JP2014531458A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014531458A5 JP2014531458A5 JP2014533218A JP2014533218A JP2014531458A5 JP 2014531458 A5 JP2014531458 A5 JP 2014531458A5 JP 2014533218 A JP2014533218 A JP 2014533218A JP 2014533218 A JP2014533218 A JP 2014533218A JP 2014531458 A5 JP2014531458 A5 JP 2014531458A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- triazolo
- general formula
- pyrido
- pyrazin
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 126
- 125000005842 heteroatom Chemical group 0.000 claims 35
- 125000000623 heterocyclic group Chemical group 0.000 claims 27
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 229910052717 sulfur Inorganic materials 0.000 claims 19
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 18
- 229920006395 saturated elastomer Polymers 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 11
- -1 tert-butyl (1- (8-chloro-2-methyloxazolo [4,5-c] [1,8] naphthyridin-4-yl) azetidin-3-yl) (methyl) carbamate Chemical compound 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- MMVBKZHQTLDYKG-UHFFFAOYSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 MMVBKZHQTLDYKG-UHFFFAOYSA-N 0.000 claims 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 4
- 230000002140 halogenating effect Effects 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- ICGICUHMULRYIQ-UHFFFAOYSA-N 1-(12-bromo-2,3,4,5,8,10-hexazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=N2 ICGICUHMULRYIQ-UHFFFAOYSA-N 0.000 claims 2
- JJMSSEGSJZIYCX-UHFFFAOYSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N,N-dimethylazetidin-3-amine Chemical compound C1C(N(C)C)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 JJMSSEGSJZIYCX-UHFFFAOYSA-N 0.000 claims 2
- WASIWJNKOCZNFP-LREBCSMRSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine (2R,3R)-2,3-dihydroxybutanedioic acid Chemical compound O[C@H]([C@@H](O)C(O)=O)C(O)=O.CNC1CN(C1)c1nc2ncc(Br)cc2n2cnnc12 WASIWJNKOCZNFP-LREBCSMRSA-N 0.000 claims 2
- PVQYTONCQMWFCM-WNQIDUERSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine (2S)-2-hydroxypropanoic acid Chemical compound C[C@H](O)C(O)=O.CNC1CN(C1)c1nc2ncc(Br)cc2n2cnnc12 PVQYTONCQMWFCM-WNQIDUERSA-N 0.000 claims 2
- ZCNIOEAHXVCLCB-UHFFFAOYSA-N 1-(12-bromo-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NC=C2 ZCNIOEAHXVCLCB-UHFFFAOYSA-N 0.000 claims 2
- WNPYEYYGAWATBK-UHFFFAOYSA-N 1-(12-bromo-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NCC2 WNPYEYYGAWATBK-UHFFFAOYSA-N 0.000 claims 2
- KEHDFGJYGVMMKU-UHFFFAOYSA-N 1-(12-bromo-4-methyl-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NC(C)=C2 KEHDFGJYGVMMKU-UHFFFAOYSA-N 0.000 claims 2
- SAGHZBBBDBALED-UHFFFAOYSA-N 1-(12-bromo-4-methyl-5,6,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2C2=CC(C)=NN12 SAGHZBBBDBALED-UHFFFAOYSA-N 0.000 claims 2
- UFHKHEOAWFCXBP-UHFFFAOYSA-N 1-(12-bromo-6,8,10-triazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2C2=CC=CN12 UFHKHEOAWFCXBP-UHFFFAOYSA-N 0.000 claims 2
- HRGIIIWIMGJNML-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-amine Chemical compound C1C(N)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 HRGIIIWIMGJNML-UHFFFAOYSA-N 0.000 claims 2
