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AR040332A1 - Derivados de acido benzoico como moduladores de ppar alfa y gamma - Google Patents

Derivados de acido benzoico como moduladores de ppar alfa y gamma

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Publication number
AR040332A1
AR040332A1 ARP030102199A ARP030102199A AR040332A1 AR 040332 A1 AR040332 A1 AR 040332A1 AR P030102199 A ARP030102199 A AR P030102199A AR P030102199 A ARP030102199 A AR P030102199A AR 040332 A1 AR040332 A1 AR 040332A1
Authority
AR
Argentina
Prior art keywords
aryl
group
alkyl
optionally substituted
fluorine atoms
Prior art date
Application number
ARP030102199A
Other languages
English (en)
Inventor
Lanna Li
Original Assignee
Astrazeneca Ab
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 Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR040332A1 publication Critical patent/AR040332A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Diabetes (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Así como isómeros ópticos y racematos de los mismos, también sales, profármacos, solvatos y formas cristalinas aceptables para uso farmacéutico de los mismos, procesos para preparar dichos compuestos, su utilidad en el tratamiento de afecciones clínicas asociadas con resistencia a insulina, métodos para su uso terapéutico y composiciones farmacéuticas que contienen las mismas. Reivindicación 1: Un compuesto caracterizado porque responde a la fórmula (1) donde: R1 representa arilo sustituido optativamente con un grupo heterocíclico o un grupo heterocíclico sustituido optativamente con un arilo, donde cada arilo o grupo heterocíclico está sustituido optativamente con uno o varios de los siguientes grupos: un grupo alquilo C1-6; un grupo acilo C1-6; aril-alquilo(C1-6), donde el grupo alquilo, arilo o alquilarilo está sustituido optativamente con uno o varios Rb; halógeno, -CN y NO2, -NRcCOORa; -NRcCORa; -NRcRa; -NRcSO2Rd; -NRcCONRkRc; -NRcCSNRaRk; -ORa; -OSO2Rd; -SO2Rd; -SORd; -SRc; -SO2NRaRf; -SO2ORa; -CONRcRa; -OCONRfRa; donde Ra representa H, un grupo alquilo C1-6, un grupo arilo o aril-alquilo(C1-6) donde el grupo alquilo, arilo o aril-alquilo(C1-6) está sustituido optativamente una o más veces con Rb, donde Rb representa alquilo C1-6, arilo, aril-alquilo(C1-6), ciano, -NRcRd, =O, halo, -OH, -SH, -OC-alquilo(C1-4), -O-arilo, -O-alquilarilo C1-4, -CORc, -SRd, -SORd, o -SO2Rd, donde Rc representa H, alquilo C1-4, arilo, aril-alquilo C1-4 y Rd representa C1-4 alquilo, arilo, aril C1-4alquilo; donde Rf representa hidrógeno, alquilo C1-4, acilo C1-4, arilo, aril-alquilo(C1-4) y Ra es como se definió previamente; y Rk representa hidrógeno, alquilo C1-4, arilo, aril-alquilo(C1-4); el grupo -(CH2)mT-(CH2)m-U-(CH2)p- está unido ya sea en posición 3 ó 4 del anillo fenilo según se indica con los números en la fórmula (1) y representa un grupo seleccionado entre uno o varios de los siguientes grupos: -O(CH2)2, -O(CH2)3, NC(O)NR4(CH2)2, CH2S(O2)NR5(CH2), CH2N(R6)C(O)CH2, (CH2)2N(R6)C(O)(CH2)2, C(O)NR7CH2, C(O)NR7(CH2)2 y CH2N(R6)C(O)CH2O; V representa O, S, NR8 o a enlace simple; q representa 1, 2 ó 3; W representa O, S; N(R9)C(O), NR10 o un enlace simple; R2 representa halo, un grupo alquilo C1-4 que está sustituido optativamente con uno o varios átomos de flúor, un grupo alcoxi C1-4 que está sustituido optativamente con uno o varios átomos de flúor, un grupo acilo C1-4, arilo, un grupo aril-alquilo(C1-4), CN o NO2; r representa 0, 1, 2 ó 3; R3 representa halo, un grupo alquilo C1-4 que está sustituido optativamente con uno o varios átomos de flúor, un grupo alcoxi C1-4 que está sustituido optativamente con uno o varios átomos de flúor, un grupo acilo C1-4, arilo, un grupo aril-alquilo(C1-4) o CN; s representa 0, 1, 2, ó 3; y R4, R5, R6, R7, R8, R9 y R10 representan independientemente entre sí H, un grupo alquilo C1-10, arilo o un grupo aril-alquilo(C1-4) o, cuando m es 0 y T representa un grupo N(R6)C(O) o un grupo (R5)NS(O2) entonces R1 y R6 o R1 y R5 forman un grupo heteroarilo junto con el átomo de nitrógeno al cual están unidos; así como isómeros ópticos y racematos de los mismos, así como sales, profármacos, solvatos y formas cristalinas aceptables para uso farmacéutico de los mismos; con la condición que 1) cuando R1 es fenilo sustituido optativamente con uno o dos grupos seleccionados independientemente entre halo, un grupo alquilo C1-4 que está sustituido optativamente con uno o varios átomos de flúor, un grupo alcoxi C1-4 que está sustituido optativamente con uno o varios átomos de flúor; m es 1; T es N(R6)C(O) donde R6 representa un grupo alquilo C2-8 que está interrumpido optativamente con oxígeno; n es 1; U está ausente o representa metileno; p es 0; r es 0; V es O ó S; q es 1; y W es un enlace simple unido en posición orto al grupo ácido carboxílico, entonces s no representa 0; y 2) cuando R1 es fenilo sustituido optativamente con uno o dos grupos seleccionados independientemente entre halo, un grupo alquilo C1.4 que está sustituido optativamente con uno o varios átomos de flúor, un grupo alcoxi C1-4 que está sustituido optativamente con uno o varios átomos de flúor; m es 1; T es N(R6)C(O), donde R6 representa un grupo alquilo C2-7 no ramificado,; n es 1; U es O; p es 0; r es 0 ó 1; y cuando r es 1, R2 está unido en la posición 3 y es OCH3; V es un enlace simple; q es 2; y W es O ó S unido en posición orto al grupo ácido carboxílico; entonces s no representa 0.
ARP030102199A 2002-06-20 2003-06-20 Derivados de acido benzoico como moduladores de ppar alfa y gamma AR040332A1 (es)

