AR094550A1 - BTK INHIBITORS - Google Patents

BTK INHIBITORS

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Publication number
AR094550A1
AR094550A1 ARP140100193A ARP140100193A AR094550A1 AR 094550 A1 AR094550 A1 AR 094550A1 AR P140100193 A ARP140100193 A AR P140100193A AR P140100193 A ARP140100193 A AR P140100193A AR 094550 A1 AR094550 A1 AR 094550A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkoxy
halogen
optionally substituted
halogens
Prior art date
Application number
ARP140100193A
Other languages
Spanish (es)
Original Assignee
Merck Sharp & Dohme
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Publication date
Application filed by Merck Sharp & Dohme filed Critical Merck Sharp & Dohme
Publication of AR094550A1 publication Critical patent/AR094550A1/en

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid

Abstract

Composiciones farmacéuticas que comprenden estos compuestos y su uso en terapia. En particular, se refiere al uso de compuestos inhibidores de Btk en el tratamiento de trastornos mediados por Btk. Reivindicación 1: Un compuesto según la fórmula (1), o una sal farmacéuticamente aceptable del mismo, en la que: A¹, A², A³ y A⁴ son independientemente C, CH, CR¹¹ o N y el sistema de anillo bicíclico E-G está seleccionado del grupo que consiste en los restos del grupo de formulas (2), donde R¹¹ está independientemente seleccionado del grupo que consiste en: a) deuterio, b) H, c) halógeno, d) ciano, e) C²H₃, f) -COOH, g) -CO₂-alquilo C₁₋₆, h) -CO-alquilo C₁₋₆, i) -CONH-alcoxi C₁₋₆, j) -CONH-alquilo C₁₋₆, k) -CON-dialquilo C₁₋₆, ₗ₎ ₐₗqᵘⁱₗₒ C₁₋₆, ₘ₎ ᶜⁱᶜₗₒₐₗqᵘⁱₗₒ C₃₋₇, n) alcoxi C₁₋₆, o) arilo, p) heteroarilo C₁₋₅, q) alquenilo C₂₋₆, r) alquinilo C₂₋₆, y s) heterocicloalquilo C₄₋₇, R¹¹ está opcionalmente sustituido con uno o más grupos seleccionados de: halógeno, alquilo C₁₋₆, alcoxi C₁₋₅, hidroxilo u oxo; R¹² está independientemente seleccionado del grupo que consiste en: H, alquilo C₁₋₃. alquil C₁₋₃-NHC(O), alquil C₁₋₃-OC(O) y alquil C₁₋₃-C(O); R¹³ está independientemente seleccionado del grupo que consiste en: H y alcoxi C₁₋₄; en la que en el anillo aromático K: B¹ es N o C(R⁷); B² es N o C(R⁸); B³ es N o C(R⁹); B⁴ es N o C(R¹⁰); R⁷ es H, halógeno, OH, alquilo C₁₋₃, alcoxi C₁₋₆, cicloalcoxi C₃₋₆, heterocicloalcoxi C₁₋₅, haloalquilo C₁₋₃ o CN; en la que R⁷ puede estar opcionalmente sustituido con uno, dos o tres halógenos, OH, alquinilo C₂₋₄, -C(O)NH₂, -C(O)OH o -C(O)alquilo C₁₋₄; R⁸ es H, halógeno, OH, alquilo C₁₋₃, alcoxi C₁₋₆, cicloalcoxi C₃₋₆, heterocicloalcoxi C₁₋₅, haloalquilo C₁₋₃ o CN; en la que R⁸ puede estar opcionalmente sustituido con uno, dos o tres halógenos, OH, alquinilo C₂₋₄, -C(O)NH₂, -C(O)OH o -C(O)alquilo C₁₋₄; R⁹ es H, halógeno, OH, alquilo C₁₋₃, alcoxi C₁₋₆, cicloalcoxi C₃₋₆, heterocicloalcoxi C₁₋₅, haloalquilo C₁₋₃ o CN; en la que R⁹ puede estar opcionalmente sustituido con uno, dos o tres halógenos, OH, alquinilo C₂₋₄, -C(O)NH₂, -C(O)OH o -C(O)alquilo C₁₋₄; R¹⁰ es H, halógeno, OH, alquilo C₁₋₃, alcoxi C₁₋₆, cicloalcoxi C₃₋₆, heterocicloalcoxi C₁₋₅, haloalquilo C₁₋₃ o CN; en la que R¹⁰ puede estar opcionalmente sustituido con uno, dos o tres halógenos, OH, alquinilo C₂₋₄, -C(O)NH₂, -C(O)OH o -C(O)alquilo C₁₋₄; en la que