LV12212B - A process for the production of finasteride - Google Patents

A process for the production of finasteride Download PDF

Info

Publication number: LV12212B
Authority: LV; Latvia
Prior art keywords: finasteride; mixture; organic solvent; vvater; water
Prior art date: 1992-11-19

Application number

LVP-98-236A

Other languages

English (en)

Latvian (lv)

Other versions

LV12212A (lv

Inventor

Ulf H. Dolling

James A. Mccauley

Richard J. Varsolona

Original Assignee

Merck & Co., Inc.

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.)

1992-11-19

Filing date

1998-10-26

Publication date

1999-03-20

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26681536&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LV12212(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1998-10-26 Application filed by Merck & Co., Inc. filed Critical Merck & Co., Inc.

1999-01-20 Publication of LV12212A publication Critical patent/LV12212A/xx

1999-03-20 Publication of LV12212B publication Critical patent/LV12212B/en

Links

238000000034 method Methods 0.000 title claims abstract description 20
DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 claims abstract description 45
229960004039 finasteride Drugs 0.000 claims abstract description 41
239000003960 organic solvent Substances 0.000 claims abstract description 22
-1 magnesium halide salt Chemical class 0.000 claims abstract 5
238000004519 manufacturing process Methods 0.000 claims abstract 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
239000011877 solvent mixture Substances 0.000 claims description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
239000007790 solid phase Substances 0.000 claims description 13
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 12
229940011051 isopropyl acetate Drugs 0.000 claims description 12
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 12
229960000583 acetic acid Drugs 0.000 claims description 6
239000012362 glacial acetic acid Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 abstract description 5
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract description 3
125000001931 aliphatic group Chemical group 0.000 abstract 1
150000004792 aryl magnesium halides Chemical class 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
229910052749 magnesium Inorganic materials 0.000 abstract 1
239000011777 magnesium Substances 0.000 abstract 1
239000002904 solvent Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
238000012512 characterization method Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229940072254 proscar Drugs 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
206010020112 Hirsutism Diseases 0.000 description 1
208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
229940123934 Reductase inhibitor Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
206010000496 acne Diseases 0.000 description 1
230000032683 aging Effects 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000007704 transition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/005—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N5/00—Details of television systems
- H04N5/74—Projection arrangements for image reproduction, e.g. using eidophor
- H04N5/7416—Projection arrangements for image reproduction, e.g. using eidophor involving the use of a spatial light modulator, e.g. a light valve, controlled by a video signal
- H04N5/7458—Projection arrangements for image reproduction, e.g. using eidophor involving the use of a spatial light modulator, e.g. a light valve, controlled by a video signal the modulator being an array of deformable mirrors, e.g. digital micromirror device [DMD]

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Multimedia (AREA)
Signal Processing (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Dermatology (AREA)
Urology & Nephrology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Confectionery (AREA)
Dental Preparations (AREA)
Seasonings (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

LVP-98-236A 1992-11-19 1998-10-26 A process for the production of finasteride LV12212B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US97853592A	1992-11-19	1992-11-19
US08/010,734 US5468860A (en)	1992-11-19	1993-01-29	New finasteride processes

Publications (2)

Publication Number	Publication Date
LV12212A LV12212A (lv)	1999-01-20
LV12212B true LV12212B (en)	1999-03-20

Family

ID=26681536

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
LVP-98-236A LV12212B (en)	1992-11-19	1998-10-26	A process for the production of finasteride
LVP-00-26A LV12460B (en)	1992-11-19	2000-02-23	THE METHOD OF GETTING FINASTERITES

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
LVP-00-26A LV12460B (en)	1992-11-19	2000-02-23	THE METHOD OF GETTING FINASTERITES

Country Status (32)

