PT98731B - Processo para a preparacao de um sal de codeina de um acido carboxilico substituido - Google Patents
Processo para a preparacao de um sal de codeina de um acido carboxilico substituido Download PDFInfo
- Publication number
- PT98731B PT98731B PT98731A PT9873191A PT98731B PT 98731 B PT98731 B PT 98731B PT 98731 A PT98731 A PT 98731A PT 9873191 A PT9873191 A PT 9873191A PT 98731 B PT98731 B PT 98731B
- Authority
- PT
- Portugal
- Prior art keywords
- salt
- formula
- codeine
- dichlorophenyl
- phenyl
- Prior art date
Links
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- 238000000034 method Methods 0.000 title claims description 17
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- 150000002334 glycols Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021400 peanut butter Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229940057429 sorbitan isostearate Drugs 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
- C07D489/04—Salts; Organic complexes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Carbon And Carbon Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH273590 | 1990-08-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT98731A PT98731A (pt) | 1992-07-31 |
| PT98731B true PT98731B (pt) | 1999-01-29 |
Family
ID=4240432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT98731A PT98731B (pt) | 1990-08-23 | 1991-08-21 | Processo para a preparacao de um sal de codeina de um acido carboxilico substituido |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5190947A (en, 2012) |
| EP (1) | EP0472501B1 (en, 2012) |
| JP (1) | JPH04257587A (en, 2012) |
| KR (1) | KR920004391A (en, 2012) |
| AT (1) | ATE137753T1 (en, 2012) |
| AU (1) | AU652951B2 (en, 2012) |
| CA (1) | CA2049649A1 (en, 2012) |
| DE (1) | DE59107784D1 (en, 2012) |
| DK (1) | DK0472501T3 (en, 2012) |
| ES (1) | ES2086515T3 (en, 2012) |
| FI (1) | FI96421C (en, 2012) |
| GR (1) | GR3019872T3 (en, 2012) |
| HU (1) | HU209308B (en, 2012) |
| IE (1) | IE72479B1 (en, 2012) |
| IL (1) | IL99213A (en, 2012) |
| NO (1) | NO179175C (en, 2012) |
| NZ (1) | NZ239495A (en, 2012) |
| PT (1) | PT98731B (en, 2012) |
| TW (1) | TW225536B (en, 2012) |
| ZA (1) | ZA916642B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0498011B1 (de) * | 1991-02-07 | 1995-04-26 | HEUMANN PHARMA GMBH & CO | Neue Salze der 2-(2,6-Dichloranilino)-phenylessigsäure, Verfahren zu ihrer Herstellung und ihre Verwendung für topisch anwendbare pharmazeutische Zubereitungen |
| FR2708611B1 (fr) * | 1993-07-29 | 1995-10-27 | Meram Lab | Sel de codéine de l'acide 2-(3-benzoylphényl)propionique, procédé d'obtention et compositions pharmaceutiques le contenant. |
| DE19607395C2 (de) * | 1996-02-28 | 2002-11-21 | Lohmann Therapie Syst Lts | Salze aus einem kationischen narkotischen Analgetikum mit einem anionischen nichtnarkotischen Analgetikum, Verfahren zu deren Herstellung und die diese Salze enthaltenden pharmazeutischen Präparate |
| RS49982B (sr) * | 1997-09-17 | 2008-09-29 | Euro-Celtique S.A., | Sinergistička analgetička kombinacija analgetičkog opijata i inhibitora ciklooksigenaze-2 |
| CA2304722C (en) * | 1997-09-25 | 2005-11-22 | Lts Lohmann Therapie-Systeme Ag | Acidic addition salts of morphine alkaloids and the application thereof |
