KR20000064716A - 약학적으로유용한화합물 - Google Patents
약학적으로유용한화합물 Download PDFInfo
- Publication number
- KR20000064716A KR20000064716A KR1019980707441A KR19980707441A KR20000064716A KR 20000064716 A KR20000064716 A KR 20000064716A KR 1019980707441 A KR1019980707441 A KR 1019980707441A KR 19980707441 A KR19980707441 A KR 19980707441A KR 20000064716 A KR20000064716 A KR 20000064716A
- Authority
- KR
- South Korea
- Prior art keywords
- pyrazolo
- bond
- hydroxy
- formula
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 title claims description 285
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- -1 NR 16 R 17 Chemical group 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 16
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 11
- UTKNBHYJLFLZRD-UHFFFAOYSA-N isoquinolin-2-ium;hydroxide Chemical compound [OH-].C1=[NH+]C=CC2=CC=CC=C21 UTKNBHYJLFLZRD-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- PVFTVWLLJSNYFC-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-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(=CC=3)C(F)(F)F)[NH2+]C2=C2C=CC=CC2=C1 PVFTVWLLJSNYFC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- 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 description 3
- 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 description 3
- HMLWQFPSKPIFOI-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-[(4-methoxyphenyl)methyl]-5-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].C1=CC(OC)=CC=C1CN1C(C)=C2C=CC=CC2=C2[NH2+]N(C=3C=CC(Cl)=CC=3)C(O)=C21 HMLWQFPSKPIFOI-UHFFFAOYSA-N 0.000 claims description 3
- YLICKAKYJGCYNI-UHFFFAOYSA-N 4-(2-methylsulfanylethyl)-2-[4-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(CCSC)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C(F)(F)F)C=C1 YLICKAKYJGCYNI-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- GIVKRMJBWLSPAC-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-2-[3-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].C1=CC(OC)=CC=C1CN1C2=C(O)N(C=3C=C(C=CC=3)C(F)(F)F)[NH2+]C2=C2C=CC=CC2=C1 GIVKRMJBWLSPAC-UHFFFAOYSA-N 0.000 claims description 3
- ZCQJCHZBLNLFJY-UHFFFAOYSA-N 4-methyl-2-(4-methylthiophen-2-yl)-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC(C)=CS1 ZCQJCHZBLNLFJY-UHFFFAOYSA-N 0.000 claims description 3
- AHFMOFVTPSIFDG-UHFFFAOYSA-N 4-methyl-5-methylsulfanyl-2-[4-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C(SC)=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C(F)(F)F)C=C1 AHFMOFVTPSIFDG-UHFFFAOYSA-N 0.000 claims description 3
- KFMMQNJXOUIUCC-UHFFFAOYSA-N 9-fluoro-4-[(4-methoxyphenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-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(=CC=3)C(F)(F)F)[NH2+]C2=C2C(F)=CC=CC2=C1 KFMMQNJXOUIUCC-UHFFFAOYSA-N 0.000 claims description 3
- GLAATPMUYWMETF-UHFFFAOYSA-N CC(C)(C)c1ccc(cc1)-n1nc2c(ncc3ccccc23)c1O Chemical compound CC(C)(C)c1ccc(cc1)-n1nc2c(ncc3ccccc23)c1O GLAATPMUYWMETF-UHFFFAOYSA-N 0.000 claims description 3
- CLLHLKCMHYJZIJ-UHFFFAOYSA-N Cc1ccc(nc1)-n1nc-2c(CCc3ccccc-23)c1O Chemical compound Cc1ccc(nc1)-n1nc-2c(CCc3ccccc-23)c1O CLLHLKCMHYJZIJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- ZJAASUXBXXTWJB-UHFFFAOYSA-N Oc1c2CCc3ccccc3-c2nn1-c1ccc(cc1)C(F)(F)F Chemical compound Oc1c2CCc3ccccc3-c2nn1-c1ccc(cc1)C(F)(F)F ZJAASUXBXXTWJB-UHFFFAOYSA-N 0.000 claims description 3
