AR075367A1 - GLUCOSILCERAMIDE SINTASA INHIBITORS - Google Patents

GLUCOSILCERAMIDE SINTASA INHIBITORS

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Publication number
AR075367A1
AR075367A1 ARP100100326A ARP100100326A AR075367A1 AR 075367 A1 AR075367 A1 AR 075367A1 AR P100100326 A ARP100100326 A AR P100100326A AR P100100326 A ARP100100326 A AR P100100326A AR 075367 A1 AR075367 A1 AR 075367A1
Authority
AR
Argentina
Prior art keywords
alkyl
ring
independently
ora1
bond
Prior art date
Application number
ARP100100326A
Other languages
Spanish (es)
Original Assignee
Exelixis Inc
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 Exelixis Inc filed Critical Exelixis Inc
Publication of AR075367A1 publication Critical patent/AR075367A1/en

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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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • 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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Además comprende una composicion que contiene los compuestos, N-oxidos, y/o sus sales aceptables para uso farmacéutico, y el uso de los compuestos y las composiciones para tratar enfermedades en las cuales la GCS es un mediador o está implicada. Además comprende el uso de los compuestos en y para la preparacion de medicamentos, en particular para tratar enfermedades en las cuales la GCS es un mediador o está implicada. Reivindicacion 1: Un compuesto de la formula (1), o un estereoisomero simple o mezcla de estereoisomeros de los mismos sus N-oxidos, y además opcionalmente como su sal aceptable para uso farmacéutico, donde A es isopropilo, t-butilo, cicloalquilo C3-8, heterociclilo, arilo, o heteroarilo, donde el cicloalquilo, heterociclilo, arilo, y heteroarilo están opcionalmente sustituidos con uno, dos o tres grupos RA, donde cada RA es independientemente RA2, alquilo C1-6, haloalquilo C1-4, arilo, arilalquilo C1-4 o alquilo -C1-4-RA2, donde el arilo del grupo arilalquilo C1-4 está opcionalmente sustituido con uno, dos o tres grupos RA2 donde, cada RA2 es independientemente halogeno, ciano, nitro, -ORA1, -SRA1, -N(RA1)2, -C(O)RA1, -S(O)RA1, -S(O)2RA1, -S(O)N(RA1)2, -S(O)2N(RA1)2, -C(O)ORA1, -C(O)N(RA1)2, -N(RA1)C(O)RA1, -N(RA1)C(O)ORA1, -N(RA1)C(O)N(RA1)2, -N(RA1)S(O)2RA1, -N(RA1)C(=NRA1)N(RA1)2, -P(O)(ORA1)2, o -OP(O)(ORA1)2, donde cada RA1 es independientemente hidrogeno, alquilo C1-4, o haloalquilo C1-4, o dos RA unidos a los átomos de carbono adyacentes, tomados juntos, forman -O-(G)y-O-, donde cada G es independientemente -CH2-, -C(H)(F)-, o -CF2-, y y es 1, 2, o 3; E es -(CH2)-, -C(H)(CH3)-, o -C(O)-; L es -[C(RL)2]p-L1-[C(RL)2]g-, donde p es 1, 2, o 3; q es un entero seleccionado de 0 a (3-p); L1 es un enlace, -O- o -NH- y cada RL es independientemente hidrogeno, metilo, o halometilo; R1 es -N(R10)(R11) o un resto de formula (2), donde R10 es hidrogeno o alquilo C1-4; R11 es -R13,-cicloalquilo C3-6-N(R12)2, -cicloalquilo C3-6-R13, alquilo C1-6-N(R12)2, o alquilo C1-6-R13, donde cada R12 es independientemente hidrogeno o alquilo C1-4; y R13 es (a) un anillo heterociclilo monocíclico de 4 a 10 miembros, bicíclico fusionado de 4 a 10 miembros, bicíclico puenteado de 5 a 10 miembros, o espirobicíclico de 5 a 10 miembros, donde el anillo heterociclilo comprende uno, dos o tres átomos de nitrogeno anular, y opcionalmente comprende un oxígeno anular o átomo de azufre, o (b) un heteroarilo monocíclico de 5 o 6 miembros o un heteroarilo bicíclico fusionado de 8 a 10 miembros, donde el carbono a los cuales éstos están unidos, forman un anillo fenilo; m es 0, 1, 2 o 3; n es 1, 2, o 3; y R5 es independientemente halogeno o alquilo C1-4, donde el grupo alquilo está opcionalmente sustituido con uno, dos, o tres grupos R51 donde cada R51 es independientemente hidroxi o halogeno; siempre que cuando X1 sea -N=, E es -C(O)-, L1 es un enlace o -NH-, A es isopropilo o t-butilo, R1 es un resto de formula (2), y el anillo B es pirrolidinilo, entonces R20 no es -C(O)ORB3 o -C(O)N(RB3)2; y R21, cuando está presente, es -C(O)ORB3 o -C(O)N(RB3)2; siempre que cuando L1 es un enlace, E es -CH2- o -CH(CH3)-, y Q es -NH-, entonces A no es isopropilo o ter-butilo; siempre que cuando L1 es un enlace, A es