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AR063943A1 - Dipeptidos antagonistas de iap, una composicion farmaceutica que los comprende y el uso de los mismos para el tratamiento del cancer. - Google Patents

Dipeptidos antagonistas de iap, una composicion farmaceutica que los comprende y el uso de los mismos para el tratamiento del cancer.

Info

Publication number
AR063943A1
AR063943A1 ARP070103286A ARP070103286A AR063943A1 AR 063943 A1 AR063943 A1 AR 063943A1 AR P070103286 A ARP070103286 A AR P070103286A AR P070103286 A ARP070103286 A AR P070103286A AR 063943 A1 AR063943 A1 AR 063943A1
Authority
AR
Argentina
Prior art keywords
optionally substituted
independently
atoms
heterocycloalkyl
cycloalkyl
Prior art date
Application number
ARP070103286A
Other languages
English (en)
Inventor
Matthew G Laporte
Stephen M Condon
Susan R Rippin
Yijung Deng
Original Assignee
Tetralogic Pharmaceuticals Cor
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 Tetralogic Pharmaceuticals Cor filed Critical Tetralogic Pharmaceuticals Cor
Publication of AR063943A1 publication Critical patent/AR063943A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dipéptidos miméticos de Smac que inhiben IAPs, composicion farmacéutica que los comprende y el uso de los mismos para el tratamiento del cáncer. Reivindicacion 1: Un compuesto de la formula (1) caracterizado porque Z1a, Z2a, Z1b y Z2b son independientemente CH o N; R1a y R1b son independientemente H o hidroxilo, alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos; R2a, R2a', R2b y R2b' son independientemente H o alquilo, cicloalquilo o heterocicloalquilo opcionalmente sustituidos; o cuando R2a' es H entonces R2a y R1a pueden formar juntos un anillo aziridina o azetidina y, cuando R2b' es H entonces R2b y R1b pueden formar juntos un anillo aziridina o azetidina; R3a, R3b, R4a y R4b son independientemente H o alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos, o, R4a y R3a, o R4b y R3b, o ambos, son átomos de C ligados por un grupo alquileno o alquenileno C1-8 opcionalmente sustituido o un grupo alquenileno C1-8 donde uno a tres átomos de C pueden reemplazarse por N, O, S(O)n, o C=O; R5a, R6a, R5b, y R6b son independientemente H o hidroxilo, alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos, o, R5a y R6a, o R5b y R6b, o ambos, son átomos de C ligados por un grupo alquileno o alquenileno C1-8 opcionalmente sustituido donde uno a tres átomos de C pueden reemplazarse por N, O, S(O)n, o C=O; R7a, R7b, R8a, R8b son independientemente H o hidroxilo, alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos, o, R7a y R8a, o R7b y R8b, o ambos, pueden ligarse mediante un grupo alquileno o alquenileno C3-8 donde entre uno y tres átomos de C pueden reemplazarse por N, O, S(O)n, o C=O; cada n puede ser igual o diferente y es 0, 1, o 2; Xa es -O-, -N(La-R10a)-, -S-, -C(La-R10a)=CH- opcionalmente sustituido, -C(O)-O-, -C(O)-N(La-R10a)-, -N=C(La-R10a)-; Xb es -O-, -N(Lb-R10b)-, -S-, -C(Lb-R10b)=CH- opcionalmente sustituido, -C(O)-O-, -C(O)-N(Lb-R10b)-, -N=C(Lb-R10b)-; La y Lb son independientemente un enlace covalente o un alquileno C1-4; Wa, Wb, R10a, y R10b se definen en los párrafos (a) a (e) que siguen; (a) cuando Wa y Wb juntos son un ligante, entonces Xa o Xb son independientemente -O-, -S-, o -C(O)-O; R10a y R10b, respectivamente, están ausentes; o (b) cuando Wa y Wb juntos son un ligante, Xa es -N(La-R10a)-, -C(La-R10a)=CH-, -N=C(La-R10a)-, o -C(O)-N(La-R10a)-; Xb es -N(Lb- R10b)-, -C(Lb-R10b)=CH-, -N=C(Lb-R10b)-, o -C(O)-N(Lb-R10b)-; R10a y R10b son independientemente H o hidroxilo, alquilo, alquenilo, alquinilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituido, o (c) cuando Wa y Wb juntos son un ligante, Xa es -N(La-R10a)-, -C(La-R10a)=CH-, -N=C(La-R10a)-, o -C(O)-N(La-R10a)-; Xb es -N(Lb-R10b)-, -C(Lb-R10b)=CH-, -N=C(Lb-R10b)-, o -C(O)-N(Lb-R10b)-; R10a y R10b juntos son un ligante; o (d) cuando Wa y Wb no están covalentemente ligados, Wa y Wb son independientemente H, Cl, Br, F, CN, COOH, o hidroxilo, alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos; Xa es -N(La-R10a)-, -C(La-R10a)=CH-, -N=C(La-R10a)-, o -C(O)-N(La- R10a)-; Xb es -N(Lb-R10b)-, -C(Lb-R10b)=CH-, -N=C(Lb-R10b)-, o -C(O)-N(Lb-R10b)-; R10a y R10b juntos son un ligante; o ( e) cuando Wa y Wb no están covalentemente ligados, Wa es H, Cl, Br, F, CN, COOH, o hidroxilo, alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos; Xa es -N(La-R10a)-, -C(La-R10a)=CH-, -N=C(La-R10a)-, o -C(O)-N(La-R10a)-; Xb es -O-, -N(Lb-R10b)-, -S-, -C(Lb-R10b)=CH-, -C(O)-O, -N=C(Lb-R10b)-, -C(O)-N(Lb-R10b)-; y R10b está ausente o es H o hidroxilo, alquilo, cicloalquilo, heterocicloalquilo, arilo o heteroarilo opcionalmente sustituidos, y Wb y LaR10a juntos son un ligante; o una sal farmacéuticamente aceptable del mismo; con la condicion de que cuando Z1a es N y Z2a es CH, y Z1b es N y Zb2 CH, entonces, al menos uno de los siguientes es verdadero; (i) R5a y R6a no son ambos átomos de C ligados por un enlace covalente simple; (ii) R5a y R6a son ambos átomos de C ligados por un enlace covalente simple y R5a está disustituido; (iii) R5a y R6a son ambos átomos de C ligados por un enlace covalente simple y R6a está mono- o disustituido; (iv) R5a y R6a son ambos átomos de C ligados por un enlace covalente simple y R3a y R4a son ambos átomos de C ligados por un enlace covalente simple o por un grupo alquileno o alquenileno C1-8 opcionalmente sustituido donde 1 a 3 átomos de C pueden reemplazarse por N, O, S(O)n, o C=O; (v) R5a y R6a son ambos átomos de C ligados por un enlace covalente simple y ni R2a ni R2a' son H.
ARP070103286A 2006-07-24 2007-07-24 Dipeptidos antagonistas de iap, una composicion farmaceutica que los comprende y el uso de los mismos para el tratamiento del cancer. AR063943A1 (es)

Applications Claiming Priority (1)

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Country Link
US (2) US7985735B2 (es)
EP (2) EP2409984A1 (es)
JP (1) JP5228202B2 (es)
KR (1) KR20090041391A (es)
CN (1) CN101516904A (es)
AR (1) AR063943A1 (es)
AU (1) AU2007276760B2 (es)
BR (1) BRPI0715195A2 (es)
CA (1) CA2657706A1 (es)
CL (1) CL2007002167A1 (es)
IL (1) IL196423A0 (es)
MX (1) MX2009000824A (es)
NZ (1) NZ574311A (es)
WO (1) WO2008014263A2 (es)
ZA (1) ZA200900562B (es)

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WO2008014263A2 (en) 2008-01-31
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AU2007276760B2 (en) 2012-01-19
JP2009544728A (ja) 2009-12-17
CL2007002167A1 (es) 2009-01-23
AU2007276760A1 (en) 2008-01-31
US7985735B2 (en) 2011-07-26
WO2008014263A3 (en) 2008-03-13
US20080020986A1 (en) 2008-01-24
IL196423A0 (en) 2011-08-01
BRPI0715195A2 (pt) 2013-06-11
KR20090041391A (ko) 2009-04-28
EP2409984A1 (en) 2012-01-25
CA2657706A1 (en) 2008-01-31
US20110305777A1 (en) 2011-12-15
ZA200900562B (en) 2010-06-30
CN101516904A (zh) 2009-08-26
MX2009000824A (es) 2009-02-04
EP2049563A2 (en) 2009-04-22
EP2049563B1 (en) 2014-03-12

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