AR063277A1 - SPIROHETEROCICLIC COMPOUNDS AND USES AS THERAPEUTIC AGENTS - Google Patents

SPIROHETEROCICLIC COMPOUNDS AND USES AS THERAPEUTIC AGENTS

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Publication number
AR063277A1
AR063277A1 ARP070104538A ARP070104538A AR063277A1 AR 063277 A1 AR063277 A1 AR 063277A1 AR P070104538 A ARP070104538 A AR P070104538A AR P070104538 A ARP070104538 A AR P070104538A AR 063277 A1 AR063277 A1 AR 063277A1
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Argentina
Prior art keywords
heteroaryl
aryl
heterocyclyl
aralkyl
alkyl
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ARP070104538A
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Spanish (es)
Inventor
Mehran Seid Bagherzadeh
Mikhall Chafeev
Robert Fraser
Jianmin Fu
Rajender Kamboj
Sultan Chowdhury
Shifeng Liu
Jianyu Sum
Serguei Sviri
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Xenon Pharmaceuticals Inc
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Publication of AR063277A1 publication Critical patent/AR063277A1/en

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    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • 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
    • A61P35/00—Antineoplastic agents

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compuestos para el tratamiento y/o prevencion de hipercolesterolemia, hiperplasia prostática benigna, prurito y cáncer. Reivindicacion 1: Un método para el tratamiento o la prevencion de hipercolesterolemia en un mamífero, caracterizado porque comprende administrar al mamífero que lo necesita una cantidad terapéuticamente efectiva de un compuesto de formula (1), en donde: p es entre 1 y 4; j y k son cada uno en forma independiente 0, 1, 2 o 3; Q es -C(R1a)H-, -C(O)-, -O-, -S-, -N(R5)-, - CF2-, -C(O)O-, -C(O)N(R5)- o - N(R5)C(O)-; R1a es hidrogeno o -OR5; el anillo A es un anillo heteroarilo fusionado o un anillo heterociclilo fusionado; R1 es hidrogeno, alquilo, alquenilo, alquinilo, haloalquilo, arilo, cicloalquilo, cicloalquilalquilo, heteroarilo, heterociclilo, -R8-OR5, -R8-CN, -R9-P(O)(OR5)2, o -R9-O-R9-OR5; o R1 es aralquilo sustituido con -C(O)N(R6)R7 donde: R6 es hidrogeno, alquilo, arilo o aralquilo; y R7 es hidrogeno, alquilo, haloalquilo, -R9-CN, -R9- OR5, -R9-N(R4)R5, arilo, aralquilo, cicloalquilo, cicloalquilalquilo, heterociclilo, heterociclilalquilo, heteroarilo, heteroarilalquilo; o R6 y R7, junto con el nitrogeno al cual se encuentran unidos, forman un heterociclilo o heteroarilo; y en donde cada grupo arilo, aralquilo, cicloalquilo, cicloalquilalquilo, heterociclilo, heterociclilalquilo, heteroarilo y heteroarilo para R6 y R7 se puede sustituir opcionalmente con uno o más sustituyentes seleccionados entre el grupo que consiste de alquilo, cicloalquilo, arilo, aralquilo, halo, haloalquilo, -R8-CN, -R8-OR5, heterociclilo y heteroarilo; o R1 es aralquilo opcionalmente sustituido con -R8-OR5, -C(O)OR5, halo, haloalquilo, alquilo, nitro, ciano, arilo (sustituido opcionalmente con ciano), aralquilo (sustituido opcionalmente con uno o más grupos alquilo), heterociclilo o heteroarilo; o R1 es -R9-N(R10)R11, -R9-N(R12)C(O)R11 o -R9-N(R10)C(O)N(R10)R11 donde: cada R10 es hidrogeno, alquilo, arilo o aralquilo; cada R11 es hidrogeno, alquilo, haloalquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, heterociclilo, heterociclilalquilo. heteroarilo, heteroarilalquilo, -R9-OC(O)R5, -R9-C(O)OR5, -R9-C(O)N(R4)R5, -R9-C(O)R5, -R9-OR5, o -R9-CN; R12 es hidrogeno, alquilo, arilo, aralquilo