IL96167A - אמידים של חומצות g-]1,3- דיהידרו-h)-22(-אוקסו-7-אימידאזו]b-5 ,4[- קווינולינילוקסי[ אלקאנואיות, הכנתם ותכשירי רוקחות המכלים אותם - Google Patents
אמידים של חומצות g-]1,3- דיהידרו-h)-22(-אוקסו-7-אימידאזו]b-5 ,4[- קווינולינילוקסי[ אלקאנואיות, הכנתם ותכשירי רוקחות המכלים אותםInfo
- Publication number
- IL96167A IL96167A IL9616790A IL9616790A IL96167A IL 96167 A IL96167 A IL 96167A IL 9616790 A IL9616790 A IL 9616790A IL 9616790 A IL9616790 A IL 9616790A IL 96167 A IL96167 A IL 96167A
- Authority
- IL
- Israel
- Prior art keywords
- oxo
- dihydro
- imidazo
- quinolin
- piperazine
- Prior art date
Links
- -1 quinolinyloxy Chemical group 0.000 title claims abstract description 85
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000001408 amides Chemical class 0.000 title abstract description 13
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 210000001772 blood platelet Anatomy 0.000 claims abstract description 13
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical group C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000004848 alkoxyethyl group Chemical group 0.000 claims abstract description 8
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 claims abstract description 8
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims abstract description 7
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims abstract description 6
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 61
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 41
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 31
- 230000008878 coupling Effects 0.000 claims description 30
- 238000010168 coupling process Methods 0.000 claims description 30
- 238000005859 coupling reaction Methods 0.000 claims description 30
- XNHZEJRZFBXTOB-UHFFFAOYSA-N 4-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxy]butanoic acid Chemical compound N1=C2NC(=O)NC2=CC2=CC(OCCCC(=O)O)=CC=C21 XNHZEJRZFBXTOB-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 12
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 11
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 10
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 230000000297 inotrophic effect Effects 0.000 claims description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- LRPGNFROBDUREU-UHFFFAOYSA-N 1-(cyclohexylmethyl)piperazine Chemical compound C1CNCCN1CC1CCCCC1 LRPGNFROBDUREU-UHFFFAOYSA-N 0.000 claims description 3
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 claims description 3
- 229940095074 cyclic amp Drugs 0.000 claims description 3
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims description 2
- BMEMBBFDTYHTLH-UHFFFAOYSA-N 1-(2-methoxyethyl)piperazine Chemical compound COCCN1CCNCC1 BMEMBBFDTYHTLH-UHFFFAOYSA-N 0.000 claims description 2
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- DCEFDTKYYGMWMX-UHFFFAOYSA-N 1-(thiophen-3-ylmethyl)piperazine Chemical compound C1=CSC=C1CN1CCNCC1 DCEFDTKYYGMWMX-UHFFFAOYSA-N 0.000 claims description 2
- STZHBULOYDCZET-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine;hydron;dichloride Chemical compound Cl.Cl.C1CC2C(N)CN1CC2 STZHBULOYDCZET-UHFFFAOYSA-N 0.000 claims description 2
- SEYURSMOEWBZSA-UHFFFAOYSA-N 2-(1-ethylpyrrolidin-2-yl)ethanamine Chemical compound CCN1CCCC1CCN SEYURSMOEWBZSA-UHFFFAOYSA-N 0.000 claims description 2
- PNHGJPJOMCXSKN-UHFFFAOYSA-N 2-(1-methylpyrrolidin-2-yl)ethanamine Chemical compound CN1CCCC1CCN PNHGJPJOMCXSKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 2