isopropilo o t-butil. E es -CH2- o -CH(CH3)-, y R1 es un resto de formula (2), entonces el anillo B no es pirazolilo, indazolilo, indolilo, o bencimidazolilo; siempre que cuando E es -CH2- o -CH(CH3)-, R1 es un resto de formula (2), entonces el anillo B es un anillo heterociclilo monocíclico de 4 a 10 miembros, entonces R20 y R21, cuando están presentes, no son arilalquilo C1-4; y siempre que cuando L1 es un enlace, E es -C(O)-, R1 es -N(R10)(R11), R11 es R13, y R13 es 8-azabiciclo[3,2,1]octanillo, entonces R13A, cuando está presente, no es arilalquilo C1-4.It also comprises a composition containing the compounds, N-oxides, and / or their salts acceptable for pharmaceutical use, and the use of the compounds and compositions to treat diseases in which GCS is a mediator or is involved. It also includes the use of the compounds in and for the preparation of medicaments, in particular to treat diseases in which the GCS is a mediator or is involved. Claim 1: A compound of the formula (1), or a simple stereoisomer or mixture of stereoisomers thereof, their N-oxides, and also optionally as its salt acceptable for pharmaceutical use, wherein A is isopropyl, t-butyl, C3 cycloalkyl -8, heterocyclyl, aryl, or heteroaryl, where the cycloalkyl, heterocyclyl, aryl, and heteroaryl are optionally substituted with one, two or three RA groups, where each RA is independently RA2, C1-6 alkyl, C1-4 haloalkyl, aryl , C1-4 arylalkyl or -C1-4-RA2 alkyl, where the aryl of the C1-4 arylalkyl group is optionally substituted with one, two or three RA2 groups where, each RA2 is independently halogen, cyano, nitro, -ORA1, - SRA1, -N (RA1) 2, -C (O) RA1, -S (O) RA1, -S (O) 2RA1, -S (O) N (RA1) 2, -S (O) 2N (RA1) 2, -C (O) ORA1, -C (O) N (RA1) 2, -N (RA1) C (O) RA1, -N (RA1) C (O) ORA1, -N (RA1) C (O ) N (RA1) 2, -N (RA1) S (O) 2RA1, -N (RA1) C (= NRA1) N (RA1) 2, -P (O) (ORA1) 2, or -OP (O) (ORA1) 2, where each RA1 is independently hydrogen, C1-4 alkyl, or hal C1-4alkyl, or two RAs attached to adjacent carbon atoms, taken together, form -O- (G) and O-, where each G is independently -CH2-, -C (H) (F) -, or - CF2-, and y is 1, 2, or 3; E is - (CH2) -, -C (H) (CH3) -, or -C (O) -; L is - [C (RL) 2] p-L1- [C (RL) 2] g-, where p is 1, 2, or 3; q is an integer selected from 0 to (3-p); L1 is a bond, -O- or -NH- and each RL is independently hydrogen, methyl, or halomethyl; R1 is -N (R10) (R11) or a remainder of formula (2), where R10 is hydrogen or C1-4 alkyl; R11 is -R13, -C3-6-N (R12) 2 -cycloalkyl, C3-6-R13-cycloalkyl, C1-6-N (R12) 2 alkyl, or C1-6-R13 alkyl, where each R12 is independently hydrogen or C1-4 alkyl; and R13 is (a) a 4-10 membered monocyclic heterocyclyl ring, fused 4 to 10 membered bicyclic ring, 5 to 10 membered bridged bicyclic, or 5 to 10 membered spirobicyclic ring, wherein the heterocyclyl ring comprises one, two or three annular nitrogen atoms, and optionally comprises an annular oxygen or sulfur atom, or (b) a 5- or 6-membered monocyclic heteroaryl or an 8 to 10 membered fused bicyclic heteroaryl, where the carbon to which they are attached, form a phenyl ring; m is 0, 1, 2 or 3; n is 1, 2, or 3; and R5 is independently halogen or C1-4 alkyl, where the alkyl group is optionally substituted with one, two, or three R51 groups where each R51 is independently hydroxy or halogen; provided that when X1 is -N =, E is -C (O) -, L1 is a bond or -NH-, A is isopropyl or t-butyl, R1 is a residue of formula (2), and ring B is pyrrolidinyl, then R20 is not -C (O) ORB3 or -C (O) N (RB3) 2; and R21, when present, is -C (O) ORB3 or -C (O) N (RB3) 2; provided that when L1 is a bond, E is -CH2- or -CH (CH3) -, and Q is -NH-, then A is not isopropyl or tert-butyl; provided that when L1 is a bond, A is isopropyl or t-butyl. E is -CH2- or -CH (CH3) -, and R1 is a moiety of formula (2), then ring B is not pyrazolyl, indazolyl, indolyl, or benzimidazolyl; provided that when E is -CH2- or -CH (CH3) -, R1 is a residue of formula (2), then ring B is a monocyclic heterocyclyl ring of 4 to 10 members, then R20 and R21, when present, they are not C1-4 arylalkyl; and whenever L1 is a bond, E is -C (O) -, R1 is -N (R10) (R11), R11 is R13, and R13 is 8-azabicyclo [3,2,1] octane, then R13A , when present, it is not C1-4 arylalkyl.

