[go: up one dir, main page]

AR059365A1 - DERIVATIVES OF PIRAZOLINA, METHOD OF PREPARATION, MEDICINES CONTAINING THEM AND USES IN DISORDERS ASSOCIATED WITH CANABINOID RECEPTORS CB1. - Google Patents

DERIVATIVES OF PIRAZOLINA, METHOD OF PREPARATION, MEDICINES CONTAINING THEM AND USES IN DISORDERS ASSOCIATED WITH CANABINOID RECEPTORS CB1.

Info

Publication number
AR059365A1
AR059365A1 ARP070100522A ARP070100522A AR059365A1 AR 059365 A1 AR059365 A1 AR 059365A1 AR P070100522 A ARP070100522 A AR P070100522A AR P070100522 A ARP070100522 A AR P070100522A AR 059365 A1 AR059365 A1 AR 059365A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
unsubstituted
monosubstituted
substituted
Prior art date
Application number
ARP070100522A
Other languages
Spanish (es)
Inventor
Wilfried Buschken
Jover Antoni Torrens
Prio Josep Mas
Ruiz Jordi Ramon Quintana
Zueras Alberto Dordal
Original Assignee
Esteve Labor Dr
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 EP06008581A external-priority patent/EP1849784A1/en
Priority claimed from EP06008579A external-priority patent/EP1849783A1/en
Priority claimed from EP06008612A external-priority patent/EP1849776A1/en
Priority claimed from EP06008580A external-priority patent/EP1849775A1/en
Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr
Publication of AR059365A1 publication Critical patent/AR059365A1/en