- BBNPHMSHIGXZGV-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,11-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=CN=C(Cl)C=C2N2C1=NN=C2 BBNPHMSHIGXZGV-UHFFFAOYSA-N 0.000 claims 2
- XFMUHEUGQXUGFA-UHFFFAOYSA-N 1-(12-chloro-4-methyl-2,3,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NC(C)=N2 XFMUHEUGQXUGFA-UHFFFAOYSA-N 0.000 claims 2
- MXHBODNGTCDLFN-UHFFFAOYSA-N 1-(12-ethyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C12=NN=CN2C2=CC(CC)=CN=C2N=C1N1CC(NC)C1 MXHBODNGTCDLFN-UHFFFAOYSA-N 0.000 claims 2
- QRDLDDNULOYARY-UHFFFAOYSA-N 1-(8-chloro-2-methyl-[1,3]oxazolo[4,5-c][1,8]naphthyridin-4-yl)-n-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2C2=C1N=C(C)O2 QRDLDDNULOYARY-UHFFFAOYSA-N 0.000 claims 2
- GEZHTOGZKOZVFG-UHFFFAOYSA-N 12-bromo-11-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC(C)=C(Br)C=C2N2C1=NN=C2 GEZHTOGZKOZVFG-UHFFFAOYSA-N 0.000 claims 2
- YPOGNINXKRNIAQ-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,3,4,5,8,10-hexazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Br)C=C2N2C1=NN=N2 YPOGNINXKRNIAQ-UHFFFAOYSA-N 0.000 claims 2
- CCIBEQZUDVOXRO-UHFFFAOYSA-N 12-bromo-N-(1-methylpyrrolidin-3-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-amine Chemical compound C1N(C)CCC1NC1=NC2=NC=C(Br)C=C2N2C1=NN=C2 CCIBEQZUDVOXRO-UHFFFAOYSA-N 0.000 claims 2
- GFMFYECOOOAXQM-UHFFFAOYSA-N 12-chloro-4-methyl-7-(4-methylpiperazin-1-yl)-2,3,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NC(C)=N2 GFMFYECOOOAXQM-UHFFFAOYSA-N 0.000 claims 2
- NJPYHCCBZPKJRN-UHFFFAOYSA-N 12-chloro-7-(1,4-diazepan-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N1CCCNCC1 NJPYHCCBZPKJRN-UHFFFAOYSA-N 0.000 claims 2
- PLSIRSPTBSKMDP-UHFFFAOYSA-N 12-chloro-7-(4-methyl-1,4-diazepan-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 PLSIRSPTBSKMDP-UHFFFAOYSA-N 0.000 claims 2
- LCTNQWHKGUJFEH-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,3,4,5,8,10-hexazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=N2 LCTNQWHKGUJFEH-UHFFFAOYSA-N 0.000 claims 2
- FXKDRFDFQGJXIQ-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 FXKDRFDFQGJXIQ-UHFFFAOYSA-N 0.000 claims 2
- PVXMKQSOGUMXCY-UHFFFAOYSA-N 12-chloro-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 PVXMKQSOGUMXCY-UHFFFAOYSA-N 0.000 claims 2
- BYAVSOKLNYIJSU-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=CC=CN=C2N2C1=NN=C2 BYAVSOKLNYIJSU-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- ZOWOZQMEPXBKTA-UWVGGRQHSA-N C([C@@H]1C[C@H]2CN1C)N2C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C([C@@H]1C[C@H]2CN1C)N2C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 ZOWOZQMEPXBKTA-UWVGGRQHSA-N 0.000 claims 2
- BUVFPBCXBVKVEI-UHFFFAOYSA-N C1C(NC)CN1C1=NC2=NC=C(Br)C=C2C2=CC=NN12 Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2C2=CC=NN12 BUVFPBCXBVKVEI-UHFFFAOYSA-N 0.000 claims 2
- SFBTWVZZRINEDU-UHFFFAOYSA-N C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 SFBTWVZZRINEDU-UHFFFAOYSA-N 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- MSBQKMIKJYWQLY-UHFFFAOYSA-N N-methyl-1-(12-nitro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C([N+]([O-])=O)C=C2N2C1=NN=C2 MSBQKMIKJYWQLY-UHFFFAOYSA-N 0.000 claims 2
- PMYCLVJEHZLPHY-UHFFFAOYSA-N N-methyl-1-(12-phenyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C=3C=CC=CC=3)C=C2N2C1=NN=C2 PMYCLVJEHZLPHY-UHFFFAOYSA-N 0.000 claims 2
