JP2016500694A5 - - Google Patents
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- JP2016500694A5 JP2016500694A5 JP2015538317A JP2015538317A JP2016500694A5 JP 2016500694 A5 JP2016500694 A5 JP 2016500694A5 JP 2015538317 A JP2015538317 A JP 2015538317A JP 2015538317 A JP2015538317 A JP 2015538317A JP 2016500694 A5 JP2016500694 A5 JP 2016500694A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- spiro
- pyridin
- diaza
- chloro
- 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 decan-8-yl Chemical group 0.000 claims 39
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- WLDBKDYSWDAYMZ-UHFFFAOYSA-N decan-1-one Chemical compound CCCCCCCCC[C]=O WLDBKDYSWDAYMZ-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- LQGLKWIXYWZNGB-UHFFFAOYSA-N 1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound O1C(=O)NCC11CCNCC1 LQGLKWIXYWZNGB-UHFFFAOYSA-N 0.000 claims 3
- HHIOFHJYOIVJJK-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCNCC1 HHIOFHJYOIVJJK-UHFFFAOYSA-N 0.000 claims 3
- HRSWSISJJJDBOQ-UHFFFAOYSA-N 2-oxo-1,3-diaza-8-azoniaspiro[4.5]dec-3-en-4-olate Chemical compound N1C(=O)NC(=O)C11CCNCC1 HRSWSISJJJDBOQ-UHFFFAOYSA-N 0.000 claims 3
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- KZQKFDYIFPNXSE-UHFFFAOYSA-N 1'-[2-amino-3-chloro-5-(1-methylindazol-5-yl)pyridin-4-yl]spiro[1h-indole-3,4'-piperidine]-2-one Chemical compound O=C1NC2=CC=CC=C2C1(CC1)CCN1C1=C(Cl)C(N)=NC=C1C1=CC=C2N(C)N=CC2=C1 KZQKFDYIFPNXSE-UHFFFAOYSA-N 0.000 claims 1
- QPJLHDVDDLHLFI-UHFFFAOYSA-N 1'-[2-amino-3-chloro-5-[4-(1-methylpyrazol-4-yl)phenyl]pyridin-4-yl]spiro[1h-indole-3,4'-piperidine]-2-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(CC2)C2=CC=CC=C2NC3=O)C=C1 QPJLHDVDDLHLFI-UHFFFAOYSA-N 0.000 claims 1
- CHDMTSGOYLFAAG-UHFFFAOYSA-N 1,4,9-triazaspiro[5.5]undecan-5-one Chemical compound O=C1NCCNC11CCNCC1 CHDMTSGOYLFAAG-UHFFFAOYSA-N 0.000 claims 1
- OFXFWAVREFHCLN-UHFFFAOYSA-N 1-[2-amino-3-chloro-5-(4-morpholin-4-ylphenyl)pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=C(Cl)C(N)=NC=C1C(C=C1)=CC=C1N1CCOCC1 OFXFWAVREFHCLN-UHFFFAOYSA-N 0.000 claims 1
- HZPSENCJDYBPGS-UHFFFAOYSA-N 1-[2-amino-3-chloro-5-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC(CC2)C#N)C=C1 HZPSENCJDYBPGS-UHFFFAOYSA-N 0.000 claims 1
- GRDNENMVSPDQBD-UHFFFAOYSA-N 1-methyl-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(C)C(=O)CCC2=C1 GRDNENMVSPDQBD-UHFFFAOYSA-N 0.000 claims 1
- WODIALSWFWKWMM-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound O=C1NC(=O)CC11CCNCC1 WODIALSWFWKWMM-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- FPWYXHKGPQQAAG-UHFFFAOYSA-N 3-oxodecanal Chemical compound CCCCCCCC(=O)CC=O FPWYXHKGPQQAAG-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- QEOZRFNZVFRMOA-UHFFFAOYSA-N 5-[6-amino-5-chloro-4-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)pyridin-3-yl]-3h-1,3-benzoxazol-2-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3NC(=O)OC3=CC=2)C=1N(CC1)CCC21CCNC2=O QEOZRFNZVFRMOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- NOECPUUEJMSLDL-UHFFFAOYSA-N 8-(2-amino-3-chloro-5-phenylpyridin-4-yl)-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1CC2(C(NCC2)=O)CCN1C1=C(Cl)C(N)=NC=C1C1=CC=CC=C1 NOECPUUEJMSLDL-UHFFFAOYSA-N 0.000 claims 1
