NO309816B1 - Erytromycin A 9-0-oksimderivater som utviser antibiotisk aktivitet, og farmasøytisk preparat inneholdende disse - Google Patents
Erytromycin A 9-0-oksimderivater som utviser antibiotisk aktivitet, og farmasøytisk preparat inneholdende disse Download PDFInfo
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- NO309816B1 NO309816B1 NO972702A NO972702A NO309816B1 NO 309816 B1 NO309816 B1 NO 309816B1 NO 972702 A NO972702 A NO 972702A NO 972702 A NO972702 A NO 972702A NO 309816 B1 NO309816 B1 NO 309816B1
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- Prior art keywords
- formula
- erythromycin
- compounds
- benzyloxycarbonyl
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title description 78
- 229960003276 erythromycin Drugs 0.000 title description 72
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- 150000002923 oximes Chemical class 0.000 title description 23
- 230000003115 biocidal effect Effects 0.000 title description 10
- 230000001747 exhibiting effect Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 88
- -1 hydroxy- Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
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- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 6
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
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- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
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- RMHDLBZYPISZOI-UHFFFAOYSA-N borane;methylsulfanylmethane Chemical compound B.CSC RMHDLBZYPISZOI-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 229940125797 compound 12 Drugs 0.000 description 1
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- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
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- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- DPKDODGKXGTYBD-UHFFFAOYSA-N ethyl 2-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoylamino]acetate Chemical compound CCOC(=O)CNC(=O)CCCCCNC(=O)OC(C)(C)C DPKDODGKXGTYBD-UHFFFAOYSA-N 0.000 description 1
- MMZBRJRNWLUJRY-UHFFFAOYSA-N ethyl 2-[6-[(4-fluorobenzoyl)amino]hexanoylamino]acetate Chemical compound CCOC(=O)CNC(=O)CCCCCNC(=O)C1=CC=C(F)C=C1 MMZBRJRNWLUJRY-UHFFFAOYSA-N 0.000 description 1
- VZADFVVEJLAGMT-UHFFFAOYSA-N ethyl 2-[6-[(4-methoxybenzoyl)amino]hexanoylamino]acetate Chemical compound CCOC(=O)CNC(=O)CCCCCNC(=O)C1=CC=C(OC)C=C1 VZADFVVEJLAGMT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MLDQPOXOWLCOEC-UHFFFAOYSA-N n-hexylbenzamide Chemical compound CCCCCCNC(=O)C1=CC=CC=C1 MLDQPOXOWLCOEC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT94MI002496A IT1276901B1 (it) | 1994-12-13 | 1994-12-13 | Derivati dell'eritromicina a 9-0-ossina dotati di attivita' antibiotica |
| PCT/EP1995/004815 WO1996018633A1 (en) | 1994-12-13 | 1995-12-07 | Erythromycin a 9-0-oxime derivatives endowed with antibiotic activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO972702D0 NO972702D0 (no) | 1997-06-12 |
| NO972702L NO972702L (no) | 1997-08-13 |
| NO309816B1 true NO309816B1 (no) | 2001-04-02 |
Family
ID=11369979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO972702A NO309816B1 (no) | 1994-12-13 | 1997-06-12 | Erytromycin A 9-0-oksimderivater som utviser antibiotisk aktivitet, og farmasøytisk preparat inneholdende disse |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US5847092A (uk) |
| EP (1) | EP0797579B1 (uk) |
| JP (1) | JPH10510520A (uk) |
| KR (1) | KR100367559B1 (uk) |
| CN (1) | CN1046535C (uk) |
| AP (1) | AP739A (uk) |
| AT (1) | ATE190620T1 (uk) |
| AU (1) | AU690791B2 (uk) |
| BG (1) | BG63261B1 (uk) |
| BR (1) | BR9510015A (uk) |
| CA (1) | CA2207029A1 (uk) |
| CZ (1) | CZ289943B6 (uk) |
| DE (1) | DE69515694T2 (uk) |
| DK (1) | DK0797579T3 (uk) |
| EE (1) | EE03401B1 (uk) |
| ES (1) | ES2144154T3 (uk) |
| FI (1) | FI972493A (uk) |
| GE (1) | GEP20012391B (uk) |
| GR (1) | GR3033622T3 (uk) |
| HU (1) | HU220631B1 (uk) |
| IT (1) | IT1276901B1 (uk) |
| LT (1) | LT4276B (uk) |
| LV (1) | LV11898B (uk) |
| MD (1) | MD1788G2 (uk) |
| NO (1) | NO309816B1 (uk) |
| NZ (1) | NZ297446A (uk) |
| OA (1) | OA10491A (uk) |
| PL (1) | PL182053B1 (uk) |
| PT (1) | PT797579E (uk) |
| RO (1) | RO116282B1 (uk) |
| RU (1) | RU2152951C1 (uk) |
| SI (1) | SI9520124A (uk) |
| TJ (1) | TJ306B (uk) |
| UA (1) | UA48958C2 (uk) |
| WO (1) | WO1996018633A1 (uk) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1290447B1 (it) | 1997-03-28 | 1998-12-03 | Zambon Spa | Derivati 1,3-ossatiolanici ad attivita' antivirale |
| IT1301967B1 (it) * | 1998-07-30 | 2000-07-20 | Zambon Spa | Derivato di eritromicina ad attivita' antibiotica |
| IT1301968B1 (it) * | 1998-07-30 | 2000-07-20 | Zambon Spa | Derivati di eritromicina ad attivita' antibiotica |
| IT1306205B1 (it) * | 1999-01-15 | 2001-05-30 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| US6638908B1 (en) | 2000-08-09 | 2003-10-28 | Yale University | Crystals of the large ribosomal subunit |
| US6947844B2 (en) | 2000-08-09 | 2005-09-20 | Yale University | Modulators of ribosomal function and identification thereof |
| IL151012A0 (en) | 2001-08-03 | 2003-02-12 | Ribosomes Structure And Protei | Ribosomes structure and protein synthesis inhibitors |
| US6952650B2 (en) | 2001-08-03 | 2005-10-04 | Yale University | Modulators of ribosomal function and identification thereof |
| ITMI20021726A1 (it) | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| TW200420573A (en) | 2002-09-26 | 2004-10-16 | Rib X Pharmaceuticals Inc | Bifunctional heterocyclic compounds and methods of making and using same |
| US8202843B2 (en) | 2004-02-27 | 2012-06-19 | Rib-X Pharmaceuticals, Inc. | Macrocyclic compounds and methods of making and using the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2473525A1 (fr) * | 1980-01-11 | 1981-07-17 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| GB8521402D0 (en) | 1985-08-28 | 1985-10-02 | Beecham Group Plc | Chemical compounds |
| US4740502A (en) * | 1986-06-20 | 1988-04-26 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| DK90788A (da) | 1987-02-24 | 1988-08-25 | Beecham Group Plc | Erythromycinderivater |
| US5302705A (en) * | 1989-10-07 | 1994-04-12 | Taisho Pharmaceutical Co., Ltd. | 6-O-methylerythromycin a oxime derivatives |
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
-
1994
- 1994-12-13 IT IT94MI002496A patent/IT1276901B1/it active IP Right Grant
-
1995
- 1995-12-07 JP JP8518235A patent/JPH10510520A/ja not_active Ceased
- 1995-12-07 BR BR9510015A patent/BR9510015A/pt not_active IP Right Cessation
- 1995-12-07 KR KR1019970703968A patent/KR100367559B1/ko not_active IP Right Cessation
- 1995-12-07 RU RU97112082/04A patent/RU2152951C1/ru not_active IP Right Cessation
- 1995-12-07 PL PL95320688A patent/PL182053B1/pl not_active IP Right Cessation
- 1995-12-07 GE GEAP19953817A patent/GEP20012391B/en unknown
- 1995-12-07 TJ TJ97000477A patent/TJ306B/xx unknown
- 1995-12-07 WO PCT/EP1995/004815 patent/WO1996018633A1/en not_active Application Discontinuation
- 1995-12-07 HU HU9701826A patent/HU220631B1/hu not_active IP Right Cessation
- 1995-12-07 AT AT95941076T patent/ATE190620T1/de not_active IP Right Cessation
- 1995-12-07 SI SI9520124A patent/SI9520124A/sl not_active IP Right Cessation
- 1995-12-07 DK DK95941076T patent/DK0797579T3/da active
- 1995-12-07 CN CN95196779A patent/CN1046535C/zh not_active Expired - Fee Related
- 1995-12-07 AP APAP/P/1997/000989A patent/AP739A/en active
- 1995-12-07 EP EP95941076A patent/EP0797579B1/en not_active Expired - Lifetime
- 1995-12-07 MD MD97-0243A patent/MD1788G2/ro not_active IP Right Cessation
- 1995-12-07 EE EE9700124A patent/EE03401B1/xx not_active IP Right Cessation
- 1995-12-07 CA CA002207029A patent/CA2207029A1/en not_active Abandoned
- 1995-12-07 UA UA97073719A patent/UA48958C2/uk unknown
- 1995-12-07 RO RO97-01065A patent/RO116282B1/ro unknown
- 1995-12-07 AU AU42603/96A patent/AU690791B2/en not_active Ceased
- 1995-12-07 ES ES95941076T patent/ES2144154T3/es not_active Expired - Lifetime
- 1995-12-07 DE DE69515694T patent/DE69515694T2/de not_active Expired - Fee Related
- 1995-12-07 CZ CZ19971786A patent/CZ289943B6/cs not_active IP Right Cessation
- 1995-12-07 US US08/836,785 patent/US5847092A/en not_active Expired - Fee Related
- 1995-12-07 NZ NZ297446A patent/NZ297446A/xx unknown
- 1995-12-07 PT PT95941076T patent/PT797579E/pt unknown
-
1997
- 1997-06-05 BG BG101570A patent/BG63261B1/bg unknown
- 1997-06-12 FI FI972493A patent/FI972493A/fi not_active IP Right Cessation
- 1997-06-12 NO NO972702A patent/NO309816B1/no unknown
- 1997-06-13 OA OA70023A patent/OA10491A/en unknown
- 1997-07-07 LT LT97-116A patent/LT4276B/lt not_active IP Right Cessation
- 1997-07-10 LV LVP-97-137A patent/LV11898B/en unknown
-
2000
- 2000-06-07 GR GR20000401308T patent/GR3033622T3/el not_active IP Right Cessation
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