KR890011837A - 디데하이드로 비타민 d₃유도체 - Google Patents
디데하이드로 비타민 d₃유도체 Download PDFInfo
- Publication number
- KR890011837A KR890011837A KR1019890000513A KR890000513A KR890011837A KR 890011837 A KR890011837 A KR 890011837A KR 1019890000513 A KR1019890000513 A KR 1019890000513A KR 890000513 A KR890000513 A KR 890000513A KR 890011837 A KR890011837 A KR 890011837A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- didehydro
- hydroxy
- treatment
- compound according
- Prior art date
Links
- 150000003704 vitamin D3 derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 7
- 206010006956 Calcium deficiency Diseases 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000002503 metabolic effect Effects 0.000 claims 3
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 201000006409 renal osteodystrophy Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/32—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.3.0) system, e.g. indenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 하기 일반식(Ⅰ)의 화합물.상기식에서, R1은 수소 또는 하이드록시이고, R2는 수소 또는 불소이다.
- 제1항에 있어서, 1α,25-디하이드록시-23, 24-디데하이드로-26, 26, 26, 27, 27, 27-헥사플루오로콜레칼시페롤, 25-하이드록시-23, 24-디데하이드로-26, 26, 26, 27, 27, 27-헥사플루오로콜레칼시페롤, 1α,25-디하이드록시-23,24-디데하이드로콜레칼시페롤, 및 25-하이드록시-23,24-디데하이드로콜레칼시페롤로 이루어진 그룹의 화합물.
- 제1항 또는 제2항에 있어서, 특히 대사성 칼슘 결핍을 특징으로 하는 질환 상태 특히, 골다공증 및 신장 공이영양증(Renal Osteodystrophy)을 치료하기 위해 치료적 활성 물질로서 사용하기 위한 화합물.
- 특히, 대사성 칼슘 결핍을 특징으로 하는 질환상태 특히 골다공증 및 신장 공이영양증(Renal Osteodystrophy)을 치료하기 위한, 제1항 또는 제2항에 따르는 화합물의 약제학적 유효양, 특히 약 0.1 내지 2㎍의 용량, 및 약제학적으로 허용되는 담체물질을 함유함을 특징으로 하는 약제.
- 대사성 칼슘 결핍을 특징으로 하는 질환상태, 특히 골다공증 및 신장 공이영양증을 치료하기 위한 약제의 제조를 위한 제1항 또는 제2항에 따르는 화합물의 용도.
- 본 명세서, 특히 실시예에서 기술한 신규한 화합물, 조성물, 제조방법 및 사용방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US145,867 | 1988-01-20 | ||
US07/145,867 US4804502A (en) | 1988-01-20 | 1988-01-20 | Vitamin D compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
KR890011837A true KR890011837A (ko) | 1989-08-22 |
KR960009118B1 KR960009118B1 (en) | 1996-07-13 |
Family
ID=22514903
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR89000513A KR960009118B1 (en) | 1988-01-20 | 1989-01-19 | Didehydro-vitamin d3 derivatives |
Country Status (23)
Country | Link |
---|---|
US (1) | US4804502A (ko) |
EP (1) | EP0326875B1 (ko) |
JP (1) | JPH0764805B2 (ko) |
KR (1) | KR960009118B1 (ko) |
AR (1) | AR246253A1 (ko) |
AT (1) | ATE74125T1 (ko) |
AU (1) | AU621851B2 (ko) |
CA (1) | CA1314906C (ko) |
DE (1) | DE58901003D1 (ko) |
DK (1) | DK171966B1 (ko) |
ES (1) | ES2032613T3 (ko) |
FI (1) | FI92193C (ko) |
GR (1) | GR3004785T3 (ko) |
HU (1) | HU201736B (ko) |
IE (1) | IE60920B1 (ko) |
IL (1) | IL88988A (ko) |
MC (1) | MC1997A1 (ko) |
NO (1) | NO174547C (ko) |
NZ (1) | NZ227642A (ko) |
PH (1) | PH24442A (ko) |
PT (1) | PT89485B (ko) |
YU (1) | YU47204B (ko) |
ZA (1) | ZA8922B (ko) |
Families Citing this family (53)
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US4898855A (en) * | 1987-09-14 | 1990-02-06 | Hoffman-La Roche Inc. | Deuterated analogs of 1,25-dihydroxycholecalciferol |
ZA8923B (en) * | 1988-01-20 | 1989-09-27 | Hoffmann La Roche | 16-dehydro-vitamin d3-derivatives |
US5145846A (en) * | 1988-01-20 | 1992-09-08 | Hoffmann-La Roche Inc. | Vitamin D3 analogs |
