IL90179A - תולדות n-)2-אמינו-5,6,7,8-טטראהידרופירידו-]b-2,3[ פירימידין-6איל-אציל( של חומצה l -גלוטמית, הכנתן, תכשירי רוקחות המכ - Google Patents
תולדות n-)2-אמינו-5,6,7,8-טטראהידרופירידו-]b-2,3[ פירימידין-6איל-אציל( של חומצה l -גלוטמית, הכנתן, תכשירי רוקחות המכInfo
- Publication number
- IL90179A IL90179A IL9017989A IL9017989A IL90179A IL 90179 A IL90179 A IL 90179A IL 9017989 A IL9017989 A IL 9017989A IL 9017989 A IL9017989 A IL 9017989A IL 90179 A IL90179 A IL 90179A
- Authority
- IL
- Israel
- Prior art keywords
- amino
- pyrimidin
- hydroxy
- tetrahydropyrido
- glutamic acid
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 229960002989 glutamic acid Drugs 0.000 title claims description 50
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000006239 protecting group Chemical group 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004956 cyclohexylene group Chemical group 0.000 claims abstract description 6
- 150000002306 glutamic acid derivatives Chemical class 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 241000124008 Mammalia Species 0.000 claims abstract description 5
- 150000001721 carbon Chemical group 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- -1 2-amino-4-hydroxy-5 ,6,7, 8-tetrahydropyrido[2 , 3-d] - pyrimidin-6-yl Chemical group 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
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- 230000003301 hydrolyzing effect Effects 0.000 claims 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 55
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- 241000699670 Mus sp. Species 0.000 description 12
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- HERPVHLYIHBEFW-ZETCQYMHSA-N diethyl (2s)-2-aminopentanedioate Chemical compound CCOC(=O)CC[C@H](N)C(=O)OCC HERPVHLYIHBEFW-ZETCQYMHSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- RWNJOXUVHRXHSD-UHFFFAOYSA-N hept-6-enoic acid Chemical compound OC(=O)CCCCC=C RWNJOXUVHRXHSD-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- JZYKFLLRVPPISG-UHFFFAOYSA-N hex-5-ynenitrile Chemical compound C#CCCCC#N JZYKFLLRVPPISG-UHFFFAOYSA-N 0.000 description 1
- WZBQFNAWQPYQPM-UHFFFAOYSA-N hex-5-ynoyl chloride Chemical compound ClC(=O)CCCC#C WZBQFNAWQPYQPM-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005243 lung squamous cell carcinoma Diseases 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 208000026037 malignant tumor of neck Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- YWBHXANUFSSMNL-UHFFFAOYSA-N n-(6-bromo-4-oxo-1h-pyrido[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide Chemical compound C1=C(Br)C=NC2=NC(NC(=O)C(C)(C)C)=NC(O)=C21 YWBHXANUFSSMNL-UHFFFAOYSA-N 0.000 description 1
- KLUNIYXWSVXRCD-UHFFFAOYSA-N n-(6-ethynyl-4-oxo-1h-pyrido[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide Chemical compound C1=C(C#C)C=NC2=NC(NC(=O)C(C)(C)C)=NC(O)=C21 KLUNIYXWSVXRCD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940127075 other antimetabolite Drugs 0.000 description 1
- 229960003552 other antineoplastic agent in atc Drugs 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000008791 toxic response Effects 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/198,201 US4882333A (en) | 1988-05-25 | 1988-05-25 | N-(5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl-alkanoyl)-glutamic acid derivatives |
| US07/198,207 US4882334A (en) | 1988-05-25 | 1988-05-25 | N-(5,6,7,8-tetrahydropyrido]2,3-d]pyrimidin-6-ylethl-thineyl-and furylcarbonyl)-glutamic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL90179A0 IL90179A0 (en) | 1989-12-15 |
| IL90179A true IL90179A (he) | 1994-02-27 |
Family
ID=26893557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9017989A IL90179A (he) | 1988-05-25 | 1989-05-03 | תולדות n-)2-אמינו-5,6,7,8-טטראהידרופירידו-]b-2,3[ פירימידין-6איל-אציל( של חומצה l -גלוטמית, הכנתן, תכשירי רוקחות המכ |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0343801B1 (he) |
| JP (1) | JP2818198B2 (he) |
| KR (1) | KR0131589B1 (he) |
| CN (1) | CN1025334C (he) |
| AT (1) | ATE109480T1 (he) |
| AU (1) | AU611027B2 (he) |
| CA (1) | CA1340631C (he) |
| CY (1) | CY2055B1 (he) |
| DE (1) | DE68917211T2 (he) |
| DK (1) | DK172753B1 (he) |
| ES (1) | ES2057116T3 (he) |
| HU (1) | HU205356B (he) |
| IE (1) | IE63620B1 (he) |
| IL (1) | IL90179A (he) |
| NZ (1) | NZ229242A (he) |
| PT (1) | PT90635B (he) |
| RU (1) | RU2002747C1 (he) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03173890A (ja) * | 1989-09-21 | 1991-07-29 | Takeda Chem Ind Ltd | ピロロ［２，３―ｄ］ピリミジン誘導体，その製造法，用途及び中間体 |
| IL96531A (he) * | 1989-12-11 | 1995-08-31 | Univ Princeton | תולדות של חומצה n-)דיומותמר-h1-פירולו]d-2,3[ פירימידין-3-אילאציל(-גלוטאמית, הכנתן ותכשירי רוקחות המכילים אותן |
| CA2032695A1 (en) * | 1989-12-20 | 1991-06-21 | Hiroshi Akimoto | Condensed heterocyclic compounds, their production and use |
| ZA932731B (en) * | 1992-04-23 | 1994-10-19 | Lilly Co Eli | Method of treating gar-transformylase-dependent tumors |
| US5608082A (en) * | 1994-07-28 | 1997-03-04 | Agouron Pharmaceuticals, Inc. | Compounds useful as antiproliferative agents and GARFT inhibitors |
| RU2191188C2 (ru) * | 1994-11-14 | 2002-10-20 | Варнер-Ламберт Компани | Производные 6-арилпиридо[2,3-d]-пиримидины и -нафтиридины, фармацевтическая композиция, обладающая ингибирующим действием клеточной пролиферации, вызываемой протеиновой тирозинкиназой, и способ ингибирования клеточной пролиферации |
| CA2184783A1 (en) * | 1995-09-08 | 1997-03-09 | William J. Gill | Nonclassical antifolates |
| CA2251813A1 (en) * | 1996-05-01 | 1997-11-06 | The Trustees Of Princeton University | 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidines |
| HUP0100869A3 (en) * | 1998-02-11 | 2002-12-28 | Lilly Co Eli | Processes and intermediates useful to make antifolates |
| RU2305677C2 (ru) * | 2001-12-27 | 2007-09-10 | Адзиномото Ко., Инк. | Способы получения производных глутаминовой кислоты, способы получения промежуточных соединений и новое промежуточное соединение для данных способов |
| KR101160473B1 (ko) * | 2003-01-09 | 2012-06-28 | 아지노모토 가부시키가이샤 | 글루탐산 유도체 및 피로글루탐산 유도체의 제조 방법 및신규 제조 중간체 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA861235B (en) * | 1985-03-08 | 1986-10-29 | Univ Princeton | Pyrido(2,3-d)pyrimidine derivatives |
| US4684653A (en) * | 1985-03-08 | 1987-08-04 | The Trustees Of Princeton University | Pyrido(2,3-d)pyrimidine derivatives |
| NZ219971A (en) * | 1986-06-06 | 1989-08-29 | Univ Princeton | Tetrahydropyrido (2,3-d pyrimidine derivatives and pharmaceutical compositions |
| IE60038B1 (en) * | 1986-06-30 | 1994-05-18 | Univ Princeton | 4(3H)-oxo-5, 6, 7, 8-tetrahydropyrido-[2, 3-d]pyrimidine derivatives |
-
1989
- 1989-05-02 DK DK198902152A patent/DK172753B1/da not_active IP Right Cessation
- 1989-05-03 IL IL9017989A patent/IL90179A/he not_active IP Right Cessation
- 1989-05-04 ES ES89304499T patent/ES2057116T3/es not_active Expired - Lifetime
- 1989-05-04 DE DE68917211T patent/DE68917211T2/de not_active Expired - Fee Related
- 1989-05-04 EP EP89304499A patent/EP0343801B1/en not_active Expired - Lifetime
- 1989-05-04 AT AT89304499T patent/ATE109480T1/de not_active IP Right Cessation
- 1989-05-17 CA CA000599937A patent/CA1340631C/en not_active Expired - Fee Related
- 1989-05-23 PT PT90635A patent/PT90635B/pt not_active IP Right Cessation
- 1989-05-23 NZ NZ229242A patent/NZ229242A/xx unknown
- 1989-05-24 AU AU35109/89A patent/AU611027B2/en not_active Ceased
- 1989-05-24 RU SU894614259A patent/RU2002747C1/ru active
- 1989-05-25 JP JP1132541A patent/JP2818198B2/ja not_active Expired - Lifetime
- 1989-05-25 KR KR1019890007041A patent/KR0131589B1/ko not_active Expired - Fee Related
- 1989-05-25 HU HU892684A patent/HU205356B/hu not_active IP Right Cessation
- 1989-05-25 CN CN89103686A patent/CN1025334C/zh not_active Expired - Fee Related
- 1989-06-12 IE IE176789A patent/IE63620B1/en not_active IP Right Cessation
-
1998
- 1998-06-12 CY CY9802055A patent/CY2055B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT50342A (en) | 1990-01-29 |
| NZ229242A (en) | 1990-10-26 |
| IE891767L (en) | 1989-11-25 |
| IL90179A0 (en) | 1989-12-15 |
| RU2002747C1 (ru) | 1993-11-15 |
| KR900018100A (ko) | 1990-12-20 |
| PT90635B (pt) | 1994-10-31 |
| JPH0267281A (ja) | 1990-03-07 |
| EP0343801B1 (en) | 1994-08-03 |
| EP0343801A3 (en) | 1991-05-02 |
| DE68917211T2 (de) | 1994-11-24 |
| AU611027B2 (en) | 1991-05-30 |
| DK215289A (da) | 1989-11-26 |
| AU3510989A (en) | 1989-11-30 |
| IE63620B1 (en) | 1995-05-17 |
| HK1000284A1 (en) | 1998-02-20 |
| DK215289D0 (da) | 1989-05-02 |
| HU205356B (en) | 1992-04-28 |
| DE68917211D1 (de) | 1994-09-08 |
| EP0343801A2 (en) | 1989-11-29 |
| DK172753B1 (da) | 1999-06-28 |
| CN1025334C (zh) | 1994-07-06 |
| ATE109480T1 (de) | 1994-08-15 |
| PT90635A (pt) | 1989-11-30 |
| CY2055B1 (en) | 1998-06-12 |
| ES2057116T3 (es) | 1994-10-16 |
| JP2818198B2 (ja) | 1998-10-30 |
| CA1340631C (en) | 1999-07-06 |
| KR0131589B1 (ko) | 1998-04-17 |
| CN1038098A (zh) | 1989-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| RH1 | Patent not in force |