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AR077726A1 - MODULATORS OF RECEPTORS OF THYROID HORMONE, PHARMACEUTICAL COMPOSITIONS, USE AND PROCESS OF PREPARATION OF SUCH COMPOUNDS - Google Patents

MODULATORS OF RECEPTORS OF THYROID HORMONE, PHARMACEUTICAL COMPOSITIONS, USE AND PROCESS OF PREPARATION OF SUCH COMPOUNDS

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Publication number
AR077726A1
AR077726A1 ARP100100050A ARP100100050A AR077726A1 AR 077726 A1 AR077726 A1 AR 077726A1 AR P100100050 A ARP100100050 A AR P100100050A AR P100100050 A ARP100100050 A AR P100100050A AR 077726 A1 AR077726 A1 AR 077726A1
Authority
AR
Argentina
Prior art keywords
groups
formula
alkyl
compound
aryl
Prior art date
Application number
ARP100100050A
Other languages
Spanish (es)
Inventor
Saurin Raval
Preeti Raval
Mukul Jain
Original Assignee
Cadila Healthcare Ltd
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Filing date
Publication date
Application filed by Cadila Healthcare Ltd filed Critical Cadila Healthcare Ltd
Publication of AR077726A1 publication Critical patent/AR077726A1/en

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    • 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
    • C07C233/81—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 carboxyl groups
    • C07C233/82—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/83—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than 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 carboxyl groups
    • 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
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic 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
    • C07C275/32—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 singly-bound oxygen atoms
    • C07C275/34—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 singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C275/36—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 singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
    • 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
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Reivindicacion 1: Un compuesto de la formula (1), sus tautomeros o sales farmacéuticamente aceptables caracterizado porque en donde R = OR1, NHR1, en donde R1 se selecciona de H o grupos seleccionados de grupos alquilo(C1-6)Ar, alquilo C1-6, cada uno de estos grupos se sustituyen además mediante sustituyentes adecuados; R2 representa hidrogeno, grupos hidroxilo, halo, acilo, oxo o grupos opcionalmente sustituidos seleccionados de alquilo C1-6, alcoxi, cicloalquilo C3-7, arilo, heteroarilo, ariloxi, aralquilo, aralcoxi, ácido carboxílico y sus derivados seleccionados de ésteres y amidas de alquilo C1-3, derivados de sulfenilo, derivados de sulfonilo o R2 se selecciona de grupos que representan -CONR5R6, -SO2NR5R6, en donde R5 y R6 son iguales o diferentes y en cada aparicion se seleccionan independientemente de H, o grupos seleccionados de grupos alquilo C1-6, cicloalquilo C3-7, bicicloalquilo, arilo, cada uno de estos grupos se sustituye adicionalmente por sustituyentes adecuados; o los grupos R5 y R6 junto con el átomo de nitrogeno al cual están unidos forman un anillo cíclico de cinco a ocho miembros que además y opcionalmente contiene uno o más heteroátomos seleccionados de N, S, O; R3, R4 pueden ser iguales o distintos y en cada aparicion se seleccionan independientemente de H, halogeno o grupos alquilo C1-6, que además se sustituyen con sustituyentes adecuados; 'X' representa O, -CH2-, CO; 'Z' representa un enlace o enlazador adecuado seleccionado de NH o -(CH2)n en donde 'n' representa un entero 0-2; 'Y' representa grupos seleccionados de grupos alquilo, arilo, heteroarilo, heterociclilo o cicloalquilo, cada uno de estos grupos se sustituyen además por sustituyentes adecuados; R7 se selecciona de H o grupos seleccionados de grupos alquilo C1-6, cicloalquilo C3-7, acilo, arilo, aralquilo, heteroarilo, cada uno de estos grupos se sustituye además por sustituyentes adecuados; R8 se selecciona de OR9, NHR9 o NHOH en donde, R9 en cada aparicion se selecciona de H o grupos seleccionados de alquilo C1-6, que se sustituye además con sustituyentes adecuados. Reivindicacion 10: Una composicion farmacéutica caracterizada porque comprende una cantidad terapéuticamente efectiva de un compuesto de la formula (1), tal como se reivindica en cualquiera de las reivindicaciones precedentes y un vehículo, diluyente farmacéuticamente aceptable o excipientes. Reivindicacion 13: El uso de un compuesto de la formula (1) o su composicion farmacéutica de acuerdo con cualquiera de las reivindicaciones precedentes caracterizado para la fabricacion de un medicamento para el tratamiento de la obesidad y la dislipidemia. Reivindicacion 17: Un proceso para preparar compuestos de la formula (1) caracterizado porque R2 es alquilo, arilo, R5R6NCO-, R5R6NSO2-, Z= -(CH2)n-, R8=OH, que consiste en los siguientes pasos: i) reducir el éter de biarilo adecuado de la formula (2), en donde ôGPö representa grupos protectores adecuados para dar la amina correspondiente de la formula (3); ii) hacer reaccionar la amina de la formula 3 con haloacetato de alquilo adecuado en una base o bases adecuadas en solventes adecuados para dar un compuesto de la formula (4), en donde ôAkö representa un grupo alquilo adecuado; iii) hacer reaccionar el compuesto de la formula (4) con ClCO(CH2)nY, en donde ôYö es como se definio anteriormente, en presencia de una base adecuada en solventes inertes para dar el compuesto de la formula (5), iv) desproteccion e hidrolisis del compuesto de la formula (5) para dar el compuesto de la formula (1).Claim 1: A compound of the formula (1), its tautomers or pharmaceutically acceptable salts characterized in that where R = OR1, NHR1, wherein R1 is selected from H or groups selected from alkyl groups (C1-6) Ar, C1 alkyl -6, each of these groups is further substituted by suitable substituents; R2 represents hydrogen, hydroxyl groups, halo, acyl, oxo or optionally substituted groups selected from C1-6 alkyl, alkoxy, C3-7 cycloalkyl, aryl, heteroaryl, aryloxy, aralkyl, aralkoxy, carboxylic acid and their derivatives selected from esters and amides of C1-3 alkyl, sulfenyl derivatives, sulfonyl derivatives or R2 is selected from groups representing -CONR5R6, -SO2NR5R6, where R5 and R6 are the same or different and in each occurrence they are independently selected from H, or groups selected from C1-6 alkyl, C3-7 cycloalkyl, bicycloalkyl, aryl groups, each of these groups is further substituted by suitable substituents; or the R5 and R6 groups together with the nitrogen atom to which they are attached form a five to eight membered cyclic ring that additionally and optionally contains one or more heteroatoms selected from N, S, O; R3, R4 may be the same or different and in each occurrence they are independently selected from H, halogen or C1-6 alkyl groups, which are also substituted with suitable substituents; 'X' represents O, -CH2-, CO; 'Z' represents a suitable linker or linker selected from NH or - (CH2) n where 'n' represents a 0-2 integer; 'Y' represents groups selected from alkyl, aryl, heteroaryl, heterocyclyl or cycloalkyl groups, each of these groups are further substituted by suitable substituents; R7 is selected from H or groups selected from C1-6 alkyl, C3-7 cycloalkyl, acyl, aryl, aralkyl, heteroaryl groups, each of these groups is further substituted by suitable substituents; R8 is selected from OR9, NHR9 or NHOH wherein, R9 in each occurrence is selected from H or selected groups of C1-6 alkyl, which is further substituted with suitable substituents. Claim 10: A pharmaceutical composition characterized in that it comprises a therapeutically effective amount of a compound of the formula (1), as claimed in any of the preceding claims and a carrier, pharmaceutically acceptable diluent or excipients. Claim 13: The use of a compound of the formula (1) or its pharmaceutical composition according to any of the preceding claims characterized for the manufacture of a medicament for the treatment of obesity and dyslipidemia. Claim 17: A process for preparing compounds of the formula (1) characterized in that R2 is alkyl, aryl, R5R6NCO-, R5R6NSO2-, Z = - (CH2) n-, R8 = OH, consisting of the following steps: i) reduce the suitable biaryl ether of the formula (2), wherein "GPö" represents suitable protecting groups to give the corresponding amine of the formula (3); ii) reacting the amine of the formula 3 with suitable alkyl haloacetate in a suitable base or bases in suitable solvents to give a compound of the formula (4), wherein "Akö" represents a suitable alkyl group; iii) reacting the compound of the formula (4) with ClCO (CH2) nY, wherein "Y" is as defined above, in the presence of a suitable base in inert solvents to give the compound of the formula (5), iv) deprotection and hydrolysis of the compound of the formula (5) to give the compound of the formula (1).

