FR2698873B1 - Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant. - Google Patents

Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant.

Info

Publication number
FR2698873B1
FR2698873B1 FR9214720A FR9214720A FR2698873B1 FR 2698873 B1 FR2698873 B1 FR 2698873B1 FR 9214720 A FR9214720 A FR 9214720A FR 9214720 A FR9214720 A FR 9214720A FR 2698873 B1 FR2698873 B1 FR 2698873B1
Authority
FR
France
Prior art keywords
pct
group
activators
potassium channels
benzothiepins
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
FR9214720A
Other languages
English (en)
Other versions
FR2698873A1 (fr
Inventor
Jean-Jacques Berthelon
Marc Brunet Michelnoblet
Philippe Durbin
Daniel Guerrier
Nghia Luong Trong
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sante SAS
Original Assignee
LIPHA SAS
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 LIPHA SAS filed Critical LIPHA SAS
Priority to FR9214720A priority Critical patent/FR2698873B1/fr
Priority to SI9300632A priority patent/SI9300632A/sl
Priority to LTIP1525A priority patent/LT3167B/lt
Priority to ZA939127A priority patent/ZA939127B/xx
Priority to IL10789193A priority patent/IL107891A0/xx
Priority to CN93120135A priority patent/CN1050127C/zh
Priority to US08/284,454 priority patent/US5602152A/en
Priority to PL93304719A priority patent/PL174246B1/pl
Priority to SK939-94A priority patent/SK93994A3/sk
Priority to CA002129642A priority patent/CA2129642A1/fr
Priority to DK94902708T priority patent/DK0626954T3/da
Priority to TW082110417A priority patent/TW276255B/zh
Priority to CZ941848A priority patent/CZ184894A3/cs
Priority to JP6513771A priority patent/JPH07503977A/ja
Priority to AT94902708T priority patent/ATE177742T1/de
Priority to PCT/EP1993/003445 priority patent/WO1994013658A2/fr
Priority to KR1019940702708A priority patent/KR100236810B1/ko
Priority to EP94902708A priority patent/EP0626954B1/fr
Priority to RU94040853A priority patent/RU2127268C1/ru
Priority to RO94-01321A priority patent/RO113040B1/ro
Priority to AU56975/94A priority patent/AU680856B2/en
Priority to DE69324001T priority patent/DE69324001T2/de
Priority to NZ258896A priority patent/NZ258896A/en
Priority to ES94902708T priority patent/ES2132373T3/es
Priority to HU9402302A priority patent/HUT67852A/hu
Publication of FR2698873A1 publication Critical patent/FR2698873A1/fr
Priority to LVP-94-154A priority patent/LV10451B/en
Priority to FI943646A priority patent/FI943646A/fi
Priority to NO942914A priority patent/NO942914L/no
Application granted granted Critical
Publication of FR2698873B1 publication Critical patent/FR2698873B1/fr
Priority to US08/460,866 priority patent/US5652252A/en
Priority to GR990401589T priority patent/GR3030514T3/el
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
FR9214720A 1992-07-12 1992-12-07 Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant. Expired - Fee Related FR2698873B1 (fr)

Priority Applications (30)

