RU98118998A - PHARMACEUTICAL APPLICABLE COMPOUNDS - Google Patents
PHARMACEUTICAL APPLICABLE COMPOUNDSInfo
- Publication number
- RU98118998A RU98118998A RU98118998/04A RU98118998A RU98118998A RU 98118998 A RU98118998 A RU 98118998A RU 98118998/04 A RU98118998/04 A RU 98118998/04A RU 98118998 A RU98118998 A RU 98118998A RU 98118998 A RU98118998 A RU 98118998A
- Authority
- RU
- Russia
- Prior art keywords
- pyrazolo
- hydroxy
- methyl
- hydroxide
- isoquinoline
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 20
- 150000003839 salts Chemical class 0.000 claims 74
- 239000011780 sodium chloride Substances 0.000 claims 74
- -1 NR 16 R 17 Chemical group 0.000 claims 69
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 7
- UTKNBHYJLFLZRD-UHFFFAOYSA-M C1=NC=CC2=CC=CC=C12.[OH-] Chemical compound C1=NC=CC2=CC=CC=C12.[OH-] UTKNBHYJLFLZRD-UHFFFAOYSA-M 0.000 claims 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- GYPOFOQUZZUVQL-UHFFFAOYSA-N 2H-isoquinolin-3-one Chemical compound C1=CC=C2C=NC(O)=CC2=C1 GYPOFOQUZZUVQL-UHFFFAOYSA-N 0.000 claims 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 125000004432 carbon atoms Chemical group C* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- 150000002829 nitrogen Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- ZDQCLDBVVQUHDH-UHFFFAOYSA-N 6H-isoquinolin-5-one Chemical compound N1=CC=C2C(=O)CC=CC2=C1 ZDQCLDBVVQUHDH-UHFFFAOYSA-N 0.000 claims 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- UTKNBHYJLFLZRD-UHFFFAOYSA-N isoquinolin-2-ium;hydroxide Chemical compound [OH-].C1=[NH+]C=CC2=CC=CC=C21 UTKNBHYJLFLZRD-UHFFFAOYSA-N 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 0.000 claims 2
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical compound C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 claims 1
- IXPCPXXOAVXTCX-UHFFFAOYSA-N 2-(4-chlorophenyl)-3a,4-dimethyl-5H-pyrazolo[4,3-c]isoquinolin-3-one Chemical compound O=C1C2(C)N(C)CC3=CC=CC=C3C2=NN1C1=CC=C(Cl)C=C1 IXPCPXXOAVXTCX-UHFFFAOYSA-N 0.000 claims 1
- NDPTWLATLYNZFB-UHFFFAOYSA-N 2-(4-chlorophenyl)-3a,4-dimethylpyrazolo[4,3-c]isoquinoline-3,5-dione Chemical compound O=C1C2(C)N(C)C(=O)C3=CC=CC=C3C2=NN1C1=CC=C(Cl)C=C1 NDPTWLATLYNZFB-UHFFFAOYSA-N 0.000 claims 1
- YDUONSFDPJKKOD-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methylpyrazolo[4,3-c]cinnolin-3-one Chemical compound C12=CC=CC=C2N(C)N=C(C2=O)C1=NN2C1=CC=C(Cl)C=C1 YDUONSFDPJKKOD-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- AVKONKDQIQXXTI-UHFFFAOYSA-N 3-methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]pyrazolo[4,3-c]isoquinolin-5-one Chemical compound N1=C(C2=CC=CC=C2C(=O)N2C)C2=C(OC)N1C1=CC=C(C(F)(F)F)C=C1 AVKONKDQIQXXTI-UHFFFAOYSA-N 0.000 claims 1
- CFGASVMZNHUVJV-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-2-(4-methylphenyl)-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].C1=CC(OC)=CC=C1CN1C2=C(O)N(C=3C=CC(C)=CC=3)[NH2+]C2=C2C=CC=CC2=C1 CFGASVMZNHUVJV-UHFFFAOYSA-N 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- JJQPQPJIDRVWKM-UHFFFAOYSA-N 5-(dimethylamino)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C(N(C)C)=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C(F)(F)F)C=C1 JJQPQPJIDRVWKM-UHFFFAOYSA-N 0.000 claims 1
- HUGUPCLMYOTVJT-UHFFFAOYSA-N CC(C)c1ccc(cc1)-n1nc2c(ncc3ccccc23)c1O Chemical compound CC(C)c1ccc(cc1)-n1nc2c(ncc3ccccc23)c1O HUGUPCLMYOTVJT-UHFFFAOYSA-N 0.000 claims 1
- PQLUVPOJYXZXKA-UHFFFAOYSA-N CC(C)n1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(cc1)C(F)(F)F Chemical compound CC(C)n1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(cc1)C(F)(F)F PQLUVPOJYXZXKA-UHFFFAOYSA-N 0.000 claims 1
- SOGPOPQSEHFZBX-UHFFFAOYSA-N CC1=NC2=C(O)N(N=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1 Chemical compound CC1=NC2=C(O)N(N=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1 SOGPOPQSEHFZBX-UHFFFAOYSA-N 0.000 claims 1
- KAEQUJKUSPLLOX-UHFFFAOYSA-N COc1ccc(CCc2nc3c(O)n(nc3c3ccccc23)-c2ccc(cc2)C(F)(F)F)cc1 Chemical compound COc1ccc(CCc2nc3c(O)n(nc3c3ccccc23)-c2ccc(cc2)C(F)(F)F)cc1 KAEQUJKUSPLLOX-UHFFFAOYSA-N 0.000 claims 1
- DKAKOSUOWJVWSD-UHFFFAOYSA-N COc1ccc(Cn2c3c(O)n(nc3c3ccccc3c2=O)-c2ccc(cc2)C(F)(F)F)cc1 Chemical compound COc1ccc(Cn2c3c(O)n(nc3c3ccccc3c2=O)-c2ccc(cc2)C(F)(F)F)cc1 DKAKOSUOWJVWSD-UHFFFAOYSA-N 0.000 claims 1