- GYAFLLCEXZVXRI-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-ethylindazol-5-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(CC)N=CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O GYAFLLCEXZVXRI-UHFFFAOYSA-N 0.000 claims 1
- NBEOSRCQLSILFB-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-ethylindazol-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=C2N(CC)N=CC2=CC=C1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O NBEOSRCQLSILFB-UHFFFAOYSA-N 0.000 claims 1
- LJZGQQSILUTMBY-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(C)C(=O)CCC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O LJZGQQSILUTMBY-UHFFFAOYSA-N 0.000 claims 1
- MRZZSYKABAANGP-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methyl-2-oxo-3h-indol-5-yl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CNC(=O)O2 MRZZSYKABAANGP-UHFFFAOYSA-N 0.000 claims 1
- KRWSWUYIMMBEBZ-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methyl-2-oxo-3h-indol-5-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O KRWSWUYIMMBEBZ-UHFFFAOYSA-N 0.000 claims 1
- IAXKCHNAHGGRFL-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methylindazol-5-yl)pyridin-4-yl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21NC(=O)NC2=O IAXKCHNAHGGRFL-UHFFFAOYSA-N 0.000 claims 1
- UYMBYVWSBPECIF-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methylindazol-5-yl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CNC(=O)O2 UYMBYVWSBPECIF-UHFFFAOYSA-N 0.000 claims 1
- VPJXPDLMACOGIZ-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methylindazol-5-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O VPJXPDLMACOGIZ-UHFFFAOYSA-N 0.000 claims 1
- WVMHRPYCVFNQTJ-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methylindazol-5-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CC(=O)NC2=O WVMHRPYCVFNQTJ-UHFFFAOYSA-N 0.000 claims 1
- GEZQIASUCYYJOQ-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methylindazol-6-yl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=C2N(C)N=CC2=CC=C1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CNC(=O)O2 GEZQIASUCYYJOQ-UHFFFAOYSA-N 0.000 claims 1
- RCWFVFHZIVJFRT-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-methylindazol-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=C2N(C)N=CC2=CC=C1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O RCWFVFHZIVJFRT-UHFFFAOYSA-N 0.000 claims 1
- WPSWRMGEAFKBTL-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1-propan-2-ylindazol-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=C2N(C(C)C)N=CC2=CC=C1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O WPSWRMGEAFKBTL-UHFFFAOYSA-N 0.000 claims 1
- SNFNTWHHWHKCOS-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1h-indazol-5-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3C=NNC3=CC=2)C=1N(CC1)CCC21CCNC2=O SNFNTWHHWHKCOS-UHFFFAOYSA-N 0.000 claims 1
- JXICCADVBDBLGD-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1h-indol-6-yl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3NC=CC3=CC=2)C=1N(CC1)CCC21CNC(=O)O2 JXICCADVBDBLGD-UHFFFAOYSA-N 0.000 claims 1
- ZKZCNOUDDQDUCS-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(1h-indol-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3NC=CC3=CC=2)C=1N(CC1)CCC21CCNC2=O ZKZCNOUDDQDUCS-UHFFFAOYSA-N 0.000 claims 1
