FI89261B - Nya aromatiska bicykliska foereningar, foerfarande foer deras framstaellning och kosmetiska kompositioner som innehaoller dessa foereningar - Google Patents
Nya aromatiska bicykliska foereningar, foerfarande foer deras framstaellning och kosmetiska kompositioner som innehaoller dessa foereningar Download PDFInfo
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- FI89261B FI89261B FI873148A FI873148A FI89261B FI 89261 B FI89261 B FI 89261B FI 873148 A FI873148 A FI 873148A FI 873148 A FI873148 A FI 873148A FI 89261 B FI89261 B FI 89261B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
- C07C65/36—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic containing rings other than six-membered aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/36—Polyhydroxylic alcohols containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
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- 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
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
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- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/17—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Claims (12)
1. Aromatiska bicykliska föreningar, känneteck-n a d e av att de motsvarar följande formel: Λ - I -T U> ><Χ l_5 J n där: - n är talet 0 eller l, - R’ betecknar en väteatom eller en OH-grupp, - R" betecknar en väteatom, - eller R' och R" bildar tillsammans en oxogrupp (=0), - R betecknar gruppen -CH20H eller gruppen -C0R7, II 49 89261 varvid R7 betecknar en väteatom, gruppen -0R8 eller gruppen r’ / -N \ r" varvid R8 betecknar en väteatom eller en lägre alkylgrupp och r' och r" var och en betecknar en väteatom, en lägre alkylgrupp eller en fenylgrupp som eventuellt är substi-tuerad med en eller tvä trifluormetylgrupper eller bildar tillsammans med en kväveatom, till vilken de är bundna, en med en hydroxylgrupp och en lägre alkylgrupp substituerad piperazinoring, - A betecknar en metylen- eller dimetylengrupp, som är an-tingen osubstituerad eller substituerad med en lägre alkylgrupp med 1-6 kolatomer, - R1( R2, R3 och R4 var och en betecknar en väteatom eller en lägre alkylgrupp med 1-6 kolatomer, varvid Rx och R3 tillsammans kan bilda en metylen- eller dimetylengrupp, dä A betecknar en dimetylengrupp, - R5 och R6 betecknar väteatomer eller metylgrupper, inklusive salterna av nämnda föreningar liksom deras optiska och geometriska isomerer.
2. Föreningar enligt patentkravet 1, känneteck-n a d e av att de motsvarar följande formel: där A, R, R1-R4, R' och R" har de betydelser som angivits i patentkravet 1. so 8 9 261
3. Föreningar enligt patentkravet 1, känneteck-n a d e av att de motsvarar följande formel: kA,A. », »6 "s där A, R, Rx-R6, R' och R" har de betydelser som angivits i patentkravet 1.
4. Föreningar enligt patentkravet 2, känneteck-n a d e av att de motsvarar följande formel: en 3 R' l·'' <m COR', CHj^ ^Cllj 1 där: / - A betecknar gruppen CH3-CH eller en dimetylengrupp, - R' betecknar en OH-grupp och R" betecknar en väteatom eller R' och R", tagna tillsammans, bildar en oxogrupp (=0), och - R'7 betecknar en väteatom, gruppen -0R'e eller gruppen r' / -N varvid R'8 betecknar en väteatom eller en lägre \ r" alkylgrupp, r' betecknar en väteatom och r" betecknar en lägre alkylgrupp eller en substituerad fenylgrupp eller r' och r" bildar tillsammans en 4-(2-hydroxietyDpiperazino-grupp. li si 89261
5. Föreningar enligt patentkravet 3, känneteck-n a d e av att de motsvarar följande formel: ch3X/c"3 R· -R" C0R 7 där: / - A betecknar gruppen CH3-CH eller en diraetylengrupp, \ - R' betecknar en OH-grupp och R" betecknar en väteatom eller R' och R" bildar tillsammans en oxogrupp (=0), - R6 betecknar en väteatom eller en metylgrupp, och r' / - R1 η betecknar gruppen -0R'8 eller gruppen -N varvid r" R'8:n betecknar en väteatom eller en lägre alkylgrupp, r' betecknar en väteatom och r" betecknar en lägre alkylgrupp .