| AU2002305816B2 (en) * | 2001-06-05 | 2008-04-10 | Psivida Us Inc. | Sustained-release analgesic compounds |
| US20030118528A1 (en) * | 2001-11-19 | 2003-06-26 | Walters Kenneth A. | Topical delivery of codrugs |
| US10004729B2 (en) | 2002-07-05 | 2018-06-26 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| US8840928B2 (en) * | 2002-07-05 | 2014-09-23 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| US8557291B2 (en) * | 2002-07-05 | 2013-10-15 | Collegium Pharmaceutical, Inc. | Abuse-deterrent pharmaceutical compositions of opioids and other drugs |
| JP4694207B2 (ja) * | 2002-07-05 | 2011-06-08 | コルジウム ファーマシューティカル， インコーポレイテッド | オピオイドおよび他の薬物に関する乱用抑止性の薬学的組成物 |
| TW200500067A (en) * | 2003-01-21 | 2005-01-01 | Control Delivery Sys Inc | Salts of codrugs and uses related thereto |
| CA2916869A1 (en) * | 2004-06-12 | 2005-12-29 | Jane C. Hirsh | Abuse-deterrent drug formulations |
| US20090291121A1 (en) * | 2008-05-23 | 2009-11-26 | Symrise, Inc. | Capsule and coated capsules as a delivery system for dietary supplements and therapeutic materials |
| BRPI1006222A2 (pt) | 2009-03-12 | 2016-08-02 | Cumberland Pharmaceuticas Inc | uso de ibuprofeno na redução de dor em pacientes humanos que são submetidos a cirurgia, uso de ibuprofeno na redução de dor cirúrgica em pacientes humanos e uso de ibuprofeno para melhorar o tempo ambulatorial após a operação em pacientes humanos que sorem procedimentos cirúrgicos ortopédicos |
| US10668060B2 (en) | 2009-12-10 | 2020-06-02 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| WO2013112456A1 (en) | 2012-01-24 | 2013-08-01 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Controlled release formulations for the induction and proliferation of blood cells |
| US9072710B2 (en) | 2012-03-16 | 2015-07-07 | Cumberland Pharmaceuticals Inc. | Injectable ibuprofen formulation |
| US9737530B1 (en) | 2016-06-23 | 2017-08-22 | Collegium Pharmaceutical, Inc. | Process of making stable abuse-deterrent oral formulations |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA537946A (en) * | 1957-03-12 | J. Lewenstein Mozes | Process for preparing improved compounds having narcotic effect | |
| US936254A (en) * | 1908-01-06 | 1909-10-05 | Belden Mfg Co | Attachment for telephones. |
| DE377588C (de) * | 1922-08-29 | 1923-06-22 | O Hinsberg Dr | Verfahren zur Darstellung einer salzartigen Verbindung des Codeins |
| US2628185A (en) * | 1949-04-01 | 1953-02-10 | Lewenstein Mozes Juda | Analgesic compounds and compositions |
| US3895063A (en) * | 1965-04-08 | 1975-07-15 | Ciba Geigy Corp | Substituted Anilino Benzyl Alcohols |
| FR2051482B1 (en, 2012) * | 1969-04-04 | 1973-06-08 | Rabot Ets David | |
| CA964192A (en) * | 1970-07-21 | 1975-03-11 | Roy H. Reiner | Long-acting narcotic antagonist formulations containing pamoate salts of dihydronormorphinone |
| FR2257606B1 (en, 2012) * | 1974-01-10 | 1978-02-24 | Sumitomo Chemical Co | |
| US4176186A (en) * | 1978-07-28 | 1979-11-27 | Boehringer Ingelheim Gmbh | Quaternary derivatives of noroxymorphone which relieve intestinal immobility |
