ES2060712T3 - Proceso para la preparacion de acidos 7-sustituido-hept-6-enoicos y -heptanoicos y derivados y compuestos intermedios de los mismos. - Google Patents
Proceso para la preparacion de acidos 7-sustituido-hept-6-enoicos y -heptanoicos y derivados y compuestos intermedios de los mismos.Info
- Publication number
- ES2060712T3 ES2060712T3 ES89118906T ES89118906T ES2060712T3 ES 2060712 T3 ES2060712 T3 ES 2060712T3 ES 89118906 T ES89118906 T ES 89118906T ES 89118906 T ES89118906 T ES 89118906T ES 2060712 T3 ES2060712 T3 ES 2060712T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- preparation
- compounds
- alkil
- chlorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title abstract 11
- 238000000034 method Methods 0.000 title abstract 6
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 6
- 239000000460 chlorine Substances 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 4
- 150000004703 alkoxides Chemical class 0.000 abstract 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Substances 0.000 abstract 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical group 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 230000001315 anti-hyperlipaemic effect Effects 0.000 abstract 1
- 230000002930 anti-sclerotic effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
- C07C223/02—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—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
- C07D209/24—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 with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Abstract
SE PRESENTA UN PROCESO PARA LA PREPARACION DE COMPUESTOS DE FORMULA (I) EN DONDE X ES -CH2CH2- O -CH=CH-; R1 ES UN GRUPO ESTER INERTE PARA LAS CONDICIONES DE REACCION; Y R ES UN RADICAL ORGANICO QUE TIENE GRUPOS QUE SON INERTES BAJO CONDICIONES DE REDUCCION ESTEREO SELECTIVA DE UN COMPUESTO CORRESPONDIENTE A LA FORMULA (II), EN LA QUE R, R1 Y X SON DEFINIDOS COMO LOS ANTERIORES Y UNA DE ENTRE Z1 Y Z2 ES OXIGENO Y LA OTRA ES HIDROXIDO E HIDROGENO. LOS COMPUESTOS DE LA FORMULA (I) SON AGENTES ANTI ESCLEROTICOS, ANTI HIPERLIPIDEMICOS Y ANTI HIPERCOLESTERODEMICOS. EL PROCESO PUEDE TAMBIEN APLICARSE A LA PREPARACION DE COMPUESTOS DE LA FORMULA (IU), EN LA QUE IU ES U -OCH2 - CH CH2 CH CH2 - COORU IU, DONDE (EQUIVALE) (EQUIVALE) OH OH U ES TRIFENILMETIL (TRITIL) Y RU ES ALIL O UN RADICAL QUE FORMA UN ESTER INERTE BAJO CONDICIONES DE REACCION, QUE SON INTERMEDIARIOS EN LA PREPARACION DE ALGUNOS DE LOS COMPUETOS DE LA FORMULA (I). TAMBIEN SE PRESENTA UN NUEVO PROCESO PARA LA PREPARACION DE INTERMEDIARIOS TEMPRANOS PARA SU USO DE LA PREPARACION POR EJEMPLO COMPUETOS DE LA FORMULA (I). NOMINALMENTE PROCESO A, QUE COMPRENDE LA PREPARACION DE COMPUESTOS DE LA FORMULA VII EN LA QUE R12 ES UN ALKIL C1 - C3, UN FENIL O UN FENIL SUSTITUIDO POR ENTRE 1 Y 3 SUSTITUYENTES CADA UNO DE LOS CUALES ES INDEPENDIENTEMENTE ALKIL C1- C3, ALKOLXIDO C1 - 3, FLUOR, CLORO, BROMO O NITRO CON UN MAXIMO DE DOS GRUPOS NITRO; Y R13 INDEPENDIENTEMENTE TIENE EL SIGNIFICADO ANTES DESCRITO EN R12, EMPEZANDO DESDE LOS COMPUESTOS CORRESPONDIENTES A LA FORMULA VII Y PROCESO B QUE COMPRENDE LA PREPARACION DE COMPUESTOS VA, EN LA QUE R5 ES HIDROGENO, ALKIL C1 -3, N - BUTIL, I - BUTIL, T-BUTIL, CICLOALKIL C3 -6, ALKOXIDO C1 -3, N- BUTOXIDO, I-BUTOXIDO, TRIFLUOROMETIL, FLUOR, CLORO, FENOXIDO O BENZILOXIDO; R6 ES HIDROGENO, ALKIL C1 -3, ALKOXIDO C1-3, TRIFLUROMETIL, FLUOR, CLORO, FENOXIDO O BENZILOXIDO; CON LA CONDICION DE QUE NO MAS DE 1 ENTRE R5 Y R6 SEA TRIFLUOROMETIL, NO MAS DE ENTRE 1 DE R5 Y R6 SEA FENOXIDO YNO MASQUE 1 DE R5 Y R6 SE BENXILOXIDO; UNO DE R7 Y R8 ES FENIL TRISUSTITUIDO POR R8, R10 Y R11 Y LA OTRA ES ALKIL C1 - 6 PRIMARIO O SECUNDARIO NO CONTENIENDO UN ATOMO DE CARBONO ASIMETRICO, CICLO ALKIL C3 -6 O FENIL -(CH2)M-; EN DONDE R9 ES HIDROGENO, ALKIL C1-3, N-BUTIL, I-BUTIL, T-BUTIL, ALKIXIDO C1-3, N-BUTOXIDO, I-BUTOXIDO, TRIFLUOROMETIL, FLUOR, CLORO, FENOXIDO O BENZILOXIDO; R10 ES HIDROGENO, ALKIL C1 -3, ALKOXIDO C1 -3, TRIFLUOROMETIL, FLUOR, CLORO, FENOXIDO O BENZILOXIDO; R11 ES HIDROGENO, ALKIL C1-2, ALKOXIDO C1-2, FLUOR, O CLORO Y M ES 1, 2 O 3; CON LA CONDICION DE QUE NO MAS DE UNO DE R9 Y R10 SEA TRIFLUOROMETIL, NO MAS DE 1 DE R9 Y R10 SEA FENOXIDO, Y NO MAS QUE UNO DE R9 Y R10 SEA BENZILOXIDO, EMPEZANDO DE UN SUBGRUPO DE COMPUESTO DE FORMULA (VII). UNA CONFORMACION ESPECIFICA DEL CONCEPTO INVENTIVO YA RELATADO SE ILUSTRA CON LA PREPARACION DE UN COMPUESTO DE FORMULA IA EN FORMA RACEIMICA U OPTICAMENTE PURA EN FORMA DE SAL DE ACIDO LIBRE, ESTER O DELTA-LACTONA, COMO POR EJ.UN ESTER INTERNO.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25747588A | 1988-10-13 | 1988-10-13 | |
| US35553189A | 1989-05-22 | 1989-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2060712T3 true ES2060712T3 (es) | 1994-12-01 |
Family
ID=26945992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES89118906T Expired - Lifetime ES2060712T3 (es) | 1988-10-13 | 1989-10-11 | Proceso para la preparacion de acidos 7-sustituido-hept-6-enoicos y -heptanoicos y derivados y compuestos intermedios de los mismos. |
Country Status (24)
| Country | Link |
|---|---|
| EP (2) | EP0363934B1 (es) |
| JP (1) | JP2853227B2 (es) |
| KR (1) | KR0162656B1 (es) |
| AT (1) | ATE99281T1 (es) |
| AU (1) | AU636122B2 (es) |
| BG (1) | BG60555B1 (es) |
| CA (1) | CA2000553C (es) |
| CZ (1) | CZ283316B6 (es) |
| DE (1) | DE68911834T2 (es) |
| DK (1) | DK175073B1 (es) |
| ES (1) | ES2060712T3 (es) |
| FI (1) | FI98063C (es) |
| HK (1) | HK49496A (es) |
| HU (1) | HU207993B (es) |
| IE (2) | IE940109L (es) |
| IL (1) | IL91941A (es) |
| MY (1) | MY105067A (es) |
| NO (1) | NO174623C (es) |
| NZ (1) | NZ230973A (es) |
| RO (1) | RO109732B1 (es) |
| SG (1) | SG139553A1 (es) |
| SK (1) | SK579789A3 (es) |
| WO (1) | WO1990003962A1 (es) |
| YU (1) | YU48466B (es) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5118853A (en) * | 1988-10-13 | 1992-06-02 | Sandoz Ltd. | Processes for the synthesis of 3-disubstituted aminoacroleins |
| US5290946A (en) * | 1988-10-13 | 1994-03-01 | Sandoz Ltd. | Processes for the synthesis of 3-(substituted indolyl-2-yl)propenaldehydes |
| CA2027179A1 (en) * | 1989-10-10 | 1991-04-11 | Barry C. Ross | Chemical compounds |
| DE4424525A1 (de) * | 1994-07-12 | 1995-01-26 | Elmar Meyer | Dauermagnet-Kolbenmotor |
| GT199800127A (es) | 1997-08-29 | 2000-02-01 | Combinaciones terapeuticas. | |
| NZ517468A (en) | 1999-08-30 | 2004-02-27 | Aventis Pharma Gmbh | Use of inhibitors of the renin-angiotensin system in the prevention of cardiovascular events |
| IL152580A0 (en) | 2000-05-26 | 2003-05-29 | Ciba Sc Holding Ag | Process for the preparation of indole derivatives and intermediates of the process |
| US7777006B2 (en) | 2002-12-31 | 2010-08-17 | Csl Behring L.L.C. | Method for purification of alpha-1-antitrypsin |
| KR20050114282A (ko) * | 2003-04-24 | 2005-12-05 | 다이셀 가가꾸 고교 가부시끼가이샤 | 광학 활성의 디히드록시헵텐산 에스테르의 분리 방법 |
| US7368581B2 (en) | 2003-06-18 | 2008-05-06 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of fluvastatin sodium crystal from XIV |
| US7368468B2 (en) | 2003-06-18 | 2008-05-06 | Teva Pharmaceutical Industries Ltd. | Fluvastatin sodium crystal forms XIV, LXXIII, LXXIX, LXXX and LXXXVII, processes for preparing them, compositions containing them and methods of using them |
| EP1719759A3 (en) | 2003-06-18 | 2007-03-21 | Teva Pharmaceutical Industries, Inc. | Fluvastatin sodium crystal form LXXIII, processes for preparing it, compositions containing it and methods of using it |
| WO2005053683A1 (en) | 2003-11-26 | 2005-06-16 | Duke University | A method of preventing or treating glaucoma |
| US7851624B2 (en) | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
| US20060211752A1 (en) | 2004-03-16 | 2006-09-21 | Kohn Leonard D | Use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune/inflammatory diseases associated with toll-like receptor overexpression |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| ES2327668T3 (es) | 2006-04-20 | 2009-11-02 | F.I.S. Fabbrica Italiana Sintetici S.P.A. | Procedimiento para la preparacion de sal sodica de fluvastatina. |
| EP2373609B1 (en) | 2008-12-19 | 2013-10-16 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
| EP2327682A1 (en) | 2009-10-29 | 2011-06-01 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
| AU2013214693B2 (en) | 2012-02-02 | 2017-02-23 | Kenneth Gek-Jin OOI | Improvements in tear film stability |
| JP2016516804A (ja) | 2013-04-17 | 2016-06-09 | ファイザー・インク | 心血管疾患を治療するためのｎ−ピペリジン−３−イルベンズアミド誘導体 |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| AU2020209215B2 (en) | 2019-01-18 | 2023-02-02 | Astrazeneca Ab | PCSK9 inhibitors and methods of use thereof |
| WO2025168652A1 (en) | 2024-02-05 | 2025-08-14 | Astrazeneca Ab | Azd-0780 in combination with a statin for use in lowering ldl-c levels and treating cardiovacular diseases |
| WO2025196153A1 (en) | 2024-03-20 | 2025-09-25 | Astrazeneca Ab | Pcsk9 inhibitors and methods of use thereof |
| WO2025196155A1 (en) | 2024-03-20 | 2025-09-25 | Astrazeneca Ab | Pcsk9 inhibitors and methods of use thereof |
| TW202539678A (zh) | 2024-03-20 | 2025-10-16 | 瑞典商阿斯特捷利康公司 | Ｐｃｓｋ９抑制劑及其使用方法 |
| WO2025238159A1 (en) | 2024-05-16 | 2025-11-20 | Astrazeneca Ab | Combination therapy comprising azd0780 and ezetimibe |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB945536A (en) * | 1961-09-08 | 1964-01-02 | Istituto Chemioterapico | Method of preparing ª -amino-acroleins |
