LV10452B - A process for the preparation of (1h-azolo-1-ylmethyl)-substituted derivatives of benzotriazoles - Google Patents

A process for the preparation of (1h-azolo-1-ylmethyl)-substituted derivatives of benzotriazoles Download PDF

Info

Publication number: LV10452B
Authority: LV; Latvia
Prior art keywords: formula; compound; alkyl; cmecb; npn
Prior art date: 1987-06-01

Application number

LVP-92-233A

Other languages

English (en)

Latvian (lv)

Other versions

LV10452A (lv

Inventor

Alfons H M Raeymaekers

Eddy J E Freyne

Gelder Josephus L H Van

Marc G Venet

Original Assignee

Janssen Pharmaceutica Nv

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.)

1987-06-01

Filing date

1992-11-27

Publication date

1995-08-20

1992-11-27 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1995-02-20 Publication of LV10452A publication Critical patent/LV10452A/xx

1995-08-20 Publication of LV10452B publication Critical patent/LV10452B/lv

Links

238000000034 method Methods 0.000 title claims 4
150000001565 benzotriazoles Chemical class 0.000 title claims 2
238000002360 preparation method Methods 0.000 title claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 4
-1 (1H-Azol-1-ylmethyl)-substituted benztriazole Chemical class 0.000 claims 22
150000001875 compounds Chemical class 0.000 claims 14
238000006243 chemical reaction Methods 0.000 claims 10
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
125000003545 alkoxy group Chemical group 0.000 claims 6
125000000217 alkyl group Chemical group 0.000 claims 6
229910052739 hydrogen Inorganic materials 0.000 claims 6
239000001257 hydrogen Substances 0.000 claims 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
239000002253 acid Substances 0.000 claims 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 4
239000012964 benzotriazole Substances 0.000 claims 4
239000003153 chemical reaction reagent Substances 0.000 claims 4
238000000746 purification Methods 0.000 claims 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
229910052736 halogen Inorganic materials 0.000 claims 3
150000002367 halogens Chemical group 0.000 claims 3
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
150000001450 anions Chemical class 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
239000012429 reaction media Substances 0.000 claims 2
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
238000007126 N-alkylation reaction Methods 0.000 claims 1
238000010934 O-alkylation reaction Methods 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
125000005133 alkynyloxy group Chemical group 0.000 claims 1
239000002585 base Substances 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
238000006477 desulfuration reaction Methods 0.000 claims 1
230000023556 desulfurization Effects 0.000 claims 1
150000004985 diamines Chemical class 0.000 claims 1
229940069417 doxy Drugs 0.000 claims 1
HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
239000000203 mixture Substances 0.000 description 22
241001669680 Dormitator maculatus Species 0.000 description 8
229910017604 nitric acid Inorganic materials 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
101100366940 Mus musculus Stom gene Proteins 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
231100001143 noxa Toxicity 0.000 description 3
101100384273 Dictyostelium discoideum clua gene Proteins 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
240000007124 Brassica oleracea Species 0.000 description 1
241001415830 Bubo Species 0.000 description 1
235000002566 Capsicum Nutrition 0.000 description 1
241000025995 Chone Species 0.000 description 1
101100440640 Drosophila melanogaster conu gene Proteins 0.000 description 1
206010019909 Hernia Diseases 0.000 description 1
241001114813 Macna Species 0.000 description 1
101150096418 Mepe gene Proteins 0.000 description 1
101100066898 Mus musculus Flna gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
MMPOTNFPDMJTRR-UHFFFAOYSA-N OOOOOOOOOOO Chemical compound OOOOOOOOOOO MMPOTNFPDMJTRR-UHFFFAOYSA-N 0.000 description 1
UIQWBVPFHHQZHH-UHFFFAOYSA-N OOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOO UIQWBVPFHHQZHH-UHFFFAOYSA-N 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
101100009643 Papaver somniferum CODM gene Proteins 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
239000006002 Pepper Substances 0.000 description 1
241001442654 Percnon planissimum Species 0.000 description 1
235000016761 Piper aduncum Nutrition 0.000 description 1
235000017804 Piper guineense Nutrition 0.000 description 1
244000203593 Piper nigrum Species 0.000 description 1
235000008184 Piper nigrum Nutrition 0.000 description 1
101150095510 TMEM35A gene Proteins 0.000 description 1
PEJHHXHHNGORMP-UHFFFAOYSA-M Umeclidinium bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 PEJHHXHHNGORMP-UHFFFAOYSA-M 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
208000016335 bubo Diseases 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1