- VFJYUWOESPOUBJ-UHFFFAOYSA-N Cc1ccc(nc1)-n1nc2c(ccc3ccccc23)c1O Chemical compound Cc1ccc(nc1)-n1nc2c(ccc3ccccc23)c1O VFJYUWOESPOUBJ-UHFFFAOYSA-N 0.000 claims 1
- LNPLYHUEZONSFN-UHFFFAOYSA-N Cc1nc2c(O)n(nc2c2c(F)cccc12)-c1ccc(Cl)cc1 Chemical compound Cc1nc2c(O)n(nc2c2c(F)cccc12)-c1ccc(Cl)cc1 LNPLYHUEZONSFN-UHFFFAOYSA-N 0.000 claims 1
- JRESQKLANNYWIE-UHFFFAOYSA-N Cc1nc2c(O)n(nc2c2c(F)cccc12)-c1ccc(cc1)C(F)(F)F Chemical compound Cc1nc2c(O)n(nc2c2c(F)cccc12)-c1ccc(cc1)C(F)(F)F JRESQKLANNYWIE-UHFFFAOYSA-N 0.000 claims 1
- JEIATIDSGKNVLE-UHFFFAOYSA-N Cn1c2c(O)n(nc2c2ccccc2c1=N)-c1ccc(cc1)C(F)(F)F Chemical compound Cn1c2c(O)n(nc2c2ccccc2c1=N)-c1ccc(cc1)C(F)(F)F JEIATIDSGKNVLE-UHFFFAOYSA-N 0.000 claims 1
- ZWUXBHZHBNBRRJ-UHFFFAOYSA-N Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(Cl)cc1 Chemical compound Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(Cl)cc1 ZWUXBHZHBNBRRJ-UHFFFAOYSA-N 0.000 claims 1
- YTCIFVOOVKTNBZ-UHFFFAOYSA-N Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(Cl)nc1 Chemical compound Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(Cl)nc1 YTCIFVOOVKTNBZ-UHFFFAOYSA-N 0.000 claims 1
- OZMVULSHMIXZBE-UHFFFAOYSA-N Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(cc1)C(F)(F)F Chemical compound Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ccc(cc1)C(F)(F)F OZMVULSHMIXZBE-UHFFFAOYSA-N 0.000 claims 1
- ZLNSKVUNWCLOFY-UHFFFAOYSA-N Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ncccn1 Chemical compound Cn1c2c(O)n(nc2c2ccccc2c1=O)-c1ncccn1 ZLNSKVUNWCLOFY-UHFFFAOYSA-N 0.000 claims 1
- JSVPBGUMJPGDOI-UHFFFAOYSA-N Cn1c2c(O)n(nc2c2ccccc2c1=S)-c1ccc(cc1)C(F)(F)F Chemical compound Cn1c2c(O)n(nc2c2ccccc2c1=S)-c1ccc(cc1)C(F)(F)F JSVPBGUMJPGDOI-UHFFFAOYSA-N 0.000 claims 1
- LBIXUTJTXJGOMF-UHFFFAOYSA-N FC(C1=CC=C(C=C1)N1N=C2C=3C=CC=NC3C=NC2=C1O)(F)F Chemical compound FC(C1=CC=C(C=C1)N1N=C2C=3C=CC=NC3C=NC2=C1O)(F)F LBIXUTJTXJGOMF-UHFFFAOYSA-N 0.000 claims 1
- SQKGWYUXMCKYQY-UHFFFAOYSA-N Oc1n(nc2c1ccc1ccccc21)-c1ccc(cc1)C(F)(F)F Chemical compound Oc1n(nc2c1ccc1ccccc21)-c1ccc(cc1)C(F)(F)F SQKGWYUXMCKYQY-UHFFFAOYSA-N 0.000 claims 1
- VTBIVAJHJQPWLO-UHFFFAOYSA-N Oc1n(nc2c1nc(Cl)c1ccccc21)-c1ccc(cc1)C(F)(F)F Chemical compound Oc1n(nc2c1nc(Cl)c1ccccc21)-c1ccc(cc1)C(F)(F)F VTBIVAJHJQPWLO-UHFFFAOYSA-N 0.000 claims 1
- LMZWHGAOYUMQEN-UHFFFAOYSA-N Oc1n(nc2c1ncc1cc(F)ccc21)-c1ccc(Cl)cc1 Chemical compound Oc1n(nc2c1ncc1cc(F)ccc21)-c1ccc(Cl)cc1 LMZWHGAOYUMQEN-UHFFFAOYSA-N 0.000 claims 1
- BGARNLFHBCDKBA-UHFFFAOYSA-N Oc1n(nc2c1ncc1cccc(F)c21)-c1ccc(Cl)cc1 Chemical compound Oc1n(nc2c1ncc1cccc(F)c21)-c1ccc(Cl)cc1 BGARNLFHBCDKBA-UHFFFAOYSA-N 0.000 claims 1
- HXJJOHMPRRNWBW-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1ccc(Cl)nc1 Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1ccc(Cl)nc1 HXJJOHMPRRNWBW-UHFFFAOYSA-N 0.000 claims 1
- KLKKZAVOZSWSRL-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)-c1ccccc1 Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)-c1ccccc1 KLKKZAVOZSWSRL-UHFFFAOYSA-N 0.000 claims 1
- AMOXWKQNJBEWNN-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)C(F)(F)C(F)(F)F Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)C(F)(F)C(F)(F)F AMOXWKQNJBEWNN-UHFFFAOYSA-N 0.000 claims 1
- MODHOZZQEZIXSZ-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)C(F)(F)F Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)C(F)(F)F MODHOZZQEZIXSZ-UHFFFAOYSA-N 0.000 claims 1
- MENMAINLQQOVDL-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1cnc2ccccc2c1 Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1cnc2ccccc2c1 MENMAINLQQOVDL-UHFFFAOYSA-N 0.000 claims 1
- LWHVBABPYWJVLG-UHFFFAOYSA-N [OH-].ClC1=CC=C(C=C1)N1[NH2+]C2=C3C=CC=NC3=CN(C2=C1O)C Chemical compound [OH-].ClC1=CC=C(C=C1)N1[NH2+]C2=C3C=CC=NC3=CN(C2=C1O)C LWHVBABPYWJVLG-UHFFFAOYSA-N 0.000 claims 1
- BIMSDSMRVMTPLI-UHFFFAOYSA-N [OH-].ClC1=CC=C(C=C1)N1[NH2+]C=2C(N(N=C3C=CC=CC23)C)=C1O Chemical compound [OH-].ClC1=CC=C(C=C1)N1[NH2+]C=2C(N(N=C3C=CC=CC23)C)=C1O BIMSDSMRVMTPLI-UHFFFAOYSA-N 0.000 claims 1