| US4739073A (en) * | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
| WO1984002131A1 (fr) * | 1982-11-22 | 1984-06-07 | Sandoz Ag | Produits analogues de mevalolactone et leurs derives, leurs procedes de production, compositions pharmaceutiques les contenant ainsi que leur utilisation en tant que produits pharmaceutiques |
| US4571428A (en) * | 1983-07-08 | 1986-02-18 | Sandoz, Inc. | 6-Substituted-4-hydroxy-tetrahydropyran-2-ones |
| US4650890A (en) * | 1984-04-03 | 1987-03-17 | Sandoz Corp. | Preparation of olefinic compounds and intermediates thereof |
| ATE62906T1 (de) * | 1984-06-22 | 1991-05-15 | Sandoz Ag | Pyrazolanaloge von mevalonolakton und abkoemmlinge davon, verfahren zu deren herstellung und deren verwendung. |
| JPS62501009A (ja) * | 1984-12-04 | 1987-04-23 | サンド・アクチエンゲゼルシヤフト | メバロノラクトンのインデン同族体及びその誘導体 |
| US4668794A (en) * | 1985-05-22 | 1987-05-26 | Sandoz Pharm. Corp. | Intermediate imidazole acrolein analogs |
| EP0244364A3 (en) * | 1986-04-30 | 1992-04-01 | Sandoz Ag | Preparation of olefinic compounds |
| PT85662B (pt) * | 1986-09-10 | 1990-06-29 | Sandoz Sa | Processo para a preparacao de derivados de aza-indol e de indolizina e de composicoes farmaceuticas que os contem |
-
1989
- 1989-10-11 AT AT89118906T patent/ATE99281T1/de not_active IP Right Cessation
- 1989-10-11 RO RO145326A patent/RO109732B1/ro unknown
- 1989-10-11 IE IE940109A patent/IE940109L/xx unknown
- 1989-10-11 DE DE68911834T patent/DE68911834T2/de not_active Expired - Lifetime
- 1989-10-11 NZ NZ230973A patent/NZ230973A/xx unknown
- 1989-10-11 EP EP89118906A patent/EP0363934B1/en not_active Expired - Lifetime
- 1989-10-11 AU AU43448/89A patent/AU636122B2/en not_active Expired
- 1989-10-11 WO PCT/EP1989/001201 patent/WO1990003962A1/en not_active Ceased
- 1989-10-11 ES ES89118906T patent/ES2060712T3/es not_active Expired - Lifetime
- 1989-10-11 MY MYPI89001403A patent/MY105067A/en unknown
- 1989-10-11 IL IL9194189A patent/IL91941A/en not_active IP Right Cessation
- 1989-10-11 SG SG200602066-3A patent/SG139553A1/en unknown
- 1989-10-11 EP EP19930106005 patent/EP0562643A3/en not_active Ceased
- 1989-10-11 KR KR1019900701243A patent/KR0162656B1/ko not_active Expired - Lifetime
- 1989-10-11 HU HU896048A patent/HU207993B/hu unknown
- 1989-10-11 IE IE327789A patent/IE63477B1/en not_active IP Right Cessation
- 1989-10-11 YU YU197389A patent/YU48466B/sh unknown
- 1989-10-11 JP JP1510605A patent/JP2853227B2/ja not_active Expired - Lifetime
- 1989-10-12 CZ CS895797A patent/CZ283316B6/cs not_active IP Right Cessation
- 1989-10-12 SK SK5797-89A patent/SK579789A3/sk unknown
- 1989-10-12 CA CA002000553A patent/CA2000553C/en not_active Expired - Lifetime
-
1990
- 1990-06-07 BG BG92179A patent/BG60555B1/bg unknown
- 1990-06-12 NO NO902598A patent/NO174623C/no unknown
- 1990-06-12 FI FI902935A patent/FI98063C/fi active IP Right Grant
- 1990-06-13 DK DK199001446A patent/DK175073B1/da not_active IP Right Cessation
-
1996
- 1996-03-21 HK HK49496A patent/HK49496A/en not_active IP Right Cessation
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