LV11028B - Novel benzimidazole and azabenzimidazole derivatives - Google Patents
Novel benzimidazole and azabenzimidazole derivatives Download PDFInfo
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- LV11028B LV11028B LVP-95-309A LV950309A LV11028B LV 11028 B LV11028 B LV 11028B LV 950309 A LV950309 A LV 950309A LV 11028 B LV11028 B LV 11028B
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- 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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
- C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- General Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Animal Behavior & Ethology (AREA)
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- Pyridine Compounds (AREA)
Claims (19)
- LV 11028 Izgudrojuma formula 1. Benzimidazola atvasinājumi ar kopējo formulu (I)kurā: A ir aromātisks cikls vai slāpekļa heterocikls; X1( X2, X3 un X4, neatkarīgi viens no otra, ir ūdeņraža atoms, halogēna atoms, Cļ.e-alkilgrupa, C3.7-cikloalkilgrupa, C^-alkoksigrupa, Cve-alkiltiogrupa, Ci.6-alkilsulfonilgrupa, C-|.6-alkilsulfinilgrupa, trifluormetilgrupa, hidroksilgrupa, nitrogrupa, oksimetilgrupa, grupa COOR’, kur R' ir ūdeņraža atoms vai C-,.6-alkilgrupa, pie kam X3 un X4 var kopā ar benzola gredzenu veidot naftalīna ciklu; B ir CR5R6, kur R5 un R6 ir ūdeņraža atoms, C^-alkilgrupa, C3.7-cikloalkilgrupa vai sēra atoms; 1 R·,, R2, R3 un R4, neatkarīgi viens no otra, ir ūdeņraža atoms, C^-alkilgrupa vai C3.7-cikloalkilgrupa, pie tam CRļR2 vai CR3R4 kopā ar B, kad tas ir CR5R6, var veidot C3.7-cikloalkilgrupu vai C3_7-cikloalkilēngrupu, bez tam vēl R^ un R3R4 var veidot C3_7-cikloalkilgrupu; n ir vesels skaitlis no 1 līdz 4 vao 0, ja R-, un R2 nav ūdeņraža atoms; D ir grupa no rindas; COOR7, kur R7 ir ūdeņraža atoms, C-|.6-alkilgrupa vai C3.7-cikloalkilgrupa; CONHR8, kur R8 ir ūdeņraža atoms, C^-alkilgrupa vai C3.7-cikloalkilgrupa; CN, kā ari 2-[1 -(4-hlorbenzil)-5-hlorimidazo[4,5-b]piridin-2-il]rnerkapto-2-metilpro-pānskābe, un minēto savienojumu sālis, jo sevišķi farmaceitiski pieņemamās sālis.
- 2. Benzimidazola atvasinājumi pēc 1. punkta, kas atšķiras ar to, ka A ir benzola gredzens.
- 3. Benzimidazola atvasinājumi pēc 1. punkta, kas atšķiras ar to, ka A ir piridina cikls.
- 4 LV 110284. Benzimidazola atvasinājumi pēc jebkura no 1.-3. punktam, kas atšķiras ar to, ka X·, ir fluora atoms.
- 5. Benzimidazola atvasinājumi pēc jebkura no 1.-3. punktam, kas atšķiras ar to, ka X·, ir hlora atoms.
- 6. Benzimidazola atvasinājumi pēc jebkura no 1.-5. punktam, kas atšķiras ar to, ka X3 ir hlora atoms.
- 7. Benzimidazola atvasinājumi pēc jebkura no 1.-5. punktam, kas atšķiras ar to, ka X3 ir metoksigrupa.
- 8. Benzimidazola atvasinājumi pēc jebkura no 1.-5. punktam, kas atšķiras ar to, ka X3 ir metiltiogrupa.
- 9. Benzimidazola atvasinājumi pēc jebkura no 1.-8. punktam, kas atšķiras ar to, ka X4 ir hlora atoms.
- 10 Benzimidazola atvasinājumi pēc jebkura no 1.-9. punktam, kas atšķiras ar to, ka D ir skābes grupa. 2 LV 11028
- 11. Benzžmidazola atvasinājumi pēc jebkura no 1.-10. punktam, kas atšķiras ar to, ka B ir metilēngrupa, R1 un R2 katrs ir metilgrupa, R3 un R4 ir ūdeņraža atoms un n ir 1.
- 12. Benzimidazola atvasinājumi pēc jebkura no 1.-10. punktam, kas atšķiras ar to, ka B ir sēra atoms.
- 13. Benzimidazola atvasinājumi pēc jebkura no 1.-10. punktam vai 12. punkta, kas atšķiras ar to, ka CR-,R2 ir ciklopentāna cikls.