Country	Link
US (3)	US5468860A (fr)
EP (3)	EP0823436A3 (fr)
JP (2)	JPH07110875B2 (fr)
CN (1)	CN1058018C (fr)
AT (2)	ATE177112T1 (fr)
AU (1)	AU658774B2 (fr)
BG (2)	BG62362B1 (fr)
CA (1)	CA2103107C (fr)
CY (1)	CY2135B1 (fr)
CZ (3)	CZ301191B6 (fr)
DE (4)	DE69323754T2 (fr)
DK (2)	DK0655458T3 (fr)
DZ (1)	DZ1733A1 (fr)
ES (2)	ES2052476T5 (fr)
FI (4)	FI107450B (fr)
GR (4)	GR940300045T1 (fr)
HR (2)	HRP931410B1 (fr)
HU (2)	HU216195B (fr)
IL (1)	IL107574A (fr)
IS (2)	IS1692B (fr)
LV (2)	LV12212B (fr)
MX (1)	MX9307222A (fr)
MY (2)	MY110410A (fr)
NO (3)	NO305912B1 (fr)
PH (1)	PH31120A (fr)
RO (2)	RO115165B1 (fr)
RU (1)	RU2120445C1 (fr)
SI (1)	SI9300603B (fr)
SK (2)	SK286488B6 (fr)
TW (1)	TW257766B (fr)
UA (1)	UA41341C2 (fr)
WO (1)	WO1994011387A2 (fr)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5468860A (en) *	1992-11-19	1995-11-21	Merck & Co., Inc.	New finasteride processes
TW408127B (en) *	1993-09-17	2000-10-11	Glaxo Inc	Androstenones
IT1270660B (it) *	1994-10-13	1997-05-07	Poli Ind Chimica Spa	Procedimento microbiologico per la preparazione di 3-oxo-4-azasteroidi-17beta-carbossi sostituiti e uso dei prodotti come inibitori dell'enzima 5alfa-riduttasi
US5670643A (en) *	1995-03-16	1997-09-23	Glaxo Wellcome Inc.	Method for preparing finasteride
US5585383A (en) *	1995-05-03	1996-12-17	Merck & Co., Inc.	Process for crystallizing a 4-azasteroid 5alpha-reductase inhibitor
EP0859761A4 (fr) *	1995-09-15	2000-01-26	Merck & Co Inc	4-azasteroides utilises pour le traitement d'etats hyperandrogeniques
GB2338234B (en) *	1998-06-10	2000-05-03	Torcan Chemical Ltd	Preparation of finasteride
ES2153789B1 (es) *	1999-07-05	2001-10-16	Raga Consultores S L	Procedimiento para la obtencion de 178-(n-terc-butlcarbamoil)-3-ona-4-aza-esteroides
EA200200524A1 (ru) *	1999-11-01	2002-10-31	Торкан Кемикал Лтд.	Получение полиморфных форм i и ii финастерида путем образования комплексов с солями металлов группы i или ii
AU2001269911B2 (en) *	2000-09-07	2006-09-21	Dr. Reddy's Laboratories Ltd.	Novel polymorphic form of 17-beta-(n-ter.butyl carbamoyl)-4-aza-5-alpha-androst-1-en-3-one and a process for preparing it
CA2422159A1 (fr) *	2000-09-07	2002-03-14	Dr. Reddy's Laboratories Ltd.	Nouvelles formes polymorphes de 17-beta-(n-ter.butyl carbamoyl)-4-aza-5-alpha-androst-1-en-3-one et leurs procedes de preparation
EP1790653A3 (fr) *	2000-09-07	2010-06-02	Dr. Reddy's Laboratories Ltd.	Nouvelles formes polymorphes de 17-beta-(n-ter.butyl carbomyol)-4-aza-5-alpha-androst-1-en-3-one et leurs procedes de preparation
KR100415858B1 (ko) *	2001-09-22	2004-01-24	한미약품 주식회사	17베타-(엔-3차-부틸카바모일)-3-온 스테로이드 화합물의제조방법
CN100428897C (zh) *	2002-08-16	2008-10-29	浙江寿峰堂生物工程有限公司	抗疲劳改善亚健康的保健食品及其制备方法
ES2206065B1 (es) *	2002-10-31	2005-08-16	Ragactives, S.L.	Procedimiento para la obtencion de la forma polimorfica i de finasterida.
AU2003217439A1 (en) *	2003-03-19	2004-10-11	Hetero Drugs Limited	Novel crystalline forms of finasteride
DE602004016170D1 (de) *	2003-07-03	2008-10-09	Cipla Ltd	Verfahren zur herstellung von finasterid form i
US20050136015A1 (en) *	2003-12-17	2005-06-23	McKie Derrick B.	Topical use of halosalicylic acid derivatives
US20070167477A1 (en) *	2006-01-13	2007-07-19	Mandava Venkata Naga Brahmeswa	Processes to prepare finasteride polymorphs
US7531658B2 (en) *	2006-01-20	2009-05-12	Apotex Pharmachem Inc.	Process for the preparation of 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones
US7897800B2 (en)	2006-02-03	2011-03-01	Jr Chem, Llc	Chemical compositions and methods of making them
JP5038331B2 (ja)	2006-02-03	2012-10-03	ジェイアールケムエルエルシー	銅と亜鉛の組成物を用いた老化防止治療
US7687650B2 (en)	2006-02-03	2010-03-30	Jr Chem, Llc	Chemical compositions and methods of making them
US7867522B2 (en)	2006-09-28	2011-01-11	Jr Chem, Llc	Method of wound/burn healing using copper-zinc compositions
US20090076058A1 (en) *	2007-09-17	2009-03-19	Protia, Llc	Deuterium-enriched finasteride
US8273791B2 (en)	2008-01-04	2012-09-25	Jr Chem, Llc	Compositions, kits and regimens for the treatment of skin, especially décolletage
HRP20120475T1 (hr) *	2008-05-05	2012-08-31	Abbott Gmbh & Co. Kg	Postupak određivanja topljivosti kristalne tvari u polimeru
WO2010085753A1 (fr)	2009-01-23	2010-07-29	Jr Chem, Llc	Traitements pour l'acné rosacée et trousses médicales pour les mettre en pratique
US8952057B2 (en)	2011-01-11	2015-02-10	Jr Chem, Llc	Compositions for anorectal use and methods for treating anorectal disorders