- PGQDQCATOKHSPS-UHFFFAOYSA-N N-methyl-1-[12-(trifluoromethyl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl]azetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C(F)(F)F)C=C2N2C1=NN=C2 PGQDQCATOKHSPS-UHFFFAOYSA-N 0.000 claims 2
- 206010028735 Nasal congestion Diseases 0.000 claims 2
- CROHFCZGWRERLS-UHFFFAOYSA-N OC(=O)C(F)(F)F.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound OC(=O)C(F)(F)F.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 CROHFCZGWRERLS-UHFFFAOYSA-N 0.000 claims 2
- CYXCYSGPIROROX-UHFFFAOYSA-N OC(=O)CC(O)(C(O)=O)CC(O)=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 CYXCYSGPIROROX-UHFFFAOYSA-N 0.000 claims 2
- IZDLCMCWQGTICB-UHFFFAOYSA-N OP(O)(O)=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound OP(O)(O)=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 IZDLCMCWQGTICB-UHFFFAOYSA-N 0.000 claims 2
- HBJWDNXPIOANHH-UHFFFAOYSA-N OS(O)(=O)=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound OS(O)(=O)=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 HBJWDNXPIOANHH-UHFFFAOYSA-N 0.000 claims 2
- DECAHPNLPIGUOJ-UHFFFAOYSA-N O[N+]([O-])=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound O[N+]([O-])=O.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 DECAHPNLPIGUOJ-UHFFFAOYSA-N 0.000 claims 2
- 208000003251 Pruritus Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 230000008030 elimination Effects 0.000 claims 2
- 238000003379 elimination reaction Methods 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 230000026030 halogenation Effects 0.000 claims 2
- 238000005658 halogenation reaction Methods 0.000 claims 2
- 229960001340 histamine Drugs 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
- YPTSSSOPRLTPQF-SNVBAGLBSA-N (3R)-1-(12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N,N-dimethylpyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 YPTSSSOPRLTPQF-SNVBAGLBSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 claims 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
- DJMOXMNDXFFONV-UHFFFAOYSA-N 1,3-dimethyl-7-[2-(n-methylanilino)ethyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(C)C1=CC=CC=C1 DJMOXMNDXFFONV-UHFFFAOYSA-N 0.000 claims 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims 1
- PMFKRDBIRGTURK-UHFFFAOYSA-N 1-(11,12-dichloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC(Cl)=C(Cl)C=C2N2C1=NN=C2 PMFKRDBIRGTURK-UHFFFAOYSA-N 0.000 claims 1
- RUYWWNNHZXPQLX-UHFFFAOYSA-N 1-(12,13-dichloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C(Cl)=C2N2C1=NN=C2 RUYWWNNHZXPQLX-UHFFFAOYSA-N 0.000 claims 1
- GJOQDWINDBYYCV-UHFFFAOYSA-N 1-(12-bromo-11-methyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC(C)=C(Br)C=C2N2C1=NN=C2 GJOQDWINDBYYCV-UHFFFAOYSA-N 0.000 claims 1
- FPWNDDCXBCRCQO-UHFFFAOYSA-N 1-(12-bromo-13-methyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C(C)=C2N2C1=NN=C2 FPWNDDCXBCRCQO-UHFFFAOYSA-N 0.000 claims 1
- ZBRDONFKRCRLOB-UHFFFAOYSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-3-methylazetidin-3-amine Chemical compound C1C(C)(N)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 ZBRDONFKRCRLOB-UHFFFAOYSA-N 0.000 claims 1
