JP2010521522A5 - - Google Patents
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- JP2010521522A5 JP2010521522A5 JP2009554036A JP2009554036A JP2010521522A5 JP 2010521522 A5 JP2010521522 A5 JP 2010521522A5 JP 2009554036 A JP2009554036 A JP 2009554036A JP 2009554036 A JP2009554036 A JP 2009554036A JP 2010521522 A5 JP2010521522 A5 JP 2010521522A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- pyridine
- optionally substituted
- dione
- 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.)
- Granted
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- -1 1,3-Benzothiazol-2-yl Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 15
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 5
- 150000005229 pyrazolopyridines Chemical class 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- YGXAYPWLSCJZRQ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-ethyl-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC=C2SC(N3NC4=CC(=O)N(CCOC)C(=C4C3=O)CC)=NC2=C1 YGXAYPWLSCJZRQ-UHFFFAOYSA-N 0.000 claims 2
- WVGSMJYPLAOVRV-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-ethyl-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(CC)N1CCCN1CCOCC1 WVGSMJYPLAOVRV-UHFFFAOYSA-N 0.000 claims 2
- NZTATZGYYCOWNR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-ethyl-5-(4-methylpiperazin-1-yl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(CC)N1N1CCN(C)CC1 NZTATZGYYCOWNR-UHFFFAOYSA-N 0.000 claims 2
- SIXSWBRHHWBRRQ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-ethyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(CC)N1CC1=CC=CC=N1 SIXSWBRHHWBRRQ-UHFFFAOYSA-N 0.000 claims 2
- SDCAMLQHQRVVAN-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-5-(oxolan-2-ylmethyl)-1-(pyridin-2-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3N=CC=CC=3)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CC1CCCO1 SDCAMLQHQRVVAN-UHFFFAOYSA-N 0.000 claims 2
- DNKYHHFCPXKFIY-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(C)N1CC1=CC=CC=N1 DNKYHHFCPXKFIY-UHFFFAOYSA-N 0.000 claims 2
- SOWDNLOMIQWAKK-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(CC)N(CCOC)C(=O)C=C2NN1C1=CC=C(F)C=C1 SOWDNLOMIQWAKK-UHFFFAOYSA-N 0.000 claims 2
- STQHYZIEXCJXHE-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CCC1=CC=CC=C1 STQHYZIEXCJXHE-UHFFFAOYSA-N 0.000 claims 2
- DKRLZUYJVLRNKH-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CCCN1CCOCC1 DKRLZUYJVLRNKH-UHFFFAOYSA-N 0.000 claims 2
- SVWXTWPIDMRQBZ-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CC1=CC=CC=N1 SVWXTWPIDMRQBZ-UHFFFAOYSA-N 0.000 claims 2
- JTHHUSZXKAATHK-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-morpholin-4-yl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1N1CCOCC1 JTHHUSZXKAATHK-UHFFFAOYSA-N 0.000 claims 2
- HKCHGZRTXYMUOB-UHFFFAOYSA-N 4-ethyl-5-(3-morpholin-4-ylpropyl)-2-[4-(trifluoromethoxy)phenyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(OC(F)(F)F)=CC=3)C(=O)C2=C(CC)N1CCCN1CCOCC1 HKCHGZRTXYMUOB-UHFFFAOYSA-N 0.000 claims 2
- JHESKYYOWZPHPU-UHFFFAOYSA-N 4-ethyl-5-(3-morpholin-4-ylpropyl)-2-[4-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(=CC=3)C(F)(F)F)C(=O)C2=C(CC)N1CCCN1CCOCC1 JHESKYYOWZPHPU-UHFFFAOYSA-N 0.000 claims 2
- GDXIFMQUTARHDA-UHFFFAOYSA-N 4-methyl-2-(2-methylphenyl)-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)N(CCCN3CCOCC3)C(=O)C=C2N1 GDXIFMQUTARHDA-UHFFFAOYSA-N 0.000 claims 2
