SK43099A3 - Hydroxamic acid derivatives, process for their preparation and their use - Google Patents
Hydroxamic acid derivatives, process for their preparation and their use Download PDFInfo
- Publication number
- SK43099A3 SK43099A3 SK430-99A SK43099A SK43099A3 SK 43099 A3 SK43099 A3 SK 43099A3 SK 43099 A SK43099 A SK 43099A SK 43099 A3 SK43099 A3 SK 43099A3
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- SK
- Slovakia
- Prior art keywords
- formula
- carbon atoms
- alkyl
- aryl
- amino
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title abstract description 10
- 239000002253 acid Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 10
- 230000001363 autoimmune Effects 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 7
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 89
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000006301 indolyl methyl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 3
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
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- 239000012044 organic layer Substances 0.000 description 5
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
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- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- 208000016036 idiopathic nephrotic syndrome Diseases 0.000 description 1
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- 238000011534 incubation Methods 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
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- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- LSCYTCMNCWMCQE-UHFFFAOYSA-N n-methylpyridin-4-amine Chemical compound CNC1=CC=NC=C1 LSCYTCMNCWMCQE-UHFFFAOYSA-N 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 208000009928 nephrosis Diseases 0.000 description 1
- 231100001027 nephrosis Toxicity 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000004768 organ dysfunction Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 229960005190 phenylalanine 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
- 206010035653 pneumoconiosis Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9620572.9A GB9620572D0 (en) | 1996-10-02 | 1996-10-02 | Organic compounds |
| GBGB9706667.4A GB9706667D0 (en) | 1997-04-02 | 1997-04-02 | Organic compounds |
| PCT/EP1997/005376 WO1998014424A1 (en) | 1996-10-02 | 1997-09-30 | Hydroxamic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK43099A3 true SK43099A3 (en) | 1999-08-06 |
Family
ID=26310147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK430-99A SK43099A3 (en) | 1996-10-02 | 1997-09-30 | Hydroxamic acid derivatives, process for their preparation and their use |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0929517B1 (es) |
| JP (1) | JP3444898B2 (es) |
| KR (1) | KR20000048811A (es) |
| CN (1) | CN1101807C (es) |
| AR (1) | AR009103A1 (es) |
| AT (1) | ATE219050T1 (es) |
| AU (1) | AU726065B2 (es) |
| BR (1) | BR9712255A (es) |
| CA (1) | CA2267415A1 (es) |
| CO (1) | CO4900034A1 (es) |
| CZ (1) | CZ113999A3 (es) |
| DE (1) | DE69713354T2 (es) |
| DK (1) | DK0929517T3 (es) |
| ES (1) | ES2178759T3 (es) |
| HK (1) | HK1021637A1 (es) |
| HU (1) | HUP9903892A3 (es) |
| ID (1) | ID22212A (es) |
| IL (1) | IL129166A0 (es) |
| MY (1) | MY127926A (es) |
| NO (1) | NO313457B1 (es) |
| NZ (1) | NZ334908A (es) |
| PE (1) | PE2099A1 (es) |
| PL (1) | PL188518B1 (es) |
| PT (1) | PT929517E (es) |
| RU (1) | RU2196131C2 (es) |
| SI (1) | SI0929517T1 (es) |
| SK (1) | SK43099A3 (es) |
| TR (1) | TR199900725T2 (es) |