6. Föreningar enligt nogät av patentkraven 1-5, k ä n -netecknade av att de har valts frän en grupp be-stäende av: (1) - (5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naftyl) - 4 -karbonylmetylbensoat, (2) - (5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naftyl)-4-karbonylbensoesyra, (3) - (5,8-metano-5,6,7,8-tetrahydro-2-naftyl)-4-karbonyl-bensaldehyd, (4) - (5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naftyl)-4-karbonylbensaldehyd, (5) - (1,1,2,3,3-pentametyl-5-indanyl)-4-karbonylmetyl-bensoat, 52 89261 (6) - (1,1,2,3,3-pentametyl-5-indanyl)-4-karbonylbensoesyra, (7) - (l,i(2,3,3-pentametyl-5-indanyl)-4-karbonylbensalde- hyd, (8) - (1,1,2,3,3-pentametyl-5-indanyl)-1-(4-hydroximetylfen- yl}-metanol, (9) - (5,5,8,8 -tetrametyl- 5,6,7,8 -tetrahydro-2-naftyl)-4-hydroximetylbensoesyra, (10) - (1,1,2,3,3-pentametyl-5-indanyl)-4-hydroximetylben- soesyra, (11) - (1,1,2,3,3-pentametyl-5-indanyl)-4-hydroximetylmetyl-bensoat, (12) - N-etyl-(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl)-4-karbonylbensamid, (13) - N-etyl-(1,1,2,3,3-pentametyl-5-indanyl)-4-karbonyl-bensamid, (14) - trans(5,8-metano-5,6,7,8-tetrahydro-2-naftyl)-4-kar-bonyletylcinnamat, (15) - trans(5,8-metano-5,6,7,8-tetrahydro-2-naftyl)-4-kar-bonylkanelsyra, (16) - trans(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl) - 4-karbonyletylcinnamat, (17) - trans(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl)-4-karbonylkanelsyra, (18) - trans(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl)-4-karbonyl-a-metyletylcinnamat, (19) - trans(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl) - 4 -karbony1-a-metylkanelsyra, (20) - trans(1,1,2,3,3-pentametyl-5-indanyl) -4-karbony1-a-metyletylcinnamat, (21) - trans(l,1,2,3,3-pentametyl-5-indanyl)-4-karbonylme-tylkanelsyra, (22) - N-etyl-trans(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naf tyl) - 4-karbonyl-ar-metylsinnamid, (23) - trans(5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl)-4-hydroximetyletylcinnamat, (24) - trans (5,5,8,8-tetrametyl-5,6,7,8-tetrahydro-2-naft-yl)-4-hydroximetylkanelsyra, II 53 89261 (25) - 4'-(2-hydroxietyl)piperazino-(5,5,8,8-tetrametyl- 5.6.7.8- tetrahydro-2-naftyl)-4-karbonylbensamid, (26) - N-(3,5-ditrifluormetyl-1-fenyl) - (5,5,8,8-tetrametyl- 5.6.7.8- tetrahydro-7-naftyl)- 4 -karbonylbensamid.
7. Förfarande för framställning av foreningar enligt nagot av patentkraven 1-6, kanne tecknat avatti ett organiskt lösningsmedel en halogenid säsom en syraklorid enligt följande formel: ci r.o ('°2\ 0) fär reagera med en aromatisk förening enligt ndgon av följande formler: MRX 3. a a (2) 3 (2^) där: A, Rx - R4 har samma betydelser som i patentkravet 1, R8 be-tecknar en lägre alkylgrupp och X betecknar Br eller Cl, att vid behov den erhällna ketoestern förtvälas till motsvarande ketosyra, och denna ketosyra därefter överföres till motsvarande amid genom inverkan av en amin med formeln: r' / HN \ r"
54 S9261 där: r' och r" har samma betydelser som i patentkravet 1, eller nämnda ketosyra därefter överföres tili hydroxisyra eller till diol och diolen sedan eventuellt oxideras tili motsva-rande ketoaldehyd.
8. Förfarande för framställning av föreningar med formeln (I) , där n=*0 och R=CHO, kännetecknat av att en syraklorid med formeln: cico ri i ett organiskt lösningsmedel fär reagera under betingelser-na för en Friedel-Crafts reaktion med en aromatisk förening med formeln -2 Co R3 R4 varefter aldehydfunktionen frigöres genom utbyte med glyoxal för erhällande av den önskade ketoaldehyden.