- LNARHFZHSCYKQV-UHFFFAOYSA-N [OH-].FC=1C=CC2=C3C(N(C=C2C1)C)=C(N([NH2+]3)C3=CC=C(C=C3)C(F)(F)F)O Chemical compound [OH-].FC=1C=CC2=C3C(N(C=C2C1)C)=C(N([NH2+]3)C3=CC=C(C=C3)C(F)(F)F)O LNARHFZHSCYKQV-UHFFFAOYSA-N 0.000 claims 1
- OEVXYGNARWOKJF-UHFFFAOYSA-N [OH-].OC=1N([NH2+]C2=C3C=CC=NC3=CN(C21)C)C2=CC=C(C=C2)C(F)(F)F Chemical compound [OH-].OC=1N([NH2+]C2=C3C=CC=NC3=CN(C21)C)C2=CC=C(C=C2)C(F)(F)F OEVXYGNARWOKJF-UHFFFAOYSA-N 0.000 claims 1
- JOJOOYOZWVNPBY-UHFFFAOYSA-N [OH-].OC=1N([NH2+]C=2C1N(C(=C1C=CC=CC21)C)C(C)C)C2=CC=C(C=C2)C(F)(F)F Chemical compound [OH-].OC=1N([NH2+]C=2C1N(C(=C1C=CC=CC21)C)C(C)C)C2=CC=C(C=C2)C(F)(F)F JOJOOYOZWVNPBY-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Claims (16)
где каждый из B, D, E и G представляет собой СН, СА или N при условии, что не более, чем один из B, D, Е и G представляет собой СА, и не более, чем один из B, D, Е и G представляет собой N; Х представляет собой С = О, С = S, С = NR15, CR3R6 или NR4; Y представляет собой N или N+R7 или CR18; Z представляет собой ОR8 или O-; R1 представляет собой ОН или С1-6-алкил, или образует связь с R2, либо с R5; R2 представляет собой Н, С1-6-алкил (необязательно замещенный фенилом, СООR9, NR10R11, OR12 или F) или С3-7-циклоалкил или образует связь с любым из R1, R3 или R4; R3 представляет собой Н или связь с R2; R4 представляет собой С1-6-алкил или связь с R2; R5 представляет собой связь с R1 или R8; R6 представляет собой Н, С1-6-алкил (необязательно замещенный фенилом), С3-7-циклоалкил, фенил, галоген, C1-6-алкокси, С1-6-алкилтио, С1-6-алкилсульфинил, циано или NR13R14; R7 представляет собой С1-6-алкил (необязательно замещенный фенилом) или С3-7-циклоалкил, каждый из которых может быть необязательно замещен галогеном, гидрокси, С1-6-алкокси, C1-6-алкилтио, С1-6-алкилсульфинилом, NR16R17, СООН, СОО(С1-6-алкилом) или циано; либо R6 и R7 вместе представляют собой С3-5-алкилен, вследствие чего Х и Y образуют 5-7-членное кольцо; R8 представляет собой Н, С1-6-алкил или связь с R5; R9, R10, R11, R12, R15, R16, R17 и R18 независимо представляют собой С1-6-алкил или Н; R13 и R14 независимо являются С1-6-алкилом, Н или вместе с атомом азота, к которому они присоединены, образуют 3-7-членное насыщенное кольцо, необязательно содержащее дополнительный атом кислорода или атом азота, необязательно замещенный С1-6-алкилом; Ar1 представляет собой фенил, пиридил, пиримидинил, 2-бензотиазолил, 2- или 3-хинолил или 2-хиноксалинил, каждый из которых необязательно замещен одним или несколькими заместителями, выбранными из: галогена, нитро, циано, фенила, фенилсульфонила, С1-6-алкила, С1-6-алкокси, С1-6-алкилтио, C1-6-алкилсульфинила, СООН, СОО(С1-6-алкила), С1-6-алкила, замещенного фенилом, или фенила, в котором алкильные, алкокси, алкилтио и алкилсульфинильные группы могут быть необязательно замещены фтором; и А представляет собой галоген, циано, амино, нитро, C1-6-алкил или С1-6-алкокси; где фенильные группы, которые присутствуют в R2, R6 или R7, либо в качестве заместителей в Ar1, могут быть необязательно замещены С1-6-алкилом, галогеном или С1-6-алкокси; при условии, что: (i) когда Х представляет собой С = О, С = S или С = NR15, тогда Y представляет собой N; (ii) когда R4 представляет собой связь с R2, тогда Y представляет собой N+R7; (iii) когда Y представляет собой N+R7, тогда Z представляет собой О-, R2 представляет собой связь с R3 или с R4, а R1 и R5 образуют связь; (iv) когда Y представляет собой N, тогда Z представляет собой ОR8; (v) когда R1 представляет собой ОН, тогда Х представляет собой С = О, Y представляет собой N, Z представляет собой ОR8, а R5 представляет собой связь с R8; (vi) когда R1 представляет собой алкил, тогда R5 представляет собой связь с R8, Y представляет собой N, R2 не является связью и Х не представляет собой NR4; (vii) когда R1 представляет собой связь с R2, тогда R5 и R8 образуют связь, и если Х представляет собой NR4, тогда R4 представляет собой алкил; (viii) когда R6 представляет собой арил, галоген, алкокси, тиоалкил, тогда R2 и R3 образуют связь; (ix) когда Y представляет собой N или N+R7 и R2 замещен любым из NR10R11, OR12 или F, тогда заместитель и кольцевой азот Y не может быть присоединен к тому же атому углерода R2; (x) когда R7 замещен любым из NR16R17, ОR12 или галогеном, тогда заместитель и