Application Number Priority Date Filing Date Title
FR9214720A FR2698873B1 (fr) 1992-12-07 1992-12-07 Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant.
SI9300632A SI9300632A (en) 1992-12-07 1993-12-03 Benzocycloheptenes, benzoxepines and benzothiepines
LTIP1525A LT3167B (en) 1992-12-07 1993-12-03 Benzocycloheptenes,benzoxepines and benzothiepines
IL10789193A IL107891A0 (en) 1992-12-07 1993-12-06 Benzocycloheptenes, benzoxepines and benzothiepines
CN93120135A CN1050127C (zh) 1992-12-07 1993-12-06 苯并环庚烯和苯并氧杂䓬其制备方法和含有它们的药物组合物
ZA939127A ZA939127B (en) 1992-12-07 1993-12-06 Benzocycloheptenes benzoxepines and benzothiepines
DE69324001T DE69324001T2 (de) 1992-12-07 1993-12-07 Benzocycloheptine, benzoxepine und benzothiepine
SK939-94A SK93994A3 (en) 1992-12-07 1993-12-07 Benzocycloheptenes, benzoxepines and benzothiepines and method their producing
CA002129642A CA2129642A1 (fr) 1992-12-07 1993-12-07 Benzocycloheptenes, benzoxepines et benzothiepines
DK94902708T DK0626954T3 (da) 1992-12-07 1993-12-07 Benzocycloheptener, benzoxepiner og benzothiepiner
TW082110417A TW276255B (fr) 1992-12-07 1993-12-07
CZ941848A CZ184894A3 (en) 1992-12-07 1993-12-07 Benzocycloheptenes, benzoxepines and benzothiepines and process for preparing thereof
JP6513771A JPH07503977A (ja) 1992-12-07 1993-12-07 ベンゾシクロヘプテン，ベンゾキセピンおよびベンゾチエピン
AT94902708T ATE177742T1 (de) 1992-12-07 1993-12-07 Benzocycloheptine, benzoxepine und benzothiepine
PCT/EP1993/003445 WO1994013658A2 (fr) 1992-12-07 1993-12-07 Benzocycloheptenes, benzoxepines et benzothiepines
KR1019940702708A KR100236810B1 (ko) 1992-12-07 1993-12-07 벤조사이클로헵텐
US08/284,454 US5602152A (en) 1992-12-07 1993-12-07 Benzoxepines
RU94040853A RU2127268C1 (ru) 1992-12-07 1993-12-07 Производные бензоциклогептена или бензоксепина, способ их получения, промежуточные соединения и фармацевтическая композиция
RO94-01321A RO113040B1 (ro) 1992-12-07 1993-12-07 Derivati heterociclici de benzocicloheptene, benzoxepine sau benzotiepine, procedeu pentru prepararea acestora, compusi intermediari si compozitie farmaceutica
AU56975/94A AU680856B2 (en) 1992-12-07 1993-12-07 Benzocycloheptenes, benzoxepines and benzothiepines
PL93304719A PL174246B1 (pl) 1992-12-07 1993-12-07 Nowe związki, pochodne benzocykloheptenu, benzoksepiny i benzotiepiny
NZ258896A NZ258896A (en) 1992-12-07 1993-12-07 Heterocyclic substituted benzoxepine and benzocycloheptene derivatives; pharmaceutical compositions thereof
ES94902708T ES2132373T3 (es) 1992-12-07 1993-12-07 Benzocicloheptenos, benzoxepinas y benzotiepinas.
HU9402302A HUT67852A (en) 1992-12-07 1993-12-07 New benzocycloheptenes, and benzoxepines, pharmaceutical compositions containing them and process for producing them
EP94902708A EP0626954B1 (fr) 1992-12-07 1993-12-07 Benzocycloheptenes, benzoxepines et benzothiepines
LVP-94-154A LV10451B (en) 1992-12-07 1994-08-05 Benzocycloheptenes, benzoxepines and benzothiepines and methods for preparation thereof
FI943646A FI943646A (fi) 1992-12-07 1994-08-05 Bentsosyklohepteenejä, bentsoksepiinejä bentsotiepiinejä
NO942914A NO942914L (no) 1992-12-07 1994-08-05 Benzosykloheptener, benzoksepiner og benzotiepiner
US08/460,866 US5652252A (en) 1992-07-12 1995-06-05 Benzocycloheptenes
GR990401589T GR3030514T3 (en) 1992-12-07 1999-06-15 Benzocycloheptenes, benzoxepines and benzothiepines.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9214720A FR2698873B1 (fr) 1992-12-07 1992-12-07 Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant.