o -C(O)R5; y en donde cada grupo arilo, aralquilo, cicloalquilo, cicloalquilalquilo, heterociclilo, heterociclilalquilo, heteroarilo y heteroarilalquilo para R10 y R11 se puede sustituir opcionalmente con uno o más sustituyentes seleccionados entre el grupo que consiste de alquilo, cicloalquilo, arilo, aralquilo, halo, haloalquilo, nitro, -R8-CN, -R8-OR5, -R8-C(O)R5, heterociclilo y heteroarilo; o R1 es heterociclilalquilo o heteroarilalquilo donde el grupo heterociclilalquilo o heteroarilalquilo está opcionalmente sustituido por uno o más sustituyentes seleccionados entre el grupo que consiste de alquilo, halo, haloalquilo, -R8-OR5, -R8-C(O)OR5, arilo y aralquilo; cada R2 se selecciona en forma independiente entre el grupo que consiste de hidrogeno, alquilo, alquenilo, alquinilo, alcoxi, halo, haloalquilo, haloalquenilo, haloalcoxi, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, aralquenilo, heterociclilo, heterociclilalquilo, heteroarilo, heteroarilalquilo, -R8-CN, -R8-NO2, -R8-OR5, -R8-N(R4)R5, -N=C(R4)R5, -S(O)mR4, -R8-C(O)R4, -C(S)R4, -C(R4)2C(O)R5, -R8-C(O)OR4, -C(S)OR4. -R8-C(O)N(R4)R5, -C(S)N(R4)R5, -N(R5)C(O)R4, -N(R5)C(S)R4, -N(R5)C(O)OR4, -N(R5)C(S)OR4, - N(R5)C(O)N(R4)R5, -N(R5)C(S)N(R4)R5, -N(R5)S(O)nR4, -N(R5)S(O)nN(R4)R5, -R8-S(O)nN(R4)R5, -N(R5)C(=NR5)N(R4)R5, y -N(R5)C(=N-CN)N(R4)R5, en donde cada m es en forma independiente 0, 1, o 2 y cada n es en forma independiente 1 o 2; y en donde cada uno de los grupos cicloalquilo, cicloalquilalquilo, arilo, aralquilo, aralquenilo, heterociclilo, heterociclilalquilo, heteroarilo y heteroarilalquilo para cada R2 se puede sustituir opcionalmente con uno o más sustituyentes seleccionados entre el grupo que consiste de alquilo, alquenilo, alquinilo, alcoxi, halo, haloalquilo, haloalquenilo, haloalcoxi, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, aralquenilo, heterociclilo, heterociclilalquilo, heteroarilo, heteroarilalquilo, -R8-CN, - R8-NO2, -R8-OR5, -R8-N(R4)R5, -S(O)mR4, -R8-C(O)R4, -R8-C(O)OR4, -R8-C(O)N(R4)R5, -N(R5)C(O)R4, y -N(R5)S(O)nR4, en donde cada m es en forma independiente 0, 1, o 2 y cada n es en forma independiente 1 o 2; o dos grupos R2 adyacentes junto con los átomos del anillo heteroarilo fusionado o del anillo heterociclilo fusionado a los cuales se encuentran unidos directamente, pueden formar un anillo fusionado seleccionado entre cicloalquilo, arilo, heterociclilo y heteroarilo, y los grupos R2 restantes, si se encuentran presentes, son de la manera que se ha descrito; R3a, R3b, R3c y R3d cada uno se selecciona en forma independiente entre el grupo que consiste de hidrogeno, alquilo, alquenilo, alquinilo, alcoxi, halo, haloalquilo, haloalquenilo, haloalcoxi, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, aralquenilo, heterociclilo, heterociclilalquilo, heteroarilo, heteroarilalquilo, -R8-CN, -R8-NO2, -R8-OR5, -R8-N(R4)R5, -N=C(R4)R5, - S(O)mR4, -R8-C(O)R4, -C(S)R4, - C(R4)2C(O)R5, R8-C(O)OR4, -C(S)OR4, -R8-C(O)N(R4)R5, -C(S)N(R4)R5, -N(R5)C(O)R4, -N(R5)C(S)R4, -N(R5)C(O)OR4, -N(R5)C(S)OR4, -N(R5)C(O)N(R4)R5, -N(R5)C(S)N(R4)R5, -N(R5)S(O)nR4, -N(R5)S(O)nN(R4)R5, -R8-S(O)nN(R4)R5, -N(R5)C(=NR5)N(R4)R5, y - N(R5)C(N=C(R4)R5)N(R4)R5, en donde cada m es en forma independiente 0, 1, o 2 y cada n es en forma independiente 1 o2; o R3a y R3b, o R3b y R3c, o R3c y R3d, junto con los átomos de carbono del anillo a los cuales están unidos directamente, pueden formar un anillo fusionado seleccionado entre cicloalquilo, heterociclilo, arilo o heteroarilo, y el grupo R3a, R3b, R3c o R3d restante