ARP100100326A 2009-02-06 2010-02-05 GLUCOSILCERAMIDE SINTASA INHIBITORS AR075367A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15043409P 2009-02-06 2009-02-06
PCT/US2010/023080 WO2010091104A1 (en) 2009-02-06 2010-02-03 Glucosylceramide synthase inhibitors

Publications (1)

Publication Number Publication Date
AR075367A1 true AR075367A1 (en) 2011-03-30

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ID=42148396

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP100100326A AR075367A1 (en) 2009-02-06 2010-02-05 GLUCOSILCERAMIDE SINTASA INHIBITORS

Country Status (3)

Country Link
AR (1) AR075367A1 (en)
TW (1) TW201040156A (en)
WO (1) WO2010091104A1 (en)

Families Citing this family (13)

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DK2685986T3 (en) * 2011-03-18 2020-03-02 Genzyme Corp GLUCOSYLCERAMIDE SYNTHASIS INHIBITORS
MA37975B2 (en) * 2012-09-11 2021-03-31 Genzyme Corp Glucosylceramide synthase inhibitors
JO3713B1 (en) * 2013-03-15 2021-01-31 Genzyme Corp SALT FORMS OF (S)-Quinuclidin-3-yl (2-(2-(4-fluorophenyl)thiazol-4-yl)propan-2-yl)carbamate
EP3318277A1 (en) 2016-11-04 2018-05-09 Institut du Cerveau et de la Moelle Epiniere-ICM Inhibitors of glucosylceramide synthase for the treatment of motor neuron diseases
CN114746422B (en) * 2019-11-15 2024-03-12 柳韩洋行 Derivatives having 1,2,3, 4-tetrahydronaphthalene moiety or pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the same
CN114829361B (en) * 2019-11-15 2024-07-16 柳韩洋行 Derivatives having 2, 3-dihydro-1H-indene or 2, 3-dihydrobenzofuran moiety or pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the same
AU2021215396A1 (en) 2020-02-03 2022-09-29 Genzyme Corporation Methods for treating neurological symptoms associated with lysosomal storage diseases
JP2023523454A (en) 2020-04-28 2023-06-05 ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガン Pyridine inhibitors of glucosylceramide synthase and methods of treatment using them
IL300090A (en) 2020-07-24 2023-03-01 Genzyme Corp Pharmaceutical compositions comprising venglustat
WO2022060763A2 (en) * 2020-09-17 2022-03-24 Merck Sharp & Dohme Corp. Modified imidazopyridines as glucosylceramide synthase inhibitors
WO2022060764A1 (en) * 2020-09-18 2022-03-24 Merck Sharp & Dohme Corp. Modified benzofuran-carboxamides as glucosylceramide synthase inhibitors
WO2023172475A2 (en) * 2022-03-11 2023-09-14 Merck Sharp & Dohme Llc Non-aromatic cyclic-pyrimidine analogs as glucosylceramide synthase inhibitors
WO2023177563A2 (en) * 2022-03-14 2023-09-21 Merck Sharp & Dohme Llc Fused pyrazole amide analogs as glucosylceramide synthase inhibitors

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US4107288A (en) 1974-09-18 1978-08-15 Pharmaceutical Society Of Victoria Injectable compositions, nanoparticles useful therein, and process of manufacturing same
US5145684A (en) 1991-01-25 1992-09-08 Sterling Drug Inc. Surface modified drug nanoparticles
GB0400812D0 (en) 2004-01-14 2004-02-18 Celltech R&D Ltd Novel compounds
JP2008519840A (en) 2004-11-10 2008-06-12 ジェンザイム・コーポレイション How to treat diabetes
ES2277745B1 (en) * 2005-06-14 2008-06-01 Laboratorios Almirall S.A. N-AMIDA DERIVATIVES OF 8-AZABICICLO /3.2.1/OCT-3-ILO AS AN ANTIGONISTS OF CCR1.
EP2594564B1 (en) * 2007-05-31 2016-09-28 Genzyme Corporation 2-acylaminopropanol-type glucosylceramide synthase inhibitors

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TW201040156A (en) 2010-11-16
WO2010091104A1 (en) 2010-08-12
WO2010091104A8 (en) 2011-04-07

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