US5087619A (en) * | 1988-01-20 | 1992-02-11 | Hoffman-La Roche Inc. | Vitamin D3 analogs |
US4927815A (en) * | 1988-04-29 | 1990-05-22 | Wisconsin Alumni Research Foundation | Compounds effective in inducing cell differentiation and process for preparing same |
DE69005897D1 (de) * | 1989-05-18 | 1994-02-24 | Hoffmann La Roche | Dehydrocholecalciferolderivate. |
GB9017890D0 (en) * | 1990-08-15 | 1990-09-26 | Leo Pharm Prod Ltd | Chemical compounds i |
US5258559A (en) * | 1990-11-27 | 1993-11-02 | Hoffmann-La Roche Inc. | Process for the preparation of [1R-(1β(R*), 3aα, 4β, 7aβ)] octahydro-1-(5-hydroxy-1,5-dimethylhexyl)-7a-methyl-4H-inden-4-one |
US20040009958A1 (en) * | 1991-01-08 | 2004-01-15 | Bone Care International, Inc. | Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2 |
WO1992012165A1 (en) * | 1991-01-08 | 1992-07-23 | Lunar Corporation | METHODS FOR PREPARATION AND USE OF 1α,24-DIHYDROXY VITAMIN D¿2? |
AU650751B2 (en) * | 1991-05-28 | 1994-06-30 | Wisconsin Alumni Research Foundation | Novel synthesis of 19-nor vitamin D compounds |
DE69213844T2 (de) * | 1991-07-05 | 1997-04-10 | Duphar Int Res | Vitamin-D Derivat, Verfahren zu dessen Herstellung sowie Zwischenprodukte dafür |
IL99368A (en) * | 1991-09-02 | 1996-01-19 | Teva Pharma | Preparations for the treatment of psoriasis and atopic dermatitis, which contain the result of xanthine |
US5200536A (en) * | 1992-02-10 | 1993-04-06 | Daikin Industries Ltd. | Fluorine-containing vitamin D3 analogues |
ES2091515T3 (es) * | 1992-05-20 | 1996-11-01 | Hoffmann La Roche | Analogos fluorados de la vitamina d3. |
DE4220757A1 (de) * | 1992-06-24 | 1994-01-05 | Schering Ag | Derivate in der Vitamin D-Reihe mit Modifikationen in der 20-Position, Verfahren zu ihrer Herstellung, Zwischenprodukte für dieses Verfahren, diese Derivate enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
DE4221961A1 (de) * | 1992-06-30 | 1994-01-05 | Schering Ag | 22-En-25-oxa-Derivate in der Vitamin D-Reihe, Verfahren zu ihrer Herstellung, diese Derivate enthaltenen pharmazeutische Präparate sowie deren Verwendung als Arzneimittel |
US5753638A (en) * | 1992-10-07 | 1998-05-19 | Hoffmann-La Roche Inc. | Method of treating hyperproliferative skin disease with Vitamin D3 fluorinated analogs |
CA2096105A1 (en) * | 1992-10-07 | 1994-04-08 | Enrico Giuseppe Baggiolini (Deceased) | Vitamin d3 fluorinated analogs |
GB9223061D0 (en) * | 1992-11-04 | 1992-12-16 | Leo Pharm Prod Ltd | Chemical compounds |
TW267161B (ko) * | 1992-11-20 | 1996-01-01 | Hoffmann La Roche | |
US5547947A (en) * | 1993-03-11 | 1996-08-20 | Hoffmann-La Roche Inc. | Methods of treatment |
GB9314400D0 (en) * | 1993-07-12 | 1993-08-25 | Leo Pharm Prod Ltd | Produktionsaktieselskab) chemical compounds |
US5401733A (en) * | 1993-10-01 | 1995-03-28 | Hoffmann-La Roche Inc. | Stable and active metabolites of 1,25-dihydroxy-16-ene-cholecalciferol |
US5428029A (en) * | 1993-11-24 | 1995-06-27 | Hoffmann-La Roche Inc. | Vitamin D3 fluorinated analogs |
US6121469A (en) * | 1993-12-23 | 2000-09-19 | The Regents Of The University Of California | Therapeutically effective 1α,25-dihydroxyvitamin D3 analogs |
