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AR052666A1 - DERIVATIVES OF 1H-IMIDAZOL AS MODULATORS OF THE CANNABINOID CB2 RECEIVER - Google Patents

DERIVATIVES OF 1H-IMIDAZOL AS MODULATORS OF THE CANNABINOID CB2 RECEIVER

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Publication number
AR052666A1
AR052666A1 ARP060100463A ARP060100463A AR052666A1 AR 052666 A1 AR052666 A1 AR 052666A1 AR P060100463 A ARP060100463 A AR P060100463A AR P060100463 A ARP060100463 A AR P060100463A AR 052666 A1 AR052666 A1 AR 052666A1
Authority
AR
Argentina
Prior art keywords
group
substituted
alkyl
substituents
hydroxy
Prior art date
Application number
ARP060100463A
Other languages
Spanish (es)
Inventor
Josephus H M Lange
Stuivenberg Herman H Van
Vliet Bernard J Van
Original Assignee
Solvay Pharm Bv
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 Solvay Pharm Bv filed Critical Solvay Pharm Bv
Publication of AR052666A1 publication Critical patent/AR052666A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Se refiere a un grupo de derivados de 1H-imidazol que son moduladores de receptores cannabinoides CB2, a métodos para la preparacion de estos compuestos, a nuevos compuestos intermedios utiles para la síntesis de dichos derivados de imidazol, a métodos para la preparacion de estos compuestos intermedios, a composiciones farmacéuticas que contienen uno o más de estos derivados de 1H-imidazol como ingrediente activo, como así también al uso de estas composiciones farmacéuticas para el tratamiento de trastornos en los cuales están implicados receptores cannabinoides CB2. Reivindicacion 1: compuestos derivados de 1H-imidazol, caracterizados por la formula general (1) donde R1 representa H o halogeno o alquilo C1-3, alquilo C1-3 que puede contener 1-3 átomos de F o un grupo hidroxi o amino, o R1 representa alquinilo C2-3, alquenilo C2-3, alquinilo C2-3 o alquinilo C2-3 que puede contener 1-3 átomos de F, o R1 representa acetilo, ciclopropilo, ciano, metilsulfonilo, etilsulfonilo, metilsulfinilo, etilsulfinilo, trifluorometilsulfanilo, metilsulfanilo, etilsulfanilo, formilo o heteroalquilo C2-4; R2 representa fenilo que puede estar substituido con 1, 2, 3, 4 o 5 sustituyentes Y, que pueden ser iguales o diferentes, seleccionados del grupo formado por metilo, etilo, propilo, metoxi, etoxi, hidroxi, Cl, I, Br, F, trifluorometilo, trifluorometoxi, metilsulfonilo, carbamoilo, fenilo y ciano, o R2 representa heteroarilo, heteroarilo que puede estar sustituido con 1, 2, o 3 sustituyentes Y, donde Y tiene el significado arriba definido, con la condicion de que R2 no es un grupo 6-metil-2-piridilo, o R2 representa un sistema anular carbocíclico de 4-10 miembros, mono- insaturado o completamente saturado, monocíclico, bicíclico fusionado o tricíclico fusionado, o R2 representa un sistema anular heterocíclico de 4-10 miembros, mono-insaturado o completamente saturado, monocíclico, bicíclico fusionado o tricíclico fusionado, sistema anular carbocíclico o heterocíclico que puede estar sustituido con 1-5 sustituyentes seleccionados entre metilo, etilo, amino, hidroxi o F, o R2 representa un grupo de formula general CH2-R5 donde R5 representa fenilo que está sustituido con 1, 2, 3, 4 o 5 sustituyentes y arriba definidos, o R5 representa un heteroarilo o un grupo 1,2,3,4-tetrahidronaftilo o indanilo, heteroarilo o grupo 1,2,3,4-tetrahidronaftilo o indanilo que puede estar sustituido con 1, 2 o 3 sustituyentes Y arriba definidos o R5 representa un sistema anular carbocíclico de 4-10 miembros, mono-insaturado o completamente saturado, monocíclico, bicíclico fusionado o tricíclico fusionado, o R5 representa un sistema anular heterocíclico de 4-10 miembros, mono-insaturado o