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AR032256A1 - Derivados de la urea como antagonistas de integrin alfa 4". - Google Patents

Derivados de la urea como antagonistas de integrin alfa 4".

Info

Publication number
AR032256A1
AR032256A1 ARP020100181A ARP020100181A AR032256A1 AR 032256 A1 AR032256 A1 AR 032256A1 AR P020100181 A ARP020100181 A AR P020100181A AR P020100181 A ARP020100181 A AR P020100181A AR 032256 A1 AR032256 A1 AR 032256A1
Authority
AR
Argentina
Prior art keywords
aryl
cycloalkyl
heteroaryl
4alkyl
heterocyclyl
Prior art date
Application number
ARP020100181A
Other languages
English (en)
Original Assignee
Almirall Prodesfarma Sa
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 Almirall Prodesfarma Sa filed Critical Almirall Prodesfarma Sa
Publication of AR032256A1 publication Critical patent/AR032256A1/es

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    • 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
    • C07D213/40—Acylated substituent nitrogen atom
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • 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
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    • 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
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    • 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
    • C07C275/40—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 nitrogen atoms not being part of nitro or nitroso groups
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    • C07C275/42—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 carboxyl groups
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Abstract

Un antagonista novedoso de integrin a4b1 y/o integrin a4b7 de la formula (1) o una sal farmacéuticamente aceptable de la misma, donde R1 es C3-10alquilo, C3-10alquenilo, C3-10alquinilo, cicloalquilo, cicloalquilo-C1-10alquilo, cicloalquilo-C2-10alquenilo, cicloalquilo-C2-10alquinilo, heterociclilo, heterociclilo-C1-10alquilo, heterociclilo-C2-10alquenilo, heterociclilo-C2-10alquinilo, arilo, arilo-C1-10alquilo, arilo-C2-10alquenilo, arilo-C2-10alquinilo, heteroarilo, heteroarilo-C1-10alquilo, heteroariloC2-10alquenilo, o heteroarilo- C2-10alquinilo; donde dichos grupos o fracciones alquilo, alquenilo y alquinilo son no sustituidos o sustituidos con desde uno a cuatro sustituyentes, los que pueden ser los mismos o diferentes y que son independientemente seleccionados desde Ra; y donde dichos grupos o fracciones cicloalquilo, heterociclilo, arilo, y heteroarilo son no sustituidos o sustituidos con desde uno a cuatro sustituyentes, los que pueden ser los mismos o diferentes y que son independientemente seleccionados desde Rb; R2 es hidrogeno, C1-6alquilo, C0-2-alquilocicloalquilo, C0-2alquilarilo, C0-2alquilheteroarilo, cicloalquil-C0-2alquilo, arilo-C0-2alquilo o heteroarilo-C0-2alquilo, donde dichos grupos o fracciones arilo y heteroarilo no son sustituidos o sustituidos desde uno hasta cuatro sustituyentes, los cuales pueden ser los mismos o diferentes y que son independientemente seleccionados desde Ra; R3 y R4 son independientemente hidrogeno o C1-4alquilo; R2 y R3 junto a los átomos a los que ellos están adjuntos pueden formar un anillo de 4 a 8 miembros; R5 es C1-6alquilo, cicloalquilo, cicloalquilo-C1-4alquilo, heterociclilo, heterociclilo-C1-4alquilo, arilo, arilo-C1-4alquilo, heteroarilo, o heteroarilo-C1-4alquilo; donde dichos grupos o fracciones alquilo son no sustituidos o sustituidos con desde uno hasta cuatro sustituyentes, los cuales pueden ser