- ACNKCRPPBHDURQ-UHFFFAOYSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N,3-dimethylazetidin-3-amine Chemical compound C1C(NC)(C)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 ACNKCRPPBHDURQ-UHFFFAOYSA-N 0.000 claims 1
- IMAPROMTHHFNMX-UHFFFAOYSA-N 1-(12-bromo-2,8,10-triazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=CC=C2 IMAPROMTHHFNMX-UHFFFAOYSA-N 0.000 claims 1
- CNQCMTPWHZVXMN-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N,N-dimethylazetidin-3-amine Chemical compound C1C(N(C)C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 CNQCMTPWHZVXMN-UHFFFAOYSA-N 0.000 claims 1
- WIWASHXVJIOYQI-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 WIWASHXVJIOYQI-UHFFFAOYSA-N 0.000 claims 1
- KUVCTILQZQIXQN-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=CC=C(Cl)N=C2N2C1=NN=C2 KUVCTILQZQIXQN-UHFFFAOYSA-N 0.000 claims 1
- FIRPUJYYXYHEHM-UHFFFAOYSA-N 1-(12-chloro-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NC=C2 FIRPUJYYXYHEHM-UHFFFAOYSA-N 0.000 claims 1
- ZUESIEDHNAEKDJ-UHFFFAOYSA-N 1-(12-chloro-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2C2=NC=NN12 ZUESIEDHNAEKDJ-UHFFFAOYSA-N 0.000 claims 1
- KDXQZJSWOFTCDE-UHFFFAOYSA-N 1-(12-chloro-4-methyl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2C2=NC(C)=NN12 KDXQZJSWOFTCDE-UHFFFAOYSA-N 0.000 claims 1
- NCUKOAXZZQWVCK-UHFFFAOYSA-N 1-(12-ethenyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C=C)C=C2N2C1=NN=C2 NCUKOAXZZQWVCK-UHFFFAOYSA-N 0.000 claims 1
- AJHJVKGCVDFCNX-UHFFFAOYSA-N 1-(12-ethynyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C#C)C=C2N2C1=NN=C2 AJHJVKGCVDFCNX-UHFFFAOYSA-N 0.000 claims 1
- SGQVHLLHCYFWEE-UHFFFAOYSA-N 1-(12-iodo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(I)C=C2N2C1=NN=C2 SGQVHLLHCYFWEE-UHFFFAOYSA-N 0.000 claims 1
- YYYIJFMHVKLXPK-UHFFFAOYSA-N 1-(12-methoxy-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(OC)C=C2N2C1=NN=C2 YYYIJFMHVKLXPK-UHFFFAOYSA-N 0.000 claims 1
- QUDLOIFPNJDOEM-UHFFFAOYSA-N 1-(8-chloro-2-methylpyrazolo[3,4-c][1,8]naphthyridin-4-yl)-n-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2C2=CN(C)N=C12 QUDLOIFPNJDOEM-UHFFFAOYSA-N 0.000 claims 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- MPWMAHNETDBXLC-UHFFFAOYSA-N 1-[12-(difluoromethoxy)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl]-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(OC(F)F)C=C2N2C1=NN=C2 MPWMAHNETDBXLC-UHFFFAOYSA-N 0.000 claims 1
- DVKBWONYFFCHMU-UHFFFAOYSA-N 1-[12-(difluoromethyl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl]-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C(F)F)C=C2N2C1=NN=C2 DVKBWONYFFCHMU-UHFFFAOYSA-N 0.000 claims 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- MYRLDCFZZRCYHU-UHFFFAOYSA-N 11,12-dichloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC(Cl)=C(Cl)C=C2N2C1=NN=C2 MYRLDCFZZRCYHU-UHFFFAOYSA-N 0.000 claims 1
- FEHVAJUHQQKIBN-UHFFFAOYSA-N 11,12-dichloro-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound N1=C(Cl)C(Cl)=CC(N2C=NN=C22)=C1N=C2N1CCNCC1 FEHVAJUHQQKIBN-UHFFFAOYSA-N 0.000 claims 1
- HFZKBCNDCXWASD-UHFFFAOYSA-N 11-chloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CN=C2N2C1=NN=C2 HFZKBCNDCXWASD-UHFFFAOYSA-N 0.000 claims 1
- MPECOUXNLZZITG-UHFFFAOYSA-N 11-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=CC(C)=CN=C2N2C1=NN=C2 MPECOUXNLZZITG-UHFFFAOYSA-N 0.000 claims 1