Applications Claiming Priority (1)

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SE0201937A SE0201937D0 (sv) 2002-06-20 2002-06-20 Therapeutic agents

Publications (1)

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AR040332A1 true AR040332A1 (es) 2005-03-30

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US (1) US7521461B2 (es)
EP (1) EP1517680A1 (es)
JP (1) JP4327085B2 (es)
KR (1) KR20050014014A (es)
CN (1) CN100400512C (es)
AR (1) AR040332A1 (es)
AU (1) AU2003240101B2 (es)
BR (1) BR0311840A (es)
CA (1) CA2490687A1 (es)
IL (1) IL165672A0 (es)
IS (1) IS7639A (es)
MX (1) MXPA04012694A (es)
NO (1) NO20045222L (es)
NZ (1) NZ536972A (es)
PL (1) PL375078A1 (es)
RU (1) RU2339613C2 (es)
SE (1) SE0201937D0 (es)
TW (1) TW200403209A (es)
UA (1) UA77527C2 (es)
WO (1) WO2004000295A1 (es)
ZA (1) ZA200409690B (es)

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US7521461B2 (en) 2009-04-21
BR0311840A (pt) 2005-03-15
JP4327085B2 (ja) 2009-09-09
AU2003240101A1 (en) 2004-01-06
TW200403209A (en) 2004-03-01
SE0201937D0 (sv) 2002-06-20
NO20045222L (no) 2005-01-19
PL375078A1 (en) 2005-11-14
CN1662230A (zh) 2005-08-31
RU2339613C2 (ru) 2008-11-27
IL165672A0 (en) 2006-01-15
KR20050014014A (ko) 2005-02-05
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US20050267149A1 (en) 2005-12-01
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IS7639A (is) 2005-01-12
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CA2490687A1 (en) 2003-12-31
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