кольцевой азот Y не может быть присоединен к тому же самому атому углерода R7; (хi) когда один из В, D, Е и G представляет собой N, тогда Х не представляет собой NR4; (xii) когда Y представляет собой СR18, тогда Х представляет собой СR3R6; при дополнительном условии, что: когда В, D, Е и G представляют собой СН, Х представляет собой СНR3, Y представляет собой N, R1 и R5 образуют связь, R8 представляет собой Н, и R2 и R3 вместе представляют собой связь, тогда Ar1 не представляет собой 4-хлорфенил, 4-фторфенил или 4-метоксифенил.1. The compound of formula I or its pharmaceutically acceptable derivative for use as a pharmaceutical preparation
where each of B, D, E and G represents CH, CA or N, provided that no more than one of B, D, E and G represents CA, and no more than one of B, D, E and G is N; X represents C = O, C = S, C = NR 15 , CR 3 R 6 or NR 4 ; Y is N or N + R 7 or CR 18 ; Z is OR 8 or O - ; R 1 is OH or C 1-6 -alkyl, or forms a bond with R 2 , or with R 5 ; R 2 is H, C 1-6 alkyl (optionally substituted with phenyl, COOR 9 , NR 10 R 11 , OR 12 or F) or C 3-7 cycloalkyl or forms a bond with any of R 1 , R 3 or R 4 ; R 3 is H or a bond to R 2 ; R 4 is C 1-6 alkyl or a bond with R 2 ; R 5 is a bond to R 1 or R 8 ; R 6 is H, C 1-6 alkyl (optionally substituted by phenyl), C 3-7 cycloalkyl, phenyl, halogen, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, cyano or NR 13 R 14 ; R 7 is C 1-6 alkyl (optionally substituted by phenyl) or C 3-7 cycloalkyl, each of which may be optionally substituted with halogen, hydroxy, C 1-6 alkoxy, C 1-6 alkylthio, C 1 -6- alkylsulfinyl, NR 16 R 17 , COOH, COO (C 1-6 alkyl) or cyano; or R 6 and R 7 together represent C 3-5 -alkylene, as a result of which X and Y form a 5-7-membered ring; R 8 is H, C 1-6 alkyl or a bond to R 5 ; R 9 , R 10 , R 11 , R 12 , R 15 , R 16 , R 17 and R 18 are independently C 1-6 alkyl or H; R 13 and R 14 are independently C 1-6 alkyl, H or, together with the nitrogen atom to which they are attached, form a 3-7 membered saturated ring, optionally containing an additional oxygen atom or nitrogen atom, optionally substituted with C 1-6 -alkyl; Ar 1 is phenyl, pyridyl, pyrimidinyl, 2-benzothiazolyl, 2- or 3-quinolyl or 2-quinoxalinyl, each of which is optionally substituted with one or more substituents selected from: halogen, nitro, cyano, phenyl, phenylsulfonyl, C 1 -6- alkyl, C 1-6 -alkoxy, C 1-6 -alkylthio, C 1-6 -alkylsulfinyl, COOH, COO (C 1-6 -alkyl), C 1-6 -alkyl, substituted by phenyl, or phenyl in which the alkyl, alkoxy, alkylthio and alkylsulfinyl groups may be optionally substituted with fluorine; and A represents halogen, cyano, amino, nitro, C 1-6 alkyl or C 1-6 alkoxy; wherein the phenyl groups that are present in R 2 , R 6 or R 7 , or as substituents in Ar 1 , may be optionally substituted with C 1-6 alkyl, halogen or C 1-6 alkoxy; provided that: (i) when X is C = O, C = S or C = NR 15 , then Y is N; (ii) when R 4 is a bond to R 2 , then Y is N + R 7 ; (iii) when Y is N + R 7 , then Z is O - , R 2 is a bond to R 3 or R 4 , and R 1 and R 5 form a bond; (iv) when Y is N, then Z is OR 8 ; (v) when R 1 is OH, then X is C = O, Y is N, Z is OR 8 , and R 5 is a bond to R 8 ; (vi) when R 1 is alkyl, then R 5 is a bond to R 8 , Y is N, R 2 is not a bond, and X is not NR 4 ; (vii) when R 1 is a bond to R 2 , then R 5 and R 8 form a bond, and if X is NR 4 , then R 4 is alkyl; (viii) when R 6 is aryl, halogen, alkoxy, thioalkyl, then R 2 and R 3 form a bond; (ix) when Y is N or N + R 7 and R 2 is substituted by any of NR 10 R 11 , OR 12 or F, then the substituent and ring nitrogen Y cannot be attached to the same carbon atom of R 2 ; (x) when R 7 is substituted with any of NR 16 R 17 , OR 12 or halogen, then the substituent and ring nitrogen Y cannot be attached to the same carbon atom of R 7 ; (xi) when one of B, D, E, and G is N, then X is not NR 4 ; (xii) when Y is CR 18 , then X is CR 3 R 6 ; with the additional condition that: when B, D, E, and G are CH, X is CHR 3 , Y is N, R 1 and R 5 form a bond, R 8 is H, and R 2 and R 3 together represent a bond, then Ar 1 does not represent 4-chlorophenyl, 4-fluorophenyl or 4-methoxyphenyl.
