AR073881A1 - PRAZOLOPIRIMIDINE DERIVATIVES ANTAGONIST RECEIVER H4 - Google Patents

PRAZOLOPIRIMIDINE DERIVATIVES ANTAGONIST RECEIVER H4

Info

Publication number
AR073881A1
AR073881A1 ARP090103979A ARP090103979A AR073881A1 AR 073881 A1 AR073881 A1 AR 073881A1 AR P090103979 A ARP090103979 A AR P090103979A AR P090103979 A ARP090103979 A AR P090103979A AR 073881 A1 AR073881 A1 AR 073881A1
Authority
AR
Argentina
Prior art keywords
alkyl
aryl
optionally substituted
groups
heteroaryl
Prior art date
Application number
ARP090103979A
Other languages
Spanish (es)
Inventor
Bernado Marina Virgili
Gonzalez Elena Carceller
Original Assignee
Palau Pharma 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 Palau Pharma Sa filed Critical Palau Pharma Sa
Publication of AR073881A1 publication Critical patent/AR073881A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Abstract

Derivados de pirazolopirimidina utiles como antagonistas del receptor H4 de la histamina. Se proveen además composiciones farmacéuticas que los comprenden, su uso en la fabricacion de un medicamento para el tratamiento de enfermedades relacionadas y un proceso para su preparacion. Reivindicacion 1: Un compuesto caracterizado por la formula (1) donde: R1 y R2 forman, junto con el átomo de N al que estén unidos, un grupo heterocíclico saturado seleccionado de: (i) un grupo heterocíclico que contiene 2 átomos de N y no contiene ningun otro heteroátomo, donde dicho grupo heterocíclico puede estar opcionalmente sustituido con uno o más grupos alquilo C1-4; y (ii) un grupo heterocíclico que contiene 1 átomo de N y no contiene ningun otro heteroátomo, donde dicho grupo heterocíclico está sustituido con un grupo -NRaRb y puede estar opcionalmente sustituido con uno o más grupos alquilo C1-4; pudiendo ser dichos grupos heterocíclicos (i) y (ii) monocíclicos de 4 a 7 miembros, bicíclicos con puente de 7 a 8 miembros o bicíclicos condensados de 8 a 12 miembros; o R1 representa H o alquilo C1-4, y R2 representa azetidinilo, pirrolidinilo, piperidinilo o azepanilo, que puede estar opcionalmente sustituido con uno o más grupos alquilo C1-4; Ra representa H o alquilo C1-4; Rb representa H o alquilo C1-4; o Ra y Rb forman, junto con el átomo de N al que están unidos, un grupo azetidinilo, pirrolidinilo, piperidinilo o azepanilo que puede estar opcionalmente sustituido con uno o más grupos alquilo C1-4; R3 representa H o NH2; R5 puede estar situado o en N1 o N2 del anillo de pirazol; cuando R5 está unido a N1, o R4 representa R6 y R5 representa R7, o R4 representa R7 y R5 representa R8, o R4 y R5 pueden estar unidos juntos formando un grupo alquileno C3-5 que puede estar opcionalmente sustituido con uno o más grupos alquilo C1-8; cuando R5 está unido a N2, R4 representa R6 y R5 representa R7; R6 representa H, alquilo C1-11, cicloalquil C3-8-alquilo C0-11, heterocicloalquil C3-8-alquilo C0-11, aril-C0-11alquilo, heteroaril-C0-11alquilo, aril-NH-alquilo C0-11, heteroaril-NH-alquilo C0-11, R9-alquilo C0-11 o R10-W-alquilo C0-11; R7 representa H, alquilo C1-6, cicloalquil C3-8-alquilo C0-6, alcoxi C1-6-alquilo C1-6 o (cicloalquil C3-8-alquil C0-6)-O-alquilo C1-6, R8 representa cicloalquil C3-8-alquilo C0-11, heterocicloalquil C3-8-alquilo C0-11, aril-C0-11alquilo, heteroaril-C0-11alquilo, aril-NH-alquilo C2-11, heteroaril-NH-alquilo C2-11, R9-alquilo C2-11 o R10-W-alquilo C2-11; R9 representa -CONR11R11, -NR11COR11, -NR11SO2R11, -SO2NR11R11, -NR11CONR11R11, -CONHSO2R11, -CO2R11, -SO2R11, -NR11R11 o 1H-tetrazol-5-ilo; R10 representa H, alquilo C1-11, R11-O-alquilo C1-11, cicloalquil C3-8-alquilo C0-11, heterocicloalquil C3-8-alquilo C0-11, aril-C0-11-alquilo, heteroaril-C0-11 alquilo, aril-NH-C2-11 alquilo, heteroaril-NH-C2-11 alquilo o R9-C1-11 alquilo; R11 representa H, alquilo C1-6, cicloalquil C3-8-alquilo C0-6 o aril-C0-6-alquilo; W representa O, S, SO o SO2; donde, en R6, R8 y R10 cualquier grupo alquilo puede estar opcionalmente sustituido con uno o más átomos de halogeno, y cualquier grupo cicloalquilo y heterocicloalquilo pueden estar opcionalmente sustituidos con uno o más sustituyentes seleccionados independientemente de alquilo C1-6, halogeno, arilo y R9; arilo representa fenilo opcionalmente sustituido con uno o más grupos R12; heteroarilo representa un anillo aromático, monocíclico de 5 o 6 miembros o bicíclico