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NZ211145A (en) *	1984-02-27	1988-10-28	Merck & Co Inc	4-aza-5-alpha-androst-1-en-3-ones and pharmaceutical compositions
US4760071A (en) *	1984-02-27	1988-07-26	Merck & Co., Inc.	17β-N-monosubstituted carbamoyl-4-aza-5α-androst-1-en-3-ones which are active as testosterone 5α-reductase inhibitors
DE3888378T2 (de) *	1987-04-03	1994-09-29	Merck & Co Inc	Behandlung von Prostatacarcinoma mit 17-beta-n-monosubstituierten-Carbamoyl-4-aza-5-alpha-Androst-1-en-3-onen.
NZ225100A (en)	1987-06-29	1991-09-25	Merck & Co Inc	Reaction of steroids (including 4-azasteroids) with a silylating agent in the presence of a quinone to introduce a delta' double bond and silylated intermediates
US5084574A (en) *	1988-04-18	1992-01-28	Merck & Co., Inc.	Dehydrogenation process
US5237061A (en) *	1988-10-31	1993-08-17	Merck & Co., Inc.	Methods of synthesizing benign prostatic hypertropic agents and their intermediates
US5021575A (en) *	1989-11-13	1991-06-04	Merck & Co., Inc.	Method for introducing a 1,2 double bond into azasteroids
JP3282731B2 (ja) *	1990-06-15	2002-05-20	メルクエンドカムパニーインコーポレーテッド	結晶の構造および大きさを改良する結晶化方法
EP0462662A3 (en) *	1990-06-20	1992-08-19	Merck & Co. Inc.	17beta-n-monosubstituted adamantyl/norbornanyl carbamoyl-4-aza-5alpha-androst-1-en-3-ones and androstan-3-ones
US5120847A (en) †	1990-08-27	1992-06-09	Merck & Co., Inc.	Process for iodinating or brominating the α-methylenic carbon of a secondary amide
US5091534A (en)	1990-08-27	1992-02-25	Merck & Co., Inc.	Trialkylsilyl trifluoromethanesulfonate mediated α-methylenic carbon functionalization of 4-AZA-5α-androstan-3-one steroids
CA2050824A1 (fr) *	1990-09-24	1992-03-25	John M. Williams	Methode de preparation de 3-oxo-4-azaandrost-1-en-17.beta.-ones
US5061801A (en) *	1990-09-24	1991-10-29	Merck & Co., Inc.	Intermediate for making 3-oxo-4-aza-androst-1-ene 17β-ketones
US5468860A (en) *	1992-11-19	1995-11-21	Merck & Co., Inc.	New finasteride processes

