CZ291702B6 - Cyklický peptid, způsob jeho přípravy, farmaceutický prostředek s jeho obsahem a použití - Google Patents
Cyklický peptid, způsob jeho přípravy, farmaceutický prostředek s jeho obsahem a použití Download PDFInfo
- Publication number
- CZ291702B6 CZ291702B6 CZ19973102A CZ310297A CZ291702B6 CZ 291702 B6 CZ291702 B6 CZ 291702B6 CZ 19973102 A CZ19973102 A CZ 19973102A CZ 310297 A CZ310297 A CZ 310297A CZ 291702 B6 CZ291702 B6 CZ 291702B6
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- CZ
- Czechia
- Prior art keywords
- group
- formula
- phenyl
- substituted
- alkoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 65
- 108010069514 Cyclic Peptides Proteins 0.000 title claims description 40
- 102000001189 Cyclic Peptides Human genes 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 29
- 230000008569 process Effects 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
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- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims abstract description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 34
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000006239 protecting group Chemical group 0.000 claims description 25
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
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- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 4
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 1
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- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 150000003009 phosphonic acids Chemical class 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract description 24
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- 229910052740 iodine Inorganic materials 0.000 abstract description 2
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- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 16
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- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical compound CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41834195A | 1995-04-07 | 1995-04-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ310297A3 CZ310297A3 (cs) | 1998-06-17 |
| CZ291702B6 true CZ291702B6 (cs) | 2003-05-14 |
Family
ID=23657711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19973102A CZ291702B6 (cs) | 1995-04-07 | 1996-04-03 | Cyklický peptid, způsob jeho přípravy, farmaceutický prostředek s jeho obsahem a použití |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5646111A (en:Method) |
| EP (1) | EP0736541B1 (en:Method) |
| JP (1) | JPH11504005A (en:Method) |
| KR (1) | KR19980703646A (en:Method) |
| CN (1) | CN1185739A (en:Method) |
| AR (2) | AR002731A1 (en:Method) |
| AT (1) | ATE228535T1 (en:Method) |
| AU (1) | AU702841B2 (en:Method) |
| BR (1) | BR9604906A (en:Method) |
| CA (1) | CA2217048A1 (en:Method) |
| CO (1) | CO4700480A1 (en:Method) |
| CZ (1) | CZ291702B6 (en:Method) |
| DE (1) | DE69624966T2 (en:Method) |
| EA (1) | EA000464B1 (en:Method) |
| ES (1) | ES2187617T3 (en:Method) |
| HU (1) | HUP9800809A3 (en:Method) |
| IL (1) | IL117749A (en:Method) |
| IN (1) | IN181897B (en:Method) |
| MX (1) | MX9707611A (en:Method) |
| MY (1) | MY132116A (en:Method) |
| NO (1) | NO974562L (en:Method) |
| NZ (1) | NZ305735A (en:Method) |
| PE (1) | PE39097A1 (en:Method) |
| PL (1) | PL322821A1 (en:Method) |
| TR (1) | TR199701122T1 (en:Method) |
| UA (1) | UA46759C2 (en:Method) |
| WO (1) | WO1996031228A1 (en:Method) |
| YU (1) | YU22496A (en:Method) |