- GKJXCCOFBMRZRU-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(2-oxo-1,3-dihydroindol-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3NC(=O)CC3=CC=2)C=1N(CC1)CCC21CCNC2=O GKJXCCOFBMRZRU-UHFFFAOYSA-N 0.000 claims 1
- WQZNIUAKZLJCGJ-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(2-oxo-3,4-dihydro-1h-quinolin-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3CCC(=O)NC3=CC=2)C=1N(CC1)CCC21CCNC2=O WQZNIUAKZLJCGJ-UHFFFAOYSA-N 0.000 claims 1
- XVQGZXKVZJABRU-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(2-oxo-3,4-dihydro-1h-quinolin-6-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound ClC=1C(N)=NC=C(C=2C=C3CCC(=O)NC3=CC=2)C=1N(CC1)CCC21CC(=O)NC2=O XVQGZXKVZJABRU-UHFFFAOYSA-N 0.000 claims 1
- HMVPVIOIRAADKF-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(2-oxo-3h-1,3-benzoxazol-5-yl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound ClC=1C(N)=NC=C(C=2C=C3NC(=O)OC3=CC=2)C=1N(CC1)CCC21CNC(=O)O2 HMVPVIOIRAADKF-UHFFFAOYSA-N 0.000 claims 1
- RPQTXWJXCHWVBS-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-(4-morpholin-4-ylphenyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1CC2(C(NCC2)=O)CCN1C1=C(Cl)C(N)=NC=C1C(C=C1)=CC=C1N1CCOCC1 RPQTXWJXCHWVBS-UHFFFAOYSA-N 0.000 claims 1
- WLNUDRFOSHWBNG-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-(1-methylpyrazol-4-yl)phenyl]pyridin-4-yl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(CC2)C(NC(=O)N3)=O)C=C1 WLNUDRFOSHWBNG-UHFFFAOYSA-N 0.000 claims 1
- UXSVDQPKNXQICD-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-(1-methylpyrazol-4-yl)phenyl]pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(OC(=O)NC3)CC2)C=C1 UXSVDQPKNXQICD-UHFFFAOYSA-N 0.000 claims 1
- FORSEVCTEGJHQK-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-(1-propan-2-ylpyrazol-4-yl)phenyl]pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=NN(C(C)C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(OC(=O)NC3)CC2)C=C1 FORSEVCTEGJHQK-UHFFFAOYSA-N 0.000 claims 1
- GHHDMQJYDMQTDY-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-[1-(2-hydroxy-2-methylpropyl)pyrazol-4-yl]phenyl]pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=NN(CC(C)(O)C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(C(NCC3)=O)CC2)C=C1 GHHDMQJYDMQTDY-UHFFFAOYSA-N 0.000 claims 1
- APUBCHAZOCQBHU-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-[1-(2-hydroxyethyl)pyrazol-4-yl]phenyl]pyridin-4-yl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound C1CC2(C(NC(=O)N2)=O)CCN1C1=C(Cl)C(N)=NC=C1C(C=C1)=CC=C1C=1C=NN(CCO)C=1 APUBCHAZOCQBHU-UHFFFAOYSA-N 0.000 claims 1
- PZXIDSYVQYAQHR-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-[1-(2-hydroxyethyl)pyrazol-4-yl]phenyl]pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1CC2(OC(=O)NC2)CCN1C1=C(Cl)C(N)=NC=C1C(C=C1)=CC=C1C=1C=NN(CCO)C=1 PZXIDSYVQYAQHR-UHFFFAOYSA-N 0.000 claims 1
- JWAWMHOKDKSMQR-UHFFFAOYSA-N 8-[2-amino-3-chloro-5-[4-[1-(2-methylsulfonylethyl)pyrazol-4-yl]phenyl]pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=NN(CCS(=O)(=O)C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(C(NCC3)=O)CC2)C=C1 JWAWMHOKDKSMQR-UHFFFAOYSA-N 0.000 claims 1