- MWPVFFBPURHQLC-UHFFFAOYSA-N 12-bromo-13-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Br)C(C)=C2N2C1=NN=C2 MWPVFFBPURHQLC-UHFFFAOYSA-N 0.000 claims 1
- SUJNCELQINVQLY-UHFFFAOYSA-N 12-bromo-7-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1C2CN(C)CC2CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 SUJNCELQINVQLY-UHFFFAOYSA-N 0.000 claims 1
- AAGGRTPMBWISNV-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 AAGGRTPMBWISNV-UHFFFAOYSA-N 0.000 claims 1
- LPKFGUUUKOUOML-UHFFFAOYSA-N 12-bromo-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Br)=CN=C2N=C1N1CCNCC1 LPKFGUUUKOUOML-UHFFFAOYSA-N 0.000 claims 1
- QBHCQEPPGQIINH-UHFFFAOYSA-N 12-chloro-11-ethoxy-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C12=NN=CN2C=2C=C(Cl)C(OCC)=NC=2N=C1N1CCN(C)CC1 QBHCQEPPGQIINH-UHFFFAOYSA-N 0.000 claims 1
- NAGYFKMYWLJUMW-UHFFFAOYSA-N 12-chloro-11-methoxy-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C12=NN=CN2C=2C=C(Cl)C(OC)=NC=2N=C1N1CCN(C)CC1 NAGYFKMYWLJUMW-UHFFFAOYSA-N 0.000 claims 1
- ZXZURXJLMUCTMW-UHFFFAOYSA-N 12-chloro-11-methoxy-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C12=NN=CN2C=2C=C(Cl)C(OC)=NC=2N=C1N1CCNCC1 ZXZURXJLMUCTMW-UHFFFAOYSA-N 0.000 claims 1
- SHVWOUAQFIVYLU-UHFFFAOYSA-N 12-chloro-3-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2C SHVWOUAQFIVYLU-UHFFFAOYSA-N 0.000 claims 1
- ZSHGPJMGIVDHRC-UHFFFAOYSA-N 12-chloro-3-methyl-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound N=1C2=NC=C(Cl)C=C2N2C(C)=NN=C2C=1N1CCNCC1 ZSHGPJMGIVDHRC-UHFFFAOYSA-N 0.000 claims 1
- NKENEEDRJGMPRZ-UHFFFAOYSA-N 12-chloro-4-(methoxymethyl)-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=C(COC)N=C2C2=CC(Cl)=CN=C2N=C1N1CCN(C)CC1 NKENEEDRJGMPRZ-UHFFFAOYSA-N 0.000 claims 1
- RETNOQVKSOUDLS-UHFFFAOYSA-N 12-chloro-4-cyclopropyl-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NC(C3CC3)=NN12 RETNOQVKSOUDLS-UHFFFAOYSA-N 0.000 claims 1
- DILJIYOWMILJQS-UHFFFAOYSA-N 12-chloro-4-cyclopropyl-7-piperazin-1-yl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=C(C3CC3)N=C2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 DILJIYOWMILJQS-UHFFFAOYSA-N 0.000 claims 1
- LZCULMVMPNXCPI-UHFFFAOYSA-N 12-chloro-4-cyclopropyl-N,N-diethyl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-amine Chemical compound N=1N2C(N(CC)CC)=NC3=NC=C(Cl)C=C3C2=NC=1C1CC1 LZCULMVMPNXCPI-UHFFFAOYSA-N 0.000 claims 1
- FSZACHAIFINHRW-UHFFFAOYSA-N 12-chloro-4-methyl-7-piperazin-1-yl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=C(C)N=C2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 FSZACHAIFINHRW-UHFFFAOYSA-N 0.000 claims 1
- GKOJQCIFYJTODN-UHFFFAOYSA-N 12-chloro-7-(1-methyl-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b]pyridin-6-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1C2N(C)CCCC2CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 GKOJQCIFYJTODN-UHFFFAOYSA-N 0.000 claims 1
- HKCSBHXQPLYUKS-UHFFFAOYSA-N 12-chloro-7-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1C2CN(C)CC2CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 HKCSBHXQPLYUKS-UHFFFAOYSA-N 0.000 claims 1
