LT3769B - Heterocyclic compounds - Google Patents

Heterocyclic compounds Download PDF

Info

Publication number
LT3769B
LT3769B LTIP1233A LTIP1233A LT3769B LT 3769 B LT3769 B LT 3769B LT IP1233 A LTIP1233 A LT IP1233A LT IP1233 A LTIP1233 A LT IP1233A LT 3769 B LT3769 B LT 3769B
Authority
LT
Lithuania
Prior art keywords
phenyl
dihydropyridazin
dihydro
formula
compound
Prior art date
Application number
LTIP1233A
Other languages
English (en)
Lithuanian (lt)
Inventor
Heimo Olavi Haikala
Pentti Tapio Nore
Erkki Juhani Honkanen
Jarmo Johan Pystynen
Kari Kalevi Loennberg
Anne Maria Luiro
Aino Kyllikki Pippuri
Original Assignee
Orion Yhtymae Oy
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.)
Filing date
Publication date
Application filed by Orion Yhtymae Oy filed Critical Orion Yhtymae Oy
Publication of LTIP1233A publication Critical patent/LTIP1233A/xx
Publication of LT3769B publication Critical patent/LT3769B/lt

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Detergent Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Cephalosporin Compounds (AREA)
LTIP1233A 1989-02-11 1993-09-28 Heterocyclic compounds LT3769B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB898903130A GB8903130D0 (en) 1989-02-11 1989-02-11 Substituted pyridazinones

Publications (2)

Publication Number Publication Date
LTIP1233A LTIP1233A (en) 1995-04-25
LT3769B true LT3769B (en) 1996-03-25

Family

ID=10651554

Family Applications (1)

Application Number Title Priority Date Filing Date
LTIP1233A LT3769B (en) 1989-02-11 1993-09-28 Heterocyclic compounds

Country Status (24)