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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

LVP-92-233A 1987-06-01 1992-11-27 A process for the preparation of (1h-azolo-1-ylmethyl)-substituted derivatives of benzotriazoles LV10452B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US5602187A	1987-06-01	1987-06-01

Publications (2)

Publication Number	Publication Date
LV10452A LV10452A (lv)	1995-02-20
LV10452B true LV10452B (en)	1995-08-20

Family

ID=22001654

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-92-233A LV10452B (en)	1987-06-01	1992-11-27	A process for the preparation of (1h-azolo-1-ylmethyl)-substituted derivatives of benzotriazoles

Country Status (24)

Country	Link
EP (1)	EP0293978B1 (da)
JP (1)	JPH0662612B2 (da)
KR (1)	KR970000952B1 (da)
CN (1)	CN1022184C (da)
AU (1)	AU603446B2 (da)
BG (2)	BG50278A3 (da)
CA (1)	CA1307271C (da)
CY (1)	CY1866A (da)
DE (1)	DE3884055T2 (da)
DK (1)	DK175218B1 (da)
ES (1)	ES2059490T3 (da)
FI (1)	FI90078C (da)
HK (1)	HK114795A (da)
HU (2)	HU201056B (da)
IE (1)	IE61823B1 (da)
IL (1)	IL86551A (da)
LT (1)	LT3950B (da)
LV (1)	LV10452B (da)
NO (1)	NO169900C (da)
NZ (1)	NZ224714A (da)
PT (1)	PT87623B (da)
RU (1)	RU1838308C (da)
UA (1)	UA11192A (da)
ZA (1)	ZA883861B (da)