en el anillo heteroaromático L: W es CH, N o S; X es C(R⁶ᵃ), N, O ó S; Y es C(R⁶), N(R⁶ᵇ), O ó S; Z es C(R⁶ᵃ), N o un enlace; R⁵ es H, halógeno, ciano, alquilo C₁₋₄, alcoxi C₁₋₅, cicloalquilo C₃₋₆, cicloalcoxi C₃₋₆ o -C(O)O-alquilo C₁₋₃; en la que R⁵ puede estar opcionalmente sustituido con uno, dos o tres halógenos, OH o alcoxi C₁₋₃; o R⁵ es arilo C₆₋₁₀, heteroarilo C₁₋₅ o heterocicloalquilo C₂₋₆, en la que R⁵ puede estar opcionalmente sustituido con halógeno, alquilo C₁₋₆ o alcoxi C₁₋₃; R⁶ es H, halógeno, ciano, alquilo C₁₋₆ o alcoxi C₁₋₆; en la que R⁶ puede estar opcionalmente sustituido con uno, dos o tres halógenos o ciano; R⁶ᵃ es H, alquilo C₁₋₄ o cicloalquilo C₃₋₆; R⁶ᵇ es H, alquilo C₁₋₃, cicloalquilo C₃₋₆ o -C(O)O-alquilo C₁₋₄; o R⁵ y R⁶ pueden formar juntos un anillo de 5 a 6 miembros carbocíclico o heterocíclico, y opcionalmente estar insaturado o ser aromático; o R⁵ y R⁶ pueden formar juntos cicloalquenilo C₃₋₇ o heterocicloalquenilo C₂₋₆; cada uno opcionalmente sustituido con alquilo C₁₋₃ o con uno o más halógenos; Q es C=O, C(Rᶠ)₂ o C=N(Rʰ); T es C(Rᵉ)₂, O, NRᵉ o un enlace; U es C(Rᵈ)₂, O ó NRᵈ; V es C(Rᵍ)₂, O ó un enlace; Rᶜ, Rᵈ, Rᵉ y Rᶠ están seleccionados cada uno independientemente de H, halógeno, alquilo C₁₋₆, hidroxilo, alquenilo C₁₋₆ o -C(O)Rᶻ, en la que Rᶻ está independientemente seleccionado de heteroarilo C₁₋₅, arilo e hidroxilo, cualquier grupo alquilo de Rᶜ, Rᵈ, Rᵉ o Rᶠ puede estar opcionalmente sustituido con hidroxi, -C(O)alcoxi C₁₋₃ o -C(O)OH; Rᵍ está independientemente seleccionado de H, halógeno, alquilo C₁₋₆, alcoxi C₁₋₆, haloalquilo C₁₋₆ o hidroxilo; Rʰ está independientemente seleccionado de H o CN; con la condición de que: 1) hasta 2 átomos de X, Y y Z puedan ser simultáneamente un heteroátomo; 2) cuando un átomo seleccionado de X o Y sea O ó S, entonces Z sea un enlace y el otro átomo seleccionado de X o Y no pueda ser O ó S; 3) cuando Z sea CH o N, entonces Y sea C(R⁶) o N y X sea CH o N; 4) en el anillo K, hasta 2 de B¹, B², B³ y B⁴ puedan ser N; 5) cuando Q sea C(Rᶠ)₂, entonces T sea C(Rᵉ)₂; 6) cuando T es NRᵉ, entonces Rᵉ no es halógeno; y 7) cuando U es NRᵈ, entonces Rᵈ no es halógeno.Pharmaceutical compositions comprising these compounds and their use in therapy. In particular, it refers to the use of Btk inhibitor compounds in the treatment of Btk mediated disorders. Claim 1: A compound according to formula (1), or a pharmaceutically acceptable salt thereof, wherein: A¹, A², A³ and A⁴ are independently C, CH, CR¹¹ or N and the bicyclic ring system EG is selected from group consisting of the remains of the group of formulas (2), where R¹¹ is independently selected from the group consisting of: a) deuterium, b) H, c) halogen, d) cyano, e) C²H₃, f) -COOH, g) -CO₂-C₁₋₆ alkyl, h) -CO-C₁₋₆ alkyl, i) -CONH-C₁₋₆ alkoxy, j) -CONH-C₁₋₆ alkyl, k) -CON-C₁₋₆ dialkyl, ₗ₎ ₐₗqᵘⁱₗₒ C₁₋₆, ₘ₎ ᶜⁱᶜₗₒₐₗqᵘⁱₗₒ C₃₋₇, n) C₁₋₆ alkoxy, o) aryl, p) C₁₋₅ heteroaryl, q) C₂₋₆ alkenyl, r) C₂₋₆ alkynyl, and s) C₄ heterocycloalkyl ₋₇, R¹¹ is optionally substituted with one or more groups selected from: halogen, C₁₋₆ alkyl, C₁₋₅ alkoxy, hydroxyl or oxo; R¹² is independently selected from the group consisting of: H, C₁₋₃ alkyl. C₁₋₃-NHC (O) alkyl, C₁₋₃-OC (O) alkyl and