Publications (2)

Publication Number Publication Date
FR2698873A1 FR2698873A1 (fr) 1994-06-10
FR2698873B1 true FR2698873B1 (fr) 1995-02-24

Family

ID=9436308

Family Applications (1)

Application Number Title Priority Date Filing Date
FR9214720A Expired - Fee Related FR2698873B1 (fr) 1992-07-12 1992-12-07 Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant.

Country Status (29)

Country Link
US (2) US5602152A (fr)
EP (1) EP0626954B1 (fr)
JP (1) JPH07503977A (fr)
KR (1) KR100236810B1 (fr)
CN (1) CN1050127C (fr)
AT (1) ATE177742T1 (fr)
AU (1) AU680856B2 (fr)
CA (1) CA2129642A1 (fr)
CZ (1) CZ184894A3 (fr)
DE (1) DE69324001T2 (fr)
DK (1) DK0626954T3 (fr)
ES (1) ES2132373T3 (fr)
FI (1) FI943646A (fr)
FR (1) FR2698873B1 (fr)
GR (1) GR3030514T3 (fr)
HU (1) HUT67852A (fr)
IL (1) IL107891A0 (fr)
LT (1) LT3167B (fr)
LV (1) LV10451B (fr)
NO (1) NO942914L (fr)
NZ (1) NZ258896A (fr)
PL (1) PL174246B1 (fr)
RO (1) RO113040B1 (fr)
RU (1) RU2127268C1 (fr)
SI (1) SI9300632A (fr)
SK (1) SK93994A3 (fr)
TW (1) TW276255B (fr)
WO (1) WO1994013658A2 (fr)
ZA (1) ZA939127B (fr)

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US6107494A (en) * 1994-09-13 2000-08-22 G.D. Searle And Company Substituted 5-aryl-benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US6642268B2 (en) 1994-09-13 2003-11-04 G.D. Searle & Co. Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors
US6262277B1 (en) 1994-09-13 2001-07-17 G.D. Searle And Company Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US6268392B1 (en) 1994-09-13 2001-07-31 G. D. Searle & Co. Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors
JP3304093B2 (ja) * 1994-09-13 2002-07-22 モンサント カンパニー 回腸の胆汁酸輸送及びタウロコール酸塩吸収の阻害活性を有する新規ベンゾチエピン類
US5952326A (en) * 1997-12-10 1999-09-14 Pfizer Inc. Tetralin and chroman derivatives useful in the treatment of asthma, arthritis and related diseases
US6221897B1 (en) 1998-06-10 2001-04-24 Aventis Pharma Deutschland Gmbh Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use
BR9916564A (pt) * 1998-12-23 2002-01-29 Searle Llc Combinações para indicações cardiovasculares
EP1340510A1 (fr) 1998-12-23 2003-09-03 G.D. Searle LLC. Combinaisons d'inhibiteurs de la protéine de transfert de l'ester de cholestéryle utilisées dans le cadre de troubles cardio-vasculaires
EA004231B1 (ru) * 1998-12-23 2004-02-26 Джи.Ди.Сирл Ллс Сочетание ингибиторов белка, переносящего эфир холестерила, и производных фибриновой кислоты для сердечно-сосудистых показаний
ES2189529T3 (es) * 1998-12-23 2003-07-01 Searle Llc Combinaciones de inhiidores para el transporte de acidos biliares en el ileon y agentes complejantes para indicaciones cardiovasculares.
HUP0201972A3 (en) * 1998-12-23 2005-06-28 G D Searle Llc Chicago Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein inhibitors for cardiovascular indications
BR9916565A (pt) * 1998-12-23 2002-01-29 Searle Llc Combinações de inibidores do transporte ácido da bile ileal e derivados do ácido fìbrico para indicações cardiovasculares
WO2000038722A1 (fr) 1998-12-23 2000-07-06 G.D. Searle & Co. COMBINAISONS D'INHIBITEURS DE LA PROTEINE DE TRANSFERT DE L'ESTER DE CHOLESTERYLE ET D'INHIBITEURS DE LA HMG CoA-REDUCTASE UTILISEES DANS LE CADRE DE TROUBLES CARDIO-VASCULAIRES
PT1140184E (pt) * 1998-12-23 2003-10-31 Searle Llc Combinacoes de inibidores de proteina de transferencia de ester de colesterilo com derivados de acido nicotinico para indicacoes cardiovasculares
AU2001240115A1 (en) 2000-03-10 2001-09-24 Pharmacia Corporation Method for the preparation of tetrahydrobenzothiepines
AU2001247331A1 (en) * 2000-03-10 2001-09-24 Pharmacia Corporation Combination therapy for the prophylaxis and treatment of hyperlipidemic conditions and disorders
US20040077625A1 (en) * 2001-07-25 2004-04-22 Tremont Samuel J. Novel 1,4-benzothiazepine and 1,5-benzothiazepine compounds as inhibitors of apical sodium codependent bile acid transport abd taurocholate uptake
WO2003040127A1 (fr) * 2001-11-02 2003-05-15 G.D. Searle Llc Composes benzothiepine mono- et di-fluores en tant qu'inhibiteurs du transport d'acides biliaires a co-dependance sodique apicale (asbt) et de reprise de taurocholate
CA2471639A1 (fr) 2002-01-17 2003-07-31 Pharmacia Corporation Nouveaux composes d'alkyl/aryl hydroxy ou cetothiepine servant d'inhibiteurs du transport des acides biliaires de type ileal et de l'absorption de taurocholate
BR112014010223B8 (pt) 2011-10-28 2021-02-23 Lumena Pharmaceuticals Llc uso de uma composição compreendendo inibidores de reciclagem de ácido de bílis e forma de dosagem pediátrica
WO2013152170A1 (fr) 2012-04-04 2013-10-10 Catylix, Inc. Modulateurs sélectifs de récepteur d'androgène