ARP100100050A 2009-01-09 2010-01-08 MODULATORS OF RECEPTORS OF THYROID HORMONE, PHARMACEUTICAL COMPOSITIONS, USE AND PROCESS OF PREPARATION OF SUCH COMPOUNDS AR077726A1 (en)

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CN116745279A (en) * 2021-02-02 2023-09-12 株式会社Lg化学 Novel compounds as protein kinase inhibitors

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GB9828442D0 (en) 1998-12-24 1999-02-17 Karobio Ab Novel thyroid receptor ligands and method II
US6344481B1 (en) 1999-03-01 2002-02-05 Pfizer Inc. Thyromimetic antiobesity agents
US6787652B1 (en) 1999-09-30 2004-09-07 Pfizer, Inc. 6-Azauracil derivatives as thyroid receptor ligands
TR200202249T2 (en) 2000-03-31 2003-01-21 Pfizer Products Inc. Malonic acids and their derivatives as thyroid receptor ligands
TW200504021A (en) * 2003-01-24 2005-02-01 Bristol Myers Squibb Co Substituted anilide ligands for the thyroid receptor
JP2007512359A (en) 2003-11-19 2007-05-17 メタバシス・セラピューティクス・インコーポレイテッド Novel phosphorus-containing thyroid hormone-like substance
RU2007148927A (en) 2005-05-26 2009-07-10 Метабэйзис Терапьютикс, Инк. (Us) NEW TYREOMIMETICS CONTAINING PHOSPHIC ACID
CA2606499C (en) 2005-05-26 2017-06-13 Metabasis Therapeutics, Inc. Thyromimetics for the treatment of fatty liver diseases
WO2007132475A1 (en) 2006-05-15 2007-11-22 Cadila Healthcare Limited Selective tr-beta 1 agonist
WO2008021210A2 (en) 2006-08-11 2008-02-21 Combinatorx, Incorporated Methods and compositions for the treatment of neurodegenerative disorders
PT2079678E (en) * 2006-10-31 2013-03-05 Cadila Healthcare Ltd Selective tr-beta 1 agonist
WO2009089093A1 (en) 2008-01-04 2009-07-16 Quatrx Pharmaceuticals Company Thyroid hormone receptor agonists

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