DK252282A - Fremgangsmaade til fremstilling af 1,3-bis-(1,2,4-triazol-1-yl)-2-(2,4-difluorphenyl)propan-2-ol eller far aceutisk acceptable salte deraf - Google Patents
Fremgangsmaade til fremstilling af 1,3-bis-(1,2,4-triazol-1-yl)-2-(2,4-difluorphenyl)propan-2-ol eller far aceutisk acceptable salte deraf Download PDFInfo
- Publication number
- DK252282A DK252282A DK252282A DK252282A DK252282A DK 252282 A DK252282 A DK 252282A DK 252282 A DK252282 A DK 252282A DK 252282 A DK252282 A DK 252282A DK 252282 A DK252282 A DK 252282A
- Authority
- DK
- Denmark
- Prior art keywords
- aceutic
- difluorphenyl
- triazol
- propan
- hazardous
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
-
- 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
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8117379 | 1981-06-06 | ||
GB8117379 | 1981-06-06 | ||
GB8131370 | 1981-10-17 | ||
GB8131370 | 1981-10-17 | ||
GB8206329 | 1982-03-04 | ||
GB8206329 | 1982-03-04 |
Publications (3)
Publication Number | Publication Date |
---|---|
DK252282A true DK252282A (da) | 1982-12-07 |
DK149849B DK149849B (da) | 1986-10-13 |
DK149849C DK149849C (da) | 1987-04-27 |
Family
ID=27261198
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK252282A DK149849C (da) | 1981-06-06 | 1982-06-04 | Analogifremgangsmaade til fremstilling af 1,3-bis-(1,2,4-triazol-1-yl)-2-(2,4-difluorphenyl)-propan-2-ol eller farmaceutisk acceptable salte deraf |
Country Status (27)
Country | Link |
---|---|
US (1) | US4404216A (da) |
EP (1) | EP0069442B1 (da) |
KR (1) | KR850001132B1 (da) |
AU (1) | AU529987B2 (da) |
CA (1) | CA1181076A (da) |
DE (1) | DE3262386D1 (da) |
DK (1) | DK149849C (da) |
EG (1) | EG17222A (da) |
ES (2) | ES512882A0 (da) |
FI (1) | FI71134C (da) |
GR (1) | GR76491B (da) |
HK (1) | HK8488A (da) |
HU (1) | HU189143B (da) |
IE (1) | IE53144B1 (da) |
IL (1) | IL65963A (da) |
IN (1) | IN158113B (da) |
LU (1) | LU88329I2 (da) |
MX (1) | MX7119E (da) |
MY (1) | MY8800094A (da) |
NL (1) | NL930061I2 (da) |
NO (2) | NO156128C (da) |
NZ (1) | NZ200864A (da) |
PH (1) | PH18015A (da) |
PL (1) | PL130909B1 (da) |
PT (1) | PT75017B (da) |
SG (1) | SG80887G (da) |
YU (1) | YU42770B (da) |
Families Citing this family (77)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5395942A (en) * | 1980-06-02 | 1995-03-07 | Zeneca Limited | Heterocyclic compounds |
US5466821A (en) * | 1981-03-18 | 1995-11-14 | Zeneca Limited | Heterocyclic compounds |
DE3218130A1 (de) * | 1982-05-14 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide |
US4510148A (en) * | 1982-06-12 | 1985-04-09 | Pfizer Inc. | 2-Heterocyclic-1,3-bis(1H-1,2,4-triazol-1-yl)-propan-2-ols as antifungal agents |
US4466974A (en) * | 1982-11-16 | 1984-08-21 | Pfizer Inc. | Bistriazole antifungal agents |
GB8302500D0 (en) * | 1983-01-29 | 1983-03-02 | Pfizer Ltd | Antifungal agents |
GB8304282D0 (en) * | 1983-02-16 | 1983-03-23 | Pfizer Ltd | Antifungal agents |
GB8305377D0 (en) * | 1983-02-25 | 1983-03-30 | Pfizer Ltd | Antifungal agents |
DE3307218A1 (de) * | 1983-03-02 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Substituierte diazolylalkyl-carbinole, verfahren zu ihrer herstellung und ihre verwendung als antimykotische mittel |
DE3307216A1 (de) * | 1983-03-02 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Fungizide mittel |
DE3307217A1 (de) * | 1983-03-02 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Substituierte 1,3-diazolyl-2-propanole, verfahren zu ihrer herstellung und ihre verwendung als antimykotische mittel |