US6103709A (en) * | 1993-12-23 | 2000-08-15 | The Regents Of The University Of California | Therapeutically effective 1α,25-dihydroxyvitamin D3 analogs and methods for treatment of vitamin D diseases |
AU7295696A (en) * | 1995-10-27 | 1997-05-22 | F. Hoffmann-La Roche Ag | Pharmaceutical composition for treating osteoporosis |
US5696103A (en) * | 1995-11-17 | 1997-12-09 | Syntex (U.S.A.) Inc. | Method for treating osteoporosis |
US5939408A (en) | 1996-05-23 | 1999-08-17 | Hoffman-La Roche Inc. | Vitamin D3 analogs |
NO971934L (no) * | 1996-05-23 | 1997-11-24 | Hoffmann La Roche | Flourinerte vitamin D3 -analoger |
US6100294A (en) * | 1997-05-16 | 2000-08-08 | Women And Infants Hospital | Cyclic ether vitamin D3 compounds, 1α(OH) 3-epi-vitamin D3 compounds and uses thereof |
EP0981514B1 (en) * | 1997-05-16 | 2006-04-05 | Woman & Infants Hospital | 3-epi vitamin d2 compounds and uses thereof |
US20010007907A1 (en) * | 1997-05-16 | 2001-07-12 | Women And Infants Hospital | 3-epi compounds of vitamin d3 and uses thereof |
US6087350A (en) | 1997-08-29 | 2000-07-11 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Use of pretreatment chemicals to enhance efficacy of cytotoxic agents |
JP4219553B2 (ja) * | 1997-09-08 | 2009-02-04 | エフ.ホフマン−ラ ロシュ アーゲー | 1,3−ジヒドロキシ−20,20−ジアルキル−ビタミンd3類似体 |
US5919986A (en) * | 1997-10-17 | 1999-07-06 | Hoffmann-La Roche Inc. | D-homo vitamin D3 derivatives |
ES2368824T3 (es) | 1998-03-27 | 2011-11-22 | Oregon Health & Science University | Vitamina d y sus análogos en el tratamiento de tumores y otros desórdenes hiperproliferativos. |
AU2001278744A1 (en) * | 2000-08-17 | 2002-02-25 | Chugai Seiyaku Kabushiki Kaisha | Remedial agent for osteoporosis |
GB0305332D0 (en) * | 2003-03-10 | 2003-04-09 | Leuven K U Res & Dev | Biological evaluation of novel vitamin D analogues |
GB0422929D0 (en) * | 2004-10-15 | 2004-11-17 | Leuven K U Res & Dev | Bioactive vitamin D analogues |
US20060003950A1 (en) * | 2004-06-30 | 2006-01-05 | Bone Care International, Inc. | Method of treating prostatic diseases using a combination of vitamin D analogues and other agents |
US7094775B2 (en) * | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
JP2008519808A (ja) | 2004-11-12 | 2008-06-12 | ビオエクセル エスピーエー | 膀胱癌治療のためのビタミンd誘導体及び抗増殖薬の併用 |
EP1879449A4 (en) * | 2005-05-10 | 2009-12-16 | Dermipsor Ltd | SKIN CARE COMPOSITIONS AND METHODS |
BRPI0609630A2 (pt) * | 2005-05-10 | 2010-04-20 | Dermipsor Ltd | composições e métodos para tratamento de doenças epidérmicas hiperproliferativas |
CN101405249B (zh) * | 2006-03-15 | 2013-05-29 | 日本迈科洛生物制药有限公司 | 茚衍生物的制备方法及其制备中间体 |
KR20090082257A (ko) | 2006-11-02 | 2009-07-29 | 메루샹가부시키가이샤 | 1-히드록시-19-노르시클로비타민 d 유도체의 제조방법 및 그 제조 중간체 |
CA2981549A1 (en) * | 2009-01-27 | 2010-08-05 | Berg Llc | Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy |
SG10201404883YA (en) | 2009-08-14 | 2014-10-30 | Berg Llc | Vitamin d3 and analogs thereof for treating alopecia |
PL2634171T3 (pl) | 2010-10-25 | 2015-12-31 | Teijin Ltd | 23-ynowa pochodna witaminy D3 |
AU2014274099A1 (en) | 2013-05-29 | 2015-12-24 | Berg Llc | Preventing or mitigating chemotherapy induced alopecia using vitamin D |