1993
- 1993-01-29 US US08/010,734 patent/US5468860A/en not_active Expired - Fee Related
- 1993-11-05 UA UA95058438A patent/UA41341C2/uk unknown
- 1993-11-05 RO RO99-00785A patent/RO115165B1/ro unknown
- 1993-11-05 IS IS4286A patent/IS1692B/is unknown
- 1993-11-05 RU RU95112521A patent/RU2120445C1/ru active
- 1993-11-05 CZ CZ20003686A patent/CZ301191B6/cs not_active IP Right Cessation
- 1993-11-05 RO RO95-00940A patent/RO115164B1/ro unknown
- 1993-11-05 US US08/411,685 patent/US5652365A/en not_active Expired - Lifetime
- 1993-11-05 CZ CZ20003685A patent/CZ301160B6/cs not_active IP Right Cessation
- 1993-11-05 CZ CZ19951268A patent/CZ287842B6/cs not_active IP Right Cessation
- 1993-11-05 SK SK1897-2000A patent/SK286488B6/sk not_active IP Right Cessation
- 1993-11-05 WO PCT/US1993/010659 patent/WO1994011387A2/fr not_active Ceased
- 1993-11-05 SK SK659-95A patent/SK281765B6/sk unknown
- 1993-11-11 MY MYPI93002365A patent/MY110410A/en unknown
- 1993-11-11 TW TW082109464A patent/TW257766B/zh not_active IP Right Cessation
- 1993-11-11 MY MYPI96001019A patent/MY110411A/en unknown
- 1993-11-11 IL IL10757493A patent/IL107574A/xx not_active IP Right Cessation
- 1993-11-12 DE DE69323754T patent/DE69323754T2/de not_active Expired - Fee Related
- 1993-11-12 AT AT95200270T patent/ATE177112T1/de not_active IP Right Cessation
- 1993-11-12 AT AT93203163T patent/ATE164850T1/de active
- 1993-11-12 EP EP97201712A patent/EP0823436A3/fr not_active Withdrawn
- 1993-11-12 DE DE0599376T patent/DE599376T1/de active Pending
- 1993-11-12 ES ES93203163T patent/ES2052476T5/es not_active Expired - Lifetime
- 1993-11-12 DE DE69317856T patent/DE69317856T2/de not_active Expired - Lifetime
- 1993-11-12 EP EP93203163A patent/EP0599376B2/fr not_active Expired - Lifetime
- 1993-11-12 DE DE0655458T patent/DE655458T1/de active Pending
- 1993-11-12 EP EP95200270A patent/EP0655458B1/fr not_active Expired - Lifetime
- 1993-11-12 ES ES95200270T patent/ES2072848T3/es not_active Expired - Lifetime
- 1993-11-12 DK DK95200270T patent/DK0655458T3/da active
- 1993-11-12 DK DK93203163T patent/DK0599376T4/da active
- 1993-11-15 CA CA2103107A patent/CA2103107C/fr not_active Expired - Lifetime
- 1993-11-16 IS IS4094A patent/IS1671B/is unknown
- 1993-11-17 DZ DZ930120A patent/DZ1733A1/fr active
- 1993-11-18 JP JP5289536A patent/JPH07110875B2/ja not_active Expired - Fee Related