GB8306351D0 (en) * | 1983-03-08 | 1983-04-13 | Ici Plc | Azole fungicides |
US4992454A (en) * | 1983-03-16 | 1991-02-12 | Pfizer Inc. | Antifungal 1,3-bis (1H-1,2,4-triazol-1-yl)-2-aryl butan-2-ols and derivatives thereof |
DK159205C (da) * | 1983-03-16 | 1991-03-04 | Pfizer | Bis(triazol)alkanol-forbindelser, anvendelse af disse, farmaceutiske praeparater og landbrugsfungicider indeholdende disse og fremgangsmaade til behandling af planter eller froe, som har en svampeinfektion |
DE3313073A1 (de) * | 1983-04-12 | 1984-10-18 | Bayer Ag, 5090 Leverkusen | 1-azolyl-3-pyrazolyl-2-propanol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
GB8313235D0 (en) * | 1983-05-13 | 1983-06-22 | Pfizer Ltd | Antifungal agents |
US4482564A (en) * | 1983-06-03 | 1984-11-13 | Schering Corporation | Triazolyl-substituted propane derivatives |
DE3332415A1 (de) * | 1983-09-08 | 1985-03-28 | Messerschmitt-Bölkow-Blohm GmbH, 8012 Ottobrunn | Steuerbares stroemungsumlenksystem |
USH672H (en) | 1986-12-31 | 1989-09-05 | E. R. Squibb & Sons, Inc. | Stable antifungal capsule formulation |
US4916134A (en) * | 1987-03-25 | 1990-04-10 | Janssen Pharmacuetica N.V. | 4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-azolylmethyl)-1,3-dioxolan-4-yl]me]phenyl]-1-piperazinyl]phenyl]triazolones |
GB9002375D0 (en) * | 1990-02-02 | 1990-04-04 | Pfizer Ltd | Triazole antifungal agents |
DE4134125C2 (de) * | 1991-10-15 | 1995-02-02 | Mack Chem Pharm | Triazol-Derivate enthaltende pharmazeutische Zusammensetzungen zur rektalen Applikation |
EP0548553A1 (en) * | 1991-11-25 | 1993-06-30 | Takeda Chemical Industries, Ltd. | Optically active azole compounds, their production and use |
EP0597049A1 (en) * | 1992-03-04 | 1994-05-18 | Jemlan, Inc. | Antifungal agents |
ES2040181B1 (es) * | 1992-03-30 | 1994-05-16 | Uriach & Cia Sa J | Procedimiento para la obtencion de nuevas dihidropiridinas. |
IL105200A (en) * | 1993-03-29 | 1997-03-18 | Teva Pharma | Regiospecific processes for the preparation of 1, 3-bis (1, 2, 4-triazol-1-yl)-propan- 2-ol derivatives |
CA2106032C (en) * | 1993-09-13 | 1995-11-07 | Gamini Weeratunga | Methods for the manufacture of fluconazole and forms thereof, intermediates useful in the manufacture thereof, and combinations comprising fluconazole |
US6043064A (en) * | 1993-10-22 | 2000-03-28 | Bristol-Myers Squibb Company | Enzymatic hydroxylation process for the preparation of HMG-CoA reductase inhibitors and intermediates thereof |
NZ270418A (en) | 1994-02-07 | 1997-09-22 | Eisai Co Ltd | Polycyclic triazole & imidazole derivatives, antifungal compositions |
CA2139079C (en) * | 1994-12-23 | 1996-05-28 | K.S. Keshava Murthy | Commercial process for the manufacture of fluconazole and intermediates useful in the manufacture thereof |
CN1054853C (zh) * | 1995-01-11 | 2000-07-26 | 上海三维制药公司 | 氟康唑中间体1-[2-(2,4-二氟苯基)2,3-环氧丙基]-1h-1,2,4-三氮唑及其甲磺酸盐的制备方法 |
US5770616A (en) * | 1995-06-07 | 1998-06-23 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of cancers |
US6200992B1 (en) | 1995-06-07 | 2001-03-13 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of cancers |
US5665751A (en) * | 1995-06-07 | 1997-09-09 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of cancers |
NZ272586A (en) * | 1995-07-17 | 1996-10-28 | Apotex Inc | Process for preparing fluconazole and triazolylepoxypropane precursors |
US5908855A (en) * | 1996-07-16 | 1999-06-01 | The Procter & Gamble Company | Compositions for treating viral infections |