- DTMJLSYMVBVNOW-UHFFFAOYSA-N 5-(2-morpholin-4-ylethyl)-2-pyridin-2-yl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=C2C(=O)N(C=3N=CC=CC=3)NC2=CC(=O)N1CCN1CCOCC1 DTMJLSYMVBVNOW-UHFFFAOYSA-N 0.000 claims 2
- RYPVHNJGJGSXHH-UHFFFAOYSA-N 5-benzyl-4-ethyl-2-(4-fluorophenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CC1=CC=CC=C1 RYPVHNJGJGSXHH-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- OPWIRJKWKBGRBM-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-4-methyl-5-[3-(2-oxopyrrolidin-1-yl)propyl]-2-phenylpyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C(=CC=CC=3)Cl)N(C=3C=CC=CC=3)C(=O)C2=C(C)N1CCCN1CCCC1=O OPWIRJKWKBGRBM-UHFFFAOYSA-N 0.000 claims 1
- RQLIJUQDJIWPSW-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-5-[2-(1h-imidazol-5-yl)ethyl]-4-methyl-2-phenylpyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C=CC(Cl)=CC=3)N(C=3C=CC=CC=3)C(=O)C2=C(C)N1CCC1=CN=CN1 RQLIJUQDJIWPSW-UHFFFAOYSA-N 0.000 claims 1
- GQGQOPNIMHBAOH-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-5-[2-(1h-indol-3-yl)ethyl]-4-methyl-2-phenylpyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1N1C(=O)C2=C(C)N(CCC=3C4=CC=CC=C4NC=3)C(=O)C=C2N1CC1=CC=C(F)C=C1 GQGQOPNIMHBAOH-UHFFFAOYSA-N 0.000 claims 1
- FDPVGRGPQDYSEQ-UHFFFAOYSA-N 2,4-diphenyl-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1C1=C2C(=O)N(C=3C=CC=CC=3)NC2=CC(=O)N1CC1=CC=CN=C1 FDPVGRGPQDYSEQ-UHFFFAOYSA-N 0.000 claims 1
- HAUIRJQRGRMAIV-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-1-[(2-chlorophenyl)methyl]-4-methyl-5-(3-morpholin-4-ylpropyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C(=CC=CC=3)Cl)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CCCN1CCOCC1 HAUIRJQRGRMAIV-UHFFFAOYSA-N 0.000 claims 1
- XHGZXAVUEWBNHE-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-1-[(2-chlorophenyl)methyl]-4-methyl-5-morpholin-4-ylpyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C(=CC=CC=3)Cl)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1N1CCOCC1 XHGZXAVUEWBNHE-UHFFFAOYSA-N 0.000 claims 1
- RYDRQKFTQARJHP-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-1-[(4-bromophenyl)methyl]-4-methyl-5-(2-morpholin-4-ylethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C=CC(Br)=CC=3)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CCN1CCOCC1 RYDRQKFTQARJHP-UHFFFAOYSA-N 0.000 claims 1
- VDGVQFKQALNCIZ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-1-[(4-fluorophenyl)methyl]-4-methyl-5-(3-morpholin-4-ylpropyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C=CC(F)=CC=3)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CCCN1CCOCC1 VDGVQFKQALNCIZ-UHFFFAOYSA-N 0.000 claims 1
- XYRKERQLRYSNDV-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-1-benzyl-4-methyl-5-(oxolan-2-ylmethyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C=CC=CC=3)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CC1CCCO1 XYRKERQLRYSNDV-UHFFFAOYSA-N 0.000 claims 1
- HSSPTKKINZIHTL-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-1-benzyl-5-(furan-2-ylmethyl)-4-methylpyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2N(CC=3C=CC=CC=3)N(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CC1=CC=CO1 HSSPTKKINZIHTL-UHFFFAOYSA-N 0.000 claims 1
- QALRXLQBQWGLSW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-ethyl-5-[1-[(4-methylphenyl)methyl]piperidin-4-yl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(CC)N1C(CC1)CCN1CC1=CC=C(C)C=C1 QALRXLQBQWGLSW-UHFFFAOYSA-N 0.000 claims 1
- GDODCCPBPFSXIK-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-1-[(3-methylphenyl)methyl]-5-(3-morpholin-4-ylpropyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=CC=CC(CN2C3=CC(=O)N(CCCN4CCOCC4)C(C)=C3C(=O)N2C=2SC3=CC=CC=C3N=2)=C1 GDODCCPBPFSXIK-UHFFFAOYSA-N 0.000 claims 1
- SDYDERKEOSPKDV-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-1-[(4-methylphenyl)methyl]-5-(3-morpholin-4-ylpropyl)pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(C)=CC=C1CN1C2=CC(=O)N(CCCN3CCOCC3)C(C)=C2C(=O)N1C1=NC2=CC=CC=C2S1 SDYDERKEOSPKDV-UHFFFAOYSA-N 0.000 claims 1
- YZVZFGKBBHGZOI-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-5-(2-methylbutyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC=C2SC(N3NC=4C(C3=O)=C(C)N(C(C=4)=O)CC(C)CC)=NC2=C1 YZVZFGKBBHGZOI-UHFFFAOYSA-N 0.000 claims 1
- CWLBYWBQCRLXAZ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-5-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CCC1=CC=CC=C1 CWLBYWBQCRLXAZ-UHFFFAOYSA-N 0.000 claims 1
- QMJQNCDSPCPHQO-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CCCN1CCOCC1 QMJQNCDSPCPHQO-UHFFFAOYSA-N 0.000 claims 1
- WUKFZNWYWGZKRP-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methyl-5-morpholin-4-yl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1N1CCOCC1 WUKFZNWYWGZKRP-UHFFFAOYSA-N 0.000 claims 1
- PLLXXGHEDZWKGG-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-5-[2-(1h-imidazol-5-yl)ethyl]-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CCC1=CN=CN1 PLLXXGHEDZWKGG-UHFFFAOYSA-N 0.000 claims 1
- BMWFXSPRYOHMMZ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-5-[2-(1h-indol-3-yl)ethyl]-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC=C2SC(N3NC4=CC(=O)N(CCC=5C6=CC=CC=C6NC=5)C(=C4C3=O)C)=NC2=C1 BMWFXSPRYOHMMZ-UHFFFAOYSA-N 0.000 claims 1
- PWDYNBQZRITTAZ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-5-[2-(4-hexanoylpiperazin-1-yl)ethyl]-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1CN(C(=O)CCCCC)CCN1CCN1C(=O)C=C(NN(C=2SC3=CC=CC=C3N=2)C2=O)C2=C1C PWDYNBQZRITTAZ-UHFFFAOYSA-N 0.000 claims 1
- KJYCIPWGCPJWMD-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-5-[2-(4-methoxyphenyl)ethyl]-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)C=C(NN(C=2SC3=CC=CC=C3N=2)C2=O)C2=C1C KJYCIPWGCPJWMD-UHFFFAOYSA-N 0.000 claims 1
- CYIITHFCXXBOEQ-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-4-ethyl-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=C(F)C=3)F)C(=O)C2=C(CC)N1CCCN1CCOCC1 CYIITHFCXXBOEQ-UHFFFAOYSA-N 0.000 claims 1
- WLTPZDWPBFJKEF-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-ethyl-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C(CC)N1CC1=CC=CN=C1 WLTPZDWPBFJKEF-UHFFFAOYSA-N 0.000 claims 1
- UFSBBXSERZQNHQ-UHFFFAOYSA-N 4-[[2-(1,3-benzothiazol-2-yl)-4-methyl-3,6-dioxo-1h-pyrazolo[4,3-c]pyridin-5-yl]methyl]benzoic acid Chemical compound O=C1C=C2NN(C=3SC4=CC=CC=C4N=3)C(=O)C2=C(C)N1CC1=CC=C(C(O)=O)C=C1 UFSBBXSERZQNHQ-UHFFFAOYSA-N 0.000 claims 1
- SCPLVJAUOOAQQS-UHFFFAOYSA-N 4-ethyl-2-(2-methoxyphenyl)-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)OC)C(=O)C2=C(CC)N1CCCN1CCOCC1 SCPLVJAUOOAQQS-UHFFFAOYSA-N 0.000 claims 1
- MOCCDBAWHYEHAG-UHFFFAOYSA-N 4-ethyl-5-morpholin-4-yl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(CC)N1N1CCOCC1 MOCCDBAWHYEHAG-UHFFFAOYSA-N 0.000 claims 1