| ZA (1) | ZA962598B (en:Method) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6384013B1 (en) | 1992-03-19 | 2002-05-07 | Eli Lilly And Company | Cyclic peptide antifungal agents and process for preparation thereof |
| US6743777B1 (en) | 1992-03-19 | 2004-06-01 | Eli Lilly And Company | Cyclic peptide antifungal agents and process for preparation thereof |
| US5965525A (en) * | 1992-03-19 | 1999-10-12 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| AU1851797A (en) * | 1996-02-01 | 1997-08-22 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| WO1999006062A1 (en) * | 1997-08-04 | 1999-02-11 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| FR2784993B1 (fr) * | 1998-10-26 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'echinocandine, leur procede de preparation et leur application comme fongicides |
| UA72200C2 (uk) * | 1997-12-10 | 2005-02-15 | Авентіс Фарма С.А. | Похідні ехінокандину, спосіб їх одержання, їх застосування, проміжні сполуки та фармацевтична композиція |
| AU2003200556B2 (en) * | 1997-12-10 | 2005-12-01 | Novexel | Echinocandin derivative and their preparation method |
| US6323176B1 (en) | 1998-02-25 | 2001-11-27 | Eli Lilly And Company | Cyclic peptide antifungal agents |
| MA26663A1 (fr) | 1998-07-23 | 2004-12-20 | Hoffmann La Roche | Nouvelles aerothricines et leurs applications antifongiques |
| EP1107981B1 (en) | 1998-08-20 | 2005-01-26 | Eli Lilly & Company | Synthesis of ring-modified cyclic peptide analogs |
| PT1137663E (pt) | 1998-12-09 | 2006-12-29 | Lilly Co Eli | Purificação de compostos ciclopéptidos equinocandina |
| IL145185A0 (en) * | 1999-03-03 | 2002-06-30 | Lilly Co Eli | Echinocandin pharmaceutical formulations containing micelle-forming surfactants |
| DK1157030T3 (da) | 1999-03-03 | 2003-12-22 | Lilly Co Eli | Enchinocanidin/carbohydratkomplekser |
| IL145188A0 (en) | 1999-03-03 | 2002-06-30 | Lilly Co Eli | Processes for making pharmaceutical oral ecb formulations and compositions |
| JP4063497B2 (ja) | 1999-03-03 | 2008-03-19 | イーライ リリー アンド カンパニー | エキノカンジンアンモニウム塩結晶の形成およびアニオン交換 |
| FR2794747B1 (fr) * | 1999-06-09 | 2004-04-16 | Hoechst Marion Roussel Inc | Nouveaux derives de l'echinocandine, leur procede de preparation et leur application comme anti-fongiques |
| KR100474161B1 (ko) | 2000-01-17 | 2005-03-10 | 바실리어 파마슈티카 아게 | 에어로트리신 유도체, 이의 제조 방법 및 이를 함유하는 약학조성물 |
| FR2833596B1 (fr) * | 2001-12-14 | 2005-02-18 | Aventis Pharma Sa | Procede de preparation de derives d'echinocandine |
| US6991800B2 (en) * | 2002-06-13 | 2006-01-31 | Vicuron Pharmaceuticals Inc. | Antifungal parenteral products |
| CN101602795B (zh) * | 2009-07-20 | 2011-12-21 | 中国人民解放军第二军医大学 | 环六脂肽胺类抗真菌化合物及其盐类和制备方法 |
| CN103570530B (zh) * | 2012-07-26 | 2016-08-10 | 鲁南新时代生物技术有限公司 | 一种阿尼芬净侧链中间体的制备方法 |
| CN104003895B (zh) * | 2014-05-29 | 2016-02-24 | 黑龙江大学 | 一种钯催化的串联反应合成三联苯类化合物的方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293488A (en) * | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912B nucleus |
| US4320052A (en) * | 1979-12-13 | 1982-03-16 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4293489A (en) * | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US5166135A (en) * | 1988-09-12 | 1992-11-24 | Merck & Company, Inc. | Method for the control of pneumocystis carinii |
| DK173802B1 (da) * | 1988-09-12 | 2001-11-05 | Merck & Co Inc | Præparat til behandling af Pneumocystis carinii infeksioner og anvendelse af et cyclohexapeptid til fremstilling af et lægemiddel mod Pneumocystis carinii infektioner |
| CA2037957A1 (en) * | 1990-03-12 | 1991-09-13 | Merck & Co., Inc. | N-acylated cyclohexapeptide compounds |
| GB2241956A (en) * | 1990-03-16 | 1991-09-18 | Merck & Co Inc | N-acylated cyclohexapeptide compounds |
| IL97347A0 (en) * | 1990-03-19 | 1992-05-25 | Merck & Co Inc | Lipopeptide derivatives and antimicrobial compositions containing them |
| US5310726A (en) * | 1990-03-19 | 1994-05-10 | Merck & Co., Inc. | Lipopeptide compounds |
| US5386009A (en) * | 1990-03-19 | 1995-01-31 | Merck & Co. Inc. | Lipopeptide derivatives |
| US5330973A (en) * | 1990-03-19 | 1994-07-19 | Merck & Co., Inc. | Lipopeptide derivatives |
| US5049546A (en) * | 1990-03-19 | 1991-09-17 | Merck & Co., Inc. | Antibiotic agents |
| IE910892A1 (en) * | 1990-03-19 | 1991-09-25 | Merck & Co Inc | Lipopeptide compounds |
| IL98506A (en) * | 1990-06-18 | 1996-09-12 | Fujisawa Pharmaceutical Co | Cyclic peptide antibiotics processes for the preparation thereof and pharmaceutical compositions containing them |
| EP0486011A3 (en) * | 1990-11-16 | 1992-07-15 | Fujisawa Pharmaceutical Co., Ltd. | Pharmaceutical composition against pneumocystis carinii |
| US5369093A (en) * | 1991-03-15 | 1994-11-29 | Merck & Co., Inc. | Lipopeptide derivatives |
| US5233023A (en) * | 1991-07-30 | 1993-08-03 | Merck & Co., Inc. | Process for phosphate ester compounds of certain cyclohexapeptides |
| NZ512085A (en) * | 1992-03-19 | 2003-08-29 | Lilly Co Eli | Methods employing cyclic peptide antifungal agents |
-
1996
- 1996-03-07 US US08/612,208 patent/US5646111A/en not_active Expired - Fee Related
- 1996-04-01 PE PE1996000229A patent/PE39097A1/es not_active Application Discontinuation
- 1996-04-01 ZA ZA9602598A patent/ZA962598B/xx unknown
- 1996-04-01 IL IL11774996A patent/IL117749A/xx not_active IP Right Cessation
- 1996-04-02 IN IN591CA1996 patent/IN181897B/en unknown
- 1996-04-03 HU HU9800809A patent/HUP9800809A3/hu unknown
- 1996-04-03 AR ARP960102057A patent/AR002731A1/es unknown
- 1996-04-03 DE DE69624966T patent/DE69624966T2/de not_active Expired - Fee Related
- 1996-04-03 NZ NZ305735A patent/NZ305735A/xx unknown
- 1996-04-03 BR BR9604906A patent/BR9604906A/pt not_active IP Right Cessation
- 1996-04-03 CZ CZ19973102A patent/CZ291702B6/cs not_active IP Right Cessation
- 1996-04-03 UA UA97104915A patent/UA46759C2/uk unknown
- 1996-04-03 EA EA199700307A patent/EA000464B1/ru not_active IP Right Cessation
- 1996-04-03 JP JP8530439A patent/JPH11504005A/ja not_active Ceased
- 1996-04-03 ES ES96302362T patent/ES2187617T3/es not_active Expired - Lifetime
- 1996-04-03 PL PL96322821A patent/PL322821A1/xx unknown
- 1996-04-03 AU AU53834/96A patent/AU702841B2/en not_active Ceased
- 1996-04-03 MX MX9707611A patent/MX9707611A/es unknown
- 1996-04-03 EP EP96302362A patent/EP0736541B1/en not_active Expired - Lifetime
- 1996-04-03 TR TR97/01122T patent/TR199701122T1/xx unknown
- 1996-04-03 KR KR1019970707045A patent/KR19980703646A/ko not_active Ceased
- 1996-04-03 WO PCT/US1996/004543 patent/WO1996031228A1/en not_active Application Discontinuation
- 1996-04-03 AT AT96302362T patent/ATE228535T1/de not_active IP Right Cessation
- 1996-04-03 AR ARP960102058A patent/AR004170A1/es not_active Application Discontinuation
- 1996-04-03 CN CN96194199A patent/CN1185739A/zh active Pending
- 1996-04-03 CA CA002217048A patent/CA2217048A1/en not_active Abandoned
- 1996-04-03 CO CO96016384A patent/CO4700480A1/es unknown
- 1996-04-05 YU YU22496A patent/YU22496A/sh unknown
- 1996-04-06 MY MYPI96001310A patent/MY132116A/en unknown
-
1997
- 1997-10-02 NO NO974562A patent/NO974562L/no not_active Application Discontinuation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20050403 |