- 14. Benzimidazola atvasinājumi pēc jebkura no 1.-11. punktam, kas atšķiras ar to, ka tie ņemti no rindas: » 1 *ΟιCOOH Cl3COOH
- 15. Paņēmiens savienojumu ar formulu (I) pēc jebkura no 1.-14. punktam iegūšanai, kas atšķiras ar to, ka: A) ja B ir sēra atoms, apstrādā halogēnaizvietotas alkānkarbonkābes alkilesteri ar merkaptobenzimidazolu vai merkaptoazabenzimidazolu bāzes, piemēram, nātrija vai kālija alkoholāta, nātrija vai litija hidrida vai kālija karbonāta, klātienē spirta, dimetilformamīda, acetona vai butan-2-ona vidē, vai arī B) ja B ir grupa CR5R6, divpakāpju reakcijā vispirms skābes hlorīdu ar formulu (VIII) Ο ι R. R, R. CICO—C—ΟΙ I R. R, Formula (VIII) kurā Rļ, R2, R3, R4i R5, R6 un n ir ar jau minētajām nozīmēm un D ir estera vai nitrila grupa, apstrādā ar diamīnu, kura formulā (IV) ΝΉ, X, ’NH X. 4- K-7 x, Formula (IV) A, Xļ, X2, X3 un X4 ir ar jau minētajām nozīmēm, tālāk ciklizējot iegūto produktu skābā vidē, 5 vai ari diamīnu ar formulu (IV) apstrādā ar aldehīdu ar formulu (VIII’): I ο ι R. co3r7 R, R I I OHC—C—ΟΙ I R. R* kurā R,, R2, R3i R4, Rs, R$ un n ir ar jau minētajām nozīmēm, bet R7 ir C-,_6'alkilgrupa etiķskābes un spirta vidē, par spirtu lietojot, piemēram, metanolu, etanolu vai metoksietanolu, un iegūto atvasinājumu tālāk oksidē ar oksidētāju, piemēram, jodu vai bārija manganātu, tālāk ar skābi vai bāzi hidrolizē estera vai nitrila grupu, iegūstot skābes atvasinājumus.
- 16. Farmaceitiskā kompozīcija, kas atšķiras ar to, ka tā satur ārstnieciski darbīgu daudzumu vismaz viena savienojuma ar formulu (I) pēc jebkura no 1.-14. punktam, vai tā farmaceitiski pieņemamas sāls, kas neobligāti iesaistīts farmaceitiski pieņemamā pildvielā, atšķaidītājā vai nesējā.
- 17. Farmaceitiskā kompozīcija ar tromboksāna receptora antagonista īpašībām, kas sevišķi piemērota tādu slimību ārstēšanai kā, piemēram, mio-karda infarkts, išēmiskā slimība, trieka, migrēna, asinsizplūdums smadzenēs, ateroskleroze, plaušu embolija, bronhiālā astma, bronhīts, pneimonija, dažādas izcelsmes asinsrites šoks (asinsizplūdums, asins saindēšanās, sirds mazspēja, trauma, akūts pankreatīts, apdegumi, bakteriāla infekcija), nefrīts, pārstādītu audu atgrūšana un vēža metastāzes, kas atšķiras ar to, ka tā satur ārstnieciski darbīgu daudzumu vismaz viena savienojuma ar formulu (I), kā tas aprakstīts jebkura no 1,-14. punktam, vai tā farmaceitiski pieņemamās sāls, kas neobligāti iesaistīts farmaceitiski pieņemamā pildvielā, atšķaidītājā vai nesējā.
- 18. Paņēmiens farmaceitiskās kompozīcijas pagatavošanai, kas atšķiras ar to, ka ārstnieciski darbīgu daudzumu vismaz viena savienojuma ar formulu (I), kā tas aprakstīts jebkura no 1.-14. punktam, vai tā farmaceitiski pieņemamās sāls, iesaistīta farmaceitiski pieņemamā pildvielā, atšķaidītājā vai nesējā.