de 8 a 12 miembros, que contiene hasta cuatro heteroátomos seleccionados independientemente de nitrogeno, oxigeno y azufre, que puede estar opcionalmente sustituido con uno o más grupos R12; y cada R12 representa independientemente alquilo C1-6, halogeno, alcoxi C1-6, haloalquilo C1-6, haloalcoxi C1-6, CN, hidroxi-C0-6 alquilo, CO2R11-alquilo C0-6, CONHSO2R11-alquilo C1-6, (1H-tetrazol-5-il)-alquilo C0-6, -CONR11R11, -SO2NR11R11, -SO2-alquilo C1-6, -NR11SO2-alquilo C1-6, -NR11CONR11R11, -NR11COR11 o -NR11R11; o una de sus sales.Pyrazolopyrimidine derivatives useful as histamine H4 receptor antagonists. Pharmaceutical compositions are also provided that comprise them, their use in the manufacture of a medicament for the treatment of related diseases and a process for their preparation. Claim 1: A compound characterized by the formula (1) wherein: R1 and R2 form, together with the N atom to which they are attached, a saturated heterocyclic group selected from: (i) a heterocyclic group containing 2 N atoms and it does not contain any other heteroatom, wherein said heterocyclic group may be optionally substituted with one or more C1-4 alkyl groups; and (ii) a heterocyclic group containing 1 N atom and not containing any other heteroatom, wherein said heterocyclic group is substituted with a -NRaRb group and may be optionally substituted with one or more C1-4 alkyl groups; said heterocyclic (i) and (ii) monocyclic groups having 4 to 7 members, bicyclics with bridges of 7 to 8 members or condensed bicyclics of 8 to 12 members; or R1 represents H or C1-4 alkyl, and R2 represents azetidinyl, pyrrolidinyl, piperidinyl or azepanyl, which may be optionally substituted with one or more C1-4 alkyl groups; Ra represents H or C1-4 alkyl; Rb represents H or C1-4 alkyl; or Ra and Rb together with the N atom to which they are attached, an azetidinyl, pyrrolidinyl, piperidinyl or azepanyl group which may be optionally substituted with one or more C1-4 alkyl groups; R3 represents H or NH2; R5 may be located or in N1 or N2 of the pyrazole ring; when R5 is attached to N1, or R4 represents R6 and R5 represents R7, or R4 represents R7 and R5 represents R8, or R4 and R5 can be joined together forming a C3-5 alkylene group which may be optionally substituted with one or more groups C1-8 alkyl; when R5 is attached to N2, R4 represents R6 and R5 represents R7; R 6 represents H, C 1-11 alkyl, C 3-8 cycloalkyl-C 0-11 alkyl, C 3-8 heterocycloalkyl-C 0-11 alkyl, aryl-C 0-11 alkyl, heteroaryl-C 0-11 alkyl, aryl-NH-C 0-11 alkyl, heteroaryl-NH-C0-11 alkyl, R9-C0-11 alkyl or R10-W-C0-11 alkyl; R7 represents H, C1-6 alkyl, C3-8 cycloalkyl-C0-6 alkyl, C1-6 alkoxy-C1-6 alkyl or (cycloalkyl C3-8-C0-6 alkyl) -O-C1-6 alkyl, R8 represents C3-8 cycloalkyl-C0-11 alkyl, heterocycloalkyl C3-8-C0-11 alkyl, aryl-C0-11 alkyl, heteroaryl-C0-11 alkyl, aryl-NH-C2-11 alkyl, heteroaryl-NH-C2-11 alkyl, R9-C2-11 alkyl or R10-W-C2-11 alkyl; R9 represents -CONR11R11, -NR11COR11, -NR11SO2R11, -SO2NR11R11, -NR11CONR11R11, -CONHSO2R11, -CO2R11, -SO2R11, -NR11R11 or 1H-tetrazol-5-yl; R10 represents H, C1-11 alkyl, R11-O-C1-11 alkyl, C3-8 cycloalkyl-C0-11 alkyl, C3-8 heterocycloalkyl-C0-11 alkyl, aryl-C0-11-alkyl, heteroaryl-C0- 11 alkyl, aryl-NH-C2-11 alkyl, heteroaryl-NH-C2-11 alkyl or R9-C1-11 alkyl; R11 represents H, C1-6 alkyl, C3-8 cycloalkyl-C0-6 alkyl or aryl-C0-6-alkyl; W represents O, S, SO or SO2; where, in R6, R8 and R10 any alkyl group may be optionally substituted with one or more halogen atoms, and any cycloalkyl and heterocycloalkyl group may be optionally substituted with one or more substituents independently selected from C1-6 alkyl, halogen, aryl and R9; aryl represents phenyl optionally substituted with one or more R12 groups; heteroaryl represents an aromatic, monocyclic 5 or 6 membered or bicyclic ring of 8 to 12 members, containing up to four heteroatoms independently selected from nitrogen, oxygen and sulfur, which may be optionally substituted with one or more R12 groups; and each R12 independently represents C1-6 alkyl, halogen, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, CN, hydroxy-C0-6 alkyl, CO2R11-C0-6 alkyl, CONHSO2R11-C1-6 alkyl, (1H-tetrazol-5-yl) -C0-6 alkyl, -CONR11R11, -SO2NR11R11, -SO2-C1-6 alkyl, -NR11SO2-C1-6 alkyl, -NR11CONR11R11, -NR11COR11 or -NR11R11; or one of its salts.