- LQKZUGFOYSPFDU-UHFFFAOYSA-N 12-chloro-7-(3,4,5-trimethylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1C(C)N(C)C(C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 LQKZUGFOYSPFDU-UHFFFAOYSA-N 0.000 claims 1
- OQQGEPOZNNENRL-UHFFFAOYSA-N 12-chloro-7-(4-cyclopropylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N(CC1)CCN1C1CC1 OQQGEPOZNNENRL-UHFFFAOYSA-N 0.000 claims 1
- QQRLMVIXUGRZJU-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-11-(2,2,2-trifluoroethoxy)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC(OCC(F)(F)F)=C(Cl)C=C2N2C1=NN=C2 QQRLMVIXUGRZJU-UHFFFAOYSA-N 0.000 claims 1
- YYKWNLJXOJLGIA-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene-11-carbonitrile Chemical compound C1CN(C)CCN1C1=NC2=NC(C#N)=C(Cl)C=C2N2C1=NN=C2 YYKWNLJXOJLGIA-UHFFFAOYSA-N 0.000 claims 1
- XPZHBXVKJVWYBZ-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NC=C2 XPZHBXVKJVWYBZ-UHFFFAOYSA-N 0.000 claims 1
- KDUDYHWDYABNRM-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-3,4,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NN=CN12 KDUDYHWDYABNRM-UHFFFAOYSA-N 0.000 claims 1
- JAXUIZVKVLIYLB-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NC=NN12 JAXUIZVKVLIYLB-UHFFFAOYSA-N 0.000 claims 1
- MLLMVCNLOSRTGN-VIFPVBQESA-N 12-chloro-7-[(3S)-3,4-dimethylpiperazin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)[C@@H](C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 MLLMVCNLOSRTGN-VIFPVBQESA-N 0.000 claims 1
- XTLJUFPQIDCEOY-UHFFFAOYSA-N 12-chloro-7-[3-(methylamino)azetidin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene-11-carbonitrile Chemical compound C1C(NC)CN1C1=NC2=NC(C#N)=C(Cl)C=C2N2C1=NN=C2 XTLJUFPQIDCEOY-UHFFFAOYSA-N 0.000 claims 1
- HUHOQSHFJOASLB-UHFFFAOYSA-N 12-chloro-7-piperazin-1-yl-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NC=CN2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 HUHOQSHFJOASLB-UHFFFAOYSA-N 0.000 claims 1
- QHQIWQFWYHVEDH-UHFFFAOYSA-N 12-chloro-7-piperazin-1-yl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=CN=C2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 QHQIWQFWYHVEDH-UHFFFAOYSA-N 0.000 claims 1
- KJARIWMPADKIOR-UHFFFAOYSA-N 12-iodo-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(I)C=C2N2C1=NN=C2 KJARIWMPADKIOR-UHFFFAOYSA-N 0.000 claims 1
- UJXROVRCLVSQDF-UHFFFAOYSA-N 12-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(C)C=C2N2C1=NN=C2 UJXROVRCLVSQDF-UHFFFAOYSA-N 0.000 claims 1
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims 1
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 claims 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims 1
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims 1
- KIRBDSPJSABLQU-UHFFFAOYSA-N 2-[(12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)amino]ethanol Chemical compound OCCNC1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 KIRBDSPJSABLQU-UHFFFAOYSA-N 0.000 claims 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims 1
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims 1
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims 1
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 claims 1
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 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