- 19. Paņēmiens pēc 18. punkta, kas atšķiras ar to, ka farmaceitiskā kompozīcija ir izveidota kā želatīna kapsulas vai tabletes, kuras satur no 1 līdz 200 mg aktīvās vielas, vai kā injicējams šķīdums, kurš satur no 0,01 līdz 10 mg aktīvās vielas. 6
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9001925A FR2658511B1 (fr) | 1990-02-16 | 1990-02-16 | Nouveaux derives de benzimidazole et d'azabenzimidazole, antagonistes des recepteurs au thromboxane; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV11028A LV11028A (lv) | 1996-02-20 |
| LV11028B true LV11028B (en) | 1996-06-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-95-309A LV11028B (en) | 1990-02-16 | 1995-10-12 | Novel benzimidazole and azabenzimidazole derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5021443A (lv) |
| EP (1) | EP0442820B1 (lv) |
| JP (1) | JPH05155858A (lv) |
| KR (1) | KR910021382A (lv) |
| AT (1) | ATE127794T1 (lv) |
| AU (1) | AU638096B2 (lv) |
| CA (1) | CA2035710A1 (lv) |
| DE (1) | DE69112863T2 (lv) |
| DK (1) | DK0442820T3 (lv) |
| ES (1) | ES2080919T3 (lv) |
| FR (1) | FR2658511B1 (lv) |
| GR (1) | GR3018000T3 (lv) |
| IE (1) | IE910339A1 (lv) |
| IL (2) | IL97191A0 (lv) |
| LV (1) | LV11028B (lv) |
| NZ (1) | NZ237121A (lv) |
| PT (1) | PT96792A (lv) |
| ZA (1) | ZA911061B (lv) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5128359A (en) * | 1990-02-16 | 1992-07-07 | Laboratoires Upsa | Benzimidazole and azabenzimidazole derivatives which are thromboxane receptor antagonists, their methods of preparation |
| DE4200954A1 (de) * | 1991-04-26 | 1992-10-29 | Bayer Ag | Heterocyclisch substituierte phenylessigsaeurederivate |
| TW300219B (lv) * | 1991-09-14 | 1997-03-11 | Hoechst Ag | |
| US5187159A (en) * | 1991-10-07 | 1993-02-16 | Merck & Co., Inc. | Angiotensin II antagonists incorporating a substituted 1,3-benzodioxole or 1,3-benzodithiole |
| US5468757A (en) * | 1994-01-31 | 1995-11-21 | Eli Lilly And Company | 6-azaindole thromboxane synthase inhibitors |
| US6284748B1 (en) | 1997-03-07 | 2001-09-04 | Metabasis Therapeutics, Inc. | Purine inhibitors of fructose 1,6-bisphosphatase |
| EP1402895A1 (en) * | 1997-03-07 | 2004-03-31 | Metabasis Therapeutics, Inc. | Benzimidazole inhibitors of fructose 1,6-biphosphatase |
| DE69819311T2 (de) | 1997-03-07 | 2004-07-29 | Metabasis Therapeutics Inc., San Diego | Neue benzimidazol inhibitoren der fructose-1,6-bisphosphatase |
| KR20010033248A (ko) * | 1997-12-17 | 2001-04-25 | 폴락 돈나 엘. | 인테그린 수용체 길항제 |
| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| US20050267148A1 (en) * | 1998-07-15 | 2005-12-01 | Teijin Limited | Benzimidazole derivative |
| HUP0103256A3 (en) * | 1998-07-15 | 2002-05-28 | Teijin Ltd | Thiobenzimidazole derivatives and pharmaceutical compositions containing the compounds |
| US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US20030083315A1 (en) * | 2000-01-17 | 2003-05-01 | Naoki Tsuchiya | Human chymase inhibitors |
| AU2001264729A1 (en) * | 2000-05-22 | 2001-12-03 | Nitromed, Inc. | Thromboxane inhibitors, compositions and methods of use related applications |
| CZ20032691A3 (en) * | 2001-03-12 | 2004-04-14 | Avanir Pharmaceuticals | Benzimidazole compounds for modulating ige and inhibiting cellular proliferation |
| JP4173098B2 (ja) * | 2001-08-24 | 2008-10-29 | 帝人株式会社 | キマーゼ阻害剤及びａｃｅ阻害剤を有効成分として含有する薬剤 |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| WO2004010996A1 (ja) * | 2002-07-29 | 2004-02-05 | Shizuoka Coffein Co., Ltd. | 1,3アゾール誘導体及び同誘導体を含む血栓症治療のための医薬組成物 |
| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| WO2004024655A2 (en) | 2002-09-12 | 2004-03-25 | Avanir Pharmaceuticals | Phenyl-indole compounds for modulating ige and inhibiting cellular proliferation |
| WO2004032861A2 (en) * | 2002-10-11 | 2004-04-22 | Bristol-Myers Squibb Company | Hexahydro-benzimidazolone compounds useful as anti-inflammatory agents |
| EP1651198A2 (en) * | 2003-08-08 | 2006-05-03 | Avanir Pharmaceuticals | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