Country Link
US (2) US5019575A (sk)
EP (1) EP0383449B1 (sk)
JP (1) JP3011955B2 (sk)
CN (1) CN1036265C (sk)
AT (1) ATE127456T1 (sk)
AU (1) AU619648B2 (sk)
CA (1) CA2009678C (sk)
CZ (1) CZ286036B6 (sk)
DD (1) DD293112A5 (sk)
DE (1) DE69022078T2 (sk)
DK (1) DK0383449T3 (sk)
ES (1) ES2078939T3 (sk)
FI (1) FI96511C (sk)
GB (2) GB8903130D0 (sk)
GR (1) GR3017510T3 (sk)
HU (2) HU206692B (sk)
LT (1) LT3769B (sk)
LU (1) LU90921I2 (sk)
NO (2) NO178067C (sk)
NZ (1) NZ232257A (sk)
PT (1) PT93111B (sk)
RU (3) RU2048467C1 (sk)
SK (1) SK55790A3 (sk)
ZA (1) ZA90681B (sk)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8824458D0 (en) * 1988-10-19 1988-11-23 Orion Yhtymae Oy Substituted pyridazinones
IE62890B1 (en) * 1988-12-06 1995-03-08 Hafslund Nycomed Pharma New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure
GB8903130D0 (en) * 1989-02-11 1989-03-30 Orion Yhtymae Oy Substituted pyridazinones
GB2251615B (en) * 1991-01-03 1995-02-08 Orion Yhtymae Oy (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]pro panedinitrile
GB2266841A (en) * 1992-05-06 1993-11-17 Orion Yhtymae Oy Compounds for use as anti-ischemic medicaments
DE4239540A1 (de) * 1992-11-25 1994-05-26 Asta Medica Ag Neue heterocyclische Verbindungen mit antiasthmatischer/antiallergischer, entzündungshemmender, positiv inotroper und blutdrucksenkender Wirkung
TW309520B (sk) * 1994-04-26 1997-07-01 Mitsubishi Chem Corp
DE19514568A1 (de) 1995-04-20 1996-10-24 Merck Patent Gmbh Arylalkyl-pyridazinone
GB9606474D0 (en) * 1996-03-27 1996-06-05 Orion Yhytmo Oy Method for obtaining pure enantiomers of a pyridazinone derivative
GB9626472D0 (en) 1996-12-20 1997-02-05 Aperia Anita C New use of comt inhibitors
FI973804A (fi) * 1997-09-26 1999-03-27 Orion Yhtymae Oy Levosimendaanin oraalisia koostumuksia
FI980901A (fi) * 1998-04-23 1999-10-24 Orion Yhtymae Oyj Levosimendaania säädellysti vapauttavia oraalisia koostumuksia
FI980902A (fi) 1998-04-23 1999-10-24 Orion Yhtymae Oyj Levosimendaanin stabiileja koostumuksia
FI105389B (fi) * 1998-04-23 2000-08-15 Orion Yhtymae Oyj Menetelmä levosimendaaniannon siedettävyyden seuraamiseksi
FI104718B (fi) * 1998-06-18 2000-03-31 Orion Yhtymae Oyj [[4-(2-atsido-3-metyyli-5-oksotetrahydrofuran-2-yyli)fenyyli]hydratsono]propaanidinitriili käytettäväksi referenssiaineena levosimendaanierien analyysissä
FI20000577A0 (fi) 2000-03-13 2000-03-13 Orion Yhtymae Oy Pyridatsinyylifenyylihydratsoneja
FI20002525A (fi) 2000-11-17 2002-05-18 Orion Yhtymae Oyj Tulehduksenvastaisia aineita
WO2002072099A1 (fr) * 2001-03-14 2002-09-19 Mitsubishi Pharma Corporation Agent therapeutique et / ou prophylactique pour la cardiopathie ischemique diabetique
WO2004087641A1 (ja) * 2003-03-31 2004-10-14 Daiichi Pharmaceutical Co., Ltd. ヒドラゾン誘導体
DE102004011512B4 (de) 2004-03-08 2022-01-13 Boehringer Ingelheim Vetmedica Gmbh Pharmazeutische Zubereitung enthaltend Pimobendan
EP1579862A1 (en) 2004-03-25 2005-09-28 Boehringer Ingelheim Vetmedica Gmbh Use of PDE III inhibitors for the reduction of heart size in mammals suffering from heart failure
US8980894B2 (en) 2004-03-25 2015-03-17 Boehringer Ingelheim Vetmedica Gmbh Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure
US20060293395A1 (en) * 2004-05-28 2006-12-28 Weil Max H Methods for treating a mammal before, during and after cardiac arrest
EP1951227B1 (en) 2005-11-14 2017-04-12 Boehringer Ingelheim Vetmedica GmbH Use of pimobendan for the treatment of asymptomatic (occult) heart failure
NZ574873A (en) 2006-07-25 2012-03-30 Cephalon Inc Pyridazinone derivatives as h3 inhibitors
EP1920785A1 (en) 2006-11-07 2008-05-14 Boehringer Ingelheim Vetmedica Gmbh Liquid preparation comprising a complex of pimobendan and cyclodextrin
FR2917975B1 (fr) 2007-06-26 2009-10-16 Ceva Sante Animale Sa Compositions et traitement de l'insuffisance cardiaque chez les animaux mammiferes non humains
CA2645772A1 (en) * 2007-12-05 2009-06-05 Tagawa Greenhouse Enterprises, Llc Collapsible support apparatus and methods
US8664252B2 (en) 2008-11-25 2014-03-04 Boehringer Ingelheim Vetmedica Gmbh Phosphodiesterase type III (PDE III) inhibitors or CA2+-sensitizing agents for the treatment of hypertrophic cardiomyopathy
EP2825159B1 (en) 2012-03-15 2022-06-22 Boehringer Ingelheim Vetmedica GmbH Pharmaceutical tablet formulation for the veterinary medical sector, method of production and use thereof
EA034395B1 (ru) * 2013-01-18 2020-02-04 Бристол-Майерс Сквибб Компани Фталазиноны и изохинолиноны в качестве ингибиторов rock
MX2016000727A (es) 2013-07-19 2016-04-13 Boehringer Ingelheim Vetmed Composicion farmaceutica acuosa liquida que contiene derivados de ciclodextrina eterificada con conservante.
HUE056143T2 (hu) 2013-12-04 2024-01-28 Boehringer Ingelheim Vetmedica Gmbh Pimobendán javított gyógyászati készítményei
US10537570B2 (en) 2016-04-06 2020-01-21 Boehringer Ingelheim Vetmedica Gmbh Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease
EP3424908A1 (en) 2017-07-07 2019-01-09 Melody Healthcare Pvt. Ltd. Process for preparation of levosimendan
KR102128509B1 (ko) * 2018-12-19 2020-07-01 한국과학기술연구원 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도
CN111548310B (zh) * 2020-05-12 2021-07-02 成都欣捷高新技术开发股份有限公司 一种左西孟旦钠晶型及其制备方法
US11760730B2 (en) 2021-01-11 2023-09-19 Navinta, Llc Process for the preparation of high purity Levosimendan