| WO (1) | WO1998014424A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003294917A1 (en) * | 2002-12-20 | 2004-07-14 | Novartis Ag | Device and method for delivering mmp inhibitors |
| EP2287326A1 (en) | 2003-08-08 | 2011-02-23 | Arriva Pharmaceuticals, Inc. | Methods of protein production in yeast |
| WO2005086915A2 (en) | 2004-03-09 | 2005-09-22 | Arriva Pharmaceuticals, Inc. | Treatment of chronic obstructive pulmonary disease by low dose inhalation of protease inhibitor |
| CN1951912B (zh) * | 2005-10-18 | 2010-05-05 | 上海五洲药业股份有限公司 | 手性脂环烃异羟肟酸衍生物的制备方法 |
| GB0818907D0 (en) * | 2008-10-15 | 2008-11-19 | Isis Innovation | Histone lysine demethylase inhibitors |
| RU2021110237A (ru) * | 2016-04-18 | 2021-05-06 | Виворион Терапьютикс Аг | Новые ингибиторы меприна альфа и бета |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9223904D0 (en) * | 1992-11-13 | 1993-01-06 | British Bio Technology | Inhibition of cytokine production |
| DE19581347T1 (de) * | 1994-01-20 | 1996-12-05 | British Biotech Pharm | Metalloproteinase-Inhibitoren |
| WO1995019961A1 (en) * | 1994-01-22 | 1995-07-27 | British Biotech Pharmaceuticals Limited | Metalloproteinase inhibitors |
| GB9416897D0 (en) * | 1994-08-20 | 1994-10-12 | British Biotech Pharm | Metalloproteinase inhibitors |
| GB9423914D0 (en) * | 1994-11-26 | 1995-01-11 | British Biotech Pharm | Polyether derivatives as metalloproteinase inhibitors |
-
1997
- 1997-09-30 WO PCT/EP1997/005376 patent/WO1998014424A1/en not_active Application Discontinuation
- 1997-09-30 DE DE69713354T patent/DE69713354T2/de not_active Expired - Lifetime
- 1997-09-30 HU HU9903892A patent/HUP9903892A3/hu unknown
- 1997-09-30 KR KR1019990702806A patent/KR20000048811A/ko not_active Application Discontinuation
- 1997-09-30 NZ NZ334908A patent/NZ334908A/xx unknown
- 1997-09-30 TR TR1999/00725T patent/TR199900725T2/xx unknown
- 1997-09-30 PE PE1997000874A patent/PE2099A1/es not_active Application Discontinuation
- 1997-09-30 SK SK430-99A patent/SK43099A3/sk unknown
- 1997-09-30 PT PT97909339T patent/PT929517E/pt unknown
- 1997-09-30 PL PL97332477A patent/PL188518B1/pl not_active IP Right Cessation
- 1997-09-30 CZ CZ991139A patent/CZ113999A3/cs unknown
- 1997-09-30 SI SI9730357T patent/SI0929517T1/xx unknown
- 1997-09-30 AR ARP970104491A patent/AR009103A1/es unknown
- 1997-09-30 BR BR9712255A patent/BR9712255A/pt not_active Application Discontinuation
- 1997-09-30 ID IDW990143D patent/ID22212A/id unknown
- 1997-09-30 RU RU99108792/04A patent/RU2196131C2/ru not_active IP Right Cessation
- 1997-09-30 AT AT97909339T patent/ATE219050T1/de not_active IP Right Cessation
- 1997-09-30 IL IL12916697A patent/IL129166A0/xx not_active IP Right Cessation
- 1997-09-30 EP EP97909339A patent/EP0929517B1/en not_active Expired - Lifetime
- 1997-09-30 ES ES97909339T patent/ES2178759T3/es not_active Expired - Lifetime
- 1997-09-30 JP JP51623698A patent/JP3444898B2/ja not_active Expired - Fee Related
- 1997-09-30 CA CA002267415A patent/CA2267415A1/en not_active Abandoned
- 1997-09-30 DK DK97909339T patent/DK0929517T3/da active
- 1997-09-30 CN CN97198511A patent/CN1101807C/zh not_active Expired - Fee Related
- 1997-09-30 AU AU47068/97A patent/AU726065B2/en not_active Ceased
- 1997-10-01 CO CO97057298A patent/CO4900034A1/es unknown
- 1997-10-01 MY MYPI97004587A patent/MY127926A/en unknown
-
1999
- 1999-03-30 NO NO19991559A patent/NO313457B1/no not_active IP Right Cessation
-
2000
- 2000-01-20 HK HK00100370A patent/HK1021637A1/xx not_active IP Right Cessation
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