los mismos o diferentes y que son independientemente seleccionados desde Ra; donde dichos grupos o fracciones cicloalquilo, heterociclilo, arilo y heteroarilo son no sustituidos o sustituidos con desde uno hasta cuatro sustituyentes, los cuales pueden ser los mismos o diferentes y que son independientemente seleccionados desde Rb; L1 es ûS-, -S(O)-, -S(O)2-, -C(O)-, -C(O)O-, -C(S)-, -N(Rc)-, CH2-, -CH2N(Rc)-, -CON(Rc)-, CSN(Rc)-, -N(Rc)CO-, -N(Rc)CS-, -S(O)2N(Rc)- o ûN(Rc)S(O)2-; L2 es una union covalente, -O-, -S-, -S(O)-, -S(O)2-, -C(O)-, -C(O)O-, -OC(O)-, -C(S)-, -N(Rc)-, -CON(Rc)-, -OC(O)N(Rc), -CSN(Rc)-, N(Rc)CO-, -N(Rc)C(O)O-, -N(Rc)CS-, -S(O)2N(Rc)-, -S(O)2N(Rc)-, -N(Rc)S(O)2-, -N(Rc)CON(Rc)-, o N(Rc)CSN(Rc)-, donde si dos sustituyentes Rc están presentes ellos pueden ser lo mismos o diferentes; W es O, S, NH, N(Rc) o NCN; X es û(CH2)arilo o û(CH2)n heteroarilo-; donde dichos grupos o fracciones arilo y heteroarilo son no sustituidos o sustituidos con desde uno a cuatro sustituyentes, los cuales pueden ser los mismos o diferentes y que son independientemente seleccionados desde Rb; Y es arilo monocíclico o heteroarilo monocíclico conteniendo uno o dos heteroátomos seleccionados desde N, O y S, donde dichas fracciones arilo y heteroarilo son no sustituidos o sustituidos con desde uno a cuatro sustituyentes, los cuales pueden ser los mismos o diferentes y que son independientemente seleccionados desde Rb; Z es ûC(O)ORd, -P(O)2Ord, -S(O)2ORd, -S(O)2N(Rd)(Rd), -C(O)NH2, -C(O)N(Re)S(O)2Rd, -S(O)2N(Re)C(O)Rd, -5-tetrazolilo, o ûC(O)Rd; donde si dos grupos Rd están presentes ellos pueden ser los mismos o diferentes; Ra es ûOH, -ORe, -NO2, halogeno, -S(O)Re, -S(O)2Re, -SRe, -S(O)2ORe, -S(O)NReRe, -S(O)2NReRe, -NReRe, -O(CReRe)mNReRe, -C(O)Re, CO2Re, -CO2 (CReRe)nCONReRe, -OC(O)Re, -CN, -C(O)NReRe, -NReC(O)Re, -OC(O)NReRe, -NReC(O)ORe, -NReC(O)NReRe, -CRe(N-ORe), -CFH2, -CF2HRa, o ûCF3; donde si dos grupos Re están presentes ellos pueden ser lo mismo o diferentes; Rb es un grupo seleccionado desde: -OH, ORe, -NO2, halogeno, -S(O)Re, -S(O)2Re, -SRe, -S(O)2ORe, -S(O)NReRe, -S(O)2NReRe, -NReRe,-O(CReRe)mNReRe, -C(O)Re, -CO2Re, -CO2(CReRe)mCONReRe, -OC(O)Re, -CN, -C(O)NReRe, -NReC(O)Re, -OC(O)NReRe, -NReC(O)ORe, -NReC(O)NReRe, -CRe(N-ORe), -CFH2 ûCF2H,Ra, -CF3, C1-6alquilo, C2-4 alquenilo, C2-4alquinilo, cicloalquilo, cicloalquilo-C1-4alquilo, heterociclilo, heteociclilo-C1-4alquilo, arilo, arilo-C1-4alquilo, heteroarilo o heteroarilo C1-4alquilo; donde dichos grupos o fracciones alquilo, alquenilo, alquinilo, cicloalquilo, heterociclilo, arilo y heteroarilo son no sustituidos o sustituidos con desde uno hasta cuatro sustituyentes los cuales pueden ser los mismos o diferentes y que son independientemente seleccionados de Ra; Rc es hidrogeno, C1-10alquilo o cicloalquilo; donde dichos grupos o fracciones de alquilo o cicloalquilo son no-sustituidos o sustituidos con desde uno hasta cuatro sustituyentes los que pueden ser los mismos o diferentes y son seleccionados de Ra; Rd es hidrogeno, C1-6alquilo, cicloalquilo, cicloalquilo-C1-4alquilo, heterociclilo-C1-4alquilo, arilo, arilo-C1-4-alquilo, heteroarilo, o heteroarilo-C1-4alquilo; donde dichos grupos o fracciones de alquilo, cicloalquilo, heterociclilo, arilo y heteroarilo son no-sustituidos o sustituidos con desde uno hasta cuatro sustituyentes los que pueden ser los mismos o diferentes y son independientemente seleccionados de Ra; Re es hidrogeno o C1-4alquilo; n es un entero de 0 a 2; m es un entero de 1 a 6.
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