completamente saturado, monocíclico, bicíclico fusionado o tricíclico fusionado, sistemas anulares carbocíclicos o heterocíclicos opcionalmente sustituidos con 1-5 sustituyentes seleccionados del grupo formado por metilo, etilo, amino, hidroxi o F, o R2 representa un grupo metilsulfonilaminoalquilo, metilsulfonilalquilo o acetamidoalquilo; R3 representa H o halogeno o un grupo formilo, alquilsulfonilo C1-6, alquilsulfinilo C1-6, alquilsulfanilo C1-6, trifluorometilsulfanilo, bencilsulfanilo, o ciano, o R3 representa alquilo C1-8, alquilo C1-8 que puede estar sustituido con 1-5 sustituyentes seleccionados del grupo formado por F, hidroxi o amino, o R3 representa alquinilo C2-6, alquenilo C2-6, alcanoilo C1-6, cicloalquilo C3-8, heterocicloalquilo C5-8 o heteroalquilo C2-6, grupos que están opcionalmente sustituidos con 1-3 grupos metilo, etilo, amino o hidroxi o con 1-3 átomos de F, o R3 representa fenilo que está sustituido con 1-5 sustituyentes Y, donde Y tiene el significado arriba definido, o R3 representa un grupo heteroarilo, heteroarilo que puede estar sustituido con 1, 2 o 3 sustituyentes Y, donde Y tiene el significado arriba definido, o R3 representa bencilo o heteroarilmetilo, bencilo o heteroarilmetilo que puede estar sustituido con 1, 2 o 3 sustituyentes Y; R4 representa uno de los subgrupos (i) o (ii) donde R6 representa alquilo C4-8 ramificado o lineal, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-2, heterocicloalquil C5-7- alquilo C1-2, bicicloalquilo C5-10, bicicloalquil C5-10-alquilo C1-2, heterobicicloalquil C5-10-alquilo C1-2, tricicloalquilo C6-10, tricicloalquil C6-10-alquilo C1-2, heterotricicloalquil C6-10-alquilo C1-2, grupos que pueden estar sustituidos con 1-5 sustituyentes seleccionados de metilo, hidroxi, etilo, trifluormetilo o F, o R6 representa fenilo, bencilo, naftilo o fenetilo, grupos que pueden estar sustituidos en su sistema anular aromático con 1-3 sustituyentes Y arriba definidos, con la condicion de que R6 no es un grupo 2-metilfenilo, o R6 representa un grupo piridilo o tienilo; R7 representa H o alquilo C1-6 lineal, alquilo C1-6 lineal que puede estar sustituido con 1-3 átomos de F o R7 representa un grupo isopropilo, naftilmetilo o heteroariletilo que puede estar sustituido con 1-3 sustituyentes Y, donde Y tiene el significado arriba mencionado, o R8 representa un grupo piperidinilo, azepanilo, morfolinilo, azabiciclo[3.3.0]octanilo, 4-hidroxipiperidinilo o pirrolidinilo, con la condicion de que R8 ni es un grupo 6-metoxi-benzotiazol-2-ilo ni un grupo [3-cloro-5-(trifluorometil)pirid-2-il]metilo, o R7 y R8 -conjuntamente con el átomo de N al cual están ligados- forman un grupo heterocíclico monocíclico, bicíclico o tricíclico, no aromático o parcialmente aromático, saturado o no saturado, que tiene de 7 a 10 átomos en el anillo, grupo heterocíclico monocíclico, bicíclico o tricíclico, no aromático o parcialmente aromático, saturado o no saturado que puede estar sustituido con 1-5 sustituyentes seleccionados del grupo formado por alquilo C1-3, hidroxi, metoxi, ciano, fenilo, trifluorometilo o halogeno, o R7 y R8 -conjuntamente con el átomo de N al cual están ligados- forman un grupo heterocíclico monocíclico saturado, que contiene opcionalmente otro heteroátomo (seleccionado entre N, O S), que tiene de 5 a 6 átomos en el anillo, grupo heterocíclico que está sustituido con 1-5 sustituyentes seleccionados del grupo formado por alquilo C1-3, hidroxi, amino, fenilo, bencilo o F, con la condicion de que R7 y R8 -conjuntamente con el átomo de N al cual están ligados- no forman un grupo azabiciclo[3.2.1]octanilo trimetil- sustituido, y los tautomeros, estereoisomeros y N- oxidos de los mismos, como así también a las sales, hidratos y solvatos farmacologicamente aceptables de dichos compuestos de formula (1) y sus tautomeros, estereoisomeros y N-oxidos.It refers to a group of 1H-imidazole derivatives that are modulators of CB2 cannabinoid receptors, to methods for the preparation of these compounds, to new intermediate compounds useful for the synthesis of said imidazole derivatives, to methods for the preparation of these compounds intermediates, to pharmaceutical compositions containing one or more of these 1H-imidazole derivatives as an active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of disorders in which CB2 cannabinoid receptors are involved. Claim 1: compounds derived from 1H-imidazole, characterized by the general formula (1) wherein R 1 represents H or halogen or C 1-3 alkyl, C 1-3 alkyl which may contain 1-3 F atoms or a hydroxy or amino group, or R1 represents C2-3 alkynyl, C2-3 alkenyl, C2-3 alkynyl or C2-3 alkynyl which may contain 1-3 F atoms, or R1 represents acetyl, cyclopropyl, cyano, methylsulfonyl, ethylsulfonyl, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfanyl , methylsulfanyl, ethylsulfanyl, formyl or C2-4 heteroalkyl; R2 represents phenyl which may be substituted with 1, 2, 3, 4 or 5 substituents Y, which may be the same or different, selected from the group consisting of methyl, ethyl, propyl, methoxy, ethoxy, hydroxy, Cl, I, Br, F, trifluoromethyl, trifluoromethoxy, methylsulfonyl, carbamoyl, phenyl and cyano, or R2 represents heteroaryl, heteroaryl that may be substituted with 1, 2, or 3 substituents Y, where Y has the meaning defined above, with the proviso that R2 is not a 6-methyl-2-pyridyl group, or R2 represents a 4-10 membered, mono-unsaturated or fully saturated carbocyclic ring system, monocyclic, fused bicyclic or fused tricyclic, or R2 represents a 4-10 membered heterocyclic ring system , mono-unsaturated or fully saturated, monocyclic, fused bicyclic or fused tricyclic, carbocyclic or heterocyclic ring system that may be substituted with 1-5 substituents selected from methyl, ethyl, amino, hydroxy or F, or R2 re it has a group of general formula CH2-R5 where R5 represents phenyl which is substituted with 1, 2, 3, 4 or 5 substituents and defined above, or R5 represents a heteroaryl or a 1,2,3,4-tetrahydronaphthyl or indanyl group , heteroaryl or 1,2,3,4-tetrahydronaphthyl or indanyl group which may be substituted with 1, 2 or 3 Y-defined substituents or R5 represents a 4-10 membered, mono-unsaturated or fully saturated carbocyclic ring system, monocyclic , fused bicyclic or fused tricyclic, or R5 represents a 4-10 membered heterocyclic ring system, mono-unsaturated or fully saturated, monocyclic, fused bicyclic or fused tricyclic, carbocyclic or heterocyclic ring systems optionally substituted with 1-5 substituents selected from the group formed by methyl, ethyl, amino, hydroxy or F, or R2 represents a methylsulfonylaminoalkyl, methylsulfonylalkyl or acetamidoalkyl group; R 3 represents H or halogen or a formyl group, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfanyl, trifluoromethylsulfanyl, benzyl sulfanyl, or cyano, or R 3 represents C 1-8 alkyl, C 1-8 alkyl which may be substituted with 1 -5 substituents selected from the group consisting of F, hydroxy or amino, or R3 represents C2-6 alkynyl, C2-6 alkenyl, C1-6 alkanoyl, C3-8 cycloalkyl, C5-8 heterocycloalkyl or C2-6 heteroalkyl groups which are optionally substituted with 1-3 methyl, ethyl, amino or hydroxy groups or with 1-3 F atoms, or R3 represents phenyl which is substituted with 1-5 Y substituents, where Y has the meaning defined above, or R3 represents a group heteroaryl, heteroaryl which may be substituted with 1, 2 or 3 substituents Y, where Y