- UDKJWYFTUASSAT-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1ccc(OC(F)(F)F)cc1 Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1ccc(OC(F)(F)F)cc1 UDKJWYFTUASSAT-UHFFFAOYSA-N 0.000 claims description 3
- KLKKZAVOZSWSRL-UHFFFAOYSA-N Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)-c1ccccc1 Chemical compound Oc1n(nc2c1ncc1ccccc21)-c1ccc(cc1)-c1ccccc1 KLKKZAVOZSWSRL-UHFFFAOYSA-N 0.000 claims description 3
- KQRHWMBVDDGFJH-UHFFFAOYSA-N [OH-].OC=1N([NH2+]C=2C=1N(C=C1C=CC=CC=21)CC1=CC=C(C=C1)OC)C=1C=NC2=CC=CC=C2C=1 Chemical compound [OH-].OC=1N([NH2+]C=2C=1N(C=C1C=CC=CC=21)CC1=CC=C(C=C1)OC)C=1C=NC2=CC=CC=C2C=1 KQRHWMBVDDGFJH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- DOZCZZKHZAGMKO-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4-[(4-methoxyphenyl)methyl]-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].C1=CC(OC)=CC=C1CN1C2=C(O)N(C=3C=C(Cl)C(Cl)=CC=3)[NH2+]C2=C2C=CC=CC2=C1 DOZCZZKHZAGMKO-UHFFFAOYSA-N 0.000 claims description 2
- WISWOBVOXDOJLV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(Cl)C(Cl)=C1 WISWOBVOXDOJLV-UHFFFAOYSA-N 0.000 claims description 2
- DQXIGGIUUOIORU-UHFFFAOYSA-N 2-(4-bromophenyl)-4-[(4-methoxyphenyl)methyl]-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(Br)=CC=3)[NH2+]C2=C2C=CC=CC2=C1 DQXIGGIUUOIORU-UHFFFAOYSA-N 0.000 claims description 2
- WHNDAYMYILZNGT-UHFFFAOYSA-N 2-(4-bromophenyl)-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(Br)C=C1 WHNDAYMYILZNGT-UHFFFAOYSA-N 0.000 claims description 2
- XRYAOHFWRNRGHB-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,5-dimethyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].[NH2+]1C2=C3C=CC=CC3=C(C)N(C)C2=C(O)N1C1=CC=C(Cl)C=C1 XRYAOHFWRNRGHB-UHFFFAOYSA-N 0.000 claims description 2
- OOVMRUNJTOSPNP-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(2-methylsulfanylethyl)-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(CCSC)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(Cl)C=C1 OOVMRUNJTOSPNP-UHFFFAOYSA-N 0.000 claims description 2
- YKCAYWYLBMXVDK-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-[(4-methoxyphenyl)methyl]-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(Cl)=CC=3)[NH2+]C2=C2C=CC=CC2=C1 YKCAYWYLBMXVDK-UHFFFAOYSA-N 0.000 claims description 2
- ZIRDRYMCICGLCI-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-cyclopropyl-9-fluoro-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C3CC3)C=C3C=CC=C(F)C3=C2[NH2+]N1C1=CC=C(Cl)C=C1 ZIRDRYMCICGLCI-UHFFFAOYSA-N 0.000 claims description 2
- YJZSNRWSEWJSEE-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(Cl)C=C1 YJZSNRWSEWJSEE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- JXTZLGLKTLCHEU-UHFFFAOYSA-N 2-(4-chlorophenyl)-9-fluoro-4-[(4-methoxyphenyl)methyl]-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(Cl)=CC=3)[NH2+]C2=C2C(F)=CC=CC2=C1 JXTZLGLKTLCHEU-UHFFFAOYSA-N 0.000 claims description 2
- RDZKPSLCQMHEMV-UHFFFAOYSA-N 2-(4-iodophenyl)-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(I)C=C1 RDZKPSLCQMHEMV-UHFFFAOYSA-N 0.000 claims description 2
- HSKNESSXMAUTOB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-methyl-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C(C)(C)C)C=C1 HSKNESSXMAUTOB-UHFFFAOYSA-N 0.000 claims description 2