ARP090103979A 2008-10-15 2009-10-15 PRAZOLOPIRIMIDINE DERIVATIVES ANTAGONIST RECEIVER H4 AR073881A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08382043 2008-10-15
US14028208P 2008-12-23 2008-12-23

Publications (1)

Publication Number Publication Date
AR073881A1 true AR073881A1 (en) 2010-12-09

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AR (1) AR073881A1 (en)
TW (1) TW201026701A (en)
WO (1) WO2010043633A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012027495A1 (en) 2010-08-27 2012-03-01 University Of The Pacific Piperazinylpyrimidine analogues as protein kinase inhibitors
CA3028751A1 (en) 2016-07-01 2018-01-04 G1 Therapeutics, Inc. Pyrimidine-based antiproliferative agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL2000291C2 (en) * 2005-11-10 2009-02-17 Pfizer Prod Inc 1- (1- (2-ethoxyethyl) -3-ethyl-7- (4-methylpyridin-2-ylamino) -1 H -pyrazole (4,3-d) pyrimidin-5-yl) piperidine-4-carboxylic acid and salts thereof.
KR101315610B1 (en) * 2006-09-22 2013-10-10 파마시클릭스, 인코포레이티드 Inhibitors of bruton's tyrosine kinase
US8735411B2 (en) * 2006-10-02 2014-05-27 Abbvie Inc. Macrocyclic benzofused pyrimidine derivatives

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TW201026701A (en) 2010-07-16

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