где каждый из В, D, Е и G представляет собой СН, СА или N при условии, что не более, чем один из В, D, Е и G представляет собой СА и не более, чем один из В, D, Е и G представляет собой N; Х представляет собой С = О, С = S, С = NR15, CR3R6 или NR4; Y представляет собой N или N+R7 или CR18; Z представляет собой ОR8 или О-; R1 представляет собой ОН или С1-6-алкил, или образует связь либо с R2, либо с R5; R2 представляет собой Н, С1-6-алкил (необязательно замещенный фенилом, СООR9, NR10R11, ОR12 или F) или С3-7-циклоалкил, либо образует связь с любым из R1, R3 или R4; R3 представляет собой Н или связь с R2; R4 представляет собой С1-6-алкил или связь с R2; R5 представляет собой связь с R1 или R8; R6 представляет собой Н, С1-6-алкил (необязательно замещенный фенилом), С3-7-циклоалкил, фенил, галоген, C1-6-алкокси, С1-6-алкилтио, С1-6-алкилсульфинил, циано или NR13R14; R7 представляет собой С1-6-алкил (необязательно замещенный фенилом) или С3-7-циклоалкил, каждый из которых может быть необязательно замещен галогеном, гидрокси, С1-6-алкокси, С1-6-алкилтио, С1-6-алкилсульфинилом, NR16R17, СООН, СОО(С1-6-алкилом) или циано; либо R6 и R7 вместе представляют собой С3-5-алкилен, вследствие чего Х и Y образуют 5-7-членное кольцо; R8 представляет собой Н, С1-6-алкил или связь с R5; R9, R10, R11, R12, R15, R16, R17 и R18 независимо представляют собой С1-6-алкил или Н; R13 и R14 независимо являются С1-6-алкилом, Н или вместе с атомом азота, к которому они присоединены, образуют 3-7-членное насыщенное кольцо, необязательно содержащее дополнительный атом кислорода или атом азота, необязательно замещенный С1-6-алкилом; Ar1 представляет собой фенил, пиридил, пиримидинил, 2-бензотиазолил, 2- или 3-хинолил или 2-хиноксалинил, каждый из которых необязательно замещен одним или несколькими заместителями, выбранными из: галогена, нитро, циано, фенила, фенилсульфонила, С1-6-алкила, С1-6-алкокси, С1-6-алкилтио, C1-6-алкилсульфинила, СООН, СОО(С1-6-алкила), С1-6-алкила, замещенного фенилом, или фенила, в котором алкильные, алкокси, алкилтио и алкилсульфинильные группы могут быть необязательно замещены фтором; и А представляет собой галоген, циано, амино, нитро, С1-6-алкил или С1-6-алкокси; где фенильные группы, которые присутствуют в R2, R6 или R7, либо в качестве заместителей в Ar1 могут быть необязательно замещены С1-6-алкилом, галогеном или С1-6-алкокси; при условии, что: (i) когда Х представляет собой С = О, С = S или С = NR15, тогда Y представляет собой N; (ii) когда R4 представляет собой связь с R2, тогда Y представляет собой N+R7; (iii) когда Y представляет собой N+R7, тогда Z представляет собой О-, R2 представляет собой связь с R3 или R4, а R1 и R5 образуют связь; (iv) когда Y представляет собой N, тогда Z представляет собой ОR8; (v) когда R1 представляет собой ОН, тогда Х представляет собой С = О, Y представляет собой N, Z представляет собой ОR8, и R5 представляет собой связь с R8; (vi) когда R1 представляет собой алкил, тогда R5 представляет собой связь с R8, Y представляет собой N, R2 не является связью и Х не представляет собой NR4; (vii) когда R1 представляет собой связь с R2, тогда R5 и R8 образуют связь, и если Х представляет собой NR4, тогда R4 представляет собой алкил; (viii) когда R6 представляет собой арил, галоген, алкокси, тиоалкил, тогда R2 и R3 образуют связь; (iх) когда Y представляет собой N или N+R7 и R2 замещен любым из NR10R11, OR12 или F, тогда заместитель и кольцевой азот Y не может быть присоединен к тому же атому углерода R2; (х) когда R7 замещен любым из NR16R17, ОR12 или галогеном, тогда заместитель и кольцевой азот Y не может быть присоединен к тому же самому атому углерода R7; (хi) когда один из В, D, Е и G представляет собой N, тогда Х не представляет собой NR4; (хii) когда Y представляет собой СR18, тогда Х представляет собой СR3R6; при дополнительном условии, что: а) когда все В, D, Е и G представляют собой СН, Х представляет собой СНR3, Y представляет собой N, R1 и R5 образуют связь, R8 представляет собой Н, и R2 и R3 вместе представляют собой связь, тогда Ar1 не представляет собой незамещенный фенил, 4-хлорфенил, 4-фторфенил или 4-метоксифенил; b) когда все В, D, Е и G представляют собой СН, Х представляет собой СНR3, Y представляет собой N+R7, R1 и R5 образуют связь, R2 и R3 представляют собой связь, R8 представляет собой Н, и R7 представляет собой метил, тогда Ar1 не представляет собой незамещенный фенил; c) когда все В, D, Е и G представляют собой СН, Х представляет собой СН2, Y представляет собой N, R1 и R5 образуют связь, R8 представляет Н, и R2 представляет собой изопропил, тогда Ar1 не представляет собой незамещенный фенил или 4-бромфенил; и d) когда все В, D, Е и G представляют собой СН, Х и Y представляют собой СН2, и R1 и R5 образуют связь, тогда Ar1 не представляет собой незамещенный фенил,
или его фармацевтически приемлемое производное.2. The compound of formula I
