IL115944A - Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative - Google Patents
Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivativeInfo
- Publication number
- IL115944A IL115944A IL11594495A IL11594495A IL115944A IL 115944 A IL115944 A IL 115944A IL 11594495 A IL11594495 A IL 11594495A IL 11594495 A IL11594495 A IL 11594495A IL 115944 A IL115944 A IL 115944A
- Authority
- IL
- Israel
- Prior art keywords
- hiv
- alkyl
- hydrogen
- branched
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 208000031886 HIV Infections Diseases 0.000 title claims abstract description 11
- 238000011282 treatment Methods 0.000 title claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title description 3
- 150000003931 anilides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 239000003112 inhibitor Substances 0.000 claims abstract description 105
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims abstract description 97
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical group 0.000 claims abstract description 14
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 13
- 125000004385 trihaloalkyl group Chemical group 0.000 claims abstract description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims abstract description 10
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 230000002265 prevention Effects 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 4
- 125000000466 oxiranyl group Chemical group 0.000 claims abstract description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- 239000002777 nucleoside Substances 0.000 claims abstract description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- -1 C7-C12 alkarylalkyl Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910014585 C2-Ce Inorganic materials 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 abstract 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 125
- 102100034343 Integrase Human genes 0.000 description 123
- 241000700605 Viruses Species 0.000 description 38
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 33
- 238000004113 cell culture Methods 0.000 description 21
- 230000035772 mutation Effects 0.000 description 18
- 229960000689 nevirapine Drugs 0.000 description 16
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 15
- 230000002401 inhibitory effect Effects 0.000 description 13
- KZKYYGSZDVZKNJ-XDSPWSPCSA-N 1-[(5r,6r,8r,9r)-4-amino-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dioxo-1,7-dioxa-2$l^{6}-thiaspiro[4.4]non-3-en-8-yl]-3,5-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)C(C)=CN1[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@]2(C(=CS(=O)(=O)O2)N)[C@@H](CO[Si](C)(C)C(C)(C)C)O1 KZKYYGSZDVZKNJ-XDSPWSPCSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 10
- 235000008529 Ziziphus vulgaris Nutrition 0.000 description 9
- 244000126002 Ziziphus vulgaris Species 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 150000001413 amino acids Chemical group 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- RCSLUNOLLUVOOG-NSHDSACASA-N 4-chloro-8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2h-2,7,9a-triaza-benzo[cd]azulene-1-thione Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC(Cl)=CC1=C32 RCSLUNOLLUVOOG-NSHDSACASA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000013337 sub-cultivation Methods 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
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- 238000000034 method Methods 0.000 description 4
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 108091034117 Oligonucleotide Proteins 0.000 description 3
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- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- UMQCVRJLQBUADZ-UHFFFAOYSA-N 3-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]indol-2-one Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C=2C(N=C3C=CC=CC3=2)=O)CC1 UMQCVRJLQBUADZ-UHFFFAOYSA-N 0.000 description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
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- NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 description 1
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- MLILORUFDVLTSP-UHFFFAOYSA-N emivirine Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1C(C)C MLILORUFDVLTSP-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZSUMCRSGZQLTDK-UHFFFAOYSA-N n-phenyloxathiine-3-carboxamide Chemical class C=1C=COSC=1C(=O)NC1=CC=CC=C1 ZSUMCRSGZQLTDK-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 238000003752 polymerase chain reaction Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 238000002976 reverse transcriptase assay Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL14022495A IL140224A (en) | 1994-11-30 | 1995-11-09 | Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative |
| IL14022400A IL140224A0 (en) | 1994-11-30 | 2000-12-11 | A composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/346,721 US5968910A (en) | 1994-11-30 | 1994-11-30 | Compositions containing two or three inhibitors of different HIV reverse transcriptases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL115944A0 IL115944A0 (en) | 1996-05-14 |
| IL115944A true IL115944A (en) | 2001-10-31 |
Family
ID=23360750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11594495A IL115944A (en) | 1994-11-30 | 1995-11-09 | Composition for the treatment of hiv-1 infection containing a heterocyclyl carb (ox/thio) anilide derivative |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5968910A (de) |
| EP (1) | EP0794793B1 (de) |
| JP (1) | JP3655636B2 (de) |
| KR (1) | KR100403545B1 (de) |
| CN (1) | CN1104909C (de) |
| AU (1) | AU717025B2 (de) |
| BR (1) | BR9509925A (de) |
| CA (1) | CA2204652C (de) |
| DE (1) | DE69535366T2 (de) |
| HU (1) | HU223548B1 (de) |
| IL (1) | IL115944A (de) |
| MX (1) | MX9704024A (de) |
| NZ (1) | NZ297006A (de) |
| RU (1) | RU2227750C2 (de) |
| WO (1) | WO1996016675A2 (de) |
| ZA (1) | ZA9510108B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5696151A (en) * | 1995-11-30 | 1997-12-09 | Uniroyal Chemical Company, Inc. | Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants |
| DE69840216D1 (de) * | 1997-08-08 | 2008-12-24 | Celmed Oncology Usa Inc | Verfahren und Zubereitungen um Resistenz gegen biologische oder chemische Therapien zu Überwinden |
| ES2172303T3 (es) | 1998-01-23 | 2002-09-16 | Newbiotics Inc | Agentes terapeuticos obtenidos por catalisis enzimatica. |
| US7462605B2 (en) * | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US6683061B1 (en) * | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| IL147749A0 (en) | 1999-07-22 | 2002-08-14 | Newbiotics Inc | Methods for treating therapy-resistant tumors |
| WO2001021160A2 (en) * | 1999-09-23 | 2001-03-29 | Axxima Pharmaceuticals Aktiengesellschaft | Carboxymide and aniline derivatives as selective inhibitors of pathogens |
| UA74826C2 (en) * | 2000-05-17 | 2006-02-15 | Ortho Mcneil Pharm Inc | ?-carboline derivatives as phosphodiesterase inhibitors |
| CN101108178B (zh) * | 2006-07-20 | 2010-09-15 | 复旦大学 | 一种亲环素a抑制剂在制备抗艾滋病药物中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5268389A (en) * | 1989-10-16 | 1993-12-07 | Uniroyal Chemical Company, Inc. | Thiocarboxylate ester compounds compositions containing the same |
| IL99843A0 (en) * | 1990-11-01 | 1992-08-18 | Merck & Co Inc | Synergistic combination of hiv reverse transcriptase inhibitors |
| ATE138928T1 (de) * | 1991-09-04 | 1996-06-15 | Stichting Rega V Z W | Substituierte nukleosidderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen |
-
1994
- 1994-11-30 US US08/346,721 patent/US5968910A/en not_active Expired - Lifetime
-
1995
- 1995-11-09 IL IL11594495A patent/IL115944A/en not_active IP Right Cessation
- 1995-11-28 ZA ZA9510108A patent/ZA9510108B/xx unknown
- 1995-11-29 NZ NZ297006A patent/NZ297006A/en not_active IP Right Cessation
- 1995-11-29 CN CN95196540A patent/CN1104909C/zh not_active Expired - Lifetime
- 1995-11-29 EP EP95940258A patent/EP0794793B1/de not_active Expired - Lifetime
- 1995-11-29 WO PCT/EP1995/004704 patent/WO1996016675A2/en active IP Right Grant
- 1995-11-29 AU AU41769/96A patent/AU717025B2/en not_active Expired
- 1995-11-29 BR BR9509925A patent/BR9509925A/pt not_active IP Right Cessation
- 1995-11-29 RU RU97110670/15A patent/RU2227750C2/ru active
- 1995-11-29 KR KR1019970703579A patent/KR100403545B1/ko not_active IP Right Cessation
- 1995-11-29 DE DE69535366T patent/DE69535366T2/de not_active Expired - Lifetime
- 1995-11-29 MX MX9704024A patent/MX9704024A/es unknown
- 1995-11-29 JP JP51818896A patent/JP3655636B2/ja not_active Expired - Fee Related
- 1995-11-29 HU HU9800354A patent/HU223548B1/hu active IP Right Grant
- 1995-11-29 CA CA002204652A patent/CA2204652C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1167442A (zh) | 1997-12-10 |
| MX9704024A (es) | 1998-02-28 |
| WO1996016675A2 (en) | 1996-06-06 |
| KR100403545B1 (ko) | 2004-05-27 |
| CN1104909C (zh) | 2003-04-09 |
| DE69535366D1 (de) | 2007-02-22 |
| US5968910A (en) | 1999-10-19 |
| CA2204652A1 (en) | 1996-06-06 |
| DE69535366T2 (de) | 2007-10-11 |
| ZA9510108B (en) | 1996-06-06 |
| EP0794793B1 (de) | 2007-01-10 |
| CA2204652C (en) | 2009-04-07 |
| JP3655636B2 (ja) | 2005-06-02 |
| NZ297006A (en) | 2001-03-30 |
| HU223548B1 (hu) | 2004-09-28 |
| WO1996016675A3 (en) | 1996-08-29 |
| EP0794793A1 (de) | 1997-09-17 |
| RU2227750C2 (ru) | 2004-04-27 |
| BR9509925A (pt) | 1997-09-30 |
| IL115944A0 (en) | 1996-05-14 |
| JPH10500996A (ja) | 1998-01-27 |
| AU4176996A (en) | 1996-06-19 |
| KR987000088A (ko) | 1998-03-30 |
| HUT77573A (hu) | 1998-06-29 |
| AU717025B2 (en) | 2000-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |