazol; ylcarbamoyl
Prior art date: 1997-09-19

Application number

NO20001409A

Other languages

English (en)

Norwegian (no)

Other versions

NO20001409L (no

NO20001409D0 (no

Inventor

Roger Brodin

Robert Boigegrain

Eric Bignon

Jean-Charles Molimard

Dominique Olliero

Original Assignee

Sanofi Synthelabo

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.)

1997-09-19

Filing date

2000-03-17

Publication date

2003-03-24

1997-09-19 Priority claimed from FR9711718A external-priority patent/FR2768737B1/fr

1998-04-23 Priority claimed from FR9805106A external-priority patent/FR2777887B3/fr

2000-03-17 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

2000-03-17 Publication of NO20001409D0 publication Critical patent/NO20001409D0/no

2000-05-16 Publication of NO20001409L publication Critical patent/NO20001409L/no

2003-03-24 Publication of NO314455B1 publication Critical patent/NO314455B1/no

Links

238000000034 method Methods 0.000 title claims description 45
238000002360 preparation method Methods 0.000 title claims description 16
230000008569 process Effects 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title description 3
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239000000203 mixture Substances 0.000 claims description 185
239000011734 sodium Substances 0.000 claims description 65
-1 acetyloxy, methoxy, ethoxy, methylthio Chemical group 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 30
239000012453 solvate Substances 0.000 claims description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
229910052708 sodium Inorganic materials 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 14
229940079593 drug Drugs 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 12
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
230000008878 coupling Effects 0.000 claims description 6
238000010168 coupling process Methods 0.000 claims description 6
238000005859 coupling reaction Methods 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
NFDFTMICKVDYLQ-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5,7-dimethylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC NFDFTMICKVDYLQ-UHFFFAOYSA-N 0.000 claims description 5
ITSFURYNWBMEFN-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC ITSFURYNWBMEFN-UHFFFAOYSA-N 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
208000008589 Obesity Diseases 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
208000012661 Dyskinesia Diseases 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
159000000001 potassium salts Chemical class 0.000 claims description 3
AGOJEFQTAMTJHV-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4,5-dimethylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(C)C(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC AGOJEFQTAMTJHV-UHFFFAOYSA-N 0.000 claims description 2
WYNBPYGACGYHSD-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methoxyindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=CC(OC)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC WYNBPYGACGYHSD-UHFFFAOYSA-N 0.000 claims description 2
VZVMSBUIQNSYBC-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=CC(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC VZVMSBUIQNSYBC-UHFFFAOYSA-N 0.000 claims description 2
HYGJUCCSZDXPRF-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methoxyindol-1-yl]acetic acid Chemical compound C=1C2=CC(OC)=CC=C2N(CC(O)=O)C=1C(=O)NC(S1)=NC(C=2C(=CC(Cl)=C(OC)C=2)OC)=C1CCC1CCCCC1 HYGJUCCSZDXPRF-UHFFFAOYSA-N 0.000 claims description 2
MFWRPGPURWSDCK-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C)C=CC=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC MFWRPGPURWSDCK-UHFFFAOYSA-N 0.000 claims description 2
SXINCQCTZSUDRH-UHFFFAOYSA-N 2-[4,5-dichloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(Cl)C(Cl)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC SXINCQCTZSUDRH-UHFFFAOYSA-N 0.000 claims description 2
NZNSWXRZLJRSGW-UHFFFAOYSA-N 2-[5,7-dichloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(Cl)C=C(Cl)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC NZNSWXRZLJRSGW-UHFFFAOYSA-N 0.000 claims description 2
CUUMWIRAPXOFQO-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(Cl)C(C)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC CUUMWIRAPXOFQO-UHFFFAOYSA-N 0.000 claims description 2
YJYRFYGFCXFFOQ-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-7-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(C=C(Cl)C=C4C=3)C(F)(F)F)CC(O)=O)=N2)CCC2CCCCC2)=C1OC YJYRFYGFCXFFOQ-UHFFFAOYSA-N 0.000 claims description 2
VBRYWAAVGGWBTI-UHFFFAOYSA-N 2-[5-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]indol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(Cl)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC VBRYWAAVGGWBTI-UHFFFAOYSA-N 0.000 claims description 2
ZGZDMSJKGUFBMR-UHFFFAOYSA-N 2-[7-chloro-2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-5-methylindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=C(Cl)C=C(C)C=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC ZGZDMSJKGUFBMR-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
208000030499 combat disease Diseases 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
210000005095 gastrointestinal system Anatomy 0.000 claims description 2
150000004677 hydrates Chemical class 0.000 claims description 2
208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
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KNMAHODWYDYBNW-UHFFFAOYSA-N 2-[2-[[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)-1,3-thiazol-2-yl]carbamoyl]-4,5-dimethoxyindol-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C2=C(SC(NC(=O)C=3N(C4=CC=C(OC)C(OC)=C4C=3)CC(O)=O)=N2)CCC2CCCCC2)=C1OC KNMAHODWYDYBNW-UHFFFAOYSA-N 0.000 claims 1
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125000001309 chloro group Chemical group Cl* 0.000 claims 1
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230000009466 transformation Effects 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- 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
- 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
- C07D417/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Child & Adolescent Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