Links

Landscapes

  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicacion 1: Compuesto de pirazolina sustituido de formula general (1), en la que R1 representa un radical fenilo no sustituido o al menos monosustituido; R2 representa un radical fenilo no sustituido o al menos monosustituido; R3 representa un radical no sustituido o al menos monosustituido seleccionado del grupo que consiste en ciclononilo, ciclodecilo, cicloundecilo, ciclododecilo, ciclotridecilo, ciclotetradecilo, aziridinilo, azetidinilo; imidazolidinilo, tiomorfolinilo, pirazolidinilo, tetrahidrofuranilo, tetrahidrotiofenilo, azepanilo, diazepanilo, azocanilo, (2,5)-dihidrofuranilo, (2,5)-dihidrotiofenilo, (2,3)-dihidrofuranilo, (2,3)-dihidrofuranilo, (2,5)-dihidro-1H-pirrolilo, (2,3)-dihidro-1H-pirrolilo, tetrahidrotiopiranilo, tetrahidropiranilo, (3,4)-dihidro-2H-piranilo, (3,4)-dihidro-2H-tiopiranilo, (1,2,3,6)-tetrahidropiridinilo, (1,2,3,4)- tetrahidropiridinilo, (1,2,5,6)-tetrahidropiridinilo, [1,3]-oxazinanilo, hexahidropirimidinilo, (5,6)- dihidro-4H-pirimidinilo, oxazolidinilo, (1,3)-dioxanilo, (1,4)-dioxanilo, (1,3)-dioxolanilo, indolinilo, isoindolinilo, decahidronaftilo, (1,2,3,4)-tetrahidroquinolinilo, (12,3,4)-tetrahidroisoquinolinilo, octahidro-ciclopenta[c]pirrolilo, (1,3,4,7,9a)-hexahidro-2H-quinolizinilo, (1,2,3,5,6,8a)-hexahidro-indolizinilo, decahidroquinolinilo, dodecahidro-carbazolilo, 9H-carbazolilo, 9H-carbazolilo, decahidroisoquinolinilo, (6,7)-dihidro-4H-tieno[3,2-c]pirridinilo, (2,3)-dihidro-1H- benzo[de]isoquinolinilo, (1,2,3,4)-tetrahidroquinoxazolinilo, adamantilo, [1,2,3,4]-tetrahidronaftilo, biciclo[2.2.1]heptilo, biciclo[3.1.1]heptilo, norbornenilo, 8-aza-biciclo[3.2.1]octilo, 8-aza-espiro[4.5]decanilo y (2,3)-dihidro-1H-ciclopenta[b]- indolilo, un radical sustituido seleccionado del grupo que consiste en ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, cicloheptilo, ciclooctilo, ciclopentenilo, ciclohexenilo, cicloheptenilo, ciclooctenilo, pirrolidinilo, piperidinilo, piperazinilo, homopiperazinilo y morfolinilo, que está sustituido con 1, 2, 3, 4 o 5 sustituyente(s) independientemente seleccionado(s) del grupo que consiste en tioxo (=S), -alquilo C1-6 sustituido con uno o más grupos hidroxilo, -alquilo C1-6 sustituido con uno o más átomos de cloro, -alquilo C1-6 sustituido con uno o más grupos metoxilo y/o etoxilo, -O-alquilo C1-6 sustituido con uno o más grupos metoxilo y/o etoxilo, -S-alquilo C1-6, -C(=O)-O-alquilo C1-6, -OC(=O)-alquilo C1-6, -SCF3, - SCF2H, -SCFH2, -SH, -SO3H, -NH-C(=O)alquilo C1-6, -N(alquilo C1-6)C(=O)alquilo C1-6, -CHO, -C(=O)-perfluoroalquilo C1-6, -C(=S)-NH-alquilo C1-6, -CF2H, -CFH2, -C(=O)-NH-NRCRD, -S(=O)2-fenilo, -(alquileno C1-5)-S-alquilo C1-6, (alquileno C1-5)-S(=O)- alquilo C1-6, -(alquileno C1-5)-S(=O)2-alquilo C1-6, -NRARB, -(alquileno C1-5)NRARB, -S(=O)2-NH-alquilo C1-6, S(=O)2-NH-fenilo, ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, pirrolidinilo, piperidinilo, tiofenilo, fenoxilo y bencilo; en los que en cada caso los restos cíclicos ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, fenilo, pirrolidinilo, piperidinilo, tiofenilo, fenoxilo y bencilo pueden estar sustituidos opcionalmente con 1, 2, 3, 4 o 5 