es como se define precedentemente; cada R4 y R5 se selecciona en forma independiente entre grupo que consiste de hidrogeno, alquilo, alquenilo, alquinilo, haloalquilo, alcoxialquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, heterociclilo y heteroarilo; o cuando R4 y R5 cada se une al mismo átomo de nitrogeno, luego R4 y R5 junto con el átomo de nitrogeno al cual se encuentran unidos, pueden formar un heterociclilo o heteroarilo; y cada R8 en un enlace directo o una cadena alquileno lineal o ramificada, una cadena alquenileno lineal o ramificada o una cadena alquinileno lineal o ramificada; y cada R9 es una cadena alquileno lineal o ramificada, una cadena alquenileno lineal o ramificada o una cadena alquinileno lineal o ramificada; como un estereoisomero, enantiomero, tautomero del mismo o mezclas de los mismos; o una sal aceptable para uso farmacéutico, solvato o prodroga del mismo.Compounds for the treatment and / or prevention of hypercholesterolemia, benign prostatic hyperplasia, pruritus and cancer. Claim 1: A method for the treatment or prevention of hypercholesterolemia in a mammal, characterized in that it comprises administering to the mammal in need a therapeutically effective amount of a compound of formula (1), wherein: p is between 1 and 4; j and k are each independently 0, 1, 2 or 3; Q is -C (R1a) H-, -C (O) -, -O-, -S-, -N (R5) -, - CF2-, -C (O) O-, -C (O) N (R5) - or - N (R5) C (O) -; R1a is hydrogen or -OR5; Ring A is a fused heteroaryl ring or a fused heterocyclyl ring; R1 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, aryl, cycloalkyl, cycloalkylalkyl, heteroaryl, heterocyclyl, -R8-OR5, -R8-CN, -R9-P (O) (OR5) 2, or -R9-O- R9-OR5; or R1 is aralkyl substituted with -C (O) N (R6) R7 where: R6 is hydrogen, alkyl, aryl or aralkyl; and R7 is hydrogen, alkyl, haloalkyl, -R9-CN, -R9- OR5, -R9-N (R4) R5, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl; or R6 and R7, together with the nitrogen to which they are attached, form a heterocyclyl or heteroaryl; and wherein each aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl and heteroaryl group for R6 and R7 may optionally be substituted with one or more substituents selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, halo, haloalkyl, -R8-CN, -R8-OR5, heterocyclyl and heteroaryl; or R1 is aralkyl optionally substituted with -R8-OR5, -C (O) OR5, halo, haloalkyl, alkyl, nitro, cyano, aryl (optionally substituted with cyano), aralkyl (optionally substituted with one or more alkyl groups), heterocyclyl or heteroaryl; or R1 is -R9-N (R10) R11, -R9-N (R12) C (O) R11 or -R9-N (R10) C (O) N (R10) R11 where: each R10 is hydrogen, alkyl, aryl or aralkyl; each R11 is hydrogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, heterocyclylalkyl. heteroaryl, heteroarylalkyl, -R9-OC (O) R5, -R9-C (O) OR5, -R9-C (O) N (R4) R5, -R9-C (O) R5, -R9-OR5, or -R9-CN; R12 is hydrogen, alkyl, aryl, aralkyl or -C (O) R5; and wherein each aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl and heteroarylalkyl group for R10 and R11 may optionally be substituted with one or more substituents selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, halo, haloalkyl, nitro, -R8-CN, -R8-OR5, -R8-C (O) R5, heterocyclyl and heteroaryl; or R1 is heterocyclylalkyl or heteroarylalkyl where the heterocyclylalkyl or heteroarylalkyl group is optionally substituted by one or more substituents selected from the group consisting of alkyl, halo, haloalkyl, -R8-OR5, -R8-C (O) OR5, aryl and aralkyl ; each R2 