UA61919C2 - Амінокислотний складний ефір, що містить азол, спосіб його одержання, проміжні сполуки та фармацевтична композиція - Google Patents

Амінокислотний складний ефір, що містить азол, спосіб його одержання, проміжні сполуки та фармацевтична композиція Download PDF

Info

Publication number: UA61919C2
Authority: UA; Ukraine
Prior art keywords: formula; phenyl; triazol; methylpropyl; compounds
Prior art date: 1997-02-11

Application number

UA99020835A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Ливен Меерпоел

Ян Хеерес

Роберт Йозеф Марія Хендрікс

Original Assignee

Янссен Фармацевтика Н.В.

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.)

1997-02-11

Filing date

1998-03-02

Publication date

2003-12-15

1998-03-02 Application filed by Янссен Фармацевтика Н.В. filed Critical Янссен Фармацевтика Н.В.

2003-12-15 Publication of UA61919C2 publication Critical patent/UA61919C2/uk

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KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims abstract description 8
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WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract 4
-1 benzyloxycarbonylamino Chemical group 0.000 claims description 51
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238000000034 method Methods 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 25
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
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239000000499 gel Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
235000004554 glutamine Nutrition 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
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150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
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QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
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210000000987 immune system Anatomy 0.000 description 1
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150000007529 inorganic bases Chemical class 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
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AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229960004125 ketoconazole Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000865 liniment Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Chemical class 0.000 description 1
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230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
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239000002184 metal Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
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HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
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238000012986 modification Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
210000003899 penis Anatomy 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
229960002429 proline Drugs 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229960001153 serine Drugs 0.000 description 1
235000004400 serine Nutrition 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
230000036556 skin irritation Effects 0.000 description 1
231100000475 skin irritation Toxicity 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000009331 sowing Methods 0.000 description 1
241000894007 species Species 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229960002898 threonine Drugs 0.000 description 1
235000008521 threonine Nutrition 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

UA99020835A 1997-02-11 1998-03-02 Амінокислотний складний ефір, що містить азол, спосіб його одержання, проміжні сполуки та фармацевтична композиція UA61919C2 (uk)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
EP97200374		1997-02-11
EP97203228		1997-10-15
EP98908064A EP0958289B1 (en)	1997-02-11	1998-02-03	Amino acid ester containing azole antifungals
PCT/EP1998/000646 WO1998034934A1 (en)	1997-02-11	1998-02-03	Amino acid ester containing azole antifungals

Publications (1)

Publication Number	Publication Date
UA61919C2 true UA61919C2 (uk)	2003-12-15

Family

ID=26146124

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA99020835A UA61919C2 (uk)	1997-02-11	1998-03-02	Амінокислотний складний ефір, що містить азол, спосіб його одержання, проміжні сполуки та фармацевтична композиція

Country Status (31)

Country	Link
US (3)	US6262052B1 (id)
EP (1)	EP0958289B1 (id)
JP (1)	JP4347911B2 (id)
KR (1)	KR100509171B1 (id)
CN (1)	CN1238353C (id)
AT (1)	ATE270290T1 (id)
AU (1)	AU725302C (id)
BG (1)	BG63872B1 (id)
BR (1)	BR9809744A (id)
CA (1)	CA2262791C (id)
CZ (1)	CZ297197B6 (id)
DE (1)	DE69824834T2 (id)
DK (1)	DK0958289T3 (id)
EE (1)	EE03876B1 (id)
ES (1)	ES2224364T3 (id)
HU (1)	HU227744B1 (id)
ID (1)	ID21755A (id)
IL (2)	IL128513A (id)
MY (1)	MY129537A (id)
NO (1)	NO316668B1 (id)
NZ (1)	NZ334477A (id)
PL (1)	PL191152B1 (id)
PT (1)	PT958289E (id)
RU (1)	RU2197489C2 (id)
SI (1)	SI0958289T1 (id)
SK (1)	SK284910B6 (id)
TR (1)	TR199900584T2 (id)
TW (1)	TW495508B (id)
UA (1)	UA61919C2 (id)
WO (1)	WO1998034934A1 (id)
ZA (1)	ZA981079B (id)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0957101A1 (en)	1998-05-14	1999-11-17	Janssen Pharmaceutica N.V.	Water soluble azoles as broad-spectrum antifungals
AU1915500A (en)	1998-11-20	2000-06-13	Bristol-Myers Squibb Company	Water soluble prodrugs of azole compounds
ES2194723T3 (es)	1999-05-04	2003-12-01	Janssen Pharmaceutica Nv	Eteres antifungicos.
WO2003052117A2 (en) *	2001-09-19	2003-06-26	Massachusetts Institute Of Technology	Methods and products related to non-viral transfection
ITMI20032020A1 (it)	2003-10-17	2005-04-18	Italfarmaco Spa	Nuovi agenti antifungini azolici con diminuita interazione con i citocromi metabolici
EP2571871B1 (en) *	2010-05-19	2017-06-21	Sandoz AG	Process for the preparation of chiral triazolones
US20170290333A1 (en)	2014-12-30	2017-10-12	Dow Agrosciences Llc	Picolinamide compounds with fungicidal activity
BR102019004480B1 (pt) *	2018-03-08	2023-03-28	Dow Agrosciences Llc	Picolinamidas como fungicidas
CN111138421A (zh) *	2019-12-26	2020-05-12	上海英诺富成生物科技有限公司	抗真菌水溶性化合物及其制备方法与应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4267179A (en)	1978-06-23	1981-05-12	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles
US4791111A (en) *	1985-12-23	1988-12-13	Janssen Pharmaceutica, N.V.	[[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties
US4916134A (en)	1987-03-25	1990-04-10	Janssen Pharmacuetica N.V.	4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-azolylmethyl)-1,3-dioxolan-4-yl]me]phenyl]-1-piperazinyl]phenyl]triazolones
CA1331757C (en)	1988-02-29	1994-08-30	Janssen Pharmaceutica Naamloze Vennootschap	5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols
NZ233502A (en) *	1989-06-09	1991-11-26	Janssen Pharmaceutica Nv	4-(1,2,4-triazole- or imidazole-phenyl-substituted) -1-(1,3-dioxolan-4-ylmethoxyphenyl) piperazine derivatives; preparatory processes: fungicidal and antiviral compositions
HU221189B1 (en)	1992-03-18	2002-08-28	Janssen Pharmaceutica Nv	Itraconazole and saperconazole stereoisomers, their cyclodextrin complexes and pharmaceutical compositions containing them and process for producing them
PL181193B1 (pl)	1993-12-21	2001-06-29	Schering Corp	Nowe pochodne tetrahydrofuranowe o działaniu przeciwgrzybicznym, kompozycja farmaceutyczna do leczenia infekcji grzybiczych oraz sposób wytwarzania tych związków
NZ278882A (en) *	1994-01-24	1997-06-24	Janssen Pharmaceutica Nv	Piperazine-containing azole antifungal compounds
SK27097A3 (en) *	1995-06-02	1997-09-10	Schering Corp	Tetrahydrofuran antifungals
CA2224707A1 (en) *	1995-06-19	1997-01-03	Schering Corporation	Tetrahydrofuran antifungals