has the meaning defined above, or R3 represents benzyl or heteroarylmethyl, benzyl or heteroarylmethyl which may be substituted with 1, 2 or 3 substituents Y; R4 represents one of the subgroups (i) or (ii) where R6 represents branched or linear C4-8 alkyl, C3-8 cycloalkyl, C3-8 cycloalkyl-C1-2 alkyl, heterocycloalkylC5-7-C1-2 alkyl, bicycloalkyl C5-10, C5-10 bicycloalkyl-C1-2 alkyl, heterocyclocycloalkylC5-10-C1-2 alkyl, tricycloalkyl C6-10, tricycloalkyl C6-10-alkyl C1-2, heterocycloricalkyl C6-10-alkyl C1-2, groups which may be substituted with 1-5 substituents selected from methyl, hydroxy, ethyl, trifluoromethyl or F, or R 6 represents phenyl, benzyl, naphthyl or phenethyl, groups that may be substituted in their aromatic ring system with 1-3 Y substituents defined above , with the proviso that R6 is not a 2-methylphenyl group, or R6 represents a pyridyl or thienyl group; R7 represents H or linear C1-6 alkyl, linear C1-6 alkyl which may be substituted with 1-3 F atoms or R7 represents an isopropyl, naphthylmethyl or heteroarylethyl group which may be substituted with 1-3 Y substituents, where Y has the above-mentioned meaning, or R8 represents a piperidinyl, azepanyl, morpholinyl, azabicyclo [3.3.0] octanyl, 4-hydroxypiperidinyl or pyrrolidinyl group, with the proviso that R8 is neither a 6-methoxy-benzothiazol-2-yl group a [3-chloro-5- (trifluoromethyl) pyrid-2-yl] methyl group, or R7 and R8 - together with the N atom to which they are linked - form a monocyclic, bicyclic or tricyclic, non-aromatic or partially heterocyclic heterocyclic group aromatic, saturated or unsaturated, having 7 to 10 ring atoms, monocyclic, bicyclic or tricyclic heterocyclic group, non-aromatic or partially aromatic, saturated or unsaturated which may be substituted with 1-5 substituents selected from the group consisting of C1-3 alkyl, hydroxy, methoxy, cyano, phenyl, trifluoromethyl or halogen, or R7 and R8 - together with the N atom to which they are linked - form a saturated monocyclic heterocyclic group, optionally containing another heteroatom (selected from N, OS), which has 5 to 6 ring atoms, a heterocyclic group that is substituted with 1-5 substituents selected from the group consisting of C1-3 alkyl, hydroxy, amino, phenyl, benzyl or F, with the proviso that R7 and R8 - together with the N atom to which they are bound- do not form a tricythyl-substituted azabicyclo [3.2.1] octanyl group, and the tautomers, stereoisomers and N-oxides thereof, as well as the pharmacologically acceptable salts, hydrates and solvates of said compounds of formula (1) and their tautomers, stereoisomers and N-oxides.

ARP060100463A 2005-02-16 2006-02-09 DERIVATIVES OF 1H-IMIDAZOL AS MODULATORS OF THE CANNABINOID CB2 RECEIVER AR052666A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP05101171 2005-02-16

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AR052666A1 true AR052666A1 (en) 2007-03-28

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KR (1) KR20070107130A (en)
CN (1) CN101107233A (en)
AR (1) AR052666A1 (en)
TW (1) TW200640876A (en)
UA (1) UA92736C2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2990564A1 (en) * 2015-06-22 2016-12-29 Sumitomo Dainippon Pharma Co., Ltd. Bicyclic heterocyclic amide derivative
CA2990583A1 (en) * 2015-06-22 2016-12-29 Sumitomo Dainippon Pharma Co., Ltd. 1,4-disubstituted imidazole derivative
CN107663159A (en) * 2016-07-29 2018-02-06 上海迪诺医药科技有限公司 Polycyclic compound, its pharmaceutical composition and application

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CN101107233A (en) 2008-01-16
KR20070107130A (en) 2007-11-06
TW200640876A (en) 2006-12-01

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FA Abandonment or withdrawal