WO2017209934A1 (en) | 2016-05-13 | 2017-12-07 | Case Western Reserve University | Autophagy activators for treating or preventing skin injury |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2812741C2 (de) * | 1977-03-24 | 1987-03-12 | Wisconsin Alumni Research Foundation, Madison, Wis. | Vitamin D↓3↓-Derivate, Verfahren und Zwischenprodukte zu deren Herstellung und diese enthaltende Arzneimittel |
GB2021115B (en) * | 1978-05-19 | 1982-10-06 | Wisconsin Alumni Res Found | Vitamin d derivatives |
US4358406A (en) * | 1981-07-27 | 1982-11-09 | Wisconsin Alumni Research Foundation | 26,26,26,27,27,27-Hexafluoro-1α,25-dihydroxycholecalciferol and process for preparing same |
US4360471A (en) * | 1981-12-11 | 1982-11-23 | Wisconsin Alumni Research Foundation | 23-Dehydro-25-hydroxyvitamin D3 |
US4508651A (en) * | 1983-03-21 | 1985-04-02 | Hoffmann-La Roche Inc. | Synthesis of 1α,25-dihydroxyergocalciferol |
US4689180A (en) * | 1984-01-30 | 1987-08-25 | Wisconsin Alumni Research Foundation | 1α,25-dihydroxy-22Z-dehydroxyvitamin D compound |
US4505906A (en) * | 1984-01-30 | 1985-03-19 | Wisconsin Alumni Research Foundation | Hydroxyvitamin D2 isomers |
US4521410A (en) * | 1984-05-03 | 1985-06-04 | The General Hospital Corporation | Vitamin D glycosyl orthoesters |
US4612308A (en) * | 1984-11-29 | 1986-09-16 | Hoffmann-La Roche Inc. | 25,26-Dehydro-1α,23(S,R)-dihydroxycholecalciferol and its epimers |
US4898855A (en) * | 1987-09-14 | 1990-02-06 | Hoffman-La Roche Inc. | Deuterated analogs of 1,25-dihydroxycholecalciferol |
ZA8923B (en) * | 1988-01-20 | 1989-09-27 | Hoffmann La Roche | 16-dehydro-vitamin d3-derivatives |
-
1988
- 1988-01-20 US US07/145,867 patent/US4804502A/en not_active Expired - Fee Related
-
1989
- 1989-01-03 ZA ZA8922A patent/ZA8922B/xx unknown
- 1989-01-17 NZ NZ227642A patent/NZ227642A/en unknown
- 1989-01-17 DK DK019689A patent/DK171966B1/da not_active IP Right Cessation
- 1989-01-17 CA CA000588385A patent/CA1314906C/en not_active Expired - Fee Related
- 1989-01-17 PH PH38058A patent/PH24442A/en unknown
- 1989-01-18 HU HU89174A patent/HU201736B/hu not_active IP Right Cessation
- 1989-01-18 IL IL88988A patent/IL88988A/xx not_active IP Right Cessation
- 1989-01-18 AR AR89313012A patent/AR246253A1/es active
- 1989-01-19 NO NO890240A patent/NO174547C/no unknown
- 1989-01-19 PT PT89485A patent/PT89485B/pt not_active IP Right Cessation
- 1989-01-19 MC MC892028A patent/MC1997A1/xx unknown
- 1989-01-19 KR KR89000513A patent/KR960009118B1/ko not_active IP Right Cessation
- 1989-01-19 JP JP1008781A patent/JPH0764805B2/ja not_active Expired - Lifetime
- 1989-01-19 FI FI890282A patent/FI92193C/fi not_active IP Right Cessation
- 1989-01-19 YU YU11889A patent/YU47204B/sh unknown
- 1989-01-19 IE IE15689A patent/IE60920B1/en not_active IP Right Cessation
- 1989-01-19 AU AU28643/89A patent/AU621851B2/en not_active Ceased
- 1989-01-20 AT AT89100973T patent/ATE74125T1/de not_active IP Right Cessation
- 1989-01-20 DE DE8989100973T patent/DE58901003D1/de not_active Expired - Fee Related
- 1989-01-20 ES ES198989100973T patent/ES2032613T3/es not_active Expired - Lifetime
- 1989-01-20 EP EP89100973A patent/EP0326875B1/de not_active Expired - Lifetime
-
1992
- 1992-06-03 GR GR920401137T patent/GR3004785T3/el unknown
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