sustituyente(s) independientemente seleccionado(s) del grupo que consiste en F, CI, Br, I, -OH, -CF3, -CN, -NO2, -alquilo C1-6, -O-alquilo C1-6, -O-CF3 y -S-CF3, un resto -NR4R5 o un resto -O-R6; R4 representa un átomo de hidrogeno o un radical alifático saturado o insaturado, no sustituido o al menas monosustituido; R5 representa un radical no sustituido o al menos monosustituido seleccionado del grupo que consiste en 2-pentilo, 3-pentilo, neo-pentilo, 2-hexilo, 3-hexilo, 2-heptilo, 3-heptilo, 4-heptilo, 2- octilo, 3-octilo, 4-octilo, 2-(6-metil)-heptilo, 2-(5-metil)-heptilo, 2-(5-metil)-hexilo, 2-(4-metil)-hexilo, 2-(7-metil)-octilo; 2-(6-metil)-octilo, -O-metilo, -O-etilo, -On-propilo, -O-isopropilo, -O-n-butilo, -O-isobutilo, -O-terc-butilo, -O-n- pentilo y -O-n-hexilo; un radical sustituido seleccionado del grupo que consiste en metilo, etilo, n-propilo, isopropilo, n-butilo, sec-butilo, terc-butilo, n-pentilo, n-hexilo, n-heptilo y n-octilo, que está sustituido con 1, 2, 3, 4, 5, 6, 7, 8 o 9 sustituyentes independientemente seleccionados del grupo que consiste en -NH-alquilo C1-6, -N(alquilo C1-6)2, -C(=O)-O-alquilo C1-6 y - NH-C(=O)-alquilo C1-6, un radical no sustituido o al menos monosustituido seleccionado del grupo que consiste en adamantilo, ciclononilo, ciclodecilo, cicloundecilo, ciclododecilo, ciclotridecilo, ciclotetradecilo, aziridinilo, azetidinilo, imidazolidinilo, tiomorfolinilo, pirazolidinilo, tetrahidrofuranilo, tetrahidrotiofenilo, azepanilo, diazepanilo, azocanilo, (2,5)-dihidrofuranilo, (2,5)-dihidrotiofenilo, (2,3)-dihidrofuranilo, (2,3)-dihidrofuranilo, (2,5)-dihidro-1H-pirrolilo, (2,3)-dihidro-1H-pirrolilo, tetrahidrotiopiranilo, tetrahidropiranilo, (3,4)-dihidro-2H-piranilo, (3,4)- dihidro-2H- tiopiranilo, (1,2,3,6)-tetrahidropiridinilo, (1,2,3,4)- tetrahidropiridinilo, (1,2,5,6)-tetrahidropiridinilo, [1,3]-oxazinanilo, hexahidropirimidinilo, (5,6)-dihidro-4H-pirimidinilo, oxazolidinilo, (1,3)-dioxanilo, (1,4)-dioxanilo, (1,3)- dioxolanilo, indolinilo, isoindolinilo, decahidronaftilo, (1,2,3,4)-tetrahidroquinolinilo, (1,2,3,4)-tetrahidroisoquinolinilo, octahidro-ciclopenta[c]pirrolilo, (1,3,4,7,9a)-hexahidro-2H-quinolizinilo, (12,3,5,6,8a)-hexahidro-indolizinilo, decahidroquinolinilo, dodecahidro-carbazolilo, 9H-carbazolilo, 9H-carbazolilo, decahidroisoquinolinilo, (6,7)-dihidro-4H-tieno[3,2-c]pirridinilo, (2,3)-dihidro-1 H-benzo[de]isoquinolinilo, (1,2,3,4)- tetrahidroquinoxazolinilo, adamantilo, [1,2,3,4]- tetrahidronaftilo, biciclo[2.2.1]heptilo, biciclo[3.1.1]heptilo, norbornenilo, 8-aza-biciclo(3.2 1]octilo, 8-aza- espiro[4.5]decanilo y (2,3)-dihidro-1H-ciclopenta[b]-indolilo, un radical sustituido seleccionado del grupo que consiste en ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, cicloheptilo, ciclooctilo, ciclopentenilo, ciclohexenilo, cicloheptenilo, ciclooctenilo, pirrolidinilo, piperidinilo, piperazinilo, homopiperazinilo y morfolinilo, que está sustituido con 1, 2, 3, 4 o 5 sustituyente(s) independientemente seleccionado(s) del grupo que consiste en tioxo (=S), -alquilo C1-6 sustituido con uno o más grupos hidroxilo, -alquilo C1-6 sustituido con uno o más átomos de cloro, -alquilo C1-6 sustituido con uno o más grupos metoxilo y/o