SK6772001A3 - Benzoxazole derivatives and drugs containing the same as the active ingredient - Google Patents

Benzoxazole derivatives and drugs containing the same as the active ingredient Download PDF

Info

Publication number: SK6772001A3
Authority: SK; Slovakia
Prior art keywords: group; chloro; homopiperazinyl; compound; benzoxazole
Prior art date: 1998-11-20

Application number

SK677-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Sojiro Shiokawa

Yasuo Sato

Masaaki Izumi

Satoshi Yoshida

Hiroshi Murakami

Tomoko Ito

Tetsutaro Niisato

Original Assignee

Meiji Seika Kaisha

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.)

1998-11-20

Filing date

1999-11-19

Publication date

2001-12-03

1999-11-19 Application filed by Meiji Seika Kaisha filed Critical Meiji Seika Kaisha

2001-12-03 Publication of SK6772001A3 publication Critical patent/SK6772001A3/sk

Links

239000003814 drug Substances 0.000 title claims abstract description 21
239000004480 active ingredient Substances 0.000 title claims abstract description 10
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title description 16
229940079593 drug Drugs 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 181
150000003839 salts Chemical class 0.000 claims abstract description 38
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
206010012735 Diarrhoea Diseases 0.000 claims abstract description 19
125000003277 amino group Chemical group 0.000 claims abstract description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
125000005843 halogen group Chemical group 0.000 claims abstract description 17
210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 12
230000003449 preventive effect Effects 0.000 claims abstract description 12
125000001424 substituent group Chemical group 0.000 claims abstract description 12
125000006239 protecting group Chemical group 0.000 claims abstract description 11
230000001225 therapeutic effect Effects 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 70
238000000034 method Methods 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 20
-1 1-homopiperazinyl Chemical group 0.000 claims description 16
QPKABSXJDCZNKQ-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-7-methyl-1,3-benzoxazole Chemical compound O1C=2C(C)=CC(Cl)=CC=2N=C1N1CCCNCC1 QPKABSXJDCZNKQ-UHFFFAOYSA-N 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000012453 solvate Substances 0.000 claims description 12
208000035475 disorder Diseases 0.000 claims description 11
102000035037 5-HT3 receptors Human genes 0.000 claims description 9
108091005477 5-HT3 receptors Proteins 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
239000002111 antiemetic agent Substances 0.000 claims description 7
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 claims description 7
VLXAVBHLFBHNEA-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]acetamide Chemical compound O1C=2C(NC(=O)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 VLXAVBHLFBHNEA-UHFFFAOYSA-N 0.000 claims description 6
DTRMFUAUYNIOEZ-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-6-methyl-1,3-benzoxazole Chemical compound N=1C=2C=C(Cl)C(C)=CC=2OC=1N1CCCNCC1 DTRMFUAUYNIOEZ-UHFFFAOYSA-N 0.000 claims description 5
230000003474 anti-emetic effect Effects 0.000 claims description 5
230000036961 partial effect Effects 0.000 claims description 5
229940076279 serotonin Drugs 0.000 claims description 5
BBENGKGAKVSDCZ-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-6,7-dimethyl-1,3-benzoxazole Chemical compound O1C2=C(C)C(C)=C(Cl)C=C2N=C1N1CCCNCC1 BBENGKGAKVSDCZ-UHFFFAOYSA-N 0.000 claims description 4
UNRCLDQBGKUOMP-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-7-ethyl-1,3-benzoxazole Chemical compound O1C=2C(CC)=CC(Cl)=CC=2N=C1N1CCCNCC1 UNRCLDQBGKUOMP-UHFFFAOYSA-N 0.000 claims description 4
AHPVBWOWLNLLQH-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-7-methoxy-1,3-benzoxazole Chemical compound O1C=2C(OC)=CC(Cl)=CC=2N=C1N1CCCNCC1 AHPVBWOWLNLLQH-UHFFFAOYSA-N 0.000 claims description 4
239000012190 activator Substances 0.000 claims description 4
125000006242 amine protecting group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
LOYJLGODJCVFLT-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-amine Chemical compound O1C=2C(N)=CC(Cl)=CC=2N=C1N1CCCNCC1 LOYJLGODJCVFLT-UHFFFAOYSA-N 0.000 claims description 3
ZCXNEHHRRBCEPK-UHFFFAOYSA-N 5-chloro-2-(1,4-diazepan-1-yl)-n-ethyl-1,3-benzoxazol-7-amine Chemical compound O1C=2C(NCC)=CC(Cl)=CC=2N=C1N1CCCNCC1 ZCXNEHHRRBCEPK-UHFFFAOYSA-N 0.000 claims description 3
YZVOXCBEYYKZNK-UHFFFAOYSA-N [5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]methanol Chemical compound O1C=2C(CO)=CC(Cl)=CC=2N=C1N1CCCNCC1 YZVOXCBEYYKZNK-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
XBEWYQHJENXEIF-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]methanesulfonamide Chemical compound O1C=2C(NS(=O)(=O)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 XBEWYQHJENXEIF-UHFFFAOYSA-N 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 2
MOPZJYDOQRNABV-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]benzamide Chemical compound C=12OC(N3CCNCCC3)=NC2=CC(Cl)=CC=1NC(=O)C1=CC=CC=C1 MOPZJYDOQRNABV-UHFFFAOYSA-N 0.000 claims description 2
IWWLKUZVMOTTFP-UHFFFAOYSA-N tert-butyl n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]carbamate Chemical compound O1C=2C(NC(=O)OC(C)(C)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 IWWLKUZVMOTTFP-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229940125904 compound 1 Drugs 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
PBIFALKTLDJESI-UHFFFAOYSA-N n-[5-chloro-2-(1,4-diazepan-1-yl)-1,3-benzoxazol-7-yl]-2-methylpropanamide Chemical compound O1C=2C(NC(=O)C(C)C)=CC(Cl)=CC=2N=C1N1CCCNCC1 PBIFALKTLDJESI-UHFFFAOYSA-N 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 5
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 60
239000000203 mixture Substances 0.000 description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
230000002829 reductive effect Effects 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
238000005160 1H NMR spectroscopy Methods 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000002904 solvent Substances 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
238000012360 testing method Methods 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 25
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
230000000694 effects Effects 0.000 description 24
238000001914 filtration Methods 0.000 description 24
238000003756 stirring Methods 0.000 description 24
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
230000000052 comparative effect Effects 0.000 description 21
102000005962 receptors Human genes 0.000 description 19
108020003175 receptors Proteins 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
230000003213 activating effect Effects 0.000 description 16
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 14
239000010410 layer Substances 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 12
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239000007787 solid Substances 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
150000004677 hydrates Chemical class 0.000 description 8
230000000968 intestinal effect Effects 0.000 description 8
210000004185 liver Anatomy 0.000 description 8
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GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
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229910017604 nitric acid Inorganic materials 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
208000011580 syndromic disease Diseases 0.000 description 7
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- 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
- A61P1/12—Antidiarrhoeals
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