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JP3018386B2 (ja) * 1990-01-24 2000-03-13 吉富製薬株式会社 光学活性なベンゾチエピノピリダジン化合物の製造法

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FI943646A0 (fi) 1994-08-05
RO113040B1 (ro) 1998-03-30
AU5697594A (en) 1994-07-04
CN1050127C (zh) 2000-03-08
CN1097752A (zh) 1995-01-25
ES2132373T3 (es) 1999-08-16
NO942914L (no) 1994-08-05
PL304719A1 (en) 1995-01-09
CA2129642A1 (fr) 1994-06-23
RU2127268C1 (ru) 1999-03-10
LTIP1525A (en) 1994-07-15
NO942914D0 (fr) 1994-08-05
CZ184894A3 (en) 1995-02-15
ATE177742T1 (de) 1999-04-15
IL107891A0 (en) 1994-04-12
LT3167B (en) 1995-02-27
EP0626954B1 (fr) 1999-03-17
GR3030514T3 (en) 1999-10-29
DE69324001T2 (de) 1999-10-07
RU94040853A (ru) 1996-07-10
DE69324001D1 (de) 1999-04-22
WO1994013658A2 (fr) 1994-06-23
HUT67852A (en) 1995-05-29
LV10451A (lv) 1995-02-20
EP0626954A1 (fr) 1994-12-07
NZ258896A (en) 1996-03-26
SK93994A3 (en) 1995-04-12
LV10451B (en) 1995-12-20
FR2698873A1 (fr) 1994-06-10
KR950700278A (ko) 1995-01-16
HU9402302D0 (en) 1994-10-28
TW276255B (fr) 1996-05-21
ZA939127B (en) 1994-08-05
DK0626954T3 (da) 1999-10-11
JPH07503977A (ja) 1995-04-27
FI943646A (fi) 1994-08-05
WO1994013658A3 (fr) 1994-08-04
US5652252A (en) 1997-07-29
AU680856B2 (en) 1997-08-14
PL174246B1 (pl) 1998-07-31
SI9300632A (en) 1994-09-30
US5602152A (en) 1997-02-11
KR100236810B1 (ko) 2000-02-01

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