wherein each of B, D, E, and G is CH, CA, or N, provided that no more than one of B, D, E, and G is CA and no more than one of B, D, E, and G is N; X represents C = O, C = S, C = NR 15 , CR 3 R 6 or NR 4 ; Y is N or N + R 7 or CR 18 ; Z is OR 8 or O - ; R 1 is OH or C 1-6 -alkyl, or forms a bond with either R 2 or R 5 ; R 2 is H, C 1-6 alkyl (optionally substituted with phenyl, COOR 9 , NR 10 R 11 , OR 12 or F) or C 3-7 cycloalkyl, or forms a bond with any of R 1 , R 3 or R 4 ; R 3 is H or a bond to R 2 ; R 4 is C 1-6 alkyl or a bond with R 2 ; R 5 is a bond to R 1 or R 8 ; R 6 is H, C 1-6 alkyl (optionally substituted by phenyl), C 3-7 cycloalkyl, phenyl, halogen, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, cyano or NR 13 R 14 ; R 7 is C 1-6 alkyl (optionally substituted by phenyl) or C 3-7 cycloalkyl, each of which may be optionally substituted with halogen, hydroxy, C 1-6 alkoxy, C 1-6 alkylthio, C 1 -6- alkylsulfinyl, NR 16 R 17 , COOH, COO (C 1-6 alkyl) or cyano; or R 6 and R 7 together represent C 3-5 -alkylene, as a result of which X and Y form a 5-7-membered ring; R 8 is H, C 1-6 alkyl or a bond to R 5 ; R 9 , R 10 , R 11 , R 12 , R 15 , R 16 , R 17 and R 18 are independently C 1-6 alkyl or H; R 13 and R 14 are independently C 1-6 alkyl, H or, together with the nitrogen atom to which they are attached, form a 3-7 membered saturated ring, optionally containing an additional oxygen atom or nitrogen atom, optionally substituted with C 1-6 -alkyl; Ar 1 is phenyl, pyridyl, pyrimidinyl, 2-benzothiazolyl, 2- or 3-quinolyl or 2-quinoxalinyl, each of which is optionally substituted with one or more substituents selected from: halogen, nitro, cyano, phenyl, phenylsulfonyl, C 1 -6- alkyl, C 1-6 -alkoxy, C 1-6 -alkylthio, C 1-6 -alkylsulfinyl, COOH, COO (C 1-6 -alkyl), C 1-6 -alkyl, substituted by phenyl, or phenyl in which the alkyl, alkoxy, alkylthio and alkylsulfinyl groups may be optionally substituted with fluorine; and A is halogen, cyano, amino, nitro, C 1-6 alkyl or C 1-6 alkoxy; wherein the phenyl groups that are present in R 2 , R 6 or R 7 , or as substituents in Ar 1, may be optionally substituted with C 1-6 alkyl, halogen or C 1-6 alkoxy; provided that: (i) when X is C = O, C = S or C = NR 15 , then Y is N; (ii) when R 4 is a bond to R 2 , then Y is N + R 7 ; (iii) when Y is N + R 7 , then Z is O - , R 2 is a bond to R 3 or R 4 , and R 1 and R 5 form a bond; (iv) when Y is N, then Z is OR 8 ; (v) when R 1 is OH, then X is C = O, Y is N, Z is OR 8 , and R 5 is a bond to R 8 ; (vi) when R 1 is alkyl, then R 5 is a bond to R 8 , Y is N, R 2 is not a bond, and X is not NR 4 ; (vii) when R 1 is a bond to R 2 , then R 5 and R 8 form a bond, and if X is NR 4 , then R 4 is alkyl; (viii) when R 6 is aryl, halogen, alkoxy, thioalkyl, then R 2 and R 3 form a bond; (ix) when Y is N or N + R 7 and R 2 is substituted with any of NR 10 R 11 , OR 12 or F, then the substituent and ring nitrogen Y cannot be attached to the same carbon atom of R 2 ; (x) when R 7 is substituted with any of NR 16 R 17 , OR 12 or halogen, then the substituent and ring nitrogen Y cannot be attached to the same carbon atom of R 7 ; (xi) when one of B, D, E, and G is N, then X is not NR 4 ; (xii) when Y is CR 18 , then X is CR 3 R 6 ; with the additional proviso that: a) when all B, D, E and G are CH, X is CHR 3 , Y is N, R 1 and R 5 form a bond, R 8 is H, and R 2 and R 3 together represents a bond, then Ar 1 does not represent unsubstituted phenyl, 4-chlorophenyl, 4-fluorophenyl or 4-methoxyphenyl; b) when all B, D, E and G are CH, X is CHR 3 , Y is N + R 7 , R 1 and R 5 form a bond, R 2 and R 3 are a bond, R 8 is H, and R 7 is methyl, then Ar 1 is not unsubstituted phenyl; c) when all B, D, E and G are CH, X is CH 2 , Y is N, R 1 and R 5 form a bond, R 8 is H, and R 2 is isopropyl, then Ar 1 is not is unsubstituted phenyl or 4-bromophenyl; and d) when all B, D, E and G are CH, X and Y are CH 2 , and R 1 and R 5 form a bond, then Ar 1 is not unsubstituted phenyl,
or a pharmaceutically acceptable derivative thereof.
и их фармацевтически приемлемые соли.15. The compound according to claim 2, which is: 3-hydroxy-4 - [(4-methoxyphenyl) methyl] -2- (4-trifluoromethyl-phenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 2- (4-chlorophenyl) -2,5-dihydro-5-methyl-3H-pyrazolo [4, 3-c] -cinnol-3-one, 2- (4-chlorophenyl) -2,3a, 4,5-tetrahydro-3a, 4-dimethylpyrazolo- [4,3-c] isoquinolin-3-one, 2- (4-chlorophenyl) -3a, 4-dihydro-3a, 4-dimethyl-2H-pyrazolo- [4,3-c] isoquinoline-3,5-dione, 2- (4-chlorophenyl) -2,4-dihydro -3-hydroxy-4-methylpyrazolo- [4,3-c] isoquinolin-5-one, 3-hydroxy-4 - [(4-methoxyphenyl) methyl] -2- (3-quinolyl) -2H-pyraz Lo [4,3-c] isoquinolinium hydroxide, inner salt, 2- (3-quinolyl) -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 2- (3,4-dichlorophenyl) -3-hydroxy -4 - [(4-methoxyphenyl) methyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 2- (3,4-dichlorophenyl) -2H-pyrazolo [4,3-с] isoquinoline-3 -ol, 2 ([1,1'-biphenyl] -4-yl) -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 3-hydroxy-4 - [(4-methoxyphenyl) methyl] - 2- (4-methylphenyl) -2H-pyrazolo [4,3-c] isoquinolinium hydroxide, internal salt, 2- (4-methylphenyl) -2H-pyrazolo [4,3-с] isoquinolin-3-ol, 2- ( 4-bromophenyl) -3-hydroxy-4 - [(4-methoxyphenyl) methyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal iya salt, 2- (4-bromophenyl) -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 2- (3-trifluoromethylphenyl) -3-hydroxy-4 - [(4-methoxyphenyl) -methyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 2- (3-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 2- {4- (1,1- dimethylethyl) phenyl] -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 2- (4-trifluoromethoxyphenyl) -2H-pyrazolo [4,3-с] isoquinolin-3-ol, 2- (4- chlorophenyl) -3-hydroxy-4-methyl-2H-pyrazolo [4,3-c] -isoquinoline hydroxide, internal salt, 2- (4-chlorophenyl) -3-hydroxy-4-methyl-2H-pyrazolo [4,3 -c] -cinnolinium hydroxide, internal salt, 2- (4-chlorophenyl) -3-hydroxy-4 - [(4-methoxyfe nyl) methyl-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4-methyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt , 3-hydroxy-4-methyl-2- (3-quinolyl) -2H-pyrazolo [4,3-c] -isoquinoline hydroxide, internal salt, 