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CA2002859C (en) *	1988-11-29	1998-12-29	Jean P. F. Van Wauwe	Method of treating epithelial disorders
US5157046A (en) *	1988-11-29	1992-10-20	Janssen Pharmaceutica N.V.	Method of treating epithelial disorders
GB8827820D0 (en) *	1988-11-29	1988-12-29	Janssen Pharmaceutica Nv	(1h-azol-1-ylmethyl)substituted quinoline derivatives
EP0408509B1 (de) *	1989-07-14	1996-03-06	Ciba-Geigy Ag	Substituierte Benzonitrile
US5066656A (en) *	1989-11-01	1991-11-19	Janssen Pharmaceutica N.V.	Pharmacologically active (6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1H-benzotriazole derivatives
CA2026792A1 (en) *	1989-11-01	1991-05-02	Michael N. Greco	(6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives
NZ236440A (en) *	1989-12-15	1993-07-27	Merck & Co Inc	Reversal of sexual phenotype in poultry using an inhibitor of steroid biotransformation and/or aromatase inhibitor, poultry produced by this process
AU7124691A (en) *	1990-02-27	1991-08-29	Ciba-Geigy Ag	Benzofurans
DE4010797A1 (de) *	1990-04-04	1991-10-10	Hoechst Ag	Substituierte azole, verfahren zu deren herstellung, diese enthaltende mittel und deren verwendung
EP0457716A1 (de) *	1990-04-20	1991-11-21	Ciba-Geigy Ag	Naphthalinderivate
TW224461B (da) *	1990-09-18	1994-06-01	Ciba Geigy Ag
US5162337A (en) *	1990-10-05	1992-11-10	Merck & Co., Inc.	Animal growth promotion
TW210334B (da) *	1990-12-12	1993-08-01	Ciba Geigy Ag
CH683151A5 (de) *	1991-04-24	1994-01-31	Ciba Geigy Ag	Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus.
FI940988L (fi) *	1991-09-02	1994-04-05	Yamanouchi Pharma Co Ltd	Triatsolyloitu tertiäärinen amiiniyhdiste ja sen suola
US5635521A (en) *	1991-09-23	1997-06-03	Sandoz Ltd.	Imidazolylmethyl-pyridines
JP2700595B2 (ja) *	1992-05-21	1998-01-21	呉羽化学工業株式会社	アゾール誘導体を含有する抗アロマターゼ剤
PL176059B1 (pl) *	1992-11-10	1999-03-31	Janssen Pharmaceutica Nv	Sposób wytwarzania enancjomerycznie czystego 6-[(4-chlorofenylo) (1H-1,2,4-triazol-1-ilo)-metylo]-1-metylo-1H-benzotriazolu
AU682947B2 (en) *	1994-05-27	1997-10-23	Mochida Pharmaceutical Co., Ltd.	Novel azolyl methyl phenyl derivatives having aromatase inhibitory activity
AU6821196A (en) *	1995-08-14	1997-03-12	Janssen Pharmaceutica N.V.	Transdermal administration of vorozole
IT1286866B1 (it) *	1996-10-28	1998-07-17	Menarini Farma Ind	Composti furano-eterociclici,loro preparazione ed uso come inibitori di aromatasi
WO1998028257A1 (en) *	1996-12-24	1998-07-02	Chugai Seiyaku Kabushiki Kaisha	Aromatic amine derivatives having nos inhibitory effect
WO2002000648A1 (en) *	2000-06-28	2002-01-03	Ssp Co., Ltd.	Imidazole derivatives or salts thereof and drugs containing the derivatives or the salts
US7521447B2 (en) *	2003-03-03	2009-04-21	Array Biopharma Inc.	P38 inhibitors and methods of use thereof
US7135575B2 (en)	2003-03-03	2006-11-14	Array Biopharma, Inc.	P38 inhibitors and methods of use thereof
MX2007008781A (es)	2005-01-21	2007-09-11	Astex Therapeutics Ltd	Compuestos farmaceuticos.
KR20080000584A (ko) *	2005-04-29	2008-01-02	얀센 파마슈티카 엔.브이.	카나비노이드 수용체 길항제로서의 벤조트리아졸 유도체
US7572807B2 (en)	2005-06-09	2009-08-11	Bristol-Myers Squibb Company	Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors
WO2007031833A2 (en)	2005-09-15	2007-03-22	Council Of Scientific And Industrial Research	Novel series of imidazolyl substituted steroidal and indan-1-one derivatives
RS52298B (sr)	2006-01-31	2012-12-31	Array Biopharma Inc.	Inhibitori kinaze i postupak njihove upotrebe
WO2008044041A1 (en)	2006-10-12	2008-04-17	Astex Therapeutics Limited	Pharmaceutical combinations
EP2073807A1 (en)	2006-10-12	2009-07-01	Astex Therapeutics Limited	Pharmaceutical combinations
US9394290B2 (en) *	2010-10-21	2016-07-19	Universitaet Des Saarlandes Campus Saarbruecken	Selective CYP11B1 inhibitors for the treatment of cortisol dependent diseases

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GR75101B (da) *	1980-10-23	1984-07-13	Pfizer
EP0165781A1 (en) *	1984-06-18	1985-12-27	Eli Lilly And Company	Aromatase inhibiting N-substituted imidazole derivatives
US4609666A (en) *	1984-06-18	1986-09-02	Eli Lilly And Company	Aromatase inhibiting derivatives of α,α-bis(4-halophenyl)methyltetrazoles and triazoles
US4602025A (en) *	1984-06-18	1986-07-22	Eli Lilly And Company	Aromatase inhibitors
US4659730A (en) *	1984-06-18	1987-04-21	Eli Lilly And Company	Aromatase inhibiting imidazole derivatives
US4801594A (en) *	1984-06-18	1989-01-31	Eli Lilly And Company	Aromatase inhibitors
DE3744589C1 (de)	1987-12-31	1988-12-29	Albrecht Josef Bohrfutter	Nachspannendes Bohrfutter

