AR058779A1 - Derivados de tiazol y oxazol como inhibidores de ptp-1b, composiciones farmaceuticas - Google Patents

Derivados de tiazol y oxazol como inhibidores de ptp-1b, composiciones farmaceuticas

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Publication number
AR058779A1
AR058779A1 ARP060104051A ARP060104051A AR058779A1 AR 058779 A1 AR058779 A1 AR 058779A1 AR P060104051 A ARP060104051 A AR P060104051A AR P060104051 A ARP060104051 A AR P060104051A AR 058779 A1 AR058779 A1 AR 058779A1
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Argentina
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alkyl
group
aryl
iii
halo
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ARP060104051A
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Torrent Pharmaceuticals Ltd
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Publication of AR058779A1 publication Critical patent/AR058779A1/es

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6536Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539Five-membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42Oxazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425Thiazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/48Drugs for disorders of the endocrine system of the pancreatic hormones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D263/48Nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38Nitrogen atoms
    • C07D277/42Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/06Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic 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
    • C07D413/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/12Heterocyclic 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 chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

La presente también comprende un proceso para preparar dicho compuesto, composiciones farmacéuticas y métodos para el tratamiento o la prevención de enfermedades causadas por la PTP-1B. Composiciones farmacéuticas. Reivindicación 1: Un compuesto representado por la fórmula (1) donde: A es un miembro seleccionado del grupo formado por las fórmulas (2) a (38); B es un resto seleccionado del grupo de fórmulas (39); L se selecciona entre -NH-, -NH-CH₂-, -NH-CH(CH₃)-, -NH-CH-C(O)NH-, -NH-CH₂-CH₂-, -NHNH-, -NH-CH(COOH)-CH₂, -N(CH₂COOH)-; C es un miembro seleccionado del grupo formado por (i) fenilo, (ii) naftilo, (iii) indolilo, (iv) tiazolilo, y (v) bencimidazolilo; Y se selecciona del grupo formado por las fórmulas (40) a (43); p es 1, 2 ó 3; R¹ se selecciona del grupo formado por: i) H, ii) -CH₂COOR⁴, iii) -X(CH₂)ₙ-arilo, donde n se selecciona entre 0, 1 ó 2, y X se selecciona entre S, NH u O, iv) -S-alquilo, v) -OR⁴, vi) OCH₂-cicloalquilo, donde cicloalquilo se selecciona entre ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, cicloheptilo o ciclooctilo, vii) -CH₂CONH₂, viii) -CN, ix) halo, x) alquilo, xi) -SO₂-arilo, xii) -CF₃, xiii) -CO₂R⁴, xiv) -CO-alquilo, xv) -NH₂, xvi) -NO₂, xvii) -CH₂CONH-PhCH₂COOR⁴, xviii) tetrazolilo, xix) triazolilo, xx) pirrolilo, xxi) bencimidazolilo, xxii) pirazolilo, xxiii) ftalamoilo, xxiv) fenilo opcionalmente sustituido con uno o más grupos seleccionados entre ciano, amino, carboxi, halo, nitro, alquilo, hidroxilo, -O-alquilo, xxv) bifenilo, xxvi) -OCH₂CO₂R⁴, xxvii) piridilo, xxviii) tienilo, xxix) dimetilamino, xxx) -CH₂OH, xxxi) -CF₂H, xxxii) -SO₂NHR⁴, xxxiii) NHCO-alquilo, xxxiv) -OCF₃, o es un resto seleccionado del grupo de fórmulas (44), donde X es como se definió anteriormente; R² y R³ son seleccionados independientemente del grupo formado por: i) H, ii) -CH₂COOR⁴, iii) -S-alquilo, iv) -OR⁴, v) -CH₂CONH₂, vi) -CN, vii) halo, viii) alquilo, ix) -CF₃, x) -COOR⁴, xi) arilo, xii) -CO-alquilo, xiii) -NH₂, xiv) -NO₂, xv) -CF₂H, xvi) tienilo, xvii) NHCO-alquilo, y xviii) -OCF₃; R⁴ se selecciona entre H o alquilo; R⁵ se selecciona del grupo formado por i) -COOR⁴, donde R⁴ es como se definió anteriormente, ii) -C(O)C(O)OH, o iii) un compuesto de fórmula (45), donde Z se selecciona entre arilo o heteroarilo, opcionalmente sustituido por un grupo seleccionado independientemente entre H, alquilo, halo, nitro, -OR⁴, CF₃ y CONHR⁴, iv) un resto de fórmula (46), v) un resto de fórmula (47), vi) -CONHOH, vii) -SO₂NHCO-alquilo, viii) -SO₂NH-alquilo, ix) -CONHSO₂-alquilo, x) OH, xi) -NHCO-alquilo, y xii) -SO₂NHR⁴; R⁶ se selecciona del grupo formado por i) H, ii) -OR⁴, iii) alquilo, iv) halo, v) heterociclilo, vi) -S-alquilo, vii) -S-arilo, viii) -COOH, ix) bencilo, y x) heteroarilo; R⁷ se selecciona del grupo formado por: i) alquilo, ii) H, y iii) halo; o R⁶ y R⁷ juntos pueden formar un anillo cicloalcano seleccionado del grupo de ciclopentano, ciclohexano, ciclobutano; R⁸ y R⁹ son seleccionados independientemente del grupo formado por: i) H, ii) halo, iii) -OR⁴, iv) alquilo, v) -CONHR⁴, vi) -COOR⁴, y vii) -CO-alquilo; R¹⁰ se selecciona del grupo formado por: i) alquilo, ó ii) arilo; R¹¹ se selecciona del grupo formado por: i) H, ii) alquilo, y iii) arilo; y con la condición de que: a) cuando R⁵ es -C(O)C(O)OH, entonces Y es el resto de fórmula (40), y p es nulo; b) cuando A es fenilo y está sustituido por R¹ en la posición cuarta entonces R¹ no es -X(CH₂)ₙ-arilo; o una sal farmacéuticamente aceptable o prodroga del mismo.
ARP060104051A 2005-09-16 2006-09-15 Derivados de tiazol y oxazol como inhibidores de ptp-1b, composiciones farmaceuticas AR058779A1 (es)