- FJPUXMVNLPHRCZ-UHFFFAOYSA-N 4-methyl-2-(2-methylphenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)N(CC=3N=CC=CC=3)C(=O)C=C2N1 FJPUXMVNLPHRCZ-UHFFFAOYSA-N 0.000 claims 1
- ICYYTFBMNVALJS-UHFFFAOYSA-N 4-methyl-2-phenyl-5-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CCC1=CC=CC=C1 ICYYTFBMNVALJS-UHFFFAOYSA-N 0.000 claims 1
- ISLQXEIRVZXLJA-UHFFFAOYSA-N 4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CN=C1 ISLQXEIRVZXLJA-UHFFFAOYSA-N 0.000 claims 1
- KQWPBXREZDLGMX-UHFFFAOYSA-N 4-methyl-2-phenyl-5-(thiophen-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CS1 KQWPBXREZDLGMX-UHFFFAOYSA-N 0.000 claims 1
- JNUCVMRXTBMHRQ-UHFFFAOYSA-N 4-methyl-5-(2-morpholin-4-ylethyl)-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CCN1CCOCC1 JNUCVMRXTBMHRQ-UHFFFAOYSA-N 0.000 claims 1
- IXQAPEWDNTZIAO-UHFFFAOYSA-N 4-methyl-5-(oxolan-2-ylmethyl)-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1CCCO1 IXQAPEWDNTZIAO-UHFFFAOYSA-N 0.000 claims 1
- QAABOTJXRMFONY-UHFFFAOYSA-N 4-methyl-5-morpholin-4-yl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1N1CCOCC1 QAABOTJXRMFONY-UHFFFAOYSA-N 0.000 claims 1
- ANUFFQUQIIVNIW-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-ylmethyl)-4-methyl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(CC=3C=C4OCOC4=CC=3)C(=O)C=C2NN1C1=CC=CC=C1 ANUFFQUQIIVNIW-UHFFFAOYSA-N 0.000 claims 1
- MIRFIMNUTDFIPW-UHFFFAOYSA-N 5-(furan-2-ylmethyl)-4-methyl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CO1 MIRFIMNUTDFIPW-UHFFFAOYSA-N 0.000 claims 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 108010035114 procamine Proteins 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 229960000281 trometamol Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2002835A1 (en) * | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2000176A1 (en) | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole derivatives as NADPH Oxidase inhibitors |
| EP2166010A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166008A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2165707A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166009A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as nadph oxidase inhibitors |
| US20120141461A1 (en) * | 2009-07-17 | 2012-06-07 | The Regents Of The University Of Michigan | Compositions and methods for diagnosing and treating fibrotic disorders |
| EP2305679A1 (en) * | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| EP2512242B8 (en) * | 2009-12-18 | 2015-12-09 | GlaxoSmithKline Intellectual Property Limited | Novel compounds |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP2361912A1 (en) * | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| WO2012173952A1 (en) | 2011-06-13 | 2012-12-20 | Emory University | Piperazine derivatives, compositions, and uses related thereto |
| GB2494679A (en) * | 2011-09-15 | 2013-03-20 | Univ Jw Goethe Frankfurt Main | Treatment of neuropathic pain and nerve injury by Nox4 inhibition |
| EP2591782A1 (en) * | 2011-11-11 | 2013-05-15 | Johann Wolfgang Goethe-Universität | Nadph oxidase 4 inhibitors and use thereof |
| WO2014153227A1 (en) * | 2013-03-14 | 2014-09-25 | Eastern Virginia Medical School | Methods of preserving and protecting pancreatic beta cells and treating or preventing diabetes by inhibiting nox-1 |
| EP2857399A1 (en) | 2013-10-03 | 2015-04-08 | GenKyoTex SA | Compounds useful for the treatment of PDE5 inhibitor-poorly responsive erectile dysfunction |
| EP3098220A1 (en) | 2015-05-28 | 2016-11-30 | GenKyoTex SA | Process for the preparation of a nadph oxidase inhibitor and its polymorphs and uses thereof |
| TW201713650A (en) * | 2015-06-22 | 2017-04-16 | Actelion Pharmaceuticals Ltd | NADPH oxidase 4 inhibitors |
| CA3027097C (en) * | 2016-05-10 | 2023-11-28 | Georgia State University Research Foundation, Inc. | Bicyclic fused pyrazole derivatives for the treatment of rsv |
| US11084796B2 (en) | 2016-05-10 | 2021-08-10 | Georgia State University Research Foundation, Inc. | Heterocyclic derivatives for the treatment of RSV |
| US10280164B2 (en) | 2016-09-09 | 2019-05-07 | Incyte Corporation | Pyrazolopyridone compounds and uses thereof |
| UA125650C2 (uk) | 2016-09-09 | 2022-05-11 | Інсайт Корпорейшн | Регулятори нрk1 на основі похідних піразолопіридину та їх застосування для лікування раку |
| AR109595A1 (es) | 2016-09-09 | 2018-12-26 | Incyte Corp | Compuestos de pirazolopirimidina y usos de estos como inhibidores de hpk1 |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| US20180228786A1 (en) | 2017-02-15 | 2018-08-16 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| BR112019023109A2 (pt) | 2017-05-04 | 2020-05-26 | Glenmark Pharmaceuticals S.A. | Composto, composição farmacêutica e método para tratar uma doença, distúrbio, síndrome ou afecção mediada por nadph oxidase em um indivíduo |
| WO2019023448A1 (en) | 2017-07-26 | 2019-01-31 | Emory University | INHIBITORS OF NADPH OXIDASE AND THEIR USE |
| WO2019051199A1 (en) | 2017-09-08 | 2019-03-14 | Incyte Corporation | 6-CYANO-INDAZOLE COMPOUNDS AS HEMATOPOIETIC PROGENITOR KINASE 1 (HPK1) MODULATORS |
| EP3479843A1 (en) | 2017-11-01 | 2019-05-08 | GenKyoTex Suisse SA | Use of nox inhibitors for treatment of cancer |
| HRP20220833T1 (hr) | 2018-02-20 | 2022-10-28 | Incyte Corporation | Derivati n-(fenil)-2-(fenil)pirimidin-4-karboksamida i odgovarajući spojevi kao inhibitori hpk1 za liječenje raka |
| WO2019164847A1 (en) | 2018-02-20 | 2019-08-29 | Incyte Corporation | Indazole compounds and uses thereof |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| CN109846900B (zh) * | 2018-05-25 | 2021-07-23 | 四川大学 | 还原型烟酰胺腺嘌呤二核苷酸磷酸在制备抗病毒药物中的用途 |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| US20220112187A1 (en) * | 2018-09-11 | 2022-04-14 | Hoffmann-La Roche Inc. | Pyrazolopyridine amine compounds for the treatment of autoimmune disease |
| TW202028207A (zh) | 2018-09-25 | 2020-08-01 | 美商英塞特公司 | 吡唑并嘧啶化合物及其用途 |
| MX2022001562A (es) | 2019-08-06 | 2022-04-26 | Incyte Corp | Formas solidas de un inhibidor de la cinasa 1 del progenitor hematopoyetico (hpk1). |
| US11896719B2 (en) | 2022-01-24 | 2024-02-13 | Calliditas Therapeutics Ab | Pharmaceutical compositions |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931407A (en) * | 1973-03-01 | 1976-01-06 | American Hoechst Corporation | Method of treatment with and compositions containing condensed pyrroles bearing an N-phenyl substituent |
| DE3728278A1 (de) | 1986-12-17 | 1988-06-23 | Bayer Ag | Herbizide und fungizide mittel auf basis von substituierten pyrazolin-5-on derivaten |
| DE19518082A1 (de) * | 1995-05-17 | 1996-11-21 | Merck Patent Gmbh | 4(-Arylaminomethylen)-2,4-dihydropyrazol-3-one |