9. Förfarande för framställning av föreningar med formeln: n där: Rx - R4, Rg och R0 har de i patentkravet 1 angivna betydel-serna, kännetecknat av att en ketoaldehyd som framställts t.ex. enligt patentkravet 7 eller 8 och som har Il : 55 89261 följande formel: R. R, o där: A och Rx - R4 har de betydelser som angivits i patentkravet I, far reagera med ett alkylfosfonacetat med formeln: O R6 Il I (AIKO)2 P - CH C02 R8 i närvaro av natriumhydrid i THF och att den erhallna omät-tade ketoestern underkastas konventionella reaktionsbetin-gelser för att ge de olika betydelserna av radikalerna med formel (I) enligt patentkravet 1.
10. Kosmetisk komposition som är avsedd för kropps- och härhygien, kännetecknad av att den i en lämplig kosmetisk bärare innehaller minst en förening med formeln (I). II. Kosmetisk komposition enligt patentkravet 10, k ä n -netecknad av att den innehaller föreningen med formel (I) i en koncentration av mellan 0,0005 och 2 vikt-%, företrädesvis mellan 0,01 och 1 vikt-%.
12. Komposition enligt patentkravet 10, kännetecknad av att den dessutom innehaller minst en inert tillsats eller en kosmetiskt aktiv tillsats säsom ett hydratiseringsme-del, ett antiseborremedel, ett antiaknemedel, ett medel som gynnar härtillväxten, en karotenoid, ett smakämne, ett konser-veringsmedel, ett stabiliseringsmedel, ett medel för regiering av fuktighet, ett medel för regiering av pH, ett medel för regiering av osmotiskt tryck, ett emulgermedel, ett UV-A- eller UV-B-filtreringsmedel eller en antioxidant.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8610423 | 1986-07-17 | ||
FR8610423A FR2601670B1 (fr) | 1986-07-17 | 1986-07-17 | Nouveaux derives bicycliques aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
Publications (4)
Publication Number | Publication Date |
---|---|
FI873148A0 FI873148A0 (fi) | 1987-07-16 |
FI873148A FI873148A (fi) | 1988-01-18 |
FI89261B true FI89261B (fi) | 1993-05-31 |
FI89261C FI89261C (sv) | 1993-09-10 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI873148A FI89261C (sv) | 1986-07-17 | 1987-07-16 | Nya aromatiska bicykliska föreningar, förfarande för deras framställni ng och kosmetiska kompositioner som innehåller dessa föreningar |
Country Status (17)
Country | Link |
---|---|
US (1) | US4833240A (sv) |
EP (1) | EP0260162B1 (sv) |
JP (1) | JP2731148B2 (sv) |
AT (1) | ATE58367T1 (sv) |
AU (1) | AU597396B2 (sv) |
CA (2) | CA1296352C (sv) |
DE (2) | DE3766198D1 (sv) |
DK (1) | DK171965B1 (sv) |
ES (1) | ES2002463T3 (sv) |
FI (1) | FI89261C (sv) |
FR (1) | FR2601670B1 (sv) |
GR (2) | GR880300123T1 (sv) |
IE (1) | IE62598B1 (sv) |
NO (2) | NO167141C (sv) |
NZ (1) | NZ221112A (sv) |
PT (1) | PT85339B (sv) |
ZA (1) | ZA875261B (sv) |
Families Citing this family (62)
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FR2599031B1 (fr) * | 1986-05-23 | 1988-07-22 | Oreal | Nouveaux composes naphtyl aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
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US4877915A (en) * | 1989-01-27 | 1989-10-31 | Union Camp Corporation | Process for preparing polyalkyl tetrahydronaphthalenes |
US4877916A (en) * | 1989-01-27 | 1989-10-31 | Union Camp Corporation | Process for preparing polyalkyl tetrahydronaphthalenes |
US4877914A (en) * | 1989-01-27 | 1989-10-31 | Union Camp Corporation | Process for preparing polyalkyl tetrahydronaphthalenes |
US4877913A (en) * | 1989-01-27 | 1989-10-31 | Union Camp Corporation | Process for preparing polyalkyl tetrahydronaphthalenes |
US4877911A (en) * | 1989-01-27 | 1989-10-31 | Union Camp Corporation | Process for preparing polyalkyl tetrahydronaphthalenes |
US5194664A (en) * | 1989-02-10 | 1993-03-16 | Basf Aktiengesellschaft | Aromatic keto compounds, the preparation thereof, and drugs and cosmetics containing these |
DE3903992A1 (de) * | 1989-02-10 | 1990-08-16 | Basf Ag | Aromatische ketoverbindungen, ihre herstellung und arzneimittel sowie kosmetika daraus |
