UA61919C2 - Амино-кислотный эстер, содержащий азоловые противогрибковые составляющие - Google Patents
Амино-кислотный эстер, содержащий азоловые противогрибковые составляющие Download PDFInfo
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- UA61919C2 UA61919C2 UA99020835A UA99020835A UA61919C2 UA 61919 C2 UA61919 C2 UA 61919C2 UA 99020835 A UA99020835 A UA 99020835A UA 99020835 A UA99020835 A UA 99020835A UA 61919 C2 UA61919 C2 UA 61919C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- phenyl
- triazol
- methylpropyl
- compounds
- Prior art date
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- 229960002743 glutamine Drugs 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000006872 improvement Effects 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
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 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
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- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 239000002207 metabolite Substances 0.000 description 1
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- 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
- 229960004452 methionine Drugs 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 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
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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)
Abstract
Настоящее изобретение касается новых соединений формулы , азотнокислых форм, их фармацевтически приемлемых аддитивных солей и стереохимических изомерных форм, где -А-В-образовывают двухвалентный радикал формулы: -N=CH- (a), -CH=N- (b), -СН=СН- (с), L - ацильная составляющая аминокислоты, D - азол, который содержит производные 1,3- или 1,4-диоксолана, как широкий спектр антигрибковых соединений, их получение, композиции, которая их содержат, и их использование в медицине.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97200374 | 1997-02-11 | ||
| EP97203228 | 1997-10-15 | ||
| PCT/EP1998/000646 WO1998034934A1 (en) | 1997-02-11 | 1998-02-03 | Amino acid ester containing azole antifungals |
| EP98908064A EP0958289B1 (en) | 1997-02-11 | 1998-02-03 | Amino acid ester containing azole antifungals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA61919C2 true UA61919C2 (ru) | 2003-12-15 |
Family
ID=26146124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA99020835A UA61919C2 (ru) | 1997-02-11 | 1998-03-02 | Амино-кислотный эстер, содержащий азоловые противогрибковые составляющие |
Country Status (31)
| Country | Link |
|---|---|
| US (3) | US6262052B1 (ru) |
| EP (1) | EP0958289B1 (ru) |
| JP (1) | JP4347911B2 (ru) |
| KR (1) | KR100509171B1 (ru) |
| CN (1) | CN1238353C (ru) |
| AT (1) | ATE270290T1 (ru) |
| AU (1) | AU725302C (ru) |
| BG (1) | BG63872B1 (ru) |
| BR (1) | BR9809744A (ru) |
| CA (1) | CA2262791C (ru) |
| CZ (1) | CZ297197B6 (ru) |
| DE (1) | DE69824834T2 (ru) |
| DK (1) | DK0958289T3 (ru) |
| EE (1) | EE03876B1 (ru) |
| ES (1) | ES2224364T3 (ru) |
| HU (1) | HU227744B1 (ru) |
| ID (1) | ID21755A (ru) |
| IL (2) | IL128513A (ru) |
| MY (1) | MY129537A (ru) |
| NO (1) | NO316668B1 (ru) |
| NZ (1) | NZ334477A (ru) |
| PL (1) | PL191152B1 (ru) |
| PT (1) | PT958289E (ru) |
| RU (1) | RU2197489C2 (ru) |
| SI (1) | SI0958289T1 (ru) |
| SK (1) | SK284910B6 (ru) |
| TR (1) | TR199900584T2 (ru) |
| TW (1) | TW495508B (ru) |
| UA (1) | UA61919C2 (ru) |
| WO (1) | WO1998034934A1 (ru) |
| ZA (1) | ZA981079B (ru) |
Families Citing this family (8)
| 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 |
| WO2000030655A1 (en) | 1998-11-20 | 2000-06-02 | Bristol-Myers Squibb Company | Water soluble prodrugs of azole compounds |
