AR044934A1 - DERIVATIVES OF PROPIOANILIDS, ITS USE AS MODULATORS OF ANDROGEN RECEPTORS. PHARMACEUTICAL COMPOSITIONS. - Google Patents

DERIVATIVES OF PROPIOANILIDS, ITS USE AS MODULATORS OF ANDROGEN RECEPTORS. PHARMACEUTICAL COMPOSITIONS.

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Publication number
AR044934A1
AR044934A1 ARP040102263A ARP040102263A AR044934A1 AR 044934 A1 AR044934 A1 AR 044934A1 AR P040102263 A ARP040102263 A AR P040102263A AR P040102263 A ARP040102263 A AR P040102263A AR 044934 A1 AR044934 A1 AR 044934A1
Authority
AR
Argentina
Prior art keywords
alkyl
halo
alkenyl
aryl
independently
Prior art date
Application number
ARP040102263A
Other languages
Spanish (es)
Original Assignee
Orion Corp
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
Priority claimed from FI20030958A external-priority patent/FI20030958A0/en
Application filed by Orion Corp filed Critical Orion Corp
Publication of AR044934A1 publication Critical patent/AR044934A1/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
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • C07C235/04—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 being acyclic and saturated
    • C07C235/18—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 being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/24—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 being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides 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
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • 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
    • 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
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen 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
    • 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
    • C07C323/10—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 singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—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 singly-bound oxygen atoms 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
    • C07C323/20—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 singly-bound oxygen atoms 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 with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • 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
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/68—One oxygen atom attached in position 4

Abstract

Los compuestos de fórmula (1) tienen utilidad como moduladores del receptor androgénico (SARM) con selectividad tisular y son útiles para la terapia hormonal, por ejemplo en el tratamiento o prevención del hipogonadismo masculino y condiciones relacionadas con la edad tales como la andropausia. Reivindicación 1: Compuestos caracterizados porque responden a la fórmula (1) en donde R1 es (C1-7)alquilo, hidroxi(C1-7)alquilo o -(CH2)n-CHO, en donde n es 0-6; R2 es nitro, ciano o halógeno; R3 es H, (C1-7)alquilo o halo(C1-7)alquilo; R4 es H, (C1-7)alquilo, COR10 o SO2R13; X es O o NH; A es un grupo seleccionado entre: los compuestos de formulas (2) en donde R5, R6, R7, R8 y R9 son en forma independiente H, halógeno, nitro, ciano, (C1-7)alquilo, halo(C1-7)alquilo, ciano(C1-7)alquilo, amino, mono- o di(C1-7)alquilamino, amino(C1-7)alquilo, hidroxi(C1-7)alquilo, (C1-7)alcoxi(C1-7)alquilo, -NHCOR10, -N(COR10)2, -COR11-, OR12, -OSO2R13, -SO2R14, -NHSO2R13 o -SR15 o un anillo imida, o R5 y R6, R6 y R7, R7 y R8, o R8 y R9 forman junto con cualquiera del o los átomo/s del anillo al que están unidos, un anillo carbocíclico alifático o aromático condensado de 5 a 7 miembros o un anillo heterocíclico condensado de 5 a 7 miembros que contiene 1 a 3 heteroátomo/s seleccionados entre N, O y S; R10 y R11 son en forma independiente (C1-7)alquilo, (C2-7)alquenilo, halo(C1-7)alquilo, amino(C1-7)alquilo, mono- o di(C1-7)alquilamino(C1-7)alquilo, (C6-10)arilo, -N(R16)2 o -OR17; R12 y R15 son de forma independiente H, (C1-7)alquilo, (C2-7)alquenilo, halo(C1-7)alquilo, amino (C1-7)alquilo, mono- o di(C1-7)alquilamino(C1-7)alquilo, (C6-10)arilo, -COR18; R13 y R14 son de forma independiente (C1-7)alquilo o (C2-7)alquenilo, halo(C1-7)alquilo 0 (C6-10)arilo; R16 y R17 son de forma independiente H, (C1-7)alquilo, (C2-7)alquenilo, halo(C1-7)alquilo, amino(C1-7)alquilo o (C6-10)arilo; r18 es (C1-7)alquilo, (C2-7)alquenilo, halo(C1-7)alquilo o (C6-10)arilo; R19 y R20 son en forma independiente H, halógeno,(C1-7)alquilo o (C2-7)alquenilo; y en donde cada arilo o residuo del anillo según se ha definido puede estar sustituido, y sus sales y ésteres aceptables para uso farmacéutico.The compounds of formula (1) have utility as androgenic receptor modulators (MRSA) with tissue selectivity and are useful for hormonal therapy, for example in the treatment or prevention of male hypogonadism and age-related conditions such as andropause. Claim 1: Compounds characterized in that they respond to formula (1) wherein R1 is (C1-7) alkyl, hydroxy (C1-7) alkyl or - (CH2) n-CHO, wherein n is 0-6; R2 is nitro, cyano or halogen; R3 is H, (C1-7) alkyl or halo (C1-7) alkyl; R4 is H, (C1-7) alkyl, COR10 or SO2R13; X is O or NH; A is a group selected from: the compounds of formulas (2) wherein R5, R6, R7, R8 and R9 are independently H, halogen, nitro, cyano, (C1-7) alkyl, halo (C1-7) alkyl, cyano (C1-7) alkyl, amino, mono- or di (C1-7) alkylamino, amino (C1-7) alkyl, hydroxy (C1-7) alkyl, (C1-7) alkoxy (C1-7) alkyl, -NHCOR10, -N (COR10) 2, -COR11-, OR12, -OSO2R13, -SO2R14, -NHSO2R13 or -SR15 or an imide ring, or R5 and R6, R6 and R7, R7 and R8, or R8 and R9 together with any of the atom (s) of the ring to which they are attached, an aliphatic or aromatic carbocyclic ring fused from 5 to 7 members or a fused heterocyclic ring of 5 to 7 members containing 1 to 3 heteroatom / s selected from N, O and S; R10 and R11 are independently (C1-7) alkyl, (C2-7) alkenyl, halo (C1-7) alkyl, amino (C1-7) alkyl, mono- or di (C1-7) alkylamino (C1- 7) alkyl, (C6-10) aryl, -N (R16) 2 or -OR17; R12 and R15 are independently H, (C1-7) alkyl, (C2-7) alkenyl, halo (C1-7) alkyl, amino (C1-7) alkyl, mono- or di (C1-7) alkylamino ( C1-7) alkyl, (C6-10) aryl, -COR18; R13 and R14 are independently (C1-7) alkyl or (C2-7) alkenyl, halo (C1-7) alkyl 0 (C6-10) aryl; R16 and R17 are independently H, (C1-7) alkyl, (C2-7) alkenyl, halo (C1-7) alkyl, amino (C1-7) alkyl or (C6-10) aryl; r18 is (C1-7) alkyl, (C2-7) alkenyl, halo (C1-7) alkyl or (C6-10) aryl; R19 and R20 are independently H, halogen, (C1-7) alkyl or (C2-7) alkenyl; and wherein each aryl or ring residue as defined may be substituted, and its salts and esters acceptable for pharmaceutical use.