| US5763496A (en) | 1995-11-27 | 1998-06-09 | The Research Foundation Of State University Of New York | Prevention of atherosclerosis using NADPH oxidase inhibitors |
| TW432073B (en) | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
| WO1998037068A1 (en) * | 1997-02-21 | 1998-08-27 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| IL144468A0 (en) | 2000-07-27 | 2002-05-23 | Pfizer Prod Inc | Use of growth hormone secretagogues for improvement of functional health status |
| JP4196678B2 (ja) | 2001-04-26 | 2008-12-17 | 味の素株式会社 | 複素環化合物 |
| EP1291017A3 (en) | 2001-09-10 | 2003-07-02 | Warner-Lambert Company | Use of statins to inhibit formation of osteoclasts |
| KR20040097375A (ko) * | 2002-04-23 | 2004-11-17 | 시오노기 앤드 컴파니, 리미티드 | 피라졸로[1, 5-에이]피리미딘 유도체 및 이를 함유한엔에이디(피)에이취 산화효소 저해제 |
| WO2004005267A2 (en) | 2002-07-03 | 2004-01-15 | Janssen Pharmaceutica, N.V. | Heteroaryl compounds useful in treating inflammatory disorders |
| EP1603543A4 (en) | 2003-02-28 | 2009-03-04 | Florey Howard Inst | THERAPEUTIC COMPOSITIONS |
| US20070082910A1 (en) | 2003-04-08 | 2007-04-12 | Mitsubishi Pharma Corporation | Specific nad(p)h oxidase inhibitor |
| TW200533356A (en) | 2004-02-24 | 2005-10-16 | Mitsubishi Pharma Corp | Fused pyridazine derivatives |
| EP1809601B1 (en) | 2004-10-04 | 2014-09-10 | Manfredi, John | Compounds for alzheimer's disease |
| FR2882654B1 (fr) | 2005-03-01 | 2007-04-27 | Servier Lab | Utilisation de derives de la diosmetine pour le traitement et la prevention des pathologies thrombotiques |
| US7759337B2 (en) | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
| US7576053B2 (en) | 2005-06-13 | 2009-08-18 | Rigel Pharmaceuticals, Inc. | Methods and compositions for treating degenerative bone disorders |
| US20070014739A1 (en) | 2005-07-14 | 2007-01-18 | Eldridge Gary R | Compositions and methods for controlling biofilms and bacterial infections |
| DE102005048897A1 (de) * | 2005-10-12 | 2007-04-19 | Sanofi-Aventis Deutschland Gmbh | Diacylindazol-derivate als Inhibitoren von Lipasen und Phospholipasen |
| JP2009532501A (ja) * | 2006-04-04 | 2009-09-10 | ミリアド ジェネティクス， インコーポレイテッド | 疾患および障害のための化合物 |
| EP2002835A1 (en) | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2000176A1 (en) | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole derivatives as NADPH Oxidase inhibitors |
| PE20091093A1 (es) | 2007-12-03 | 2009-08-25 | Takeda Pharmaceutical | Compuesto heterociclico que contiene nitrogeno y su uso |
| US20090163452A1 (en) | 2007-12-20 | 2009-06-25 | Schwartz Janice B | Compositions and methods for lowering serum cholesterol |
| FR2929276B1 (fr) | 2008-04-01 | 2010-04-23 | Servier Lab | Nouveaux derives de diosmetine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP2166010A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166008A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166009A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as nadph oxidase inhibitors |
| EP2165707A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| WO2011085293A1 (en) | 2010-01-08 | 2011-07-14 | Beth Israel Deaconess Medical Center | Methods and compositions for the treatment of migraine headaches |
| EP2361912A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP2591782A1 (en) | 2011-11-11 | 2013-05-15 | Johann Wolfgang Goethe-Universität | Nadph oxidase 4 inhibitors and use thereof |
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