GB2010836B - Stilbene derivatives - Google Patents

Stilbene derivatives

Info

Publication number
GB2010836B
GB2010836B GB7849418A GB7849418A GB2010836B GB 2010836 B GB2010836 B GB 2010836B GB 7849418 A GB7849418 A GB 7849418A GB 7849418 A GB7849418 A GB 7849418A GB 2010836 B GB2010836 B GB 2010836B
Authority
GB
United Kingdom
Prior art keywords
stilbene derivatives
stilbene
derivatives
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
Application number
GB7849418A
Other versions
GB2010836A (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB2010836A publication Critical patent/GB2010836A/en
Application granted granted Critical
Publication of GB2010836B publication Critical patent/GB2010836B/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/34Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/47Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing ten carbon atoms
    • C07C13/48Completely or partially hydrogenated naphthalenes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/34Monohydroxylic alcohols containing six-membered aromatic rings and other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/03Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14Unsaturated ethers
    • C07C43/164Unsaturated ethers containing six-membered aromatic rings
    • C07C43/168Unsaturated ethers containing six-membered aromatic rings containing six-membered aromatic rings and other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/64Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/52Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/548Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings having unsaturation outside the six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/798Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring containing rings other than six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/66Polycyclic acids with unsaturation outside the aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/54Quaternary phosphonium compounds
    • C07F9/5456Arylalkanephosphonium compounds
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12CBEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00Fermentation processes for beer
    • C12C11/02Pitching yeast
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
GB7849418A 1977-12-22 1978-12-21 Stilbene derivatives Expired GB2010836B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LU78751 1977-12-22
CH1159078 1978-11-10

Publications (2)

Publication Number Publication Date
GB2010836A GB2010836A (en) 1979-07-04
GB2010836B true GB2010836B (en) 1982-08-04

Family

ID=25708596

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7849418A Expired GB2010836B (en) 1977-12-22 1978-12-21 Stilbene derivatives

Country Status (32)

Country Link
EP (1) EP0002742B1 (en)
JP (1) JPS54109955A (en)
AR (1) AR224357A1 (en)
AT (1) AT361459B (en)
AU (1) AU525419B2 (en)
BR (1) BR7808470A (en)
CA (1) CA1123839A (en)
CS (1) CS208158B2 (en)
CU (1) CU35002A (en)
CY (1) CY1277A (en)
DE (2) DE2861748D1 (en)
DK (1) DK159967C (en)
DO (1) DOP1978002760A (en)
ES (1) ES476224A1 (en)
FI (1) FI68804C (en)
FR (1) FR2422620A1 (en)
GB (1) GB2010836B (en)
GR (1) GR71656B (en)
HK (1) HK30185A (en)
HU (1) HU180786B (en)
IE (1) IE47617B1 (en)
IL (1) IL56219A (en)
IT (1) IT1102753B (en)
KE (1) KE3504A (en)
MC (1) MC1230A1 (en)
MY (1) MY8500248A (en)
NL (1) NL7812312A (en)
NO (1) NO146322C (en)
NZ (1) NZ189203A (en)
PT (1) PT68965A (en)
SE (1) SE7813212L (en)
SG (1) SG5485G (en)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI67386C (en) * 1979-06-21 1985-03-11 Hoffmann La Roche FOERFARANDE FOER FRAMSTAELLNING AV NYA THERAPEUTIC EQUIPMENT
DE3266442D1 (en) * 1982-01-23 1985-10-24 Basf Ag Phenylethylene derivatives, their preparation and use as medicines
US4588750A (en) * 1982-07-02 1986-05-13 Hoffmann-La Roche Inc. Therapeutic compositions for reducing sebum secretion
DK158947C (en) * 1982-07-06 1991-01-21 Hoffmann La Roche TETRAHYDRONAPHTHALIN, BENZOFURAN AND BENZOTHIOPHENDER DERIVATIVES, PREPARATION AND USE THEREOF, AND RODENTICID CONTAINING SUCH DERIVATIVES
US4808597A (en) * 1983-07-05 1989-02-28 Pfizer Inc. Method for inhibiting the degradation of cartilage
EP0155940A1 (en) * 1983-08-08 1985-10-02 Sri International Benzonorbornenyl, benzopyranyl and benzothiopyranyl retinoic acid analogues
FR2555571B1 (en) * 1983-11-28 1986-11-28 Interna Rech Dermatolo Centre NAPHTHALENE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THE THERAPEUTIC FIELD
FR2562539B1 (en) * 1984-04-06 1987-04-17 Chauvin Blache Lab NOVEL VINYL-4 BENZOIC ACID DERIVATIVES, PREPARATION METHOD THEREOF AND THERAPEUTIC APPLICATIONS THEREOF AND AS LIGANDS
JPS6122046A (en) * 1984-07-07 1986-01-30 Koichi Shiyudo Stilbene derivative
DE3580134D1 (en) * 1984-07-07 1990-11-22 Shudo Koichi Prof Dr Chem BENZOESAEUR DERIVATIVES.
DE3434946A1 (en) 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen DIARYLACETYLENE, THEIR PRODUCTION AND USE
DE3438386A1 (en) * 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen PHOSPHORSAEUREVINYLBENZYLESTER, THEIR PRODUCTION AND USE
DE3434942A1 (en) * 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen TETRALINE DERIVATIVES, THEIR PRODUCTION AND USE
DE3434944A1 (en) * 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen L-SUBSTITUTED TETRALIN DERIVATIVES, THEIR PRODUCTION AND USE
DE3434948A1 (en) * 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen VINYLTETRAZOLYLPHENYL DERIVATIVES, THEIR PRODUCTION AND USE
LU85558A1 (en) * 1984-09-28 1986-04-03 Oreal NOVEL RETINOICALLY ACTIVE NAPHTHALENIC DERIVATIVES, PREPARATION METHODS THEREOF, AND MEDICINAL AND COSMETIC COMPOSITIONS CONTAINING THEM
LU85726A1 (en) * 1985-01-10 1986-08-04 Cird NOVEL NAPHTHALENIC DERIVATIVES OF BENZONORBORNENE, PROCESS FOR THEIR PREPARATION AND MEDICINAL AND COSMETIC COMPOSITIONS CONTAINING THEM
CA1268125A (en) * 1985-06-28 1990-04-24 F. Hoffmann-La Roche Ag Use of a retinoid
ZW7487A1 (en) * 1986-05-23 1987-12-16 Hoffmann La Roche Tetrahydronaphthaline and indane derivatives
US4885282A (en) * 1987-07-02 1989-12-05 Thornfeldt Carl R Treatment of hyperhidrosis, ichthyosis and wrinkling
DE3726806A1 (en) * 1987-08-12 1989-02-23 Basf Ag ARYLPHOSPHOR DERIVATIVES, THEIR PRODUCTION AND USE
CA1298309C (en) * 1987-11-06 1992-03-31 Michael Klaus Benzocycloheptene derivatives
US5250562A (en) * 1988-02-24 1993-10-05 Hoffmann-La Roche Inc. Stilbene derivatives
AU618590B2 (en) * 1988-04-11 1992-01-02 Allergan, Inc. Tetralin esters of phenols or benzoic acids having retinoid like activity
US5196532A (en) * 1989-02-08 1993-03-23 Basf Aktiengesellschaft Diaryl-substituted heterocyclic compounds, their preparation and drugs and cosmetics obtained therefrom
DE3903993A1 (en) * 1989-02-10 1990-08-16 Basf Ag DIARYL SUBSTITUTED HETEROCYCLIC COMPOUNDS, THEIR PRODUCTION AND MEDICINAL PRODUCTS THEREOF
DE3903989A1 (en) * 1989-02-10 1990-09-20 Basf Ag DIPHENYLHETEROALKYL DERIVATIVES, THEIR PREPARATION, AND MEDICAMENTS AND COSMETICS THEREOF
DE3926148A1 (en) * 1989-08-08 1991-02-28 Basf Ag DIARYLACETYLENE, THEIR MANUFACTURE AND USE
JPH0579665U (en) * 1992-03-27 1993-10-29 株式会社のもと Reading assistance sheet
CA2129773C (en) * 1993-09-02 2007-05-01 Michael Klaus Aromatic carboxylic acid derivatives
FR2743560B1 (en) * 1996-01-17 1998-04-03 Europ De Bioprospective Centre RETINOID-TYPE AROMATIC POLYCYCLIC DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR USE FOR THE MANUFACTURE OF PHARMACEUTICAL AND COSMETIC COMPOSITIONS
US7226951B2 (en) * 2003-12-17 2007-06-05 Allergan, Inc. Compounds having selective cytochrome P450RAI-1 or selective cytochrome P450RAI-2 inhibitory activity and methods of obtaining the same
HUE031712T2 (en) * 2007-01-15 2017-08-28 Chongxi Yu Positively charged water-soluble prodrugs of retinoids and retinoid-like compounds with very high skin penetration rates
US20190112272A1 (en) * 2016-04-07 2019-04-18 High Force Research Limited Synthetic retinoids for use in rar mediated conditions

Also Published As

Publication number Publication date
GB2010836A (en) 1979-07-04
CU35002A (en) 1982-08-24
HU180786B (en) 1983-04-29
CS208158B2 (en) 1981-08-31
MY8500248A (en) 1985-12-31
IE782472L (en) 1979-06-22
HK30185A (en) 1985-04-26
AU525419B2 (en) 1982-11-04
NO146322C (en) 1982-09-15
BR7808470A (en) 1979-08-21
JPS54109955A (en) 1979-08-29
EP0002742A1 (en) 1979-07-11
NO146322B (en) 1982-06-01
MC1230A1 (en) 1979-10-26
ATA917578A (en) 1980-08-15
FI68804C (en) 1985-11-11
IE47617B1 (en) 1984-05-02
NZ189203A (en) 1984-07-06
DE2861748D1 (en) 1982-05-27
IL56219A0 (en) 1979-03-12
ES476224A1 (en) 1979-11-16
DE2854354A1 (en) 1979-07-05
DK159967C (en) 1991-06-03
DOP1978002760A (en) 1990-05-28
IL56219A (en) 1983-05-15
DK536178A (en) 1979-06-23
JPH0146493B2 (en) 1989-10-09
NL7812312A (en) 1979-06-26
AT361459B (en) 1981-03-10
SE7813212L (en) 1979-06-23
GR71656B (en) 1983-06-20
FI68804B (en) 1985-07-31
KE3504A (en) 1985-03-08
AU4286178A (en) 1979-06-28
IT1102753B (en) 1985-10-07
NO784329L (en) 1979-06-25
EP0002742B1 (en) 1982-04-14
CA1123839A (en) 1982-05-18
FR2422620A1 (en) 1979-11-09
DK159967B (en) 1991-01-07
SG5485G (en) 1985-06-14
IT7831277A0 (en) 1978-12-22
FR2422620B1 (en) 1981-09-18
AR224357A1 (en) 1981-11-30
PT68965A (en) 1979-01-01
CY1277A (en) 1985-07-05
FI783863A (en) 1979-06-23

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Legal Events

Date Code Title Description
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19921221