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 claims 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 claims 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 claims 1
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 claims 1
- GVAOMJUJOPOKOV-UHFFFAOYSA-N 7-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1C2CCCNC2CN1C1=NC2=NC=C(Cl)C=C2N2C=NN=C21 GVAOMJUJOPOKOV-UHFFFAOYSA-N 0.000 claims 1
- JEWSSXKQNAONAY-UHFFFAOYSA-N 7-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)-12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN2CCCC2CN1C1=NC2=NC=C(Br)C=C2N2C=NN=C21 JEWSSXKQNAONAY-UHFFFAOYSA-N 0.000 claims 1
- AXFIGHQVVHSIJW-UHFFFAOYSA-N 7-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)-12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN2CCCC2CN1C1=NC2=NC=C(Cl)C=C2N2C=NN=C21 AXFIGHQVVHSIJW-UHFFFAOYSA-N 0.000 claims 1
- YOXGDLHOYVVDST-UHFFFAOYSA-N 7-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)-12-iodo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN2CCCC2CN1C1=NC2=NC=C(I)C=C2N2C=NN=C21 YOXGDLHOYVVDST-UHFFFAOYSA-N 0.000 claims 1
- QYLPXOBUJFBVNW-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-12-(trifluoromethyl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(C(F)(F)F)C=C2N2C1=NN=C2 QYLPXOBUJFBVNW-UHFFFAOYSA-N 0.000 claims 1
- YVRBEXPZVHWNLE-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=CC=C2N2C1=NN=C2 YVRBEXPZVHWNLE-UHFFFAOYSA-N 0.000 claims 1
- YHVNTCSNXMQVCT-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene-12-carbonitrile Chemical compound C1CN(C)CCN1C1=NC2=NC=C(C#N)C=C2N2C1=NN=C2 YHVNTCSNXMQVCT-UHFFFAOYSA-N 0.000 claims 1
- VBENIBBZNCUUPY-UHFFFAOYSA-N 7-[3-(methylamino)azetidin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-12-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(N)C=C2N2C1=NN=C2 VBENIBBZNCUUPY-UHFFFAOYSA-N 0.000 claims 1
- QQNDKPIQZUOLSZ-UHFFFAOYSA-N 7-[3-(methylamino)azetidin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-12-ol Chemical compound CNC1CN(C1)c1nc2ncc(O)cc2n2cnnc12 QQNDKPIQZUOLSZ-UHFFFAOYSA-N 0.000 claims 1
- QGNOAFHQPYWXPP-UHFFFAOYSA-N 7-[3-(methylamino)azetidin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene-12-carbonitrile Chemical compound C1C(NC)CN1C1=NC2=NC=C(C#N)C=C2N2C1=NN=C2 QGNOAFHQPYWXPP-UHFFFAOYSA-N 0.000 claims 1
- OPNSWNNEUULZMB-UHFFFAOYSA-N 7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene-12-carbonitrile Chemical compound C12=NN=CN2C2=CC(C#N)=CN=C2N=C1N1CCNCC1 OPNSWNNEUULZMB-UHFFFAOYSA-N 0.000 claims 1
- VTBILOZFUGWSBC-UHFFFAOYSA-N 8-chloro-2-methyl-4-(4-methylpiperazin-1-yl)-[1,3]oxazolo[4,5-c][1,8]naphthyridine Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=C1N=C(C)O2 VTBILOZFUGWSBC-UHFFFAOYSA-N 0.000 claims 1
- DHUKNTBDLLAUQK-UHFFFAOYSA-N 8-chloro-2-methyl-4-(4-methylpiperazin-1-yl)pyrazolo[3,4-c][1,8]naphthyridine Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=CN(C)N=C12 DHUKNTBDLLAUQK-UHFFFAOYSA-N 0.000 claims 1
- XLFFUJQQSWLOSM-UHFFFAOYSA-N 8-chloro-2-methyl-4-piperazin-1-ylpyrazolo[3,4-c][1,8]naphthyridine Chemical compound N=1N(C)C=C(C2=CC(Cl)=CN=C2N=2)C=1C=2N1CCNCC1 XLFFUJQQSWLOSM-UHFFFAOYSA-N 0.000 claims 1
- XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 claims 1
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 claims 1
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 claims 1