NO20001409A 1997-09-19 2000-03-17 Karboksamidotiazolderivater, fremgangsmåter for fremstilling derav og farmasöytiske blandinger NO314455B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR9711718A FR2768737B1 (fr)	1997-09-19	1997-09-19	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant
FR9805106A FR2777887B3 (fr)	1998-04-23	1998-04-23	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant
PCT/FR1998/002007 WO1999015525A1 (fr)	1997-09-19	1998-09-18	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant

Publications (3)

Publication Number	Publication Date
NO20001409D0 NO20001409D0 (no)	2000-03-17
NO20001409L NO20001409L (no)	2000-05-16
NO314455B1 true NO314455B1 (no)	2003-03-24

Family

ID=26233812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20001409A NO314455B1 (no)	1997-09-19	2000-03-17	Karboksamidotiazolderivater, fremgangsmåter for fremstilling derav og farmasöytiske blandinger

Country Status (27)

Country	Link
US (1)	US6380230B1 (fr)
EP (1)	EP1017693A1 (fr)
JP (1)	JP3456970B2 (fr)
KR (1)	KR20010030629A (fr)
CN (1)	CN1276790A (fr)
AR (1)	AR013494A1 (fr)
AU (1)	AU746707B2 (fr)
BG (1)	BG104254A (fr)
BR (1)	BR9812653A (fr)
CA (1)	CA2304397A1 (fr)
CO (1)	CO4970713A1 (fr)
EA (1)	EA003093B1 (fr)
EE (1)	EE200000168A (fr)
HR (1)	HRP20000153A2 (fr)
HU (1)	HUP0100225A3 (fr)
ID (1)	ID25528A (fr)
IL (1)	IL134961A (fr)
IS (1)	IS5409A (fr)
MY (1)	MY141444A (fr)
NO (1)	NO314455B1 (fr)
NZ (1)	NZ503339A (fr)
PL (1)	PL339292A1 (fr)
SK (1)	SK4052000A3 (fr)
TR (1)	TR200001218T2 (fr)
TW (1)	TW430664B (fr)
UY (1)	UY25180A1 (fr)
WO (1)	WO1999015525A1 (fr)