C₁₋₃-C (O) alkyl; R¹³ is independently selected from the group consisting of: H and C₁₋₄ alkoxy; wherein in the aromatic ring K: B¹ is N or C (R⁷); B² is N or C (R⁸); B³ is N or C (R⁹); B⁴ is N or C (R¹⁰); R⁷ is H, halogen, OH, C₁₋₃ alkyl, C₁₋₆ alkoxy, C₃₋₆ cycloalkoxy, C₁₋₅ heterocycloalkoxy, C₁₋₃ haloalkyl or CN; wherein R⁷ may be optionally substituted with one, two or three halogens, OH, C₂₋₄ alkynyl, -C (O) NH₂, -C (O) OH or -C (O) C₁₋₄ alkyl; R⁸ is H, halogen, OH, C₁₋₃ alkyl, C₁₋₆ alkoxy, C₃₋₆ cycloalkoxy, C₁₋₅ heterocycloalkoxy, C₁₋₃ haloalkyl or CN; wherein R⁸ may be optionally substituted with one, two or three halogens, OH, C₂₋₄ alkynyl, -C (O) NH₂, -C (O) OH or -C (O) C₁₋₄ alkyl; R⁹ is H, halogen, OH, C₁₋₃ alkyl, C₁₋₆ alkoxy, C₃₋₆ cycloalkoxy, C₁₋₅ heterocycloalkoxy, C₁₋₃ haloalkyl or CN; wherein R⁹ may be optionally substituted with one, two or three halogens, OH, C₂₋₄ alkynyl, -C (O) NH₂, -C (O) OH or -C (O) C₁₋₄ alkyl; R¹⁰ is H, halogen, OH, C₁₋₃ alkyl, C₁₋₆ alkoxy, C₃₋₆ cycloalkoxy, C₁₋₅ heterocycloalkoxy, C₁₋₃ haloalkyl or CN; wherein R¹⁰ may be optionally substituted with one, two or three halogens, OH, C₂₋₄ alkynyl, -C (O) NH₂, -C (O) OH or -C (O) C₁₋₄ alkyl; wherein in the heteroaromatic ring L: W is CH, N or S; X is C (R⁶ᵃ), N, O or S; Y is C (R⁶), N (R⁶ᵇ), O or S; Z is C (R⁶ᵃ), N or a bond; R⁵ is H, halogen, cyano, C₁₋₄ alkyl, C₁₋₅ alkoxy, C₃₋₆ cycloalkyl, C₃₋₆ cycloalkoxy or -C (O) O-C₁₋₃ alkyl; wherein R⁵ may be optionally substituted with one, two or three halogens, OH or C₁₋₃ alkoxy; or R⁵ is C₆₋₁₀ aryl, C₁₋₅ heteroaryl or C₂₋₆ heterocycloalkyl, in which R⁵ may be optionally substituted with halogen, C₁₋₆ alkyl or C₁₋₃ alkoxy; R⁶ is H, halogen, cyano, C₁₋₆ alkyl or C₁₋₆ alkoxy; wherein R⁶ may be optionally substituted with one, two or three halogens or cyano; R⁶ᵃ is H, C₁₋₄ alkyl or C₃₋₆ cycloalkyl; R⁶ᵇ is H, C₁₋₃ alkyl, C₃₋₆ cycloalkyl or -C (O) O-C₁₋₄ alkyl; or R⁵ and R⁶ can together form a 5 to 6 carbocyclic or heterocyclic ring, and optionally be unsaturated or aromatic; or R⁵ and R⁶ can together form C₃₋₇ cycloalkenyl or C₂₋₆ heterocycloalkenyl; each optionally substituted with C₁₋₃ alkyl or with one or more halogens; Q is C = O, C (Rᶠ) ₂ or C = N (Rʰ); T is C (Rᵉ) ₂, O, NRᵉ or a bond; U is C (Rᵈ) ₂, O or NRᵈ; V is C (Rᵍ) ₂, O or a link; Rᶜ, Rᵈ, Rᵉ and Rᶠ are each independently selected from H, halogen, C₁₋₆ alkyl, hydroxyl, C₁₋₆ or -C (O) Rᶻ alkenyl, wherein Rᶻ is independently selected from C₁₋₅ heteroaryl, aryl and hydroxyl, any alkyl group of Rᶜ, Rᵈ, Rᵉ or Rᶠ may be optionally substituted with hydroxy, -C (O) C₁₋₃ alkoxy or -C (O) OH; Rᵍ is independently selected from H, halogen, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl or hydroxyl; Rʰ is independently selected from H or CN; with the proviso that: 1) up to 2 atoms of X, Y and Z can simultaneously be a heteroatom; 2) when an atom selected from X or Y is O or S, then Z is a bond and the other atom selected from X or Y cannot be O or S; 3) when Z is CH or N, then Y is C (R⁶) or N and X is CH or N; 4) in ring K, up to 2 of B¹, B², B³ and B⁴ can be N; 5) when Q is C (Rᶠ) ₂, then T is C (Rᵉ) ₂; 6) when T is NRᵉ, then Rᵉ is not halogen; and 7) when U is NRᵈ, then Rᵈ is not halogen.