- UQBSWCUGMJBYTB-IUCAKERBSA-N C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N1[C@H](CN2)C[C@H]2C1 Chemical compound C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N1[C@H](CN2)C[C@H]2C1 UQBSWCUGMJBYTB-IUCAKERBSA-N 0.000 claims 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 claims 1
- HURMPUPQNGGCEV-QMMMGPOBSA-N C1CN[C@@H](C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C1CN[C@@H](C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 HURMPUPQNGGCEV-QMMMGPOBSA-N 0.000 claims 1
- UKFUSIFHDFKEEM-MRVPVSSYSA-N C1[C@H](N)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C1[C@H](N)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 UKFUSIFHDFKEEM-MRVPVSSYSA-N 0.000 claims 1
- NSLIFGJYZMGKTP-SECBINFHSA-N C1[C@H](NC)CCN1C1=NC2=CC(Cl)=CN=C2N2C1=NN=C2 Chemical compound C1[C@H](NC)CCN1C1=NC2=CC(Cl)=CN=C2N2C1=NN=C2 NSLIFGJYZMGKTP-SECBINFHSA-N 0.000 claims 1
- NZGDTAMAUCZAFI-SECBINFHSA-N C1[C@H](NC)CCN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound C1[C@H](NC)CCN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 NZGDTAMAUCZAFI-SECBINFHSA-N 0.000 claims 1
- AALXPCRBVDDIHT-SECBINFHSA-N C1[C@H](NC)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C1[C@H](NC)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 AALXPCRBVDDIHT-SECBINFHSA-N 0.000 claims 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 claims 1
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 claims 1
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- RKJNMZGWZUCZID-UHFFFAOYSA-N Cl.C12=NN=CN2C2=CC(Br)=CN=C2N=C1OCC1CNC1 Chemical compound Cl.C12=NN=CN2C2=CC(Br)=CN=C2N=C1OCC1CNC1 RKJNMZGWZUCZID-UHFFFAOYSA-N 0.000 claims 1
- APVUNDUKYPELCP-UHFFFAOYSA-N Cl.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 Chemical compound Cl.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 APVUNDUKYPELCP-UHFFFAOYSA-N 0.000 claims 1
- JJAFTHLKVUVWPE-UHFFFAOYSA-N Cl.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=N2 Chemical compound Cl.C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=N2 JJAFTHLKVUVWPE-UHFFFAOYSA-N 0.000 claims 1
- OEBVYNULNKSONR-UHFFFAOYSA-N ClC1=C(CN2C(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)(C)C)=O)C(=CC=C1)F Chemical compound ClC1=C(CN2C(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)(C)C)=O)C(=CC=C1)F OEBVYNULNKSONR-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 229940126657 Compound 17 Drugs 0.000 claims 1
- 229940126639 Compound 33 Drugs 0.000 claims 1
- 229940127007 Compound 39 Drugs 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 206010015943 Eye inflammation Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000027601 Inner ear disease Diseases 0.000 claims 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 claims 1
- QKPZJMGEYADHCT-UHFFFAOYSA-N N-[1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-yl]-N-methylhydroxylamine Chemical compound C1C(N(O)C)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 QKPZJMGEYADHCT-UHFFFAOYSA-N 0.000 claims 1
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 claims 1
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims 1
- DSURYHHMNFJXFL-UHFFFAOYSA-N N-methyl-1-(12-methyl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C)C=C2N2C1=NN=C2 DