ES8701778A1 - Procedimiento para la preparacion de 13-alquil-ll b -fenil-gonamos - Google Patents
Procedimiento para la preparacion de 13-alquil-ll b -fenil-gonamosInfo
- Publication number
- ES8701778A1 ES8701778A1 ES551625A ES551625A ES8701778A1 ES 8701778 A1 ES8701778 A1 ES 8701778A1 ES 551625 A ES551625 A ES 551625A ES 551625 A ES551625 A ES 551625A ES 8701778 A1 ES8701778 A1 ES 8701778A1
- Authority
- ES
- Spain
- Prior art keywords
- representing
- alkyl
- carbon atoms
- group
- radical
- 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
Links
- -1 phenyl gonanes Chemical class 0.000 title abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 10
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 abstract 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 2
- 239000011630 iodine Substances 0.000 abstract 2
- NKCCODPFBDGPRJ-UHFFFAOYSA-N nitridocarbon(1+) Chemical compound N#[C+] NKCCODPFBDGPRJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- 241000221961 Neurospora crassa Species 0.000 abstract 1
- 241000189165 Nigrospora sphaerica Species 0.000 abstract 1
- 241000593945 Streptomyces platensis Species 0.000 abstract 1
- 241000546283 Streptomyces toyocaensis Species 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000033444 hydroxylation Effects 0.000 abstract 1
- 238000005805 hydroxylation reaction Methods 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000002906 microbiologic effect Effects 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
PROCEDIMIENTO DE PREPARACION DE 13-ALQUIL-11B-FENIL-GONANOS, DE FORMULA GENERAL (I), DONDE A Y B SON O, CH2 O UN DOBLE ENLACE; X ES O O FNOH; R1 ES UN ALQUILO SATURADO O INSATURADO, LINEAL O RAMIFICADO C1-C8; R2 ES UN METILO O ETILO EN A O B; SI R2 ESTA EN A, R3/R4 TIENEN DIFERENTES SIGNIFICADOS Y SI ESTA EN B TIENEN OTROS; R9, R10, R11 Y R12 REPRESENTAN EN CADA CASO H, OH, ALQUILO, ALCOXI O ACILOXI, EN CADA CASO C1-C4, O UN HALOGENO Y EL SUSTITUYENTE DEL 11B-FENILO ESTA EN POSICION 3 O 4. SE OBTIENEN A PARTIR DE PRECURSORES POR HIDROXILACION MICROBIOLOGICA CON STR. TOYOCAENSIS, Y/O STR. PLATENSIS Y/O NIGROSPORA SPHAERICA Y/O NEUROSPORA CRASA Y LOS COMPUESTOS HIDROXILADOS OBTENIDOS, DE FORMULA (I), SEGUN LOS CASOS SE EPIMERIZAN, ESTERIFICAN-ETERIFICAN, HALOGENAN O ALCOHILAN. LOS COMPUESTOS SON ANTAGONISTAS COMPETITIVOS DE LA PROGESTERONA Y SE USAN COMO ANTIGESTAGENOS, REGULADORES DE MENSTRUACION Y ANTIGLUCORTICOIDES.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853504421 DE3504421A1 (de) | 1985-02-07 | 1985-02-07 | Neue 11ss-phenyl-gonane, deren herstellung und diese enthaltende pharmazeutische praeparate |
| DE19853527517 DE3527517A1 (de) | 1985-07-29 | 1985-07-29 | 11ss-phenyl-gonane, deren herstellung und diese enthaltende pharmazeutische praeparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8701778A1 true ES8701778A1 (es) | 1986-12-16 |
| ES551625A0 ES551625A0 (es) | 1986-12-16 |
Family
ID=25829248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES551625A Expired ES8701778A1 (es) | 1985-02-07 | 1986-02-04 | Procedimiento para la preparacion de 13-alquil-ll b -fenil-gonamos |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5089635A (es) |
| EP (1) | EP0190759B1 (es) |
| CN (1) | CN1033753C (es) |
| AU (1) | AU580843B2 (es) |
| CA (1) | CA1310630C (es) |
| DE (1) | DE3665307D1 (es) |
| DK (1) | DK161709C (es) |
| ES (1) | ES8701778A1 (es) |
| FI (1) | FI85377C (es) |
| GR (1) | GR860342B (es) |