- 1993-11-18 AU AU50787/93A patent/AU658774B2/en not_active Expired
- 1993-11-18 MX MX9307222A patent/MX9307222A/es not_active IP Right Cessation
- 1993-11-18 HR HR931410A patent/HRP931410B1/xx not_active IP Right Cessation
- 1993-11-18 HU HU9303275A patent/HU216195B/hu unknown
- 1993-11-19 CN CN93114530A patent/CN1058018C/zh not_active Expired - Lifetime
- 1993-11-19 SI SI9300603A patent/SI9300603B/sl unknown
- 1993-11-19 PH PH47298A patent/PH31120A/en unknown
1994
- 1994-07-29 GR GR940300045T patent/GR940300045T1/el unknown
- 1994-11-07 HU HU94P/P00041P patent/HU210535A9/hu unknown
1995
- 1995-05-16 BG BG99637A patent/BG62362B1/bg unknown
- 1995-05-18 FI FI952422A patent/FI107450B/fi not_active IP Right Cessation
- 1995-05-19 NO NO951986A patent/NO305912B1/no not_active IP Right Cessation
- 1995-07-31 GR GR950300043T patent/GR950300043T1/el unknown
1996
- 1996-09-30 JP JP8259373A patent/JP2742409B2/ja not_active Expired - Lifetime
1997
- 1997-03-26 US US08/824,426 patent/US5886184A/en not_active Expired - Lifetime
1998
- 1998-04-09 GR GR980400749T patent/GR3026577T3/el unknown
- 1998-10-26 LV LVP-98-236A patent/LV12212B/en unknown
1999
- 1999-02-01 NO NO19990468A patent/NO307888B3/no not_active IP Right Cessation
- 1999-02-11 BG BG103170A patent/BG64464B1/bg unknown
- 1999-03-04 GR GR990400546T patent/GR3029554T3/el unknown
- 1999-05-28 NO NO992580A patent/NO307609B1/no not_active IP Right Cessation
- 1999-09-07 CY CY9900028A patent/CY2135B1/xx unknown
2000
- 2000-02-23 LV LVP-00-26A patent/LV12460B/en unknown
- 2000-05-12 HR HR20000295A patent/HRP20000295B1/xx not_active IP Right Cessation
2001
- 2001-02-15 FI FI20010290A patent/FI114215B/fi not_active IP Right Cessation
- 2001-02-15 FI FI20010289A patent/FI114800B/fi not_active IP Right Cessation
2004
- 2004-04-21 FI FI20040559A patent/FI116941B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
PH31120A (en)	1998-02-23
RU2120445C1 (ru)	1998-10-20
EP0599376B1 (fr)	1998-04-08
BG64464B1 (bg)	2005-03-31
DE69317856D1 (de)	1998-05-14
IS4094A (is)	1994-05-20
DZ1733A1 (fr)	2002-02-17
EP0823436A2 (fr)	1998-02-11
BG103170A (en)	1999-09-30
NO307609B1 (no)	2000-05-02
SI9300603B (sl)	2004-06-30
NO305912B1 (no)	1999-08-16
NO951986D0 (no)	1995-05-19
SK281765B6 (sk)	2001-07-10
ES2052476T3 (es)	1998-06-16
LV12212A (lv)	1999-01-20
AU5078793A (en)	1994-06-16
NO992580L (no)	1995-05-19
IS1692B (is)	1998-04-20
JPH06199889A (ja)	1994-07-19