| DE102004027821A1 (de) * | 2004-06-08 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Benzimidazole, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| CA2582347C (en) | 2004-09-30 | 2014-09-23 | Janssen Pharmaceutica N.V. | Novel benzimidazole derivatives useful as selective androgen receptor modulators (sarms) |
| WO2008153129A1 (ja) * | 2007-06-14 | 2008-12-18 | Teijin Pharma Limited | 尿酸値低下剤 |
| KR20130026504A (ko) * | 2010-07-14 | 2013-03-13 | 큠버랜드 에멀징 테크놀로지스 아이앤씨 | 트롬복산-a2 수용체 길항제를 이용한 간신증후군 및 간성뇌증의 치료방법 |
| WO2014020038A1 (en) * | 2012-08-03 | 2014-02-06 | Boehringer Ingelheim International Gmbh | Process for preparing spiro[2.5]octane-5,7-dione |
| US9682971B2 (en) | 2013-03-15 | 2017-06-20 | Janssen Pharmaceutica Nv | 1,2,5-Substituted benzimidazoles as flap modulators |
| US8952177B2 (en) | 2013-03-15 | 2015-02-10 | Janssen Pharmaceutica Nv | 1,2,6-substituted benzimidazoles as FLAP modulators |
| US11718614B2 (en) * | 2018-06-25 | 2023-08-08 | Suzhou Mednes Pharma Tech Co., Ltd. | Compounds and methods for treatment of hedgehog pathway associated conditions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1131688B (de) * | 1960-12-16 | 1962-06-20 | Hoechst Ag | Verfahren zur Herstellung von Benzimidazolderivaten |
| NL6715600A (lv) * | 1966-12-02 | 1968-06-04 | ||
| US3819640A (en) * | 1972-08-07 | 1974-06-25 | Degussa | Aza-benzimidazoles and process for their production |
| EP0178413A1 (en) * | 1984-08-17 | 1986-04-23 | Beecham Group Plc | Benzimidazoles |
| US4880804A (en) * | 1988-01-07 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking benzimidazoles |
-
1990
- 1990-02-16 FR FR9001925A patent/FR2658511B1/fr not_active Expired - Fee Related
- 1990-03-15 US US07/493,880 patent/US5021443A/en not_active Expired - Lifetime
-
1991
- 1991-01-31 IE IE033991A patent/IE910339A1/en not_active IP Right Cessation
- 1991-02-05 US US07/650,732 patent/US5124336A/en not_active Expired - Lifetime
- 1991-02-05 CA CA002035710A patent/CA2035710A1/en not_active Abandoned
- 1991-02-07 AU AU70874/91A patent/AU638096B2/en not_active Expired
- 1991-02-08 IL IL97191A patent/IL97191A0/xx unknown
- 1991-02-08 IL IL9719195A patent/IL97191A/en not_active IP Right Cessation
- 1991-02-13 ZA ZA911061A patent/ZA911061B/xx unknown
- 1991-02-14 NZ NZ237121A patent/NZ237121A/en unknown
- 1991-02-15 DE DE69112863T patent/DE69112863T2/de not_active Expired - Lifetime
- 1991-02-15 EP EP91400393A patent/EP0442820B1/fr not_active Expired - Lifetime
- 1991-02-15 JP JP3042378A patent/JPH05155858A/ja active Pending
- 1991-02-15 AT AT91400393T patent/ATE127794T1/de not_active IP Right Cessation
- 1991-02-15 PT PT96792A patent/PT96792A/pt not_active Application Discontinuation
- 1991-02-15 ES ES91400393T patent/ES2080919T3/es not_active Expired - Lifetime
- 1991-02-15 DK DK91400393.4T patent/DK0442820T3/da active
- 1991-02-18 KR KR1019910002673A patent/KR910021382A/ko not_active Withdrawn
-
1995
- 1995-10-12 LV LVP-95-309A patent/LV11028B/en unknown
- 1995-11-08 GR GR950403109T patent/GR3018000T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL97191A0 (en) | 1992-05-25 |
| EP0442820B1 (fr) | 1995-09-13 |
| IE910339A1 (en) | 1991-08-28 |
| GR3018000T3 (en) | 1996-02-29 |
| US5124336A (en) | 1992-06-23 |
| ATE127794T1 (de) | 1995-09-15 |
| JPH05155858A (ja) | 1993-06-22 |
| AU638096B2 (en) | 1993-06-17 |
| FR2658511B1 (fr) | 1992-06-19 |
| DE69112863T2 (de) | 1996-03-28 |
| ZA911061B (en) | 1991-11-27 |
| CA2035710A1 (en) | 1991-08-17 |
| DK0442820T3 (da) | 1996-02-05 |
| FR2658511A1 (fr) | 1991-08-23 |
| EP0442820A1 (fr) | 1991-08-21 |
| LV11028A (lv) | 1996-02-20 |
| ES2080919T3 (es) | 1996-02-16 |
| NZ237121A (en) | 1993-12-23 |
| IL97191A (en) | 1995-03-15 |
| DE69112863D1 (de) | 1995-10-19 |
| PT96792A (pt) | 1991-10-31 |
| KR910021382A (ko) | 1991-12-20 |
| US5021443A (en) | 1991-06-04 |
| AU7087491A (en) | 1991-08-22 |
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