| HU (1) | HU194904B (es) |
| IE (1) | IE58149B1 (es) |
| IL (1) | IL77762A (es) |
| NO (1) | NO171994C (es) |
| NZ (1) | NZ214998A (es) |
| PT (1) | PT81969B (es) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ214998A (en) * | 1985-02-07 | 1989-06-28 | Schering Ag | 13-(methyl or ethyl)-11-beta-phenyl-gonane derivatives; preparatory processes and pharmaceutical compositions |
| GB8513723D0 (en) * | 1985-05-31 | 1985-07-03 | Erba Farmitalia | 11-beta substituted steroids |
| ES2045082T3 (es) * | 1987-04-24 | 1994-01-16 | Akzo Nv | Un metodo para la preparacion de nuevos derivados 11-arilestrano y 11-arilpregnano. |
| AU625450B2 (en) * | 1987-07-16 | 1992-07-09 | Schering Aktiengesellschaft Berlin Und Bergkamen | 11beta-phenyl-4,9,15-estratrienes, their manufacture, and pharmaceutical preparations containing them |
| DE3723788A1 (de) * | 1987-07-16 | 1989-01-26 | Schering Ag | 11(beta)-phenyl-4,9,15-estratriene, deren herstellung und diese enthaltende pharmazeutische praeparate |
| EP0321010B1 (en) * | 1987-12-12 | 1993-02-03 | Akzo N.V. | New 11-arylsteroid compounds |
| DE3822770A1 (de) * | 1988-07-01 | 1990-01-04 | Schering Ag | 13-alkyl-11ss-phenylgonane |
| FR2643638B1 (fr) * | 1989-02-24 | 1991-06-14 | Roussel Uclaf | Nouveaux 19-nor steroides ayant en position 11beta une chaine carbonee comportant une fonction amide ou carbamate, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| FR2665901B2 (fr) * | 1989-02-24 | 1994-07-29 | Roussel Uclaf | Nouveaux 19-nor sterouides ayant en position 11beta une chaine carbonee comportant une fonction amide, leur preparation, leur application comme medicaments. |
| US5372996A (en) * | 1989-03-10 | 1994-12-13 | Endorecherche, Inc. | Method of treatment of androgen-related diseases |
| US5364847A (en) * | 1989-03-10 | 1994-11-15 | Endorecherche | Inhibitors of sex steroid biosynthesis and methods for their production and use |
| AU5856090A (en) * | 1989-07-07 | 1991-02-06 | Endorecherche Inc. | Androgen derivatives for use in the inhibition of sex steroid activity |
| DE69034035T2 (de) * | 1989-07-07 | 2004-01-22 | Endorecherche Inc., Ste-Foy | Methode zur behandlung androgenbedingter krankheiten |
| WO1991001958A2 (de) * | 1989-08-04 | 1991-02-21 | Schering Aktiengesellschaft Berlin Und Bergkamen | 11β-ARYL-GONA-4,9-DIEN-3-ONE |
| DE4042007A1 (de) * | 1990-12-22 | 1992-06-25 | Schering Ag | 6,7-modifizierte-11(beta)-aryl-4-estrene |
| ES2112268T3 (es) * | 1990-08-14 | 1998-04-01 | Hoechst Marion Roussel Inc | Nuevos 19-nor-esteroides que tienen en posicion 11beta una cadena carbonada que comprende una funcion amida, su preparacion, su aplicacion como medicamentos y composiciones farmaceuticas que los contienen. |
| US5407928A (en) * | 1990-08-15 | 1995-04-18 | Schering Aktiengesellschaft | 11β-aryl-gona-4,9-dien-3-ones |
| FR2688004A1 (fr) * | 1992-02-27 | 1993-09-03 | Roussel Uclaf | Nouveaux sterouides comportant en position 17 un radical methylene lactone, leur procede et des intermediaires de preparation, leur application comme medicaments. |
| CA2136304A1 (en) * | 1992-05-21 | 1993-11-25 | Fernand Labrie | Inhibitors of testosterone 5.alpha.-reductase activity |
| DE4332283A1 (de) * | 1993-09-20 | 1995-04-13 | Jenapharm Gmbh | Neue 11-Benzaldoximestradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE4332284C2 (de) * | 1993-09-20 | 1997-05-28 | Jenapharm Gmbh | 11-Benzaldoxim-17beta-methoxy-17alpha-methoxymethyl-estradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5780220A (en) * | 1994-05-19 | 1998-07-14 | Trustees Of The University Of Pennsylvania | Methods and compositions for inhibiting HIV replication |