etoxilo, -O-alquilo C1-6 sustituido con uno o más grupos metoxilo y/o etoxilo, -S-alquilo C1-6, -C(=O)-O-alquilo C1-6, -OC(=O)-alquilo C1-6, -SCF3, -SCF2H, -SCFH2, -SH, -SO3H, -NH-C(=O)alquilo C1-6, -N(alquilo C1-6)C(=O)alquilo C1-6, -CHO, -C(=O)-perfluoroalquilo C1-6, -C(=S)-NH-alquilo C1-6, -CF2H, -CFH2, -C(=O)-NH-NRCRD, -S(=O)2-fenilo, -(alquileno C1-5)-S-alquilo C1-6, (alquileno C1-5)-S(=O)-alquilo C1-6, -(alquileno C1-5)-S(=O)2-alquilo C1-6, -NRARB, -(alquileno C1- 5)NRARB, -S(=O)2-NH-alquilo C1-6, S(=O)2-NH-fenilo, ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, pirrolidinilo, piperidinilo, tiofenilo, -O-Bencilo, fenoxilo y bencilo; en los que en cada caso los restos cíclicos ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, fenilo, pirrolidinilo, piperidinilo, tiofenilo, fenoxilo y bencilo pueden estar sustituidos opcionalmente con 1, 2, 3, 4 o 5 sustituyente(s) independientemente seleccionado(s) del grupo que consiste en F, CI, Br, I, -OH, - CF3, -CN, -NO2, -alquilo C1-6, -O-alquilo C1-6, -O-CF3 y -S-CF3, un radical cicloalifático saturado o insaturado, no sustituido o al menos monosustituido, que contiene opcionalmente al menos un heteroátomo como miembro de anillo, que está unido a través de un grupo alquileno, grupo alquenileno o grupo alquinileno no sustituido o al menos monosustituido, puede estar condensado con un sistema cíclico mono o policíclico, no sustituido o al menos monosustituido y/o puede estar unido con un puente mediante al menos un grupo alquileno no sustituido o al menos monosustituido; un resto -NR7R8 un resto -P(=O)(OR9)2, un resto -C(=O)-OR10, un resto -C(=O)-NH-R11 o un resto -C(=O)-R12, R6 representa un radical alquilo C5-16, un radical alquenilo C2-16 o un radical alquinilo C2-16 no sustituido o al menos monosustituido; o un radical cicloalifático saturado o insaturado, no sustituido o al menos monosustituido, que contiene opcionalmente al menos un heteroátomo como miembro de anillo, que está unido a través de un grupo alquileno, grupo alquenileno o grupo alquinileno no sustituido o al menos monosustituido, puede estar condensado con un sistema cíclico mono o policíclico, no sustituido o al menos monosustituido y/o puede estar unido con un puente mediante al menos un grupo alquileno no sustituido o al menos monosustituido; un resto -P(=O)(OR9)2, un resto -C(=O)-OR10, un resto -C(=O)-NH-R11, o un resto -C(=O)-R12, R7 representa un átomo de hidrogeno o un radical alifático saturado o insaturado, no sustituido o al menos monosustituido; R8 representa un radical no sustituido o al menos monosustituido seleccionado del grupo que consiste en 2-pentilo, 3-pentilo, neo-pentilo, 2-hexilo, 3-hexilo, 2-heptilo, 3- heptilo, 4-heptilo, 2-octilo, 3-octilo, 4-octilo, 2-(6-metil)-heptilo, 2-(5-metil)-heptilo, 2-(5-metil)-hexilo, 2-(4-metil)-hexilo, 2-(7-metil)-octilo, 2-(6-metil)-octilo, -O-metilo, -O-etilo, -On-propilo, -O-isopropilo, -O-n-butilo, -O-isobutilo, - O-terc-butilo, -O-n-pentilo y -O-n-hexilo; un radical sustituido seleccionado del grupo que consiste en metilo, etilo, n-propilo, isopropilo, n-butilo, sec-butilo, terc-butilo, n-pentilo, n-hexilo, n-heptilo y n-octilo, que está sustituido con 1, 2, 3, 4, 5, 6, 7, 8 o 9 sustituyentes independientemente