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PT678086E (pt) * | 1993-01-11 | 2000-05-31 | Ligand Pharm Inc | Compostos com selectividade para receptores de retinoides x |
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FR2746101B1 (fr) | 1996-03-14 | 1998-04-30 | Composes bicycliques-aromatiques | |
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FR2755965B1 (fr) | 1996-11-19 | 1998-12-18 | Cird Galderma | Composes biaromatiques, compositions pharmaceutiques et cosmetiques les contenant et utilisations |
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CA2383565A1 (en) | 1999-09-14 | 2001-03-22 | Ligand Pharmaceuticals Incorporated | Rxr modulators with improved pharmacologic profile |
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FR2848451B1 (fr) * | 2002-12-17 | 2007-01-12 | Galderma Res & Dev | Procede de stabilisation chimique d'un retinoide solubilise et composition aqueuse obtenue selon le procede comprenant au moins un retinoide sous forme salifiee |
CA2510038A1 (en) * | 2002-12-17 | 2004-07-01 | Galderma Research & Development, S.N.C. | Process for the chemical stabilization of a solubilized retinoid in a solvent using a base |
US9050310B2 (en) * | 2004-06-25 | 2015-06-09 | Minas Theodore Coroneo | Treatment of ocular lesions |
US20060204474A1 (en) * | 2005-02-25 | 2006-09-14 | Coroneo Minas T | Treatment of epithelial layer lesions |
FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
FR2910320B1 (fr) | 2006-12-21 | 2009-02-13 | Galderma Res & Dev S N C Snc | Emulsion comprenant au moins un retinoide et du peroxyde de benzole |
FR2931661B1 (fr) | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide. |
EP3044216B1 (en) | 2013-08-20 | 2022-02-23 | University of Washington through its Center for Commercialization | Novel and specific inhibitors of cytochrome p450 26 retinoic acid hydroxylase |
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Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US3763233A (en) * | 1971-08-17 | 1973-10-02 | Sandoz Ag | 7-substituted-hexahydro pleiadenes |
JPS59196839A (ja) * | 1983-04-21 | 1984-11-08 | Sankyo Co Ltd | フエニル酢酸誘導体 |
IL80270A0 (en) * | 1985-10-11 | 1987-01-30 | Cird | Naphthalene derivatives,their preparation and pharmaceutical compositions containing them |
LU86387A1 (fr) * | 1986-04-04 | 1987-12-07 | Oreal | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
FR2599031B1 (fr) * | 1986-05-23 | 1988-07-22 | Oreal | Nouveaux composes naphtyl aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
-
1986
- 1986-07-17 FR FR8610423A patent/FR2601670B1/fr not_active Expired
-
1987
- 1987-07-10 EP EP87401644A patent/EP0260162B1/fr not_active Expired - Lifetime
- 1987-07-10 ES ES87401644T patent/ES2002463T3/es not_active Expired - Lifetime
- 1987-07-10 DE DE8787401644T patent/DE3766198D1/de not_active Expired - Lifetime
- 1987-07-10 AT AT87401644T patent/ATE58367T1/de not_active IP Right Cessation
- 1987-07-10 DE DE198787401644T patent/DE260162T1/de active Pending
- 1987-07-16 CA CA000542301A patent/CA1296352C/fr not_active Expired - Lifetime
- 1987-07-16 FI FI873148A patent/FI89261C/sv not_active IP Right Cessation
- 1987-07-16 NO NO872983A patent/NO167141C/no unknown
- 1987-07-16 PT PT85339A patent/PT85339B/pt not_active IP Right Cessation
- 1987-07-16 DK DK370787A patent/DK171965B1/da not_active IP Right Cessation
- 1987-07-16 IE IE192287A patent/IE62598B1/en not_active IP Right Cessation
- 1987-07-16 CA CA000542302A patent/CA1328605C/fr not_active Expired - Fee Related
- 1987-07-17 AU AU75903/87A patent/AU597396B2/en not_active Ceased
- 1987-07-17 ZA ZA875261A patent/ZA875261B/xx unknown
- 1987-07-17 US US07/074,969 patent/US4833240A/en not_active Expired - Lifetime
- 1987-07-17 JP JP62177350A patent/JP2731148B2/ja not_active Expired - Fee Related
- 1987-07-17 NZ NZ221112A patent/NZ221112A/xx unknown
-
1988
- 1988-12-16 GR GR88300123T patent/GR880300123T1/el unknown
-
1990
- 1990-06-01 NO NO902453A patent/NO168031C/no unknown
-
1991
- 1991-02-07 GR GR91400157T patent/GR3001455T3/el unknown
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