- QYTUXXMJLUJTBO-UHFFFAOYSA-N 8-[2-amino-3-fluoro-5-(1-methylindazol-5-yl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(F)=C1N(CC1)CCC21CCNC2=O QYTUXXMJLUJTBO-UHFFFAOYSA-N 0.000 claims 1
- ZQLQHKSTJMSAJZ-UHFFFAOYSA-N 8-[2-amino-5-(1-methyl-2-oxo-3h-indol-5-yl)-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1C1=CN=C(N)C(C(F)(F)F)=C1N(CC1)CCC21CCNC2=O ZQLQHKSTJMSAJZ-UHFFFAOYSA-N 0.000 claims 1
- XBDZVFPMNMAUFU-UHFFFAOYSA-N 8-[2-amino-5-(1-methyl-2-oxo-3h-indol-6-yl)-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=C2N(C)C(=O)CC2=CC=C1C1=CN=C(N)C(C(F)(F)F)=C1N(CC1)CCC21CCNC2=O XBDZVFPMNMAUFU-UHFFFAOYSA-N 0.000 claims 1
- NIKUYKHHRADECG-UHFFFAOYSA-N 8-[2-amino-5-(1-methylindazol-5-yl)-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(C(F)(F)F)=C1N(CC1)CCC21CCNC2=O NIKUYKHHRADECG-UHFFFAOYSA-N 0.000 claims 1
- ZDDJKIMXMVHBSP-UHFFFAOYSA-N 8-[2-amino-5-(1-methylindazol-5-yl)-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound C=1C=C2N(C)N=CC2=CC=1C1=CN=C(N)C(C(F)(F)F)=C1N(CC1)CCC21CC(=O)NC2=O ZDDJKIMXMVHBSP-UHFFFAOYSA-N 0.000 claims 1
- OEEODHWPMAZOMU-UHFFFAOYSA-N 8-[2-amino-5-(3-amino-1h-indazol-6-yl)-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2C(N)=NNC2=CC=1C1=CN=C(N)C(C(F)(F)F)=C1N(CC1)CCC21CCNC2=O OEEODHWPMAZOMU-UHFFFAOYSA-N 0.000 claims 1
- VCZWOCZZZCTWAO-UHFFFAOYSA-N 8-[2-amino-5-(3-amino-1h-indazol-6-yl)-3-chloropyridin-4-yl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound C=1C=C2C(N)=NNC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21NC(=O)NC2=O VCZWOCZZZCTWAO-UHFFFAOYSA-N 0.000 claims 1
- AVNJKHNJOUZXCO-UHFFFAOYSA-N 8-[2-amino-5-(3-amino-1h-indazol-6-yl)-3-chloropyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C=1C=C2C(N)=NNC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CNC(=O)O2 AVNJKHNJOUZXCO-UHFFFAOYSA-N 0.000 claims 1
- CGELUDGKNGUGSC-UHFFFAOYSA-N 8-[2-amino-5-(3-amino-1h-indazol-6-yl)-3-chloropyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C=1C=C2C(N)=NNC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CCNC2=O CGELUDGKNGUGSC-UHFFFAOYSA-N 0.000 claims 1
- WXFFYNALWDVRPR-UHFFFAOYSA-N 8-[2-amino-5-(3-amino-1h-indazol-6-yl)-3-chloropyridin-4-yl]-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound C=1C=C2C(N)=NNC2=CC=1C1=CN=C(N)C(Cl)=C1N(CC1)CCC21CC(=O)NC2=O WXFFYNALWDVRPR-UHFFFAOYSA-N 0.000 claims 1
- FZQAZSRDRZGHTP-UHFFFAOYSA-N 8-[2-amino-5-[4-(1-methylpyrazol-4-yl)phenyl]-3-(trifluoromethyl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(C(N)=NC=2)C(F)(F)F)N2CCC3(OC(=O)NC3)CC2)C=C1 FZQAZSRDRZGHTP-UHFFFAOYSA-N 0.000 claims 1
- NAVWVDFKHIIIDK-UHFFFAOYSA-N 8-[2-amino-5-[4-(1-methylpyrazol-4-yl)phenyl]-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(C(N)=NC=2)C(F)(F)F)N2CCC3(C(NCC3)=O)CC2)C=C1 NAVWVDFKHIIIDK-UHFFFAOYSA-N 0.000 claims 1
- JASMFRHJPBAYTM-UHFFFAOYSA-N 8-[2-amino-5-[4-(1-methylpyrazol-4-yl)phenyl]-3-(trifluoromethyl)pyridin-4-yl]-2,8-diazaspiro[4.5]decane-1,3-dione Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(C(N)=NC=2)C(F)(F)F)N2CCC3(C(NC(=O)C3)=O)CC2)C=C1 JASMFRHJPBAYTM-UHFFFAOYSA-N 0.000 claims 1
- NLLZRMAOMXUQNN-UHFFFAOYSA-N 8-[2-amino-5-[4-(1-propan-2-ylpyrazol-4-yl)phenyl]-3-(trifluoromethyl)pyridin-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1=NN(C(C)C)C=C1C1=CC=C(C=2C(=C(C(N)=NC=2)C(F)(F)F)N2CCC3(OC(=O)NC3)CC2)C=C1 NLLZRMAOMXUQNN-UHFFFAOYSA-N 0.000 claims 1