- 229940069417 doxy Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- IUMQPHHEFKTLOZ-UHFFFAOYSA-N 1-[[3-(trifluoromethyl)phenyl]methyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(CN2CCNCC2)=C1 IUMQPHHEFKTLOZ-UHFFFAOYSA-N 0.000 claims 1
- CHSINHUYLALJPT-UHFFFAOYSA-N 1-cycloheptylpiperazine Chemical compound C1CNCCN1C1CCCCCC1 CHSINHUYLALJPT-UHFFFAOYSA-N 0.000 claims 1
- WORHBDQKZCWBBV-UHFFFAOYSA-N 4-[(1-methyl-2-oxo-3h-imidazo[4,5-b]quinolin-7-yl)oxy]butanoic acid Chemical compound OC(=O)CCCOC1=CC=C2N=C(NC(N3C)=O)C3=CC2=C1 WORHBDQKZCWBBV-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/430,228 US4943573A (en) | 1989-11-01 | 1989-11-01 | Imidazo[4,5-b]quinolinyloxyalkanoic acid amides with enhanced water solubility |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96167A0 IL96167A0 (en) | 1991-07-18 |
| IL96167A true IL96167A (he) | 1994-11-11 |
Family
ID=23706624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9616790A IL96167A (he) | 1989-11-01 | 1990-10-30 | אמידים של חומצות g-]1,3- דיהידרו-h)-22(-אוקסו-7-אימידאזו]b-5 ,4[- קווינולינילוקסי[ אלקאנואיות, הכנתם ותכשירי רוקחות המכלים אותם |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4943573A (he) |
| EP (1) | EP0426180A3 (he) |
| JP (1) | JPH03169880A (he) |
| KR (1) | KR910009705A (he) |
| CN (1) | CN1025999C (he) |
| AU (1) | AU639033B2 (he) |
| CA (1) | CA2027935A1 (he) |
| EG (1) | EG19372A (he) |
| FI (1) | FI92697C (he) |
| HU (1) | HU209305B (he) |
| IE (1) | IE61579B1 (he) |
| IL (1) | IL96167A (he) |
| MY (1) | MY105308A (he) |
| NO (1) | NO175531C (he) |
| NZ (1) | NZ235868A (he) |
| OA (1) | OA09323A (he) |
| PT (1) | PT95765A (he) |
| RU (1) | RU2041210C1 (he) |
| YU (1) | YU205590A (he) |
| ZA (1) | ZA908725B (he) |
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| US8299248B2 (en) | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| JP2010502722A (ja) | 2006-09-08 | 2010-01-28 | ブレインセルス，インコーポレイティド | ４−アシルアミノピリジン誘導体を含む組み合わせ |
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| DK2170930T3 (da) | 2007-06-04 | 2012-11-05 | Synergy Pharmaceuticals Inc | Agonister af guanylatcyclase, anvendelige til behandlingen af gastrointestinale sygdomme, inflammation, cancer og andre sygdomme |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| GB0808967D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | Substitute quinazolines |
| GB0808952D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
| GB0808968D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | Substitute quinazolines |
| GB0808947D0 (en) * | 2008-05-16 | 2008-06-25 | Shire Llc | Substituted quinazolines |
| CA2730603C (en) | 2008-07-16 | 2019-09-24 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
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| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US9580471B2 (en) | 2011-03-01 | 2017-02-28 | Synergy Pharmaceuticals, Inc. | Process of preparing guanylate cyclase C agonists |
| KR101951220B1 (ko) | 2011-07-13 | 2019-02-22 | 싸이토키네틱스, 인코포레이티드 | 조합 als 치료법 |
| EP2804603A1 (en) | 2012-01-10 | 2014-11-26 | President and Fellows of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| WO2014131024A2 (en) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| AU2014274812B2 (en) | 2013-06-05 | 2018-09-27 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
| MX375926B (es) | 2013-08-09 | 2025-03-07 | Ardelyx Inc | Compuestos y metodos para inhibir el transporte de fosfato. |
| JP2022533251A (ja) | 2019-05-21 | 2022-07-21 | アルデリックス， インコーポレイテッド | 患者において血清リン酸塩を低下させるための組み合わせ |
| CN120265631A (zh) * | 2023-01-13 | 2025-07-04 | 上海超阳药业有限公司 | 喹啉酮化合物和萘啶酮化合物及其用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932407A (en) * | 1973-11-19 | 1976-01-13 | Bristol-Myers Company | Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones |
| NL7807507A (nl) * | 1977-07-25 | 1979-01-29 | Hoffmann La Roche | Tricyclische verbindingen. |
| US4490371A (en) * | 1983-02-16 | 1984-12-25 | Syntex (U.S.A.) Inc. | N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides |
| DK69285A (da) * | 1984-02-15 | 1985-08-16 | Syntex Inc | Tetrahydroimidazolderivater |
| US4668686A (en) * | 1985-04-25 | 1987-05-26 | Bristol-Myers Company | Imidazoquinoline antithrombrogenic cardiotonic agents |
| US4775674A (en) * | 1986-05-23 | 1988-10-04 | Bristol-Myers Company | Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors |
| US4701459A (en) * | 1986-07-08 | 1987-10-20 | Bristol-Myers Company | 7-amino-1,3-dihydro-2H-imidazo[4,5-b]quinolin 2-ones and method for inhibiting phosphodiesterase and blood platelet aggregation |
| US4943573A (en) * | 1989-11-01 | 1990-07-24 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyloxyalkanoic acid amides with enhanced water solubility |
-
1989
- 1989-11-01 US US07/430,228 patent/US4943573A/en not_active Expired - Fee Related
-
1990
- 1990-10-18 CA CA002027935A patent/CA2027935A1/en not_active Abandoned
- 1990-10-29 NZ NZ235868A patent/NZ235868A/en unknown
- 1990-10-29 FI FI905326A patent/FI92697C/fi not_active IP Right Cessation
- 1990-10-30 JP JP2290987A patent/JPH03169880A/ja active Pending
- 1990-10-30 IL IL9616790A patent/IL96167A/he not_active IP Right Cessation
- 1990-10-30 NO NO904689A patent/NO175531C/no unknown
- 1990-10-30 YU YU205590A patent/YU205590A/sh unknown
- 1990-10-30 MY MYPI90001900A patent/MY105308A/en unknown
- 1990-10-31 KR KR1019900017645A patent/KR910009705A/ko not_active Ceased
- 1990-10-31 ZA ZA908725A patent/ZA908725B/xx unknown
- 1990-10-31 AU AU65679/90A patent/AU639033B2/en not_active Ceased
- 1990-10-31 IE IE392390A patent/IE61579B1/en not_active IP Right Cessation
- 1990-10-31 PT PT95765A patent/PT95765A/pt not_active Application Discontinuation
- 1990-10-31 EP EP19900120952 patent/EP0426180A3/en not_active Ceased
- 1990-10-31 CN CN90108762A patent/CN1025999C/zh not_active Expired - Fee Related
- 1990-10-31 RU SU904831618A patent/RU2041210C1/ru active
- 1990-10-31 OA OA59882A patent/OA09323A/xx unknown
- 1990-11-01 HU HU906977A patent/HU209305B/hu not_active IP Right Cessation
- 1990-11-01 EG EG65590A patent/EG19372A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| IE903923A1 (en) | 1991-05-08 |
| YU205590A (sh) | 1992-09-07 |
| KR910009705A (ko) | 1991-06-28 |
| NO904689L (no) | 1991-05-02 |
| CA2027935A1 (en) | 1991-05-02 |
| EP0426180A2 (en) | 1991-05-08 |
| EG19372A (en) | 1994-12-30 |
| CN1051359A (zh) | 1991-05-15 |
| FI92697B (fi) | 1994-09-15 |
| MY105308A (en) | 1994-09-30 |
| NO175531C (no) | 1994-10-26 |
| US4943573A (en) | 1990-07-24 |
| JPH03169880A (ja) | 1991-07-23 |
| ZA908725B (en) | 1991-07-31 |
| IL96167A0 (en) | 1991-07-18 |
| AU6567990A (en) | 1991-05-23 |
| HU906977D0 (en) | 1991-05-28 |
| AU639033B2 (en) | 1993-07-15 |
| NO904689D0 (no) | 1990-10-30 |
| NO175531B (no) | 1994-07-18 |
| IE61579B1 (en) | 1994-11-16 |
| NZ235868A (en) | 1993-12-23 |
| EP0426180A3 (en) | 1992-01-08 |
| FI92697C (fi) | 1994-12-27 |
| PT95765A (pt) | 1991-09-13 |
| HUT56102A (en) | 1991-07-29 |
| FI905326A0 (fi) | 1990-10-29 |
| HU209305B (en) | 1994-04-28 |
| CN1025999C (zh) | 1994-09-28 |
| RU2041210C1 (ru) | 1995-08-09 |
| OA09323A (en) | 1992-09-15 |
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