FI80694B - Foerfarande foer framstaellning av teraoeutiskt aktiva 5,6,7,8-tetrahydroimidazo/1,5-a/pyridiner. - Google Patents

Foerfarande foer framstaellning av teraoeutiskt aktiva 5,6,7,8-tetrahydroimidazo/1,5-a/pyridiner. Download PDF

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FI80694B
FI80694B FI852399A FI852399A FI80694B FI 80694 B FI80694 B FI 80694B FI 852399 A FI852399 A FI 852399A FI 852399 A FI852399 A FI 852399A FI 80694 B FI80694 B FI 80694B
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formula
compound
reacted
hydrogen
alkyl
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FI852399A
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FI852399L (fi
FI852399A0 (fi
FI80694C (sv
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Leslie J Browne
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Ciba Geigy Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • 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
    • 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
    • A61P5/30—Oestrogens
    • 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
    • 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
    • C07D213/55—Acids; Esters
    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical 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)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Claims (4)

1. Förfarande för framställning av terapeutiskt aktiva 5,6,7,8-tetrahydroimidazo[l,5-a]pyridiner med formeln I* < 7 / \=.l ‘W ·' · IN \/ i, i vilken formel Rj^ betecknar cyano, halogen, C1-C4-alkyl el-ler amino och R2 betecknar väte, fenyl-Cj-C^-alkyl, C^-C^-alkyltio eller C1-C4-alkoxikarbonyl, och deras stereoisome-rer, blandningar av stereoisomerer eller farmaceutiskt god-tagbara salter, kännetecknat därav, att d) en förening med formeln V / \ h* (y) • r · I II 'V' i. i vilken Rj^ och R2 betecknar detsamma som ovan i formeln I* och är halogen, omsätts med en bas, eller e) en förening med formeln VI 65 8 0 6 9 4 /X . I*’ · (VI) /\ I II ‘v./’ L i vilken formel och R2 betecknar detsamma som ovan i for-meln I* och X2 är halogen, omsätts med en bas, eller f) 1 en förenlng med formeln vii / \ • · 3SSSE2 · \A> • · ** \ (VII) / \ • · I II V i,· i vilken Rj' är en i en cyanogrupp överförbar grupp och R2 betecknar detsamma som ovan i formeln I*, ' överförs i en cyanogrupp med en av de följande överföringsreaktionerna: (1) en förenlng med formeln VII, väri Rj' är formyl, omsätts med hydrazinsyra, eller (2) en förening med formeln VII, väri R1' är karbamoyl eller Cj-^-alkylkarbamoyl, omsätts med ett dehydratiseringsmedel, eller g) en förening med formeln IX 66 8 0 6 9 4 A._. ϊ=° HÄX Jl (IX ) y \ I II V i. i vilken R-j^ betecknar detsamma som ovan i formeln I*, om-sätts i närvaro av ett reducerande medel, eller h) en förening med formeln Vllc / \ __ ^00H (Vllc) I II V k, i vilken och R2 betecknar detsamma som ovan i formeln I*, dekarboxyleras, eller i) en förening med formeln I /\=. \A./* y\ <*> I n V’ t> eller ett 7,8-dihydroderivat därav, väri betecknar det- II 67 80694 samma som ovan i formeln I* eller Mr hydroximetyl, reduceras eventuellt genom att reducera samtidigt substituenten R^_ = CH2OH till gruppen = CH3; och/eller (1) för framställning av en förening med formeln I*, väri R2 Sr väte, en förening med formeln I*, väri R2 är C-l-C^-alkoxikarbonyl, omsätts först med natriumhydroxid och sedan med klorvätesyra; (2) för framställning av en förening med formeln I*, väri R2 är C^-C^-alkyltio, den motsvarande föreningen med formeln I*, väri R2 är väte, omsätts med di-C1-C4-alkyldisulfid; (3) för framställning av en förening med formeln I*, väri R2 är C1-C4-alkoxikarbonyl, den motsvarande föreningen med formeln I*, väri R2 är väte, omsätts med C1-C4-alkylhalogenfor-miat; (4) för framställning av en förening med formeln I*, väri R! är amino, den motsvarande föreningen med formeln I*, väri Rj^ är karboxi, omsätts med hydrazinsyra; (5) för framställning av en förening med formeln I*, väri R2 är fenyl-Cj-C^-alkyl, den motsvarande föreningen med formeln I*, väri R2 är väte, omsätts med fenyl-C1-C4-alkylhalogenid; (6) för framställning av en förening med formeln I*, väri Rj är cyano, den motsvarande föreningen med formeln I*, väri Rx är halogen, omsätts med ett cyanidsalt; (7) för framställning av en förening med formeln I*, väri Rj^ är cyano, den motsvarande föreningen med formeln I*, väri R1 är amino, omsätts först med ett alkalinitritsalt och sedan med koppar(I)cyanid; och/eller ett erhället sait överförs i en fri förening eller ett annat sait och/eller en fri förening överförs i ett sait 68 80694 och/eller en enantiomerisk blandning, säsom ett racemat, uppdelas i optiska isomerer.
2. Förfarande för framställning av terapeutiskt aktiva 5,6,7,8-tetrahydroimidazo[l,5-a]pyridiner med formeln Ib i 7 /\ = .l '\λ> ·' · I II V tl i vilken formel Rj betecknar cyano eller C1-C4-alkyl och R2 är väte, fenyl-C1-C4-alkyl eller C1-C4-alkyltio, stereoiso-merer, blandningar av stereoisomerer eller farmaceutiskt godtagbara salter av dessa föreningar, känneteck-n a t därav, att d) en förening med formeln Vb · · / \ • · =S5 · x>4h/</ Λ (Vb) • · I H ’V* k i vilken Rx betecknar detsamma som ovan i formeln Ib och X1 Sr halogen, omsätts med en bas, eller e) en förening med formeln VIb li 69 80694 /\_. • · |V (VIb) /\ ι' · I ιι V’ il i vilken formel R-j^ och R2 betecknar detsamma som ovan i formeln Ib och X2 är halogen, omsätts med en bas, eller f) 1 en förening med formeln Vllb / \ • »SSSS5· • · R* \ (Vllb) S \ I N V* i»· i vilken R!' är en grupp eller rest, som kan överföras i en cyanogrupp och R2 betecknar detsamma som ovan i formeln Ib, R2' överförs i cyano med en av de följande överföringsreak-tionerna: (1) en förening med formeln Vllb, väri ' är halogen, omsätts med ett cyanidsalt, (2) en förening med formeln Vllb, väri R^' är karbamoyl eller C^-C^-alkylkarbamoyl, omsätts med ett starkt dehydra-tiseringsmedel, (3) en förening med formeln Vllb, väri är formyl, omsätts med hydrazinsyra, eller 70 80694 (4) en förening med formeln Vllb, väri R^' är amino, omsätts först med ett alkalinitritsalt och sedan med koppar(I)cya-nid, eller i) en förening med formeln Ia 7 / \==.» I II V* i. eller ett 7,8-dihydroderivat därav reduceras med väte i när-varo av en hydreringskatalysator och/eller (1) för framställning av en förening med formeln Ib, väri R2 är C1-C4-alkyltio, den motsvarande föreningen med formeln Ib, väri R2 är väte, omsätts med di-C^-C^-alkyldisulfid, och/eller ett erhället sait överförs i en fri förening eller ett annat sait och/eller en fri förening med en saltbildande grupp i ett sait och/eller en erhällen racemisk blandning uppdelas i enskilda enantiomerer.
3. Förfarande enligt patentkravet 1, känneteck- n a t därav, att man framställer 5-(p-cyanofenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin, eller ett farmaceutiskt godtagbart syraadditionssalt därav
4. Förfarande enligt patentkravet 2, känneteck- n a t därav, att man framställer 5-(p-cyanofenyl)-5,6,7,8-tetrahydroimidazo[l,5-a]pyridin, eller ett farmaceutiskt godtagbart syraadditionssalt därav. il
FI852399A 1984-06-20 1985-06-17 Förfarande för framställning av terapeutiskt aktiva 5,6,7,8-tetrahydro imidazo/1,5-a/pyridiner FI80694C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI882863A FI83079C (sv) 1984-06-20 1988-06-15 Förfarande för framställning av terapeutiskt aktiva 5-fenyl-imidazo/1, 5-a/pyridiner

Applications Claiming Priority (2)

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US62242184 1984-06-20
US06/622,421 US4617307A (en) 1984-06-20 1984-06-20 Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors

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FI852399A0 FI852399A0 (fi) 1985-06-17
FI852399L FI852399L (fi) 1985-12-21
FI80694B true FI80694B (fi) 1990-03-30
FI80694C FI80694C (sv) 1990-07-10

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US (1) US4617307A (sv)
EP (1) EP0165904B1 (sv)
JP (1) JPS6112688A (sv)
KR (1) KR900008566B1 (sv)
AT (1) ATE62415T1 (sv)
AU (1) AU589565B2 (sv)
BG (7) BG60262B2 (sv)
CA (1) CA1276633C (sv)
CS (1) CS268672B2 (sv)
CY (1) CY1750A (sv)
DD (1) DD237510A5 (sv)
DE (1) DE3582452D1 (sv)
DK (1) DK170302B1 (sv)
DZ (1) DZ799A1 (sv)
ES (6) ES8702406A1 (sv)
FI (1) FI80694C (sv)
GR (1) GR851487B (sv)
HK (1) HK23494A (sv)
HU (1) HU202529B (sv)
IE (1) IE58070B1 (sv)
IL (1) IL75546A (sv)
MA (1) MA20459A1 (sv)
MX (1) MX9203369A (sv)
NO (1) NO162467C (sv)
NZ (1) NZ212483A (sv)
PH (1) PH23390A (sv)
PL (6) PL145104B1 (sv)
PT (1) PT80661B (sv)
RO (1) RO92583A (sv)
SU (6) SU1433413A3 (sv)
ZA (1) ZA854615B (sv)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4728645A (en) * 1982-12-21 1988-03-01 Ciba-Geigy Corporation Substituted imidazo[1,5-A]pyridine derivatives and other substituted bicyclic derivatives, useful as aromatase inhibitors
US5428160A (en) * 1982-12-21 1995-06-27 Ciba-Geigy Corporation Substituted imidazo[5-a]pyridine derviatives and other substituted bicyclic derivatives
US4889861A (en) * 1982-12-21 1989-12-26 Ciba-Geigy Corp. Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors
GB8510541D0 (en) * 1985-04-25 1985-05-30 Wyeth John & Brother Ltd Heterocyclic compounds
US5171858A (en) * 1985-06-05 1992-12-15 Schering A.G. Preparation of certain 5,6-dihydro-8-phenyl-imidazo[1,5-a]pyridines
US4937250A (en) * 1988-03-07 1990-06-26 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
US4749713A (en) * 1986-03-07 1988-06-07 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
US4978672A (en) * 1986-03-07 1990-12-18 Ciba-Geigy Corporation Alpha-heterocyclc substituted tolunitriles
IL83163A (en) * 1986-07-18 1991-06-10 Erba Carlo Spa Cycloalkyl-substituted 4-pyridyl derivatives,their preparation and pharmaceutical compositions containing them
GB8820730D0 (en) * 1988-09-02 1988-10-05 Erba Carlo Spa Substituted 5 6 7 8-tetrahydroimidazo/1.5-a/pyridines & process for their preparation
US5057521A (en) * 1988-10-26 1991-10-15 Ciba-Geigy Corporation Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism
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
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
MTP1076B (en) * 1990-01-12 1991-09-30 Ciba Geigy Ag Hemihydrate
US5162337A (en) * 1990-10-05 1992-11-10 Merck & Co., Inc. Animal growth promotion
CA2066369A1 (en) * 1991-04-19 1992-10-20 Alex Elbrecht Control of sex differentiation in fish
CH683151A5 (de) * 1991-04-24 1994-01-31 Ciba Geigy Ag Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus.
JPH05176659A (ja) * 1991-04-26 1993-07-20 Merck & Co Inc 家禽における雌性表現型を転換するために抗ミュラー管ホルモンを単独またはアロマターゼ阻害剤と組合せて使用する方法
WO1995028156A1 (en) * 1994-04-14 1995-10-26 Sepracor, Inc. Treating estrogen-dependent diseases with (-)-fadrozole
EP0684235A1 (en) * 1994-05-27 1995-11-29 Mochida Pharmaceutical Co., Ltd. Novel azolyl methyl phenyl derivatives having aromatase inhibitory activity
DE4432106A1 (de) * 1994-09-09 1996-03-14 Hoechst Ag Mit Heterocyclen-N-Oxid-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum, sie enthaltendes Medikament sowie Zwischenprodukte zu ihrer Herstellung
US6833373B1 (en) 1998-12-23 2004-12-21 G.D. Searle & Co. Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US6858598B1 (en) 1998-12-23 2005-02-22 G. D. Searle & Co. Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US8168616B1 (en) 2000-11-17 2012-05-01 Novartis Ag Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension
ATE345790T1 (de) * 2002-07-30 2006-12-15 Novartis Pharma Gmbh Kombination von einem aromatasehemmer mit einem bisphosphonat
ATE335744T1 (de) * 2002-08-07 2006-09-15 Novartis Pharma Gmbh Organische verbindungen als mittel zur behandlung von aldosteronbedingten zuständen
ATE398124T1 (de) * 2002-11-18 2008-07-15 Novartis Pharma Gmbh Imidazoä1,5üa pyridin-derivate und methoden zur behandlung von krankheiten in verbindung mit aldosteron
WO2005007627A1 (ja) * 2003-07-18 2005-01-27 Nihon Nohyaku Co., Ltd. フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤
GB0327839D0 (en) 2003-12-01 2003-12-31 Novartis Ag Organic compounds
TW200605867A (en) 2004-03-17 2006-02-16 Novartis Ag Use of organic compounds
BRPI0510410A (pt) * 2004-05-28 2007-10-23 Speedel Experimenta Ag compostos orgánicos
TW200616623A (en) * 2004-05-28 2006-06-01 Speedel Experimenta Ag Organic compounds
GT200600381A (es) * 2005-08-25 2007-03-28 Compuestos organicos
EP1842543A1 (en) 2006-04-05 2007-10-10 Speedel Pharma AG Pharmaceutical composition coprising an aldosterone synthase inhibitor and a mineralcorticoid receptor antagonist
MX2008015008A (es) * 2006-05-26 2008-12-05 Novartis Ag INHIBIDORES DE SINTASA DE ALDOSTERONA Y/O DE 11ß-HIDROXILASA.
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EP2095819A1 (en) * 2008-02-28 2009-09-02 Maastricht University N-benzyl imidazole derivatives and their use as aldosterone synthase inhibitors
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GB201511790D0 (en) 2015-07-06 2015-08-19 Iomet Pharma Ltd Pharmaceutical compound
JP2016074729A (ja) * 2015-12-31 2016-05-12 国立大学法人 千葉大学 イミダゾリウム塩及びそれを用いた不斉合成触媒並びにイミダゾリウム塩の製造方法
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WO2018078049A1 (en) 2016-10-27 2018-05-03 Damian Pharma Ag Aldosterone synthase inhibitor
CN114853755A (zh) * 2016-10-27 2022-08-05 达米安制药股份公司 醛固酮合酶抑制剂
UY38072A (es) 2018-02-07 2019-10-01 Novartis Ag Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos
WO2019211394A1 (en) 2018-05-03 2019-11-07 Damian Pharma Ag R-fadrozole for use in the treatment of aldostonerism
EP3887388A1 (en) 2018-11-27 2021-10-06 Novartis AG Cyclic peptides as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorders
WO2020110008A1 (en) 2018-11-27 2020-06-04 Novartis Ag Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder
UY38485A (es) 2018-11-27 2020-06-30 Novartis Ag Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación
WO2023084449A1 (en) 2021-11-12 2023-05-19 Novartis Ag Diaminocyclopentylpyridine derivatives for the treatment of a disease or disorder

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5124517B1 (sv) * 1971-03-15 1976-07-24
FR2449689A1 (fr) * 1979-02-20 1980-09-19 Logeais Labor Jacques Nouveaux derives condenses de pyrrolidine ou de piperidine, leur procede de preparation et leurs applications en therapeutique
US4444775A (en) * 1981-06-22 1984-04-24 Ciba-Geigy Corporation Substituted imidazo[1,5-A]pyridines
FI75569C (sv) * 1981-06-22 1988-07-11 Ciba Geigy Ag Analogiförfarande för framställning av terapeutiskt verkande imidazo/1 ,5-a/pyridiner.
US4361567A (en) * 1981-10-05 1982-11-30 Schering Corporation Treatment of peptic ulcer disease
US4409226A (en) * 1981-10-05 1983-10-11 Schering Corporation Imidazo[1,5-a]pyridines
US4470986A (en) * 1982-12-21 1984-09-11 Ciba-Geigy Corporation Certain imidazo (1,5-A) pyridine aliphatic carboxylic acid derivatives and their use as selective thromboxane inhibitors
US4588732A (en) * 1982-12-21 1986-05-13 Ciba-Geigy Corporation Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane synthetase inhibitors

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PT80661A (en) 1985-07-01
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