- WRXJZRDDFLTBBX-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(Cl)N=C1 WRXJZRDDFLTBBX-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- KAELQDVKOFKOQX-UHFFFAOYSA-N 3a-hydroxy-2-[4-(trifluoromethyl)phenyl]-4h-pyrazolo[4,3-c]isoquinoline-3,5-dione Chemical compound O=C1C2(O)NC(=O)C3=CC=CC=C3C2=NN1C1=CC=C(C(F)(F)F)C=C1 KAELQDVKOFKOQX-UHFFFAOYSA-N 0.000 claims description 2
- YZVCPHZBWANGLV-UHFFFAOYSA-N 4,5-dimethyl-2-[4-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].[NH2+]1C2=C3C=CC=CC3=C(C)N(C)C2=C(O)N1C1=CC=C(C(F)(F)F)C=C1 YZVCPHZBWANGLV-UHFFFAOYSA-N 0.000 claims description 2
- BDCYLEDBRGCNIA-UHFFFAOYSA-N 4-(3-hydroxy-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-2-yl)benzoic acid;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C(O)=O)C=C1 BDCYLEDBRGCNIA-UHFFFAOYSA-N 0.000 claims description 2
- LFCLBXHYRHUXPL-UHFFFAOYSA-N 4-(3-hydroxy-4-methyl-1h-pyrazolo[4,3-c]isoquinolin-1-ium-2-yl)benzonitrile;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C#N)C=C1 LFCLBXHYRHUXPL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- UFWQLPZKOGNICF-UHFFFAOYSA-N 4-cyclopropyl-9-fluoro-2-[4-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C3CC3)C=C3C=CC=C(F)C3=C2[NH2+]N1C1=CC=C(C(F)(F)F)C=C1 UFWQLPZKOGNICF-UHFFFAOYSA-N 0.000 claims description 2
- JHFCMQCVAAGCCH-UHFFFAOYSA-N 4-methyl-2-(4-methylphenyl)-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C)C=C1 JHFCMQCVAAGCCH-UHFFFAOYSA-N 0.000 claims description 2
- UHMJRIYVFOEEKI-UHFFFAOYSA-N 4-methyl-2-(4-methylsulfinylphenyl)-1h-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol;hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(S(C)=O)C=C1 UHMJRIYVFOEEKI-UHFFFAOYSA-N 0.000 claims description 2
- CMSFBHOWFRNPJY-UHFFFAOYSA-N 4-methyl-2-(4-nitrophenyl)-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C([N+]([O-])=O)C=C1 CMSFBHOWFRNPJY-UHFFFAOYSA-N 0.000 claims description 2
- HGIQSVCKZQZQHK-UHFFFAOYSA-N 4-methyl-2-(5-methylpyridin-2-yl)-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C)C=N1 HGIQSVCKZQZQHK-UHFFFAOYSA-N 0.000 claims description 2
- MYDOMCZZXQMLSS-UHFFFAOYSA-N 4-methyl-2-(6-methylpyridin-3-yl)-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C)N=C1 MYDOMCZZXQMLSS-UHFFFAOYSA-N 0.000 claims description 2
- QUZCXVQFQYDAGV-UHFFFAOYSA-N 4-methyl-2-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=CC(C(F)(F)F)=C1 QUZCXVQFQYDAGV-UHFFFAOYSA-N 0.000 claims description 2
- SNCCUKBBGGOHLY-UHFFFAOYSA-N 4-methyl-2-[4-(trifluoromethyl)phenyl]-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].OC1=C2N(C)C=C3C=CC=CC3=C2[NH2+]N1C1=CC=C(C(F)(F)F)C=C1 SNCCUKBBGGOHLY-UHFFFAOYSA-N 0.000 claims description 2
- CGHGYFODLUOFAX-UHFFFAOYSA-N 4-methyl-2-quinolin-3-yl-1H-pyrazolo[4,3-c]isoquinolin-1-ium-3-ol hydroxide Chemical compound [OH-].C1=CC=CC2=CC(N3[NH2+]C4=C5C=CC=CC5=CN(C4=C3O)C)=CN=C21 CGHGYFODLUOFAX-UHFFFAOYSA-N 0.000 claims description 2
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- MGGNIEDZABVSCC-UHFFFAOYSA-J tetrasodium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Na+].[Na+].[Na+].[Na+] MGGNIEDZABVSCC-UHFFFAOYSA-J 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- PFMBRNMAXCVTIV-UHFFFAOYSA-K trisodium hydrogen carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.OC([O-])=O.OC([O-])=O PFMBRNMAXCVTIV-UHFFFAOYSA-K 0.000 description 1
- 208000001319 vasomotor rhinitis Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9605803.7 | 1996-03-20 | ||