ARP140100193A 2013-01-23 2014-01-22 BTK INHIBITORS AR094550A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2013/070876 WO2014113932A1 (en) 2013-01-23 2013-01-23 Btk inhibitors

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AR094550A1 true AR094550A1 (en) 2015-08-12

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Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014113942A1 (en) 2013-01-23 2014-07-31 Merck Sharp & Dohme Corp. Btk inhibitors
TW201441234A (en) 2013-01-23 2014-11-01 Merck Sharp & Dohme BTK inhibitors
WO2015095102A1 (en) 2013-12-20 2015-06-25 Merck Sharp & Dohme Corp. Btk inhibitors
EP3082809B1 (en) 2013-12-20 2021-01-20 Merck Sharp & Dohme Corp. Btk inhibitors
WO2016106628A1 (en) 2014-12-31 2016-07-07 Merck Sharp & Dohme Corp. Btk inhibitors
WO2016106652A1 (en) * 2014-12-31 2016-07-07 Merck Sharp & Dohme Corp. Biarylether imidazopyrazine btk inhibitors
WO2016106629A1 (en) * 2014-12-31 2016-07-07 Merck Sharp & Dohme Corp. Btk inhibitors
WO2016106627A1 (en) * 2014-12-31 2016-07-07 Merck Sharp & Dohme Corp. Btk inhibitors
KR20180004286A (en) 2015-05-26 2018-01-10 모르포시스 아게 Combinations of Anti-CD19 Antibodies and Brutonyl Tyrosine Kinase Inhibitors and Uses Thereof
CA3028824C (en) * 2016-06-22 2023-12-12 Shanghai Fochon Pharmaceutical Co., Ltd. Substituted pyrrolo[2,3-d]pyridazin-4-ones and pyrazolo[3,4-d]pyridazin-4-ones as protein kinase inhibitors
CA3129665A1 (en) 2019-03-21 2020-09-24 Onxeo A dbait molecule in combination with kinase inhibitor for the treatment of cancer
WO2021089791A1 (en) 2019-11-08 2021-05-14 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods for the treatment of cancers that have acquired resistance to kinase inhibitors
WO2021148581A1 (en) 2020-01-22 2021-07-29 Onxeo Novel dbait molecule and its use

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AR057960A1 (en) * 2005-12-02 2007-12-26 Osi Pharm Inc BICYCLE PROTEIN QUINASE INHIBITORS
PE20070855A1 (en) * 2005-12-02 2007-10-14 Bayer Pharmaceuticals Corp DERIVATIVES OF 4-AMINO-PYRROLOTRIAZINE SUBSTITUTE AS KINASE INHIBITORS
ATE531263T1 (en) * 2006-09-22 2011-11-15 Pharmacyclics Inc BRUTON TYROSINE KINASE INHIBITORS
CA2800913C (en) * 2010-06-03 2019-07-23 Pharmacyclics, Inc. The use of inhibitors of bruton's tyrosine kinase (btk)

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