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0052442A1 (en) 1980-11-14 1982-05-26 Imperial Chemical Industries Plc Heterocyclic compounds
FI863564A (fi) 1985-09-05 1987-03-06 Boehringer Mannheim Gmbh Foerfarande foer framstaellning av heterocykliskt substituerade indoler.
US4656170A (en) 1985-05-28 1987-04-07 Warner-Lambert Company N-[4-[2-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)ethenyl]phenyl]acetamide and related compounds

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432507A (en) * 1963-12-04 1969-03-11 Upjohn Co Certain diazatricyclododecadienones and their preparation
US4353905A (en) * 1981-09-17 1982-10-12 Warner-Lambert Company Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones
US4495185A (en) * 1981-11-12 1985-01-22 Imperial Chemical Industries, Plc 1,2,4-Triazin-3(2H) ones
JPS58113180A (ja) * 1981-12-28 1983-07-05 Mitsui Toatsu Chem Inc ピリダジノン誘導体
US4581356A (en) * 1983-03-22 1986-04-08 Fujisawa Pharmaceutical Co., Ltd. Triazine derivatives, and pharmaceutical compositions comprising the same
GB8310435D0 (en) * 1983-04-18 1983-05-25 Fujisawa Pharmaceutical Co Triazine derivatives
JPS59196874A (ja) * 1983-04-22 1984-11-08 Fujisawa Pharmaceut Co Ltd トリアジン誘導体
US4599332A (en) * 1983-12-07 1986-07-08 Warner-Lambert Company 4,5-dihydro-6-[2-[4-(1H-imidazol-1-yl)phenyl]-ethenyl]-3(2H)-pyridazinones and related compounds
JPS61158969A (ja) * 1984-12-24 1986-07-18 ワーナー‐ランバート・コンパニー ４，５‐ジヒドロ‐４，４‐ジアルキル‐６‐（置換）フエニル‐３（２ｈ）‐ピリダジノン類
US4946842A (en) * 1985-07-05 1990-08-07 Smith Kline & French Laboratories Limited Novel guanidino pyridazinones as cardiac stimulants
GB8603780D0 (en) * 1986-02-15 1986-03-19 Smith Kline French Lab Chemical compounds
US4898862A (en) * 1986-03-20 1990-02-06 Sankyo Company Limited 1,2,4-triazinone derivatives, their preparation and use
IT1208003B (it) * 1987-01-08 1989-06-01 Isf Spa Procedimento per preparare derivati alcossi alchiliden, idrazino, piridazinici.
DE3706427A1 (de) * 1987-02-27 1988-09-08 Boehringer Mannheim Gmbh Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel
DE3728491A1 (de) * 1987-08-26 1989-03-09 Heumann Pharma Gmbh & Co Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JP2717687B2 (ja) * 1988-02-13 1998-02-18 日本曹達株式会社 ピリダジノン誘導体及びその製造方法
GB8903130D0 (en) * 1989-02-11 1989-03-30 Orion Yhtymae Oy Substituted pyridazinones

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0052442A1 (en) 1980-11-14 1982-05-26 Imperial Chemical Industries Plc Heterocyclic compounds
US4656170A (en) 1985-05-28 1987-04-07 Warner-Lambert Company N-[4-[2-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)ethenyl]phenyl]acetamide and related compounds
FI863564A (fi) 1985-09-05 1987-03-06 Boehringer Mannheim Gmbh Foerfarande foer framstaellning av heterocykliskt substituerade indoler.
EP0223937A1 (de) 1985-09-05 1987-06-03 Roche Diagnostics GmbH Heterocyclisch substituierte Indole, Zwischenprodukte, Verfahren zu ihrer Herstellung und Arzneimittel

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
A. A. ALOUSI, D. C. JOHNSON.: "Pharmacology of the bipyridines: amrinone and milrinone.", CIRCULATION, 1986, pages 10 - 23
ARJA ALAJOUTSIJÄRVI, ERKKI NISSINEN: "Determination of cyclic nucleotide phosphodiesterase activity by high-performance liquid chromatography", ANALYTICAL BIOCHEMISTRY, 1987, pages 128 - 132, XP024830053, DOI: doi:10.1016/0003-2697(87)90209-0
GÜNTER EGE ET AL.: "Fünfringheterocyclen, IV. Ringverengung von 5-Aryl-6H-1,3,4-thiadiazin-2(3H)-onen zu 4-Aryl-1,2,3,-thiadiazolen", JUSTUS LIEBIGS ANNALEN DER CHEMIE, 1977, pages 791 - 799
R. F. HUDSON, P. A. CHOPARD: "The Preparation of Chloromethyl Vinyl Ketones", J. ORG. CHEM., 1963, pages 2446 - 2447
WILLIAM V. CURRAN, ADMA ROSS: "6-Phenyl-4,5-dihydro-3(2H)-pyridazinones. Series of hypotensive agents", J. MED. CHEM., 1974, pages 273 - 281, XP055252332, DOI: doi:10.1021/jm00249a004

Also Published As

Publication number Publication date
AU619648B2 (en) 1992-01-30
NO2001020I1 (no) 2001-12-03
DE69022078T2 (de) 1996-02-22
HU204797B (en) 1992-02-28
JP3011955B2 (ja) 2000-02-21
EP0383449A2 (en) 1990-08-22
ES2078939T3 (es) 1996-01-01
RU2048467C1 (ru) 1995-11-20
ZA90681B (en) 1990-10-31
SK280411B6 (sk) 2000-02-14
RU1836362C (ru) 1993-08-23
ATE127456T1 (de) 1995-09-15
HUT53090A (en) 1990-09-28
JPH02288868A (ja) 1990-11-28
HU913501D0 (en) 1992-02-28
NO178067C (no) 1996-01-17
CZ55790A3 (cs) 1999-10-13
NO178067B (no) 1995-10-09
US5019575A (en) 1991-05-28
LU90921I2 (en) 2002-07-17
HUT59384A (en) 1992-05-28
EP0383449A3 (en) 1991-07-03
SK55790A3 (en) 2000-02-14
CA2009678A1 (en) 1990-08-11
GB2228004B (en) 1992-07-15
GB8903130D0 (en) 1989-03-30
DK0383449T3 (da) 1996-01-02
GR3017510T3 (en) 1995-12-31
EP0383449B1 (en) 1995-09-06
AU4929690A (en) 1990-08-16
PT93111B (pt) 1996-01-31
FI96511B (fi) 1996-03-29
HU206692B (en) 1992-12-28
GB9001853D0 (en) 1990-03-28
DD293112A5 (de) 1991-08-22
CZ286036B6 (cs) 1999-12-15
GB2228004A (en) 1990-08-15
NZ232257A (en) 1991-03-26
RU2068844C1 (ru) 1996-11-10
CN1044811A (zh) 1990-08-22
CN1036265C (zh) 1997-10-29
HU900747D0 (en) 1990-04-28
CA2009678C (en) 1998-08-11
NO900336D0 (no) 1990-01-24
FI96511C (fi) 1996-07-10
PT93111A (pt) 1990-08-31
LTIP1233A (en) 1995-04-25
FI900613A0 (fi) 1990-02-08
US5122524A (en) 1992-06-16
NO900336L (no) 1990-08-13
DE69022078D1 (de) 1995-10-12

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