| DE2935776A1 (de) * | 1979-09-05 | 1981-04-16 | Theodor Prof. Dr. 4400 Münster Eckert | Organische salze des indometacin, des naproxen und des diclofenac, ihre herstellung und sie enthaltende arzneimittel |
| AT370721B (de) * | 1981-02-24 | 1983-04-25 | Ciba Geigy Ag | Verfahren zur herstellung von neuen salzen der 2- (2,6-dichloranilino)-phenylessigsaeure, der |
| CH664085A5 (de) * | 1985-02-08 | 1988-02-15 | Ciba Geigy Ag | Pharmazeutische praeparate mit analgetischer wirksamkeit, sowie deren herstellung. |
-
1991
- 1991-07-31 TW TW080105991A patent/TW225536B/zh active
- 1991-08-14 DK DK91810645.1T patent/DK0472501T3/da active
- 1991-08-14 ES ES91810645T patent/ES2086515T3/es not_active Expired - Lifetime
- 1991-08-14 AT AT91810645T patent/ATE137753T1/de not_active IP Right Cessation
- 1991-08-14 DE DE59107784T patent/DE59107784D1/de not_active Expired - Fee Related
- 1991-08-14 EP EP91810645A patent/EP0472501B1/de not_active Expired - Lifetime
- 1991-08-16 US US07/746,676 patent/US5190947A/en not_active Expired - Fee Related
- 1991-08-16 IL IL9921391A patent/IL99213A/en unknown
- 1991-08-21 FI FI913949A patent/FI96421C/fi not_active IP Right Cessation
- 1991-08-21 CA CA002049649A patent/CA2049649A1/en not_active Abandoned
- 1991-08-21 NZ NZ239495A patent/NZ239495A/en unknown
- 1991-08-21 PT PT98731A patent/PT98731B/pt not_active IP Right Cessation
- 1991-08-21 AU AU82685/91A patent/AU652951B2/en not_active Ceased
- 1991-08-22 KR KR1019910014490A patent/KR920004391A/ko not_active Abandoned
- 1991-08-22 IE IE297391A patent/IE72479B1/en not_active IP Right Cessation
- 1991-08-22 NO NO913295A patent/NO179175C/no unknown
- 1991-08-22 HU HU912768A patent/HU209308B/hu not_active IP Right Cessation
- 1991-08-22 ZA ZA916642A patent/ZA916642B/xx unknown
- 1991-08-22 JP JP3210723A patent/JPH04257587A/ja active Pending
-
1996
- 1996-05-09 GR GR960401132T patent/GR3019872T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI96421B (fi) | 1996-03-15 |
| ZA916642B (en) | 1992-04-29 |
| NO179175B (no) | 1996-05-13 |
| IE912973A1 (en) | 1992-02-26 |
| IL99213A (en) | 1995-07-31 |
| HUT60501A (en) | 1992-09-28 |
| IE72479B1 (en) | 1997-04-23 |
| ATE137753T1 (de) | 1996-05-15 |
| PT98731A (pt) | 1992-07-31 |
| NO913295L (no) | 1992-02-24 |
| FI913949L (fi) | 1992-02-24 |
| HU209308B (en) | 1994-04-28 |
| JPH04257587A (ja) | 1992-09-11 |
| US5190947A (en) | 1993-03-02 |
| HU912768D0 (en) | 1992-01-28 |
| CA2049649A1 (en) | 1992-02-24 |
| FI913949A0 (fi) | 1991-08-21 |
| FI96421C (fi) | 1996-06-25 |
| KR920004391A (ko) | 1992-03-27 |
| EP0472501B1 (de) | 1996-05-08 |
| ES2086515T3 (es) | 1996-07-01 |
| EP0472501A3 (en) | 1993-02-24 |
| DK0472501T3 (da) | 1996-05-28 |
| AU8268591A (en) | 1992-02-27 |
| IL99213A0 (en) | 1992-07-15 |
| DE59107784D1 (de) | 1996-06-13 |
| NZ239495A (en) | 1997-05-26 |
| NO913295D0 (no) | 1991-08-22 |
| EP0472501A2 (de) | 1992-02-26 |
| GR3019872T3 (en) | 1996-08-31 |
| NO179175C (no) | 1996-08-21 |
| TW225536B (en, 2012) | 1994-06-21 |
| AU652951B2 (en) | 1994-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19920310 |
|
| FG3A | Patent granted, date of granting |
Effective date: 19981027 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20000430 |