GB9605705D0 (en) | 1996-03-19 | 1996-05-22 | Pfizer Ltd | Therapeutic agents |
TW436484B (en) * | 1996-04-24 | 2001-05-28 | Dev Center Biotechnology | 1,2,3,4-tetrahydroisoquinoline derivatives having a nitrogen-containing heterocyclic methyl substituent, the preparation process and pharmaceutical composition thereof |
DE19617282A1 (de) * | 1996-04-30 | 1997-11-06 | Bayer Ag | Triazolyl-mercaptide |
DE19617461A1 (de) * | 1996-05-02 | 1997-11-06 | Bayer Ag | Acylmercapto-triazolyl-Derivate |
DE19619544A1 (de) | 1996-05-15 | 1997-11-20 | Bayer Ag | Triazolyl-Disulfide |
DE19620407A1 (de) * | 1996-05-21 | 1997-11-27 | Bayer Ag | Thiocyano-triazolyl-Derivate |
DE19620590A1 (de) * | 1996-05-22 | 1997-11-27 | Bayer Ag | Sulfonyl-mercapto-triazolyl-Derivate |
US5710280A (en) * | 1996-07-09 | 1998-01-20 | Development Center For Biotechnology | Preparation of fluconazole and pharmaceutically acceptable salts thereof |
NZ328607A (en) * | 1996-09-09 | 1999-08-30 | Hoffmann La Roche | Heterocyclically substituted n-benzyl-azolium derivatives and fungicidal compositions |
KR100194945B1 (ko) * | 1997-01-29 | 1999-06-15 | 서치영 | 플루코나졸의 제조방법 |
GR980100028A (el) * | 1998-01-15 | 1999-09-30 | Drug Research Hellas ����� | Φαρμακευτικα προιοντα για τοπικη χρηση που περιεχουν φλουκοναζολη σε συγκεντρωσεις μεταξυ 0,2% και 5% |
CN1081189C (zh) * | 1998-07-17 | 2002-03-20 | 国家医药管理局四川抗菌素工业研究所 | 唑醇类新衍生物及其制备方法和医药用途 |
IN191188B (da) | 2000-03-07 | 2003-10-04 | Ranbaxy Lab Ltd | |
KR100423666B1 (ko) * | 2001-02-07 | 2004-03-18 | 보령제약 주식회사 | 항진균 외용 제제 |
HUP0303249A3 (en) | 2001-02-22 | 2007-03-28 | Sankyo Co | Water-soluble triazole fungicide compounds and pharmaceutical compositions containing them |
ES2252209T3 (es) * | 2001-03-23 | 2006-05-16 | Richter Gedeon Vegyeszeti Gyar R.T. | Proceso para preparar fluconazol y sus modificaciones cristalinas. |
IL157771A0 (en) * | 2001-03-27 | 2004-03-28 | Galen Chemicals Ltd | Intravaginal drug delivery devices for the administration of an antimicrobial agent |
CA2474017A1 (en) * | 2002-02-12 | 2003-08-21 | Fdc Limited | Novel anti-fungal agents |
AU2003217676B2 (en) | 2002-02-22 | 2009-06-11 | Takeda Pharmaceutical Company Limited | Active agent delivery systems and methods for protecting and administering active agents |
US8404751B2 (en) * | 2002-09-27 | 2013-03-26 | Hallux, Inc. | Subunguicide, and method for treating onychomycosis |
US20050074494A1 (en) * | 2003-10-06 | 2005-04-07 | Xiu-Xiu Cheng | Itraconazole immediate release formulation |
GB0402491D0 (en) * | 2004-02-04 | 2004-03-10 | Pfizer Ltd | Medicaments |
US20050282878A1 (en) * | 2004-04-13 | 2005-12-22 | Batchu Chandrasekhar | Process for the purification of fluconazole |
US20060252940A1 (en) * | 2005-05-05 | 2006-11-09 | Sudhakar Valluri | Crystalline 1-[2-(2,4-difluorophenyl)-oxiranyl methyl]-1h-1,2,4-triazole |
US7968579B2 (en) * | 2005-10-31 | 2011-06-28 | Daewoong Pharmaceutical Co., Ltd. | Antifungal triazole derivatives |
TWI426918B (zh) * | 2007-02-12 | 2014-02-21 | Merck Sharp & Dohme | Il-23拮抗劑於治療感染之用途 |
KR100909953B1 (ko) * | 2007-06-15 | 2009-07-31 | 한국화학연구원 | 항진균 활성을 갖는 트라이아졸 유도체, 이의 제조방법 및이를 함유하는 약학 조성물 |
US20090062357A1 (en) * | 2007-08-29 | 2009-03-05 | Protia, Llc | Deuterium-enriched fluconazole |
JP2009286756A (ja) * | 2008-05-30 | 2009-12-10 | Fujifilm Finechemicals Co Ltd | トリアゾール誘導体またはその塩 |
KR100971371B1 (ko) | 2010-02-04 | 2010-07-20 | 동국제약 주식회사 | 신규한 중간체를 이용한 보리코나졸의 제조방법 |
WO2011101862A1 (en) | 2010-02-17 | 2011-08-25 | Fdc Limited | Stabilized fluconazole polymorph iii formulation |