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IN860KO2005 2005-09-16

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AR058779A1 true AR058779A1 (es) 2008-02-20

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US (1) US20090088432A1 (es)
EP (1) EP1934192A1 (es)
JP (1) JP2009508848A (es)
KR (1) KR20080056730A (es)
CN (1) CN101268060A (es)
AR (1) AR058779A1 (es)
AU (1) AU2006290250A1 (es)
BR (1) BRPI0616217A2 (es)
CA (1) CA2622518A1 (es)
RU (1) RU2008114836A (es)
TW (1) TW200745066A (es)
WO (1) WO2007032028A1 (es)
ZA (1) ZA200802078B (es)

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CN102617564B (zh) * 2012-01-19 2015-04-29 西安交通大学 一种化合物及其制备方法
CN104059060B (zh) * 2014-05-30 2017-08-01 西安交通大学 一种5‑(1h‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用
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KR101911785B1 (ko) * 2016-08-09 2018-10-26 세종대학교 산학협력단 Ampk 억제기능에 기반한 뇌졸중 치료용 약학적 조성물
CN106946744B (zh) * 2017-03-17 2019-05-24 上海交通大学 一种新型ptp1b酶抑制剂及其制备方法和应用
CN112336719A (zh) * 2020-10-19 2021-02-09 济南大学 一种噻唑衍生物作为α-葡萄糖苷酶抑制剂及其应用

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EP1802614A1 (en) 2004-10-14 2007-07-04 F. Hoffmann-Roche AG Quinazolinylmethylenethiazolinones as cdk1 inhibitors
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WO2006047269A2 (en) 2004-10-22 2006-05-04 Exelixis, Inc. Pharmaceutical compositions

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ZA200802078B (en) 2009-08-26
BRPI0616217A2 (pt) 2011-06-14
AU2006290250A1 (en) 2007-03-22
EP1934192A1 (en) 2008-06-25
JP2009508848A (ja) 2009-03-05
WO2007032028A1 (en) 2007-03-22
WO2007032028A8 (en) 2008-07-17
CN101268060A (zh) 2008-09-17
US20090088432A1 (en) 2009-04-02
RU2008114836A (ru) 2009-10-27
KR20080056730A (ko) 2008-06-23
TW200745066A (en) 2007-12-16
CA2622518A1 (en) 2007-03-22

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