- IFEJWHLTHKRXGI-UHFFFAOYSA-N 8-[2-amino-5-[4-(6-aminopyridin-3-yl)phenyl]-3-chloropyridin-4-yl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound C1=NC(N)=CC=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(C(NCC3)=O)CC2)C=C1 IFEJWHLTHKRXGI-UHFFFAOYSA-N 0.000 claims 1
- FMDIGYNYBRKXCW-UHFFFAOYSA-N 9-[2-amino-3-chloro-5-[4-(1-methylpyrazol-4-yl)phenyl]pyridin-4-yl]-1,4,9-triazaspiro[5.5]undecan-5-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2C(=C(Cl)C(N)=NC=2)N2CCC3(CC2)C(NCCN3)=O)C=C1 FMDIGYNYBRKXCW-UHFFFAOYSA-N 0.000 claims 1
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- 125000006242 amine protecting group Chemical group 0.000 claims 1
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| PCT/EP2013/002966 WO2014063778A1 (en) | 2012-10-08 | 2013-10-02 | 2-aminopyridine compounds |
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| WO2015144290A1 (en) * | 2014-03-27 | 2015-10-01 | Merck Patent Gmbh | Pyridyl piperidines |
| CN104391058B (zh) * | 2014-11-25 | 2015-12-02 | 广东东阳光药业有限公司 | 阿法替尼及其异构体的检测方法 |
| US11285144B2 (en) * | 2016-08-03 | 2022-03-29 | The Broad Institute, Inc. | Use of CDK8 inhibitors to treat diseases of inflammation and autoimmunity |
| JP7142846B2 (ja) | 2017-01-30 | 2022-09-28 | 国立大学法人京都大学 | 新規化合物及び制御性ｔ細胞の製造方法 |
| CN111163775B (zh) | 2017-10-02 | 2023-07-11 | 勃林格殷格翰国际有限公司 | 作为cdk8/cdk19抑制剂的新型[1,6]萘啶化合物和衍生物 |
| EP4076443B1 (en) * | 2019-12-17 | 2025-09-10 | Merck Sharp & Dohme LLC | Substituted 1,3,8-triazaspiro[4,5]decane-2,4-dione compound as indoleamine 2,3-dioxygenase (ido) and/or tryptophan 2,3-dioxygenase (tdo) inhibitors |
| EP4410965A4 (en) | 2021-09-27 | 2025-09-24 | Univ Kyoto | T LYMPHOCYTE PRODUCTION PROCESS |
| KR20240130083A (ko) | 2021-11-24 | 2024-08-28 | 레그셀 가부시키가이샤 | T세포 관련 질환을 치료 또는 예방하기 위한 의약 조성물 |
| TW202330911A (zh) | 2021-11-24 | 2023-08-01 | 日商雷格細胞股份有限公司 | 人類誘導性控制性ｔ細胞及其製作方法 |
| CN114591326B (zh) * | 2022-02-28 | 2024-02-27 | 上海筛杰生物医药有限公司 | Cct-251921的中间体及其制备方法 |
| EP4497822A4 (en) | 2022-03-23 | 2026-03-18 | Univ Kyoto | PROCESS FOR THE PRODUCTION OF REGULATORY T LYMPHOCYTES |
| EP4596684A1 (en) | 2022-09-26 | 2025-08-06 | Regcell Co., Ltd. | Induced regulatory t cells containing chimeric antigen receptor (car) |
| CN120112629A (zh) | 2022-09-26 | 2025-06-06 | 国立大学法人京都大学 | T细胞产生方法 |
| US20260232799A1 (en) | 2023-02-08 | 2026-08-13 | Regcell Co., Ltd. | Pharmaceutical composition for treating or preventing pemphigus |
| CN121057812A (zh) | 2023-03-29 | 2025-12-02 | 雷格细胞股份有限公司 | 人诱导性调节性t细胞及其制作方法以及用于治疗或预防t细胞相关疾病的药物组合物 |
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| JP4272338B2 (ja) * | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
| EA200870019A1 (ru) | 2005-12-05 | 2008-12-30 | Инсайт Корпорейшн | Лактамовые соединения и способы их применения |
| WO2008122378A1 (en) * | 2007-04-04 | 2008-10-16 | Ucb Pharma, S.A. | Novel pyridine derivatives, processes for preparing them, pharmaceutical compositions thereof |
| GB0818241D0 (en) | 2008-10-06 | 2008-11-12 | Cancer Res Technology | Compounds and their use |
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