1998
- 1998-02-03 AU AU66207/98A patent/AU725302C/en not_active Expired
- 1998-02-03 SK SK1059-99A patent/SK284910B6/sk not_active IP Right Cessation
- 1998-02-03 NZ NZ334477A patent/NZ334477A/en not_active IP Right Cessation
- 1998-02-03 DK DK98908064T patent/DK0958289T3/da active
- 1998-02-03 DE DE69824834T patent/DE69824834T2/de not_active Expired - Lifetime
- 1998-02-03 JP JP53376398A patent/JP4347911B2/ja not_active Expired - Lifetime
- 1998-02-03 PT PT98908064T patent/PT958289E/pt unknown
- 1998-02-03 CN CNB988011352A patent/CN1238353C/zh not_active Expired - Lifetime
- 1998-02-03 EP EP98908064A patent/EP0958289B1/en not_active Expired - Lifetime
- 1998-02-03 SI SI9830687T patent/SI0958289T1/xx unknown
- 1998-02-03 HU HU0001050A patent/HU227744B1/hu unknown
- 1998-02-03 US US09/355,369 patent/US6262052B1/en not_active Expired - Lifetime
- 1998-02-03 ES ES98908064T patent/ES2224364T3/es not_active Expired - Lifetime
- 1998-02-03 BR BR9809744-0A patent/BR9809744A/pt not_active Application Discontinuation
- 1998-02-03 ID IDW990505A patent/ID21755A/id unknown
- 1998-02-03 WO PCT/EP1998/000646 patent/WO1998034934A1/en not_active Ceased
- 1998-02-03 IL IL12851398A patent/IL128513A/en not_active IP Right Cessation
- 1998-02-03 RU RU99106585/04A patent/RU2197489C2/ru active
- 1998-02-03 PL PL332008A patent/PL191152B1/pl unknown
- 1998-02-03 KR KR10-1999-7001983A patent/KR100509171B1/ko not_active Expired - Lifetime
- 1998-02-03 TR TR1999/00584T patent/TR199900584T2/xx unknown
- 1998-02-03 CZ CZ0283599A patent/CZ297197B6/cs not_active IP Right Cessation
- 1998-02-03 CA CA002262791A patent/CA2262791C/en not_active Expired - Lifetime
- 1998-02-03 EE EEP199900100A patent/EE03876B1/xx unknown
- 1998-02-03 AT AT98908064T patent/ATE270290T1/de active
- 1998-02-09 MY MYPI98000513A patent/MY129537A/en unknown
- 1998-02-09 TW TW087101662A patent/TW495508B/zh not_active IP Right Cessation
- 1998-02-10 ZA ZA9801079A patent/ZA981079B/xx unknown
- 1998-03-02 UA UA99020835A patent/UA61919C2/uk unknown
1999
- 1999-02-02 NO NO19990484A patent/NO316668B1/no not_active IP Right Cessation
- 1999-02-11 BG BG103171A patent/BG63872B1/bg unknown
2001
- 2001-05-04 US US09/848,989 patent/US6512116B2/en not_active Expired - Lifetime
2002
- 2002-04-23 IL IL149285A patent/IL149285A/en not_active IP Right Cessation
- 2002-11-15 US US10/298,038 patent/US6703506B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US20030158210A1 (en)	2003-08-21
PL191152B1 (pl)	2006-03-31
AU725302B2 (en)	2000-10-12
IL149285A0 (en)	2002-11-10
BG103171A (en)	1999-09-30
PL332008A1 (en)	1999-08-16
IL149285A (en)	2007-08-19
US6703506B2 (en)	2004-03-09
ES2224364T3 (es)	2005-03-01
CA2262791A1 (en)	1998-08-13
BR9809744A (pt)	2000-06-20
US20010039281A1 (en)	2001-11-08
JP4347911B2 (ja)	2009-10-21
SK105999A3 (en)	2000-06-12
HUP0001050A2 (hu)	2001-04-28
CN1236366A (zh)	1999-11-24
RU2197489C2 (ru)	2003-01-27
DK0958289T3 (da)	2004-11-01
EP0958289A1 (en)	1999-11-24
TW495508B (en)	2002-07-21
ID21755A (id)	1999-07-22
CZ283599A3 (cs)	2000-02-16
SK284910B6 (sk)	2006-02-02
DE69824834D1 (de)	2004-08-05
US6262052B1 (en)	2001-07-17
NO316668B1 (no)	2004-03-29
ZA981079B (en)	1999-08-10
DE69824834T2 (de)	2005-07-21
NZ334477A (en)	2001-05-25
AU6620798A (en)	1998-08-26
CN1238353C (zh)	2006-01-25
NO990484L (no)	1999-10-11
BG63872B1 (bg)	2003-04-30
IL128513A0 (en)	2000-01-31
KR20000068526A (ko)	2000-11-25
CA2262791C (en)	2008-10-28
HU227744B1 (en)	2012-02-28
CZ297197B6 (cs)	2006-09-13
JP2001508080A (ja)	2001-06-19
NO990484D0 (no)	1999-02-02
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PT958289E (pt)	2004-11-30
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IL128513A (en)	2002-11-10
EE9900100A (et)	1999-10-15
SI0958289T1 (en)	2004-12-31
EE03876B1 (et)	2002-10-15
TR199900584T2 (xx)	1999-10-21
WO1998034934A1 (en)	1998-08-13
HUP0001050A3 (en)	2001-07-30
AU725302C (en)	2001-08-23
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KR100509171B1 (ko)	2005-08-22

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