AR062543A1 - PIRAZOLINE COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICATIONS - Google Patents

PIRAZOLINE COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICATIONS

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Publication number
AR062543A1
AR062543A1 ARP060103040A ARP060103040A AR062543A1 AR 062543 A1 AR062543 A1 AR 062543A1 AR P060103040 A ARP060103040 A AR P060103040A AR P060103040 A ARP060103040 A AR P060103040A AR 062543 A1 AR062543 A1 AR 062543A1
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Argentina
Prior art keywords
alkyl
group
unsubstituted
monosubstituted
substituted
Prior art date
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ARP060103040A
Other languages
Spanish (es)
Inventor
Prio Jose Mas
Helmut Heinrich Buschmann
Ruiz Jordi Ramon Quintana
Zueras Alberto Dordal
Jover Antonio Torrens
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Esteve Labor Dr
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Priority claimed from EP05384018A external-priority patent/EP1743888A1/en
Priority claimed from EP06008581A external-priority patent/EP1849784A1/en
Priority claimed from EP06008580A external-priority patent/EP1849775A1/en
Priority claimed from EP06008579A external-priority patent/EP1849783A1/en
Priority claimed from EP06008612A external-priority patent/EP1849776A1/en
Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr
Publication of AR062543A1 publication Critical patent/AR062543A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Proceso de obtencion de dichos compuestos y composiciones farmacéuticas que los comprenden. 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, (1,2,3,4)- 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, (1,23,4)- 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)-C1-6 perfluoroalquilo, -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-feniIo, 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 menos 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, -O-n-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 adamantil, 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, (1,3,4,79a)- 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)-C1-6- perfluoroalquilo, -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, -O-n-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, ciProcess for obtaining said compounds and pharmaceutical compositions that comprise them. Claim 1: Substituted pyrazoline compound of general formula 1, wherein R 1 represents an unsubstituted or at least monosubstituted phenyl radical; R2 represents an unsubstituted or at least monosubstituted phenyl radical; R3 represents an unsubstituted radical or at least monosubstituted heterocycle selected from the group consisting cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, 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, (1,2,3,4) - tetrahydroisoquinolinyl, octahydro-cyclopenta [ c] pyrrolyl, (1,3,4,7,9a) -he xahidro-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, (1,23,4) -tetrahydroquinoxazolinyl, adamantyl, [1,2,3,4] -tetrahydronaphthyl, bicycles [2.2.1] heptyl, bicycles [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, 5, 3, substituent (s) independently selected (s) from the group consisting of thioxo (= S), - C1-6 alkyl substituted with one or more hydroxyl groups, - C1-6 alkyl substituted with one or more chlorine atoms, - C1- alkyl 6 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-alkyl C1-6, -OC (= O) -C1-6 alkyl, -SCF3, -SCF2H, -SCFH2, -SH, -SO3H, -NH-C (= O) -C1-6 alkyl, -N (C1 alkyl -6) -C (= O) -C 1-6 alkyl, -CHO, -C (= O) -C1-6 perfluoroalkyl, -C (= S) -NH-alkyl C1-6, - CF2H, -CFH2, -C (= O) -NH-NRCRD, -S (= O) 2-phenyl, - (C1-5 alkylene) -S-C1-6 alkyl, - (C1 alkylene -5) -S (= O) -C1-6 alkyl, - (C1-5 alkylene) -S (= O) 2-C1-6 alkyl, -NRARB, - (C1-5 alkylene) -NRARB, -S (= O) 2-NH-C 1-6 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, unsubstituted or at least monosubstituted aliphatic radical; 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; a radical unsubstituted or at least monosubstituted heterocycle selected from the group consisting of adamantyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, 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, (1,2,3,4) -tetrahydroisoquinolinyl, octahydro-cyclopenta [ c] pyrrolyl, (1,3,4,79a) - 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-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, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, pyrrolidinyl, piperidinyl, piperazinyl, which is homopiperazinyl, which is substituted for 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 atoms d and chloro, -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-C1-6 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) -C1-6- perfluoroalkyl, -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-C 1-6 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, 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 -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, ci

ARP060103040A 2005-07-15 2006-07-14 PIRAZOLINE COMPOUNDS, THEIR PREPARATION AND THEIR USE AS MEDICATIONS AR062543A1 (en)

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EP05384018A EP1743888A1 (en) 2005-07-15 2005-07-15 Carbonyl substituted pyrazoline compounds, their preparation and use as CB1 receptor modulators
US70543305P 2005-08-05 2005-08-05
EP06008581A EP1849784A1 (en) 2006-04-26 2006-04-26 Indoline-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
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

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