| GBGB9605803.7A GB9605803D0 (en) | 1996-03-20 | 1996-03-20 | Pharmaceutically-active compound |
| GBGB9610474.0A GB9610474D0 (en) | 1996-05-18 | 1996-05-18 | Pharmaceutically active compounds |
| GB9610474.0 | 1996-05-18 | ||
| GBGB9610894.9A GB9610894D0 (en) | 1996-05-24 | 1996-05-24 | Pharmaceutically useful compounds |
| GB9610894.9 | 1996-05-24 | ||
| GBGB9700862.7A GB9700862D0 (en) | 1997-01-16 | 1997-01-16 | Pharmaceutically useful compounds |
| GB9700862.7 | 1997-01-16 | ||
| PCT/SE1997/000471 WO1997034893A1 (en) | 1996-03-20 | 1997-03-20 | Pharmaceutically useful compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000064716A true KR20000064716A (ko) | 2000-11-06 |
Family
ID=27451427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980707441A Withdrawn KR20000064716A (ko) | 1996-03-20 | 1997-03-20 | 약학적으로유용한화합물 |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0888347A1 (cs) |
| JP (1) | JP2000506884A (cs) |
| KR (1) | KR20000064716A (cs) |
| CN (1) | CN1218472A (cs) |
| AR (1) | AR006520A1 (cs) |
| AU (1) | AU712141B2 (cs) |
| BR (1) | BR9708103A (cs) |
| CA (1) | CA2247814A1 (cs) |
| CZ (1) | CZ297798A3 (cs) |
| EE (1) | EE9800298A (cs) |
| ID (1) | ID16283A (cs) |
| IL (1) | IL126271A0 (cs) |
| IS (1) | IS4848A (cs) |
| NO (1) | NO984290L (cs) |
| NZ (1) | NZ331614A (cs) |
| PL (1) | PL328921A1 (cs) |
| SK (1) | SK118798A3 (cs) |
| TR (1) | TR199801861T2 (cs) |
| WO (1) | WO1997034893A1 (cs) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10110749A1 (de) * | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| JP2003002863A (ja) * | 2001-06-25 | 2003-01-08 | Nippon Soda Co Ltd | 安息香酸類の製造方法および新規化合物 |
| SE0102404D0 (sv) * | 2001-07-04 | 2001-07-04 | Active Biotech Ab | Novel immunomodulating compounds |
| US6642249B2 (en) | 2001-07-04 | 2003-11-04 | Active Biotech Ab | Immunomodulating compounds |
| DE10229762A1 (de) * | 2002-07-03 | 2004-01-22 | Aventis Pharma Deutschland Gmbh | Pyrazoloisoquinolinenderivaten zur Inhibierung von NFkappaB-induzierende Kinase |
| RU2328496C2 (ru) * | 2002-11-22 | 2008-07-10 | Эктив Байотек Аб | Пиразолхинолины с иммуномодулирующей активностью |
| AU2003287129A1 (en) * | 2002-12-16 | 2004-07-09 | Active Biotech Ab | Tetracyclic immunomodulatory compounds |
| SI1603917T1 (sl) | 2003-03-14 | 2011-04-29 | Medigene Ag | Imunomodulacijske heterociklične spojine |
| GB0325644D0 (en) | 2003-11-04 | 2003-12-10 | Avidex Ltd | Immuno ihibitory pyrazolone compounds |
| SV2005001973A (es) | 2003-12-12 | 2005-11-04 | Wyeth Corp | Quinolinas utiles en el tratamiento de enfermedades cardiovasculares ref. wyth0090-504 (am101500) |
| FR2870239B1 (fr) * | 2004-05-11 | 2006-06-16 | Sanofi Synthelabo | Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique. |
| GB0411770D0 (en) * | 2004-05-26 | 2004-06-30 | Avidex Ltd | Immuno inhibitory heterocyclic compouds |
| CN1997645B (zh) * | 2004-08-09 | 2012-05-23 | 麦迪金股份公司 | 免疫调节作为cd80抑制剂的氧代吡唑并噌啉类 |
| ES2375877T3 (es) | 2006-10-31 | 2012-03-07 | Pfizer Products Inc. | Compuestos de pirazolina como antagonistas de receptores de mineralocorticoides. |
| CN102372710A (zh) * | 2010-08-18 | 2012-03-14 | 山东轩竹医药科技有限公司 | 作为盐皮质激素受体拮抗剂的并环类化合物 |
| EP2674423A4 (en) | 2011-02-09 | 2014-07-30 | Nissan Chemical Ind Ltd | PYRAZONE DERIVATIVE AND PESTICIDES |