| CA2372691C (en) | 1999-05-04 | 2009-11-17 | Janssen Pharmaceutica N.V. | Antifungal ethers |
| 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 |
| US9040539B2 (en) * | 2010-05-19 | 2015-05-26 | Sandoz Ag | Process for the preparation of chiral triazolones |
| 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 (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4218458A (en) | 1978-06-23 | 1980-08-19 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of (4-aryloxy-methyl-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 |
| PL172358B1 (en) | 1992-03-18 | 1997-09-30 | Janssen Pharmaceutica Nv | Stereoisomeric form of itraconazole or saperconazole and method of obtaining same |
| DK0736030T3 (da) | 1993-12-21 | 2001-10-29 | Schering Corp | Fungicide tetrahydrofuraner |
| PL181947B1 (en) * | 1994-01-24 | 2001-10-31 | Janssen Pharmaceutica Nv | Water-soluble azole-type antimycotic agents |
| WO1996038443A1 (en) * | 1995-06-02 | 1996-12-05 | Schering Corporation | Tetrahydrofuran antifungals |
| AU6257396A (en) | 1995-06-19 | 1997-01-15 | Schering Corporation | Tetrahydrofuran antifungals |
-
1998
- 1998-02-03 AT AT98908064T patent/ATE270290T1/de active
- 1998-02-03 PT PT98908064T patent/PT958289E/pt unknown
- 1998-02-03 RU RU99106585/04A patent/RU2197489C2/ru active
- 1998-02-03 ID IDW990505A patent/ID21755A/id unknown
- 1998-02-03 US US09/355,369 patent/US6262052B1/en not_active Expired - Lifetime
- 1998-02-03 HU HU0001050A patent/HU227744B1/hu unknown
- 1998-02-03 ES ES98908064T patent/ES2224364T3/es not_active Expired - Lifetime
- 1998-02-03 CA CA002262791A patent/CA2262791C/en not_active Expired - Lifetime
- 1998-02-03 EP EP98908064A patent/EP0958289B1/en not_active Expired - Lifetime
- 1998-02-03 BR BR9809744-0A patent/BR9809744A/pt not_active Application Discontinuation
- 1998-02-03 CZ CZ0283599A patent/CZ297197B6/cs not_active IP Right Cessation
- 1998-02-03 IL IL12851398A patent/IL128513A/en not_active IP Right Cessation
- 1998-02-03 SI SI9830687T patent/SI0958289T1/xx unknown
- 1998-02-03 WO PCT/EP1998/000646 patent/WO1998034934A1/en active IP Right Grant
- 1998-02-03 EE EEP199900100A patent/EE03876B1/xx unknown
- 1998-02-03 AU AU66207/98A patent/AU725302C/en not_active Expired
- 1998-02-03 NZ NZ334477A patent/NZ334477A/en not_active IP Right Cessation
- 1998-02-03 KR KR10-1999-7001983A patent/KR100509171B1/ko active IP Right Grant
- 1998-02-03 PL PL332008A patent/PL191152B1/pl unknown
- 1998-02-03 CN CNB988011352A patent/CN1238353C/zh not_active Expired - Lifetime
- 1998-02-03 DK DK98908064T patent/DK0958289T3/da active
- 1998-02-03 DE DE69824834T patent/DE69824834T2/de not_active Expired - Lifetime
- 1998-02-03 SK SK1059-99A patent/SK284910B6/sk not_active IP Right Cessation
- 1998-02-03 JP JP53376398A patent/JP4347911B2/ja not_active Expired - Lifetime
- 1998-02-03 TR TR1999/00584T patent/TR199900584T2/xx unknown
- 1998-02-09 TW TW087101662A patent/TW495508B/zh not_active IP Right Cessation
- 1998-02-09 MY MYPI98000513A patent/MY129537A/en unknown
- 1998-02-10 ZA ZA9801079A patent/ZA981079B/xx unknown
- 1998-03-02 UA UA99020835A patent/UA61919C2/ru unknown
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1999
- 1999-02-02 NO NO19990484A patent/NO316668B1/no not_active IP Right Cessation
- 1999-02-11 BG BG103171A patent/BG63872B1/bg unknown
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2001
- 2001-05-04 US US09/848,989 patent/US6512116B2/en not_active Expired - Lifetime
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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
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