seleccionados del grupo que consiste en -NH-alquilo C1-6, -N(alquilo C1-6)2, -C(=O)-O-alquilo C1-6 y - NH-C(=O)-alquilo C1-6, un radical no sustituido o al menos monosustituido seleccionado del grupo que consiste en ciclononilo, ciclodecilo, cicloundecilo, ciclododecilo, ciclotridecilo, ciclotetradecilo, aziridinilo, azetidinilo, imidazolidinilo, tiClaim 1: Substituted pyrazoline compound of general formula (1), wherein R1 represents an unsubstituted or at least monosubstituted phenyl radical; R2 represents an unsubstituted or at least monosubstituted phenyl radical; R3 represents an unsubstituted or at least monosubstituted radical selected from the group consisting of cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclrideridecyl, cyclootetradecyl, aziridinyl, azetidinyl; imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5) -dihydrofuranyl, (2,5) -dihydrothiophenyl, (2,3) -dihydrofuranyl, (2,3) -dihydrofuranyl, (2 , 5) -dihydro-1H-pyrrolyl, (2,3) -dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4) -dihydro-2H-pyranyl, (3,4) -dihydro-2H-thiopyranyl, (1,2,3,6) -tetrahydropyridinyl, (1,2,3,4) -tetrahydropyridinyl, (1,2,5,6) -tetrahydropyridinyl, [1,3] -oxazinanyl, hexahydropyrimidinyl, (5.6 ) - dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3) -dioxanyl, (1,4) -dioxanyl, (1,3) -dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4) - tetrahydroquinolinyl, (12,3,4) -tetrahydroisoquinolinyl, octahydro-cyclopenta [c] pyrrolyl, (1,3,4,7,9a) -hexahydro-2H-quinolizinyl, (1,2,3,5,6,8a ) -hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro-carbazolyl, 9H-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6.7) -dihydro-4H-thieno [3,2-c] pyrridinyl, (2,3) -dihydro- 1H- benzo [de] isoquinolinyl, (1,2,3,4) -tetrahydroquinoxazolinyl, adamantyl, [1,2,3,4] -tetrahydronaphthyl, bicyclo [2.2.1] heptyl, bicyclo [3.1.1] heptyl, norbornenyl, 8-aza-bicyclo [3.2.1] octyl, 8-aza-spiro [4.5] decanyl and (2,3) -dihydro-1H-cyclopenta [b] - indolyl, a substituted radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl and morpholinyl, which is substituted with 1, 2, 3, 4 or independently selected (s) s) of the group consisting of thioxo (= S), -C 1-6 alkyl substituted with one or more hydroxyl groups, -C 1-6 alkyl substituted with one or more chlorine atoms, -C 1-6 alkyl substituted with one or more methoxy and / or ethoxy groups, -O-C 1-6 alkyl substituted with one or more methoxy and / or ethoxy groups, -S-C 1-6 alkyl, -C (= O) -O-C 1-6 alkyl, -OC (= O) -C1-6 alkyl, -SCF3, - SCF2H, -SCFH2, -SH, -SO3H, -NH-C (= O) C1-6 alkyl, -N (C1-6 alkyl) C (= O) C1-6 alkyl, -CHO, -C (= O ) -C1-6perfluoroalkyl, -C (= S) -NH-C1-6 alkyl, -CF2H, -CFH2, -C (= O) -NH-NRCRD, -S (= O) 2-phenyl, - ( C1-5 alkylene) -S-C1-6 alkyl, (C1-5 alkylene) -S (= O) - C1-6 alkyl, - (C1-5 alkylene) -S (= O) 2-C1-6 alkyl , -NRARB, - (C1-5 alkylene) NRARB, -S (= O) 2-NH-C1-6 alkyl, S (= O) 2-NH-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl , thiophenyl, phenoxy and benzyl; in which in each case the cyclic moieties cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyrrolidinyl, piperidinyl, thiophenyl, phenoxy and benzyl may be optionally substituted with 1, 2, 3, 4 or 5 independently selected substituent (s) ) of the group consisting of F, CI, Br, I, -OH, -CF3, -CN, -NO2, -C 1-6 alkyl, -O-C 1-6 alkyl, -O-CF3 and -S-CF3, a moiety -NR4R5 or a moiety -O-R6; R4 represents a hydrogen atom or a saturated or unsaturated aliphatic radical, unsubstituted or in the monosubstituted ores; R5 represents an unsubstituted or at least monosubstituted radical selected from the group consisting of 2-pentyl, 3-pentyl, neo-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3-heptyl, 4-heptyl, 2- octyl, 3-octyl, 4-octyl, 2- (6-methyl) -heptyl, 2- (5-methyl) -heptyl, 2- (5-methyl) -hexyl, 2- (4-methyl) -hexyl, 2- (7-methyl) -octyl; 2- (6-methyl) -octyl, -O-methyl, -O-ethyl, -On-propyl, -O-isopropyl, -On-butyl, -O-isobutyl, -O-tert-butyl, -On- pentyl and -On-hexyl; a substituted radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl, which is substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituents independently selected from the group consisting of -NH-C1-6 alkyl, -N (C1-6 alkyl) 2, -C (= O) -O-C 1-6 alkyl and - NH-C (= O) -C 1-6 alkyl, an unsubstituted or at least monosubstituted radical selected from the group consisting of adamantyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cycloridecyl, cyclootetradecyl, aziridinyl, azetidinyl, imidazolidinyl, thiomorpholinyl, pyrazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, azepanyl, diazepanyl, azocanyl, (2,5) -dihydrofuranyl, (2,5) -dihydrothiophenyl, (2,3) -dihydrofuranyl, (2,3) - dihydrofuranyl, (2,5) -dihydro-1H-pyrrolyl, (2,3) -dihydro-1H-pyrrolyl, tetrahydrothiopyranyl, tetrahydropyranyl, (3,4) -dihydro-2H-pyranyl, (3,4) - dihydro- 2H-thiopyranyl, (1,2,3,6) -tetrahyd ropyridinyl, (1,2,3,4) -tetrahydropyridinyl, (1,2,5,6) -tetrahydropyridinyl, [1,3] -oxazinanyl, hexahydropyrimidinyl, (5,6) -dihydro-4H-pyrimidinyl, oxazolidinyl, (1,3) -dioxanyl, (1,4) -dioxanyl, (1,3)-dioxolanyl, indolinyl, isoindolinyl, decahydronaphthyl, (1,2,3,4) -tetrahydroquinolinyl, (1,2,3,4 ) -tetrahydroisoquinolinyl, octahydro-cyclopenta [c] pyrrolyl, (1,3,4,7,9a) -hexahydro-2H-quinolizinyl, (12,3,5,6,8a) -hexahydro-indolizinyl, decahydroquinolinyl, dodecahydro- carbazolyl, 9H-carbazolyl, 9H-carbazolyl, decahydroisoquinolinyl, (6,7) -dihydro-4H-thieno [3,2-c] pyrridinyl, (2,3) -dihydro-1 H -benzo [de] isoquinolinyl, ( 1,2,3,4) - tetrahydroquinoxazolinyl, adamantyl, [1,2,3,4] - tetrahydronaphthyl, bicyclo [2.2.1] heptyl, bicyclo [3.1.1] heptyl, norbornenyl, 8-aza-bicyclo (3.2 1] octyl, 8-aza-spiro [4.5] decanyl and (2,3) -dihydro-1H-cyclopenta [b] -indolyl, a substituted radical selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl lo, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, homopiperazinyl and morpholinyl, which is substituted with 1, 2, 3, 4 or 5 substituent (s) independently selected from the group consisting of thioxo (= S), -C 1-6 alkyl substituted with one or more hydroxyl groups, -C 1-6 alkyl substituted with one or more chlorine atoms, -C 1-6 alkyl substituted with one or more methoxy and / or ethoxy groups, - O-C1-6 alkyl substituted with one or more methoxy and / or ethoxy groups, -S-C1-6 alkyl, -C (= O) -O-C1-6 alkyl, -OC (= O) -C1-alkyl 6, -SCF3, -SCF2H, -SCFH2, -SH, -SO3H, -NH-C (= O) C1-6 alkyl, -N (C1-6 alkyl) C (= O) C1-6 alkyl, -CHO , -C (= O) -C 1-6 perfluoroalkyl, -C (= S) -NH-C 1-6 alkyl, -CF2H, -CFH2, -C (= O) -NH-NRCRD, -S (= O) 2-phenyl, - (C1-5 alkylene) -S-C1-6 alkyl, (C1-5 alkylene) -S (= O) -C1-6 alkyl, - (C1-5 alkylene) -S (= O) 2-C1-6 alkyl, -NRARB, - (C1-5 alkylene) NRARB, -S (= O) 2-NH-C1-6 alkyl, S (= O) 2-NH-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperidinyl, thiophenyl, -O-benzyl, phenoxy and benzyl; in which in each case the cyclic moieties cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyrrolidinyl, piperidinyl, thiophenyl, phenoxy and benzyl may be optionally substituted with 1, 2, 3, 4 or 5 independently selected substituent (s) ) of the group consisting of F, CI, Br, I, -OH, - CF3, -CN, -NO2, -C1-6 alkyl, -O-C1-6 alkyl, -O-CF3 and -S-CF3, a saturated or unsaturated cycloaliphatic radical, unsubstituted or at least monosubstituted, optionally containing at least one heteroatom as a ring member, which is linked through an alkylene group, alkenylene group or unsubstituted or at least monosubstituted alkynylene group, may be condensed with a mono or polycyclic cyclic system, unsubstituted or at least monosubstituted and / or may be linked to a bridge by at least one unsubstituted or at least monosubstituted alkylene group; a remainder -NR7R8 a remainder -P (= O) (OR9) 2, a remainder -C (= O) -OR10, a remainder -C (= O) -NH-R11 or a remainder -C (= O) - R12, R6 represents a C5-16 alkyl radical, a C2-16 alkenyl radical or an unsubstituted or at least monosubstituted C2-16 alkynyl radical; or a saturated or unsaturated cycloaliphatic radical, unsubstituted or at least monosubstituted, optionally containing at least one heteroatom as a ring member, which is linked through an alkylene group, alkenylene group or unsubstituted or at least monosubstituted alkynylene group, may be condensed with a mono or polycyclic, unsubstituted or at least monosubstituted cyclic system and / or may be linked to a bridge by at least one unsubstituted or at least monosubstituted alkylene group; a remainder -P (= O) (OR9) 2, a remainder -C (= O) -OR10, a remainder -C (= O) -NH-R11, or a remainder -C (= O) -R12, R7 represents a hydrogen atom or a saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic radical; R8 represents an unsubstituted or at least monosubstituted radical selected from the group consisting of 2-pentyl, 3-pentyl, neo-pentyl, 2-hexyl, 3-hexyl, 2-heptyl, 3- heptyl, 4-heptyl, 2- octyl, 3-octyl, 4-octyl, 2- (6-methyl) -heptyl, 2- (5-methyl) -heptyl, 2- (5-methyl) -hexyl, 2- (4-methyl) -hexyl, 2- (7-methyl) -octyl, 2- (6-methyl) -octyl, -O-methyl, -O-ethyl, -On-propyl, -O-isopropyl, -On-butyl, -O-isobutyl, - O-tert-butyl, -On-pentyl and -On-hexyl; a substituted radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl, which is substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituents independently selected from the group consisting of -NH-C1-6 alkyl, -N (C1-6 alkyl) 2, -C (= O) -O-C 1-6 alkyl and - NH-C (= O) -C 1-6 alkyl, an unsubstituted or at least monosubstituted radical selected from the group consisting of cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cycloridecyl, cyclootetradecyl, aziridinyl, azetidinyl, imidazolidinyl, thi