| WO2020049017A1 (en) * | 2018-09-07 | 2020-03-12 | Merck Patent Gmbh | 5-morpholin-4-yl-pyrazolo[4,3-b]pyridine derivatives |
| WO2021257863A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Pyrrolotriazine compounds as jak2 v617f inhibitors |
| US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
| WO2022006456A1 (en) | 2020-07-02 | 2022-01-06 | Incyte Corporation | Tricyclic pyridone compounds as jak2 v617f inhibitors |
| PT4175719T (pt) | 2020-07-02 | 2025-06-27 | Incyte Corp | Compostos tricíclicos de ureia como inibidores v617f de jak2 |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
| US11958861B2 (en) | 2021-02-25 | 2024-04-16 | Incyte Corporation | Spirocyclic lactams as JAK2 V617F inhibitors |
| CR20240447A (es) | 2022-03-17 | 2025-01-29 | Incyte Corp | Compuestos de urea tricíclica como inhibidores de v617f de jak2. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4524146A (en) * | 1982-12-08 | 1985-06-18 | Ciba-Geigy Corporation | Certain -2-heterocycle substituted pyrazoloquinolines |
| JPS61112075A (ja) * | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| SE8903564D0 (sv) * | 1989-10-26 | 1989-10-26 | Pharmacia Ab | New use condensed quinoline compound |
| JPH05194515A (ja) * | 1991-07-31 | 1993-08-03 | Kyowa Hakko Kogyo Co Ltd | 縮合ナフチリジン誘導体 |
-
1997
- 1997-03-19 ID IDP970892A patent/ID16283A/id unknown
- 1997-03-19 AR ARP970101094A patent/AR006520A1/es unknown
- 1997-03-20 IL IL12627197A patent/IL126271A0/xx unknown
- 1997-03-20 JP JP9533412A patent/JP2000506884A/ja active Pending
- 1997-03-20 TR TR1998/01861T patent/TR199801861T2/xx unknown
- 1997-03-20 WO PCT/SE1997/000471 patent/WO1997034893A1/en not_active Application Discontinuation
- 1997-03-20 CA CA002247814A patent/CA2247814A1/en not_active Abandoned
- 1997-03-20 PL PL97328921A patent/PL328921A1/xx unknown
- 1997-03-20 CZ CZ982977A patent/CZ297798A3/cs unknown
- 1997-03-20 AU AU21867/97A patent/AU712141B2/en not_active Ceased
- 1997-03-20 CN CN97194665A patent/CN1218472A/zh active Pending
- 1997-03-20 SK SK1187-98A patent/SK118798A3/sk unknown
- 1997-03-20 BR BR9708103A patent/BR9708103A/pt unknown
- 1997-03-20 KR KR1019980707441A patent/KR20000064716A/ko not_active Withdrawn
- 1997-03-20 EP EP97914729A patent/EP0888347A1/en not_active Withdrawn
- 1997-03-20 EE EE9800298A patent/EE9800298A/xx unknown
- 1997-03-20 NZ NZ331614A patent/NZ331614A/xx unknown
-
1998
- 1998-09-16 NO NO984290A patent/NO984290L/no unknown
- 1998-09-16 IS IS4848A patent/IS4848A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2247814A1 (en) | 1997-09-25 |
| TR199801861T2 (xx) | 1998-12-21 |
| NO984290D0 (no) | 1998-09-16 |
| EE9800298A (et) | 1999-02-15 |
| ID16283A (id) | 1997-09-18 |
| NO984290L (no) | 1998-10-27 |
| CZ297798A3 (cs) | 1999-03-17 |
| JP2000506884A (ja) | 2000-06-06 |
| IL126271A0 (en) | 1999-05-09 |
| BR9708103A (pt) | 1999-07-27 |
| AU712141B2 (en) | 1999-10-28 |
| NZ331614A (en) | 2000-07-28 |
| SK118798A3 (en) | 1999-03-12 |
| EP0888347A1 (en) | 1999-01-07 |
| IS4848A (is) | 1998-09-16 |
| AR006520A1 (es) | 1999-09-08 |
| WO1997034893A1 (en) | 1997-09-25 |
| PL328921A1 (en) | 1999-03-01 |
| AU2186797A (en) | 1997-10-10 |
| CN1218472A (zh) | 1999-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19980919 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |