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AR090159A1 - 5-alquinil piridinas - Google Patents

5-alquinil piridinas

Info

Publication number
AR090159A1
AR090159A1 ARP130100586A ARP130100586A AR090159A1 AR 090159 A1 AR090159 A1 AR 090159A1 AR P130100586 A ARP130100586 A AR P130100586A AR P130100586 A ARP130100586 A AR P130100586A AR 090159 A1 AR090159 A1 AR 090159A1
Authority
AR
Argentina
Prior art keywords
alkyl
phenyl
optionally substituted
membered heteroaryl
halogen
Prior art date
Application number
ARP130100586A
Other languages
English (en)
Inventor
Bader Gerd
Reiser Ulrich
Spevak Walter
Steffen Andreas
Parkes Alastair
Original Assignee
Boehringer Ingelheim Int
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 Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR090159A1 publication Critical patent/AR090159A1/es

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    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • 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
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Su uso como miméticos SMAC, composiciones farmacéuticas que los contienen y su uso como medicamentos para el tratamiento y/o prevención de enfermedades caracterizadas por proliferación de células excesiva o anormal y afecciones asociadas tales como cáncer. Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula (1) donde R¹ es -H o -alquilo C₁₋₅; R², R²ᵃ se seleccionan de modo independiente de -H o -alquilo C₁₋₅ opcionalmente sustituido con uno o más -F; R³ se selecciona de -arilo C₆₋₁₀, heteroarilo de 5 - 14 miembros, cada uno de estos grupos se puede sustituir en forma opcional e independiente con uno o más, seleccionados de modo independiente, R⁶; o R³ se selecciona de alquilo C₁₋₆, cicloalquilo C₄₋₇, cicloalquenilo C₄₋₇, o sistema anular aromático de 5 - 14 miembros, cada uno de estos grupos se puede sustituir en forma opcional e independiente con uno o más, seleccionados de modo independiente, R⁶ᵃ; R⁶ se selecciona de -CN, halógeno, alquilo C₁₋₃, -O-alquilo C₁₋₃, -C(O)-R¹², heteroarilo de 5 - 6 miembros, tal grupo heteroarilo de 5 - 6 miembros puede estar opcionalmente sustituido con alquilo C₁₋₃; o R⁶ es fenilo, tal fenilo puede estar opcionalmente sustituido con -O-alquilo C₁₋₃; R⁶ᵃ se selecciona de =O, -CN, halógeno, alquilo C₁₋₃, -O-alquilo C₁₋₃, -C(O)-R¹², heteroarilo de 5 - 6 miembros, tal grupo heteroarilo de 5 - 6 miembros puede estar opcionalmente sustituido con alquilo C₁₋₃; o R⁶ᵃ es fenilo, tal fenilo puede estar opcionalmente sustituido con -O-alquilo C₁₋₃; R¹² se selecciona de -NH₂, -NH-alquilo C₁₋₃, heterociclilo no aromático de 5 - 7 miembros, o -O-alquilo C₁₋₃, tales grupos alquilo C₁₋₃ pueden estar opcionalmente sustituido con un heterociclilo no aromático de 5-7 miembros; R⁴ se selecciona de -H, -arilo C₆₋₁₀, heteroarilo de 5 - 14 miembros, cada uno de tales grupos está sustituido en forma opcional e independiente con uno o más, seleccionados de modo independiente, R⁷, o R⁴ se selecciona de alquilo C₁₋₆, sistema anular aromático de 5 - 14 miembros, cicloalquilo C₅₋₇, cada grupo está sustituido en forma opcional e independiente con uno o más, seleccionados de modo independiente, R⁷ᵃ, o R⁴ se selecciona de -N(R⁸,R⁹) donde R⁸, R⁹ se seleccionan de modo independiente de H, alquilo C₁₋₃, -C(O)-R¹⁰, -S(O)₂-R¹¹; R¹⁰, R¹¹ se seleccionan de modo independiente de heterociclilo no aromático de 5 - 7 miembros, cicloalquilo C₅₋₇, -arilo C₆₋₁₀, heteroarilo de 5 - 10 miembros; R⁷ se selecciona de -CN, halógeno, -CF₃, -NO₂, alquilo C₁₋₃, -S-alquilo C₁₋₃, -NH-alquilo C₁₋₃, -N(alquilo C₁₋₃)₂, -NHC(O)alquilo C₁₋₃, -C(O)-R¹³, -O-alquilo C₁₋₃, heteroarilo de 5 - 14 miembros, -O-fenilo, -CH₂-fenilo, fenilo, cada uno del grupo fenilo puede estar opcionalmente sustituido con halógeno, o heterociclilo no aromático de 5 - 6 miembros, tal heterociclilo no aromático de 5 - 6 miembros puede estar opcionalmente sustituido con alquilo C₁₋₃; R⁷ᵃ se selecciona de =O, -CN, halógeno, -CF₃, -NO₂, alquilo C₁₋₃, -S-alquilo C₁₋₃, -NH-alquilo C₁₋₃, -N(alquilo C₁₋₃)₂, -NHC(O)alquilo C₁₋₃, -C(O)-R¹³, -O-alquilo C₁₋₃, heteroarilo de 5 - 14 miembros, -O-fenilo, -CH₂-fenilo, fenilo, cada uno del grupo fenilo puede estar opcionalmente sustituido con halógeno, o heterociclilo no aromático de 5 - 6 miembros, tal heterociclilo no aromático de 5 - 6 miembros puede estar opcionalmente sustituido con alquilo C₁₋₃; donde R¹³ se selecciona de -OH, -NH₂, -NH-alquilo C₁₋₃, alquilo C₁₋₃; R⁵ se selecciona de -H, halógeno, alquilo C₁₋₃, -O-alquilo C₁₋₃, tales grupos alquilo C₁₋₃ pueden estar opcionalmente sustituido con uno o más halógeno; o R⁴ y R⁵ tomados entre sí forman un -arilo C₆₋₁₀ o heteroarilo de 5 - 14 miembros; y donde los compuestos de fórmula (1) opcionalmente pueden estar presentes en la forma de sales.
ARP130100586A 2012-02-27 2013-02-26 5-alquinil piridinas AR090159A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP12157199 2012-02-27

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AR090159A1 true AR090159A1 (es) 2014-10-22

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KR (1) KR102038585B1 (es)
CN (1) CN104169257B (es)
AP (1) AP3999A (es)
AR (1) AR090159A1 (es)
AU (1) AU2013225173B2 (es)
BR (1) BR112014021027B1 (es)
CA (1) CA2865467C (es)
CL (1) CL2014002257A1 (es)
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US9278978B2 (en) 2013-08-23 2016-03-08 Boehringer Ingelheim International Gmbh 6-Alkynyl Pyridine
US10010560B2 (en) 2014-02-26 2018-07-03 The Trustees Of The University Of Pennsylvania Small molecule HSP70 inhibitors
AR101479A1 (es) * 2014-08-11 2016-12-21 Boehringer Ingelheim Int Derivados de 6-alquinil-piridina
WO2016079527A1 (en) 2014-11-19 2016-05-26 Tetralogic Birinapant Uk Ltd Combination therapy
WO2016097773A1 (en) 2014-12-19 2016-06-23 Children's Cancer Institute Therapeutic iap antagonists for treating proliferative disorders
JP6533997B2 (ja) * 2014-12-26 2019-06-26 株式会社ヤクルト本社 Ｚｎｆ１４３阻害活性を有する化合物およびその利用
CN107709300A (zh) 2015-05-18 2018-02-16 太阳医药高级研究有限公司 新型酰胺基杂芳基芳酰基酰肼乙炔
CN109415320A (zh) * 2016-05-04 2019-03-01 百时美施贵宝公司 吲哚胺2,3-双加氧酶的抑制剂及其使用方法
EP3458441B1 (en) * 2016-05-19 2021-01-20 Boehringer Ingelheim International GmbH Process for the manufacture of 6-alkynyl-pyridine derivatives
RU2768887C2 (ru) * 2017-03-15 2022-03-25 Сан Фарма Эдвансд Рисёч Компани Лимитед Новая аморфная дисперсия (5-{ 5-[n'-(2-хлор-6-метилбензоил)гидразинокарбонил]-2-метил-фенилэтинил} -пиридин-2-ил)амида циклопропанкарбоновой кислоты
KR20190130644A (ko) * 2017-03-31 2019-11-22 베링거 인겔하임 인터내셔날 게엠베하 항암 조합 요법
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