ARP070100522A 2006-04-26 2007-02-07 DERIVATIVES OF PIRAZOLINA, METHOD OF PREPARATION, MEDICINES CONTAINING THEM AND USES IN DISORDERS ASSOCIATED WITH CANABINOID RECEPTORS CB1. AR059365A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06008581A EP1849784A1 (en) 2006-04-26 2006-04-26 Indoline-substituted pyrazoline compounds, their preparation and use as medicaments
EP06008579A EP1849783A1 (en) 2006-04-26 2006-04-26 Octahydropentalene-substituted pyrazoline compounds, their preparation and use as medicaments
EP06008612A EP1849776A1 (en) 2006-04-26 2006-04-26 Azepane- or Azocane-substituted pyrazoline compounds, their preparation and use as medicaments
EP06008580A EP1849775A1 (en) 2006-04-26 2006-04-26 Cycloalkane-substituted pyrazoline compounds, their preparation and use as medicaments

Publications (1)

Publication Number Publication Date
AR059365A1 true AR059365A1 (en) 2008-03-26

Family

ID=39272773

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP070100522A AR059365A1 (en) 2006-04-26 2007-02-07 DERIVATIVES OF PIRAZOLINA, METHOD OF PREPARATION, MEDICINES CONTAINING THEM AND USES IN DISORDERS ASSOCIATED WITH CANABINOID RECEPTORS CB1.

Country Status (1)

Country Link
AR (1) AR059365A1 (en)

Similar Documents

Publication Publication Date Title
US2554736A (en) Tertiary aminoalkyl-iminodibenzyls
UY31232A1 (en) COMPOUNDS DERIVED FROM DIBENZOTIFENILAMINO-CROMEN-4-ACTIVE WAVES REPLACED AND ITS ISOMERS AND APPLICATIONS
US2856415A (en) 3,19-dihydroxy-5-androstene derivatives
WO2022149057A1 (en) Cdk inhibitors
AR078606A1 (en) PIPERIDINE DERIVATIVES TO PREVENT AND / OR TREAT DEGENERATIVE DISORDERS OF THE CENTRAL NERVOUS SYSTEM
JP2016517409A (en) SHIP1 modulator and related compositions and methods
WO2023025091A1 (en) Hpk1 degraders, compositions thereof, and methods of using the same
AU2018268173A1 (en) Preparation of buprenorphine
AR059365A1 (en) DERIVATIVES OF PIRAZOLINA, METHOD OF PREPARATION, MEDICINES CONTAINING THEM AND USES IN DISORDERS ASSOCIATED WITH CANABINOID RECEPTORS CB1.
CR20110348A (en) PIPERIDINE DERIVATIVES
US9376447B2 (en) Transfer hydrogenation of cyclopamine analogs
AR062543A1 (en) PIRAZOLINE COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICATIONS
Jeon et al. Syntheses of sulfur and selenium analogues of pachastrissamine via double displacements of cyclic sulfate
WO2007125061A1 (en) Spirocompounds useful as modulators for dopamine d3 receptors
EP2867220A1 (en) Sulfonamide derivatives and methods of use thereof for improving the pharmacokinetics of a drug
US2542223A (en) 6-keto-delta-10-methyldecalone-1
DK173252B1 (en) Alkoxymethyl ethers of glycerols
PH12014502845A1 (en) Novel cholecystokinin receptor ligands
EP2010518A1 (en) Azabicyclo [3. 1. o] hexane derivatives as modulators of dopamine d3 receptors
EP0217736A3 (en) 1,2-disubstituted ergoline derivatives
Hong-lin et al. Chemical constituents of Phyllanthus niruri L.
WO2009158381A1 (en) Novel psymberin derivatives, compositions, and their use as antineoplastic agents
AR069113A1 (en) FURO DERIVATIVES (3,2-D) PYRIMIDINE
GB807876A (en) Manufacture of indole derivatives
Budaev et al. Synthesis and NMR spectra of new C-modified glycyrrhetic acid derivatives

Legal Events

Date Code Title Description
FB Suspension of granting procedure