ARP040102263A 2003-06-27 2004-06-25 DERIVATIVES OF PROPIOANILIDS, ITS USE AS MODULATORS OF ANDROGEN RECEPTORS. PHARMACEUTICAL COMPOSITIONS. AR044934A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48271303P 2003-06-27 2003-06-27
FI20030958A FI20030958A0 (en) 2003-06-27 2003-06-27 New compounds

Publications (1)

Publication Number Publication Date
AR044934A1 true AR044934A1 (en) 2005-10-12

Family

ID=33553916

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP040102263A AR044934A1 (en) 2003-06-27 2004-06-25 DERIVATIVES OF PROPIOANILIDS, ITS USE AS MODULATORS OF ANDROGEN RECEPTORS. PHARMACEUTICAL COMPOSITIONS.

Country Status (9)

Country Link
KR (1) KR20060035629A (en)
AR (1) AR044934A1 (en)
DE (1) DE602004026583D1 (en)
HK (1) HK1093964A1 (en)
HR (1) HRP20060036B1 (en)
IL (1) IL172279A0 (en)
IS (1) IS2752B (en)
MX (1) MXPA05013619A (en)
NO (1) NO332252B1 (en)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE28864T1 (en) * 1982-07-23 1987-08-15 Ici Plc AMIDE DERIVATIVES.
ATE423092T1 (en) * 2000-08-24 2009-03-15 Univ Tennessee Res Foundation SELECTIVE MODULATORS OF THE ANDROGEN RECEPTOR AND METHODS OF USE THEREOF
DK1463497T3 (en) * 2001-12-06 2012-01-30 Gtx Inc Treatment of muscle wasting with selective androgen receptor modulators
EP1480634B1 (en) * 2002-02-07 2011-08-03 University of Tennessee Research Foundation Selective androgen receptor modulators (SARMs) for treating benign prostate hyperplasia

Also Published As

Publication number Publication date
MXPA05013619A (en) 2006-03-10
IS2752B (en) 2011-09-15
IL172279A0 (en) 2006-04-10
NO332252B1 (en) 2012-08-06
NO20060227L (en) 2006-01-16
KR20060035629A (en) 2006-04-26
HK1093964A1 (en) 2007-03-16
IS8256A (en) 2006-01-23
HRP20060036A2 (en) 2006-03-31
HRP20060036B1 (en) 2014-04-25
DE602004026583D1 (en) 2010-05-27

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