2- (6-chloro-3-pyridyl) -3-hydroxy-4 -methyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 2- (3,4-dichlorophenyl) -3-hydroxy-4-methyl-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4-methyl-2- (4-methylphenyl) -2H-pyrazolo [4,3-c] -isoquinoline hydroxide, internal salt, 2- (4-bromophenyl) -3-hydroxy -4-methyl-2H-pyrazolo [4,3-c] -isoquinoline hydroxide, inner salt, 3-hydroxy-4-methyl-2- (3-trifluoromethylphenyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxy, inner salt, 2- [4- (1,1-dimethylethyl) phenyl] -3-hydroxy-4-methyl-2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 2- (6-chloro-3- pyridyl) -3-hydroxy-4 - [(4-methoxyphenyl) -methyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4-methyl-2- (6-methyl-3 -pyridyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-trifluoromethylphenyl) -3-hydroxy-4- (2-hydroxyethyl) -2H-pyrazolo [4,3-s] isoquinolinium hydro xis, internal salt, 3-hydroxy-4-methyl-2- (5-methyl-2-pyridyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4-methyl-2 - [4- (1-methylethyl) phenyl] -2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4-methyl-2- (4-nitrophenyl) -2H-pyrazolo [4, 3-c] isoquinoline hydroxide, inner salt, 2- (4-cyanophenyl) -3-hydroxy-4-methyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-carboxyphenyl) -3-hydroxy-4-methyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-chloro-3-trifluoromethylphenyl) -3-hydroxy-4-methyl-2H-pyrazolo [4 , 3-s] and oquinoline hydroxide, inner salt, 2- (4-trifluoromethoxyphenyl) -3-hydroxy-4-methyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, inner salt, 3-hydroxy-4-methyl-2- (4- methylthiophenyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 4-cyclopropyl-3-hydroxy-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 4-cyclopropyl-3-hydroxy-2- (6-methyl-3-pyridyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 4 - [(1,1-dimethyl-2-hydroxy) ethyl ] -3-hydroxy-2 - [(4-trifluoromethyl) phenyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal I salt, 3-hydroxy-4- (2-methoxyethyl) -2 - [(4-trifluoromethyl) phenyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-chlorophenyl) -3 -hydroxy-4- [2- (methylthio) ethyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 3-hydroxy-4- [2- (methylthio) ethyl] -2- (4-trifluoromethylphenyl ) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 4-cyclopropyl-2- (4-trifluoromethoxyphenyl) -3-hydroxy-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-chloro-3-trifluoromethylphenyl) -4-cyclopropyl-3-hydroxy-2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 4-cyclopropane drank-3-hydroxy-2- (4-methylthiophenyl) -2H-pyrazolo [4,3-c] isoquinolinium hydroxide, inner salt, 3-hydroxy-4-phenyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo- [ 4,3-c] isoquinoline hydroxide, inner salt, 4-ethyl-3-hydroxy-2- (4-trifluoromethylphenyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-trifluoromethylphenyl) -4- (1-ethoxycarbonylmethyl) -3-hydroxy-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4 - [(4-methoxyphenyl) methyl] -2-phenyl-2H-pyrazolo - [4,3-s] isoquinoline hydroxide, internal salt, 3-hydroxy-4- (1-methylethyl) -2- (4-trifluoromethylphenyl) -2H-pi split [4,3-c] isoquinolinium hydroxide, inner salt, 3-hydroxy-4- (1-methylethyl) -2- (3-trifluoromethylphenyl) -2H-pyrazolo [4,3-с] isoquinoline hydroxide, inner salt, 3- hydroxy-2- (4-iodophenyl) -4-methyl-2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 2- (6-chloro-3-pyridyl) -2H-pyrazolo [4,3- c] isoquinolin-3-ol, 2- [4- (1-methylethyl) phenyl] -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 2- (4-pentafluoroethylphenyl) -2H-pyrazolo [4 , 3-c] isoquinolin-3-ol, 2,4-dihydro-3-hydroxy-4-methyl-2- (2-pyrimidinyl) -5H-pyrazolo [4,3-c] isoquinolin-5-one, 2 - ([1,1'-biphenyl] -4-yl) -2,4-dihydro-3-hydroxy-4-methyl-5H-pyrazolo [4,3-c] isoquine lin-5-one, 2,4-dihydro-3-hydroxy-4-methyl-2- (4-trifluoromethylphenyl) -5H-pyrazolo [4,3-c] isoquinolin-5-one, 2- (6-chloro -3-pyridyl) -2,4-dihydro-3-hydroxy-4-methyl-5H-pyrazolo [4,3-c] isoquinolin-5-one, 2,4-dihydro-3-hydroxy-2- (4 -iodophenyl) -4-methyl-5H-piraeolo [4,3-c] isoquinolin-5-one, 2,4-dihydro-3-hydroxy-4- (4-methoxyphenylmethyl) -2- (4-trifluoromethylphenyl) - 5H-pyrazolo [4,3-c] isoquinolin-5-one, 2,4-dihydro-3-hydroxy-4- (1-methylethyl) -2- (4-trifluoromethylphenyl) -5H-pyrazolo [4,3- c] isoquinolin-5-one, 2,4-dihydro-3-hydroxy-4-methyl-2- [4- (1-methylethyl) -phenyl] -5H-pyrazolo [4,3-c] isoquinoline-5- he, 2,4-dihydro-3-hydroxy-2- (4-trifluoromethyl) nyl) -5H-pyrazolo [4,3-c] isoquinolin-5-one, 2,4-dihydro-3-hydroxy-2- [4- (1-methylethyl) phenyl] -5H-pyrazolo [4,3- c] isoquinolin-5-one, 2,4-dihydro-3-hydroxy-2 - ([1,1'-biphenyl] -4-yl) -5H-piraeolo [4,3-с] isoquinolin-5-one , 2- (4-chlorophenyl) -3-hydroxy-4 - [(4-methoxyphenyl) methyl] -5-megyl-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-chlorophenyl) -5-methyl-2H-pyrazolo [4,3-c] isoquinolin-3-ol, 4-cyclopropyl-3-hydroxy-5-methyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-s ] isoquinolinium hydroxide, internal salt, 3-hydroxy-4- (2-methoxyethyl) -5-methyl-2 - [(4-trifluoromethyl) -phenyl] -2H-pyrazolo [4,3-c] isoquinolinehydro oxide, inner salt, 2- (4-chlorophenyl) -3-hydroxy-4,5-dimethyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, inner salt, 5-ethyl-3-hydroxy-4-methyl -2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-5-methyl-4- (1-methylethyl) -2- (4-trifluoromethylphenyl) -2H- pyrazolo [4,3-c] isoquinolinium hydroxide, inner salt, 4-methyl-5- (1-methylethyl) -3-hydroxy-2- (4-trifluoromethylphenyl) -2H-pyrazolo- [4,3-c] isoquinoline