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halo, haloalkyl, haloalkenyl, haloalkoxy, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aralkenyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaryl-heteroaryl-heteroaryl-heteroaryl R8-CN, -R8-NO2, -R8-OR5, -R8-N (R4) R5, -N = C (R4) R5, -S (O) mR4, -R8-C (O) R4, -C (S) R4, -C (R4) 2C (O) R5, -R8-C (O) OR4, -C (S) OR4. -R8-C (O) N (R4) R5, -C (S) N (R4) R5, -N (R5) C (O) R4, -N (R5) C (S) R4, -N (R5 ) C (O) OR4, -N (R5) C (S) OR4, - N (R5) C (O) N (R4) R5, -N (R5) C (S) N (R4) R5, -N (R5) S (O) nR4, -N (R5) S (O) nN (R4) R5, -R8-S (O) nN (R4) R5, -N (R5) C (= NR5) N (R4 ) R5, and -N (R5) C (= N-CN) N (R4) R5, where each m is independently 0, 1, or 2 and each n is independently 1 or 2; and wherein each of the cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aralkenyl, heterocyclyl, heterocyclylalkyl, heteroaryl and heteroarylalkyl groups for each R2 may optionally be substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, halo, haloalkyl, haloalkenyl, haloalkoxy, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aralkenyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl, -R8-CN, - R8-NO2, -R8-OR5, -R8-R5 (-R8) R5, -S (O) mR4, -R8-C (O) R4, -R8-C (O) OR4, -R8-C (O) N (R4) R5, -N (R5) C (O) R4 , and -N (R5) S (O) nR4, where each m is independently 0, 1, or 2 and each n is independently 1 or 2; or two adjacent R2 groups together with the atoms of the fused heteroaryl ring or of the fused heterocyclyl ring to which they are directly attached, can form a fused ring selected from cycloalkyl, aryl, heterocyclyl and heteroaryl, and the remaining R2 groups, if found present, they are as described; R3a, R3b, R3c and R3d are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halo, haloalkyl, haloalkenyl, haloalkoxy, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aralkenyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl, -R8-CN, -R8-NO2, -R8-OR5, -R8-N (R4) R5, -N = C (R4) R5, - S (O) mR4, -R8-C (O) R4, -C (S) R4, - C (R4) 2C (O) R5, R8-C (O) OR4, -C (S) OR4, -R8-C (O) N (R4) R5 , -C (S) N (R4) R5, -N (R5) C (O) R4, -N (R5) C (S) R4, -N (R5) C (O) OR4, -N (R5) C (S) OR4, -N (R5) C (O) N (R4) R5, -N (R5) C (S) N (R4) R5, -N (R5) S (O) nR4, -N ( R5) S (O) nN (R4) R5, -R8-S (O) nN (R4) R5, -N (R5) C (= NR5) N (R4) R5, and - N (R5) C (N = C (R4) R5) N (R4) R5, where each m is independently 0, 1, or 2 and each n is independently 1 or 2; or R3a and R3b, or R3b and R3c, or R3c and R3d, together with the carbon atoms of the ring to which they are directly attached, can form a fused ring selected from cycloalkyl, heterocyclyl, aryl or heteroaryl, and the group R3a, R3b, R3c or R3d remaining is as defined above; each R4 and R5 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl and heteroaryl; or when R4 and R5 each bind to the same nitrogen atom, then R4 and R5 together with the nitrogen atom to which they are attached, they can form a heterocyclyl or heteroaryl; and each R8 in a direct bond or a linear or branched alkylene chain, a linear or branched alkenylene chain or a linear or branched alkynylene chain; and each R9 is a linear or branched alkylene chain, a linear or branched alkenylene chain or a linear or branched alkynylene chain; as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a salt acceptable for pharmaceutical, solvate or prodrug use thereof.

ARP070104538A 2006-10-12 2007-10-12 SPIROHETEROCICLIC COMPOUNDS AND USES AS THERAPEUTIC AGENTS AR063277A1 (en)

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