SI2788343T1 (sl) | 2011-12-11 | 2019-09-30 | Viamet Pharmaceuticals (NC), Inc. | Spojine inhibitorja metaloencimov |
US9498612B2 (en) | 2013-03-14 | 2016-11-22 | Hallux, Inc. | Method of treating infections, diseases or disorders of nail unit |
BR102013027313B1 (pt) * | 2013-10-23 | 2019-06-18 | Iharabras S.A. Indústrias Químicas | Processo para a preparação seletiva de (1h-1,2,4-triazol-1-il) alcanóis, composto hidrazinil alcanol obtido por tal processo e seu uso |
RU2538962C1 (ru) * | 2013-11-19 | 2015-01-10 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Казанский (Приволжский) Федеральный Университет" (ФГАОУ ВПО КФУ) | Противогрибковые соединения на основе производных 3,5,8-триоксабицикло[5.1.0]октана |
EA036098B1 (ru) | 2015-09-18 | 2020-09-28 | ВиПиЭс-3, ИНК. | Способ получения противогрибковых соединений |
AU2019288677A1 (en) | 2018-06-21 | 2021-01-14 | Yumanity Therapeutics, Inc. | Compositions and methods for the treatment and prevention of neurological disorders |
CN111518041B (zh) * | 2020-04-24 | 2024-07-26 | 湖南复瑞生物医药技术有限责任公司 | 一种2’4’-二氟-2-[1-(1h-1,2,4-***基)]苯乙酮的制备方法 |
CN111454227A (zh) * | 2020-05-21 | 2020-07-28 | 湖南复瑞生物医药技术有限责任公司 | 一种西洛他唑中间体的制备方法 |
CN112137972A (zh) * | 2020-09-16 | 2020-12-29 | 石家庄四药有限公司 | 一种氟康唑片剂组合物、片剂及制备方法 |
KR102434209B1 (ko) * | 2022-01-28 | 2022-08-19 | 전기열 | 천연 오일을 함유한 발모촉진 및 탈모방지용 조성물 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
-
1982
- 1982-04-22 EP EP82302075A patent/EP0069442B1/en not_active Expired
- 1982-04-22 DE DE8282302075T patent/DE3262386D1/de not_active Expired
- 1982-05-28 IE IE1285/82A patent/IE53144B1/en active Protection Beyond IP Right Term
- 1982-05-31 HU HU821755A patent/HU189143B/hu unknown
- 1982-06-01 US US06/383,866 patent/US4404216A/en not_active Expired - Lifetime
- 1982-06-02 PH PH27392A patent/PH18015A/en unknown
- 1982-06-03 PL PL1982236740A patent/PL130909B1/pl unknown
- 1982-06-03 IL IL65963A patent/IL65963A/xx not_active IP Right Cessation
- 1982-06-03 KR KR8202493A patent/KR850001132B1/ko active
- 1982-06-03 IN IN427/DEL/82A patent/IN158113B/en unknown
- 1982-06-04 FI FI822005A patent/FI71134C/fi not_active IP Right Cessation
- 1982-06-04 CA CA000404514A patent/CA1181076A/en not_active Expired
- 1982-06-04 GR GR68354A patent/GR76491B/el unknown
- 1982-06-04 DK DK252282A patent/DK149849C/da not_active IP Right Cessation
- 1982-06-04 MX MX8210108U patent/MX7119E/es unknown
- 1982-06-04 PT PT75017A patent/PT75017B/pt unknown
- 1982-06-04 AU AU84484/82A patent/AU529987B2/en not_active Expired
- 1982-06-04 YU YU1195/82A patent/YU42770B/xx unknown
- 1982-06-04 ES ES512882A patent/ES512882A0/es active Granted
- 1982-06-04 NZ NZ200864A patent/NZ200864A/en unknown
- 1982-06-04 NO NO821886A patent/NO156128C/no not_active IP Right Cessation
- 1982-06-05 EG EG319/82A patent/EG17222A/xx active
-
1983
- 1983-03-18 ES ES520794A patent/ES8404348A1/es not_active Expired
-
1987
- 1987-10-08 SG SG808/87A patent/SG80887G/en unknown
-
1988
- 1988-01-28 HK HK84/88A patent/HK8488A/xx not_active IP Right Cessation
- 1988-12-30 MY MY94/88A patent/MY8800094A/xx unknown
-
1993
- 1993-06-11 NL NL930061C patent/NL930061I2/nl unknown
- 1993-06-24 LU LU88329C patent/LU88329I2/fr unknown
-
1994
- 1994-11-02 NO NO1994019C patent/NO1994019I1/no unknown
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CTFF | Application for supplementary protection certificate (spc) filed |
Free format text: CA 1993 00020, 930603 |
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PUP | Patent expired |