hydroxy, inner salt, 3-hydroxy-4,5-dimethyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 5-chloro-2 - (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinolin-3-ol, 3a, 4-dihydro-3a-hydroxy-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-s ] isoquinoline-3,5-dione, 2,4-dihydro-3-methoxy-4-methyl-2- (4-trifluoromethylphenyl) -5H-pyrazolo [4,3-c] isoquinolin-5-one, 2- ( 4-chlorophenyl) -4- (2- (N, N-dimethylamino) ethyl} -3-hydroxy-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 3-hydroxy-4-methyl-2- ( 4-methylsulfinylphenyl) -2H-pyrazolo- [4,3-c] isoquinoline-hydroxide, internal salt, 2- (4-chlorophenyl) -3-hydroxy-4- [2- (methylsulfinyl) ethyl] -2H-pyrazolo [4, 3-C] isoquinoline hydroxide, inner salt, 3-hydroxy-4- [2- (methyl sulfinyl) ethyl] -2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 5- [2- (4-methoxyphenyl) ethyl] -2- (4-trifluoromethylphenyl) -2H -pyrazolo [4,3-c] isoquinolin-3-ol, 9-fluoro-3-hydroxy-4 - [(4-methoxyphenyl) methyl] -2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3- c] isoquinoline hydroxide, internal salt, 2- (4-chlorophenyl) -7-fluoro-3-hydroxy-4-methyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 7-fluoro-3-hydroxy -4-methyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinolinium hydroxide, internal salt, 2- (4-chlorophenyl) -4-cyclopropyl-9-fluoro-3-hydroxy-2H- pyrazolo [4,3- ] isoquinoline hydroxide, inner salt, 4-cyclopropyl-9-fluoro-3-hydroxy-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 2- (4-chlorophenyl) -9 -fluoro-3-hydroxy-4-methyl-2H-pyrazolo- [4,3-c] isoquinoline hydroxide, internal salt, 2- (4-chlorophenyl) -9-fluoro-3-hydroxy-4 - [(4-methoxyphenyl ) -methyl] -2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 9-fluoro-3-hydroxy-4-methyl- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoliniihydroxide, inner salt, 2- (4-chlorophenyl) -9-fluoro-2H-pyrazolo [4,3-c] isoquinolin-3-ol, 7-fluoro-2- (4-trifluoromethylphenyl) -2H-pyrazo Lo [4,3-c] -isoquinolin-3-ol, 2- (4-chlorophenyl) -7-fluoro-2H-pyrazolo [4,3-c] isoquinolin-3-ol, 9-fluoro-3-hydroxy -4 - [(4-methoxyphenyl) methyl] -5-methyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 2- (4-chlorophenyl) -9-fluoro -3-hydroxy-4 - [(4-methoxyphenyl) -methyl] -5-methyl-2H-pyrazolo [4,3-c] isoquinoline hydroxide, internal salt, 9-fluoro-5-methyl-2- (4-trifluoromethylphenyl ) -2H-pyrazolo- [4,3-c] isoquinolin-3-ol, 2- (4-chlorophenyl) -9-fluoro-5-methyl-2H-pyrazolo [4,3-c] -isoquinoline-3- ol, 2,4-dihydro-3-hydroxy-4-methyl-2- (4-trifluoromethylphenyl) -5H-pyrazolo [4,3-c] isoquinoline-5-thione, 3-hydroxy-4-methyl- 5-methylthio-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 2- (4-trifluoromethylphenyl) -2,4-dihydro-5-imino-4-methyl-5H -pyrazolo [4,3-c] isoquinolin-3-ol, 3-hydroxy-4- (4-methoxyphenyl) methyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo [3,4-f] [1,7 ] naphthyridinium hydroxide, inner salt, 2- (4-trifluoromethylphenyl) -2H-pyrazolo [3,4-f] [1,7] naphthyridine-3-ol, 3-hydroxy-4-methyl-2- (4-trifluoromethylphenyl ) -2H-pyrazolo- [3,4-f] [1,7] naphthyridinium hydroxide, internal salt, 2- (4-chlorophenyl) -3-hydroxy-4-methyl-2H-pyrazolo [3,4-f] - [1,7] naphthyridinium hydroxide, internal salt, 3-hydroxy-4-methyl- 5- (dimethylamino) -2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinolinium hydroxide, inner salt, 3-hydroxy-4-methyl-5-morpholinyl-2- (4-trifluoromethylphenyl) -2H -pyrazolo [4,3-s] isoquinoline hydroxide, inner salt, 3-hydroxy-4-methyl-5-piperazinyl-2- (4-trifluoromethylphenyl) -2H-pyrazolo [4,3-c] isoquinoline hydroxide, inner salt, 4 5-dihydro-2- [4- (trifluoromethyl) phenyl] -2H-benz [g] indazol-3-ol, 4,5-dihydro-2- (5-methyl-2-pyridinyl) -2H-benz [ g] indazol-3-ol, 2- [4- (trifluoromethyl) phenyl] -2H-benz [g] indazol-3-ol, 2- (5-methyl-2-pyridinyl) -2H-benz [g] indazole -3-ol
and their pharmaceutically acceptable salts.
где Х представляет собой СН2, R1 представляет собой Н, R2 представляет собой группу, соответствующую R7, которая определена в соединении формулы I в п.1, а В, D, Е и G являются такими, как они определены в п.1 и R является алкилом, с соединением формулы ХII
Ar1NHNH2
где Ar1 является таким, как он определен в п.1.16. The method of producing compounds of formula I according to claim 1 or 2, where X is CR 3 R 6 , Y is N + R 7 , Z is O - , R 3 and R 2 form a bond, R 1 and R 5 form a bond, and R 6 is H, by reacting a compound of formula XI
where X represents CH 2 , R 1 represents H, R 2 represents a group corresponding to R 7 , which is defined in the compound of formula I in claim 1, and B, D, E and G are as defined in p .1 and R is alkyl, with a compound of the formula XII
Ar 1 NHNH 2
where Ar 1 is as defined in claim 1.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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GB9605803.7 | 1996-03-20 | ||
GB9610474.0 | 1996-05-18 | ||
GB9610894.9 | 1996-05-24 | ||
GB9700862.7 | 1997-01-16 |
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RU98118998A true RU98118998A (en) | 2000-10-20 |
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RU2530775C2 (en) * | 2009-04-24 | 2014-10-10 | Санофи | DERIVATIVES OF 1H-PYRAZOLO[4,3-c]ISOQUINOLINES, METHOD OF THEIR OBTAINING AND APPLICATION IN THERAPY |
Cited By (1)
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RU2530775C2 (en) * | 2009-04-24 | 2014-10-10 | Санофи | DERIVATIVES OF 1H-PYRAZOLO[4,3-c]ISOQUINOLINES, METHOD OF THEIR OBTAINING AND APPLICATION IN THERAPY |
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