| US5639598A (en) * | 1994-05-19 | 1997-06-17 | The Trustees Of The University Of Pennsylvania | Method and kit for identification of antiviral agents capable of abrogating HIV Vpr-Rip-1 binding interactions |
| US5576310A (en) * | 1994-09-20 | 1996-11-19 | Jenapharm Gmbh | 11-benzaldoxime-17β-methoxy-17α-methoxymethyl-estrasdiene derivatives, methods for their production and pharmaceuticals containing such compounds |
| US5521166A (en) * | 1994-12-19 | 1996-05-28 | Ortho Pharmaceitical Corporation | Antiprogestin cyclophasic hormonal regimen |
| ZA9510926B (en) | 1994-12-23 | 1996-07-03 | Schering Ag | Compounds with progesterone-antagonistic and antiestrogenic action to be used together for female contraception |
| US6900193B1 (en) * | 1996-05-01 | 2005-05-31 | The United States Of America As Represented By The Department Of Health And Human Services | Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents |
| AU710139B2 (en) | 1996-05-01 | 1999-09-16 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | 21-substituted progesterone derivatives as new antiprogestational agents |
| IL122740A (en) * | 1997-01-15 | 2003-09-17 | Akzo Nobel Nv | 16-hydroxy-11-(substituted phenyl)-estra-9,4-diene derivatives, their preparation and pharmaceutical compositions containing them |
| US6090798A (en) * | 1997-12-19 | 2000-07-18 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with glucocorticoid antagonists |
| US6020328A (en) * | 1998-03-06 | 2000-02-01 | Research Triangle Institute | 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US6262042B1 (en) | 1998-05-29 | 2001-07-17 | Research Triangle Institute | 17β-amino and hydroxylamino-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| US5962444A (en) * | 1998-05-29 | 1999-10-05 | Research Triangle Institute | 17β-nitro-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
| EP1285927A3 (de) * | 2001-08-16 | 2005-06-29 | Schering Aktiengesellschaft | Verwendung von Glucocorticoid-Rezeptorantagonisten zur Vorbeugung und Behandlung von Erkrankungen des männlichen Reproduktionssystems |
| DE10236405A1 (de) * | 2002-08-02 | 2004-02-19 | Schering Ag | Progesteronrezeptormodulatoren mit erhöhter antigonadotroper Aktivität für die weibliche Fertilitätskontrolle und Hormonersatztherapie |
| DE102009034367A1 (de) * | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-benzyliden-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| ES2762243T3 (es) | 2010-05-26 | 2020-05-22 | Corcept Therapeutics Inc | Tratamiento de distrofia muscular |
| AU2016226451B2 (en) | 2015-03-02 | 2019-12-19 | Corcept Therapeutics, Inc. | Use of glucocorticoid receptor antagonist and somatostatin analogues to treat ACTH-secreting tumors |
| CN107530339B (zh) | 2015-03-30 | 2021-03-16 | 科赛普特治疗学股份有限公司 | 糖皮质激素受体拮抗剂联合糖皮质激素用于治疗肾上腺功能不全 |
| MX383318B (es) | 2015-08-13 | 2025-03-13 | Corcept Therapeutics Inc | Metodo para diagnosticar de manera diferencial el sindrome de cushing dependiente de la corticotropina. |
| KR102197526B1 (ko) | 2016-01-19 | 2020-12-31 | 코어셉트 쎄라퓨틱스 인코포레이티드 | 이소성 쿠싱 증후군의 감별 진단 |
| MX2019011543A (es) | 2017-03-31 | 2019-12-16 | Corcept Therapeutics Inc | Moduladores del receptor de glucocorticoides para el tratamiento de cancer cervical. |
| ES3043682T3 (en) | 2017-06-20 | 2025-11-25 | Corcept Therapeutics Inc | Treatment of neuroepithelial tumors using selective glucocorticoid receptor modulators |
| US20240269280A1 (en) | 2020-12-18 | 2024-08-15 | Instil Bio (Uk) Limited | Processing of tumor infiltrating lymphocytes |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377418A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 4,9-dieniques 11b-substitues, leur procede de preparation et leur application comme medicaments |
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
| FR2522328B1 (fr) * | 1982-03-01 | 1986-02-14 | Roussel Uclaf | Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments |
| DE3231827A1 (de) * | 1982-08-24 | 1984-03-01 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11ss-aryl-17(alpha)-alkinyl-17ss-hydroxy-4,9(10)- estradien-3-on-derivate, deren herstellung und diese enthaltende pharmazeutische praeparate |
| FR2573657B1 (fr) * | 1984-11-29 | 1989-05-12 | Roussel Uclaf | Produit comprenant une substance antiprogestomimetique et une substance uterotonique |
| NZ214998A (en) * | 1985-02-07 | 1989-06-28 | Schering Ag | 13-(methyl or ethyl)-11-beta-phenyl-gonane derivatives; preparatory processes and pharmaceutical compositions |
-
1986
- 1986-01-31 NZ NZ214998A patent/NZ214998A/xx unknown
- 1986-01-31 AU AU52913/86A patent/AU580843B2/en not_active Ceased
- 1986-02-02 IL IL77762A patent/IL77762A/xx not_active IP Right Cessation
- 1986-02-03 CN CN86100994A patent/CN1033753C/zh not_active Expired - Lifetime
- 1986-02-04 ES ES551625A patent/ES8701778A1/es not_active Expired
- 1986-02-05 DK DK056086A patent/DK161709C/da not_active IP Right Cessation
- 1986-02-05 GR GR860342A patent/GR860342B/el unknown
- 1986-02-05 PT PT81969A patent/PT81969B/pt not_active IP Right Cessation
- 1986-02-06 EP EP86101548A patent/EP0190759B1/de not_active Expired
- 1986-02-06 DE DE8686101548T patent/DE3665307D1/de not_active Expired
- 1986-02-06 IE IE33486A patent/IE58149B1/en not_active IP Right Cessation
- 1986-02-06 NO NO860425A patent/NO171994C/no not_active IP Right Cessation
- 1986-02-06 CA CA000501252A patent/CA1310630C/en not_active Expired - Lifetime
- 1986-02-06 HU HU86499A patent/HU194904B/hu not_active IP Right Cessation
- 1986-02-07 US US06/827,050 patent/US5089635A/en not_active Expired - Lifetime
- 1986-02-07 FI FI860559A patent/FI85377C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR860342B (en) | 1986-06-03 |
| FI860559L (fi) | 1986-08-08 |
| IE860334L (en) | 1986-08-07 |
| HU194904B (en) | 1988-03-28 |
| DK56086D0 (da) | 1986-02-05 |
| FI860559A0 (fi) | 1986-02-07 |
| HUT40453A (en) | 1986-12-28 |
| AU580843B2 (en) | 1989-02-02 |
| IL77762A (en) | 1992-08-18 |
| NZ214998A (en) | 1989-06-28 |
| DK161709B (da) | 1991-08-05 |
| NO171994B (no) | 1993-02-15 |
| FI85377C (fi) | 1992-04-10 |
| DK56086A (da) | 1986-08-08 |
| AU5291386A (en) | 1986-08-14 |
| CN86100994A (zh) | 1986-10-08 |
| EP0190759B1 (de) | 1989-08-30 |
| US5089635A (en) | 1992-02-18 |
| NO171994C (no) | 1993-05-26 |
| CN1033753C (zh) | 1997-01-08 |
| FI85377B (fi) | 1991-12-31 |
| DE3665307D1 (en) | 1989-10-05 |
| EP0190759A2 (de) | 1986-08-13 |
| NO860425L (no) | 1986-08-08 |
| IE58149B1 (en) | 1993-07-14 |
| PT81969A (de) | 1986-03-01 |
| PT81969B (pt) | 1988-03-03 |
| EP0190759A3 (en) | 1986-11-20 |
| ES551625A0 (es) | 1986-12-16 |
| DK161709C (da) | 1992-01-13 |
| CA1310630C (en) | 1992-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20041025 |