US5652365A (en)	1997-07-29
HUT66973A (en)	1995-01-30
HU216195B (hu)	1999-05-28
DE655458T1 (de)	1995-11-30
NO307888B1 (no)	2000-06-13
NO307888B3 (no)	2000-06-13
EP0599376A2 (fr)	1994-06-01
UA41341C2 (uk)	2001-09-17
WO1994011387A3 (fr)	1994-09-29
GR3026577T3 (en)	1998-07-31
US5468860A (en)	1995-11-21
RU95112521A (ru)	1997-02-10
FI107450B (fi)	2001-08-15
FI952422A0 (fi)	1995-05-18
BG99637A (bg)	1996-04-30
DK0599376T4 (da)	2008-07-28
CY2135B1 (en)	2002-05-21
DE69317856T2 (de)	1998-11-05
HRP931410A2 (en)	1996-06-30
EP0599376A3 (en)	1994-09-28
CN1058018C (zh)	2000-11-01
FI20010290L (fi)	2001-02-15
EP0599376B2 (fr)	2008-04-16
FI114800B (fi)	2004-12-31
FI116941B (fi)	2006-04-13
NO951986L (no)	1995-05-19
MY110410A (en)	1998-05-30
CZ301160B6 (cs)	2009-11-18
NO992580D0 (no)	1999-05-28
ES2052476T5 (es)	2008-11-01
JPH07110875B2 (ja)	1995-11-29
HRP931410B1 (en)	2000-06-30
WO1994011387A2 (fr)	1994-05-26
HK1008338A1 (en)	1999-05-07
BG62362B1 (bg)	1999-09-30
HRP20000295B1 (en)	2002-08-31
HRP20000295A2 (en)	2000-08-31
AU658774B2 (en)	1995-04-27
IL107574A0 (en)	1994-02-27
EP0655458A3 (fr)	1996-07-10
EP0823436A3 (fr)	1998-11-25
RO115164B1 (ro)	1999-11-30
HU210535A9 (en)	1995-04-28
MY110411A (en)	1998-05-30
SK65995A3 (en)	1995-10-11
DK0655458T3 (da)	1999-09-27
DE69323754T2 (de)	1999-10-07
IS4286A (is)	1994-05-20
GR950300043T1 (en)	1995-07-31
GR3029554T3 (en)	1999-06-30
ATE164850T1 (de)	1998-04-15
DE69323754D1 (de)	1999-04-08
CN1090583A (zh)	1994-08-10
IS1671B (is)	1997-12-19
ES2072848T3 (es)	1999-05-01
FI952422L (fi)	1995-05-18
EP0655458A2 (fr)	1995-05-31
CA2103107C (fr)	2010-09-28
FI114215B (fi)	2004-09-15
US5886184A (en)	1999-03-23
LV12460A (lv)	2000-04-20
NO990468D0 (no)	1999-02-01
SK286488B6 (sk)	2008-11-06
MX9307222A (es)	1994-07-29
JPH09235294A (ja)	1997-09-09
ES2052476T1 (es)	1994-07-16
RO115165B1 (ro)	1999-11-30
IL107574A (en)	2000-07-16
FI20040559A7 (fi)	2004-04-21
JP2742409B2 (ja)	1998-04-22
ATE177112T1 (de)	1999-03-15
TW257766B (fr)	1995-09-21
FI20010289L (fi)	2001-02-15
HU9303275D0 (en)	1994-03-28
EP0655458B1 (fr)	1999-03-03
CZ287842B6 (en)	2001-02-14
NO990468L (no)	1995-05-19
GR940300045T1 (en)	1994-07-29
SI9300603A (en)	1994-06-30
LV12460B (en)	2000-09-20
CZ301191B6 (cs)	2009-12-02
CA2103107A1 (fr)	1994-05-20
CZ126895A3 (en)	1995-12-13
DE599376T1 (de)	1994-12-08
ES2072848T1 (es)	1995-08-01

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