SK677-2001A 1998-11-20 1999-11-19 Benzoxazole derivatives and drugs containing the same as the active ingredient SK6772001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP33127498		1998-11-20
PCT/JP1999/006491 WO2000031073A1 (fr)	1998-11-20	1999-11-19	Derives de benzoxazole et produits a base de ces derniers utilises comme ingredient actif

Publications (1)

Publication Number	Publication Date
SK6772001A3 true SK6772001A3 (en)	2001-12-03

Family

ID=18241866

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK677-2001A SK6772001A3 (en)	1998-11-20	1999-11-19	Benzoxazole derivatives and drugs containing the same as the active ingredient

Country Status (23)

Country	Link
US (1)	US7045516B1 (pt)
EP (1)	EP1134220B1 (pt)
JP (1)	JP4557112B2 (pt)
KR (1)	KR100675033B1 (pt)
CN (1)	CN1333771A (pt)
AT (1)	ATE273974T1 (pt)
AU (1)	AU753797B2 (pt)
BR (1)	BR9916793A (pt)
CA (1)	CA2351446A1 (pt)
CZ (1)	CZ20011700A3 (pt)
DE (1)	DE69919575T2 (pt)
ES (1)	ES2222763T3 (pt)
HU (1)	HUP0104238A3 (pt)
ID (1)	ID30143A (pt)
IL (1)	IL143178A0 (pt)
NO (1)	NO20012443L (pt)
PL (1)	PL348426A1 (pt)
RU (1)	RU2204558C2 (pt)
SK (1)	SK6772001A3 (pt)
TR (1)	TR200101945T2 (pt)
TW (1)	TW520370B (pt)
WO (1)	WO2000031073A1 (pt)
ZA (1)	ZA200104620B (pt)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6660858B2 (en) *	2001-03-28	2003-12-09	Lion Bioscience Ag	2-aminobenzoxazole derivatives and combinatorial libraries thereof
GB0203061D0 (en) *	2002-02-08	2002-03-27	Novartis Ag	Organic compounds
EP1541172A1 (en) *	2002-08-09	2005-06-15	Ajinomoto Co., Inc.	Remedy for intestinal diseases and visceral pain
WO2007005780A2 (en) *	2005-07-01	2007-01-11	Dynogen Pharmaceuticals, Inc.	Compositions and methods for treating gastrointestinal hypomotility and associated disorders
CN101410385B (zh)	2006-03-28	2011-08-24	高点制药有限责任公司	具有组胺h3受体活性的苯并噻唑类
WO2010048514A1 (en) *	2008-10-23	2010-04-29	Albany Molecular Research, Inc.	Synthesis of 2-aminobenzoxazole compounds
KR101579688B1 (ko)	2014-07-08	2015-12-24	재단법인 전남생물산업진흥원	좁쌀풀 추출물을 유효성분으로 함유하는 과민성 대장증후군에 의한 내장 통증 억제예방 또는 치료용 약학 조성물
WO2021251565A1 (en) *	2020-06-12	2021-12-16	Hk Inno.N Corporation	Pharmaceutical composition comprising benzimidazole derivative compound

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3193560B2 (ja) *	1993-04-16	2001-07-30	明治製菓株式会社	新規ベンゾオキサゾール誘導体
JP3520177B2 (ja) *	1996-05-09	2004-04-19	明治製菓株式会社	セロトニン５−ｈｔ３受容体部分活性薬

1999
- 1999-11-18 TW TW088120112A patent/TW520370B/zh active
- 1999-11-19 CZ CZ20011700A patent/CZ20011700A3/cs unknown
- 1999-11-19 CN CN99815777A patent/CN1333771A/zh active Pending
- 1999-11-19 IL IL14317899A patent/IL143178A0/xx unknown
- 1999-11-19 WO PCT/JP1999/006491 patent/WO2000031073A1/ja active IP Right Grant
- 1999-11-19 US US09/856,372 patent/US7045516B1/en not_active Expired - Fee Related
- 1999-11-19 PL PL99348426A patent/PL348426A1/xx unknown
- 1999-11-19 JP JP2000583901A patent/JP4557112B2/ja not_active Expired - Fee Related
- 1999-11-19 TR TR2001/01945T patent/TR200101945T2/xx unknown
- 1999-11-19 CA CA002351446A patent/CA2351446A1/en not_active Abandoned
- 1999-11-19 EP EP99972633A patent/EP1134220B1/en not_active Expired - Lifetime
- 1999-11-19 AT AT99972633T patent/ATE273974T1/de not_active IP Right Cessation
- 1999-11-19 SK SK677-2001A patent/SK6772001A3/sk unknown
- 1999-11-19 KR KR1020017006249A patent/KR100675033B1/ko not_active IP Right Cessation
- 1999-11-19 AU AU11850/00A patent/AU753797B2/en not_active Ceased
- 1999-11-19 HU HU0104238A patent/HUP0104238A3/hu unknown
- 1999-11-19 ID IDW00200101321A patent/ID30143A/id unknown
- 1999-11-19 RU RU2001116715/04A patent/RU2204558C2/ru not_active IP Right Cessation
- 1999-11-19 DE DE69919575T patent/DE69919575T2/de not_active Expired - Lifetime
- 1999-11-19 ES ES99972633T patent/ES2222763T3/es not_active Expired - Lifetime
- 1999-11-19 BR BR9916793-0A patent/BR9916793A/pt not_active IP Right Cessation
2001
- 2001-05-18 NO NO20012443A patent/NO20012443L/no not_active Application Discontinuation
- 2001-06-06 ZA ZA200104620A patent/ZA200104620B/en unknown

Also Published As

Publication number	Publication date
ATE273974T1 (de)	2004-09-15
EP1134220B1 (en)	2004-08-18
CZ20011700A3 (cs)	2001-10-17
DE69919575T2 (de)	2005-09-29
ES2222763T3 (es)	2005-02-01
NO20012443L (no)	2001-07-12
PL348426A1 (en)	2002-05-20
TR200101945T2 (tr)	2001-11-21
US7045516B1 (en)	2006-05-16
KR20010086448A (ko)	2001-09-12
EP1134220A1 (en)	2001-09-19
IL143178A0 (en)	2002-04-21
ZA200104620B (en)	2002-02-04
WO2000031073A1 (fr)	2000-06-02
CN1333771A (zh)	2002-01-30
NO20012443D0 (no)	2001-05-18
JP4557112B2 (ja)	2010-10-06
DE69919575D1 (de)	2004-09-23
HUP0104238A2 (en)	2002-08-28
KR100675033B1 (ko)	2007-01-29
EP1134220A4 (en)	2001-12-19
HUP0104238A3 (en)	2003-05-28
ID30143A (id)	2001-11-08
CA2351446A1 (en)	2000-06-02
BR9916793A (pt)	2001-11-13
AU1185000A (en)	2000-06-13
TW520370B (en)	2003-02-11
AU753797B2 (en)	2002-10-31
RU2204558C2 (ru)	2003-05-20

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