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1998
- 1998-09-09 CO CO98051671A patent/CO4970713A1/es unknown
- 1998-09-12 MY MYPI98004185A patent/MY141444A/en unknown
- 1998-09-14 UY UY25180A patent/UY25180A1/es unknown
- 1998-09-16 AR ARP980104588A patent/AR013494A1/es not_active Application Discontinuation
- 1998-09-18 PL PL98339292A patent/PL339292A1/xx unknown
- 1998-09-18 AU AU91705/98A patent/AU746707B2/en not_active Ceased
- 1998-09-18 EA EA200000334A patent/EA003093B1/ru not_active IP Right Cessation
- 1998-09-18 ID IDW20000504A patent/ID25528A/id unknown
- 1998-09-18 US US09/508,830 patent/US6380230B1/en not_active Expired - Fee Related
- 1998-09-18 CN CN98810341A patent/CN1276790A/zh active Pending
- 1998-09-18 IL IL13496198A patent/IL134961A/en not_active IP Right Cessation
- 1998-09-18 BR BR9812653-9A patent/BR9812653A/pt not_active IP Right Cessation
- 1998-09-18 KR KR1020007002905A patent/KR20010030629A/ko not_active Ceased
- 1998-09-18 CA CA002304397A patent/CA2304397A1/fr not_active Abandoned
- 1998-09-18 SK SK405-2000A patent/SK4052000A3/sk unknown
- 1998-09-18 TW TW087115602A patent/TW430664B/zh active
- 1998-09-18 TR TR2000/01218T patent/TR200001218T2/xx unknown
- 1998-09-18 WO PCT/FR1998/002007 patent/WO1999015525A1/fr not_active Ceased
- 1998-09-18 EP EP98944024A patent/EP1017693A1/fr not_active Withdrawn
- 1998-09-18 HU HU0100225A patent/HUP0100225A3/hu unknown
- 1998-09-18 NZ NZ503339A patent/NZ503339A/en unknown
- 1998-09-18 JP JP2000512830A patent/JP3456970B2/ja not_active Expired - Fee Related
- 1998-09-18 EE EEP200000168A patent/EE200000168A/xx unknown
- 1998-09-18 HR HR20000153A patent/HRP20000153A2/hr not_active Application Discontinuation
2000
- 2000-03-16 IS IS5409A patent/IS5409A/is unknown
- 2000-03-17 BG BG104254A patent/BG104254A/xx unknown
- 2000-03-17 NO NO20001409A patent/NO314455B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
MY141444A (en)	2010-04-30
HRP20000153A2 (en)	2001-04-30
SK4052000A3 (en)	2001-03-12
CN1276790A (zh)	2000-12-13
NO20001409L (no)	2000-05-16
WO1999015525A1 (fr)	1999-04-01
EP1017693A1 (fr)	2000-07-12
EE200000168A (et)	2001-04-16
EA200000334A1 (ru)	2000-10-30
HUP0100225A2 (hu)	2001-09-28
JP3456970B2 (ja)	2003-10-14
IL134961A (en)	2002-07-25
UY25180A1 (es)	2001-06-29
CA2304397A1 (fr)	1999-04-01
AU9170598A (en)	1999-04-12
KR20010030629A (ko)	2001-04-16
CO4970713A1 (es)	2000-11-07
TW430664B (en)	2001-04-21
PL339292A1 (en)	2000-12-04
TR200001218T2 (tr)	2001-05-21
US6380230B1 (en)	2002-04-30
NZ503339A (en)	2002-03-28
EA003093B1 (ru)	2002-12-26
IL134961A0 (en)	2001-05-20
BR9812653A (pt)	2000-08-22
IS5409A (is)	2000-03-16
AU746707B2 (en)	2002-05-02
JP2001517667A (ja)	2001-10-09
AR013494A1 (es)	2000-12-27
ID25528A (id)	2000-10-12
HUP0100225A3 (en)	2003-05-28
NO20001409D0 (no)	2000-03-17
BG104254A (en)	2001-08-31

Legal Events

Date	Code	Title	Description
2005-06-20	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO314455B1 (no)	2003-03-24	Karboksamidotiazolderivater, fremgangsmåter for fremstilling derav og farmasöytiske blandinger
RU2059637C1 (ru)	1996-05-10	Гетероциклические производные замещенных 2-ациламино-5-тиазолов, способы их получения, производное замещенного 2-аминотиазола, производные 2-амино-4-фенилтиазола
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EP0145304B1 (fr)	1988-04-20	Dérivés de la tétrahydro bêta-carboline et procédé pour leur préparation
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