1988
- 1988-05-19 NZ NZ224714A patent/NZ224714A/xx unknown
- 1988-05-20 UA UA4355784A patent/UA11192A/uk unknown
- 1988-05-20 RU SU884355784A patent/RU1838308C/ru active
- 1988-05-23 AU AU16537/88A patent/AU603446B2/en not_active Expired
- 1988-05-25 CA CA000567618A patent/CA1307271C/en not_active Expired - Lifetime
- 1988-05-26 EP EP88201061A patent/EP0293978B1/en not_active Expired - Lifetime
- 1988-05-26 ES ES88201061T patent/ES2059490T3/es not_active Expired - Lifetime
- 1988-05-26 DE DE88201061T patent/DE3884055T2/de not_active Expired - Lifetime
- 1988-05-26 CY CY186688A patent/CY1866A/xx unknown
- 1988-05-30 IL IL86551A patent/IL86551A/xx not_active IP Right Cessation
- 1988-05-30 ZA ZA883861A patent/ZA883861B/xx unknown
- 1988-05-31 BG BG084328A patent/BG50278A3/xx unknown
- 1988-05-31 FI FI882552A patent/FI90078C/fi not_active IP Right Cessation
- 1988-05-31 PT PT87623A patent/PT87623B/pt not_active IP Right Cessation
- 1988-05-31 DK DK198802952A patent/DK175218B1/da not_active IP Right Cessation
- 1988-05-31 NO NO882390A patent/NO169900C/no not_active IP Right Cessation
- 1988-05-31 IE IE164088A patent/IE61823B1/en not_active IP Right Cessation
- 1988-06-01 CN CN88103408A patent/CN1022184C/zh not_active Expired - Lifetime
- 1988-06-01 HU HU882783A patent/HU201056B/hu unknown
- 1988-06-01 JP JP63132886A patent/JPH0662612B2/ja not_active Expired - Lifetime
- 1988-06-01 KR KR1019880006557A patent/KR970000952B1/ko not_active Expired - Lifetime
1992
- 1992-11-27 LV LVP-92-233A patent/LV10452B/lv unknown
1993
- 1993-10-18 BG BG098159A patent/BG60429B2/bg unknown
- 1993-12-16 LT LTIP1625A patent/LT3950B/lt not_active IP Right Cessation
1995
- 1995-06-29 HU HU95P/P00533P patent/HU211482A9/hu unknown
- 1995-07-13 HK HK114795A patent/HK114795A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU1653788A (en)	1988-12-01
EP0293978A3 (en)	1990-06-13
JPS63316775A (ja)	1988-12-26
DK295288D0 (da)	1988-05-31
IL86551A0 (en)	1988-11-15
ES2059490T3 (es)	1994-11-16
DE3884055D1 (de)	1993-10-21
LTIP1625A (en)	1995-07-25
LT3950B (en)	1996-05-27
EP0293978A2 (en)	1988-12-07
NO882390L (no)	1988-12-02
FI882552A0 (fi)	1988-05-31
CY1866A (en)	1988-05-26
HU211482A9 (en)	1995-11-28
UA11192A (uk)	1996-12-25
NO169900B (no)	1992-05-11
BG60429B2 (bg)	1995-03-31
NZ224714A (en)	1990-03-27
RU1838308C (ru)	1993-08-30
HU201056B (en)	1990-09-28
JPH0662612B2 (ja)	1994-08-17
PT87623A (pt)	1988-06-01
DE3884055T2 (de)	1994-01-27
FI90078C (fi)	1993-12-27
IL86551A (en)	1992-07-15
ZA883861B (en)	1990-01-31
NO882390D0 (no)	1988-05-31
NO169900C (no)	1992-08-19
KR970000952B1 (ko)	1997-01-21
LV10452A (lv)	1995-02-20
HK114795A (en)	1995-07-21
CN1022184C (zh)	1993-09-22
PT87623B (pt)	1992-09-30
BG50278A3 (bg)	1992-06-15
FI882552A7 (fi)	1988-12-02
AU603446B2 (en)	1990-11-15
DK175218B1 (da)	2004-07-12
IE881640L (en)	1988-12-01
IE61823B1 (en)	1994-11-30
HUT49132A (en)	1989-08-28
FI90078B (fi)	1993-09-15
CA1307271C (en)	1992-09-08
EP0293978B1 (en)	1993-09-15
KR890000469A (ko)	1989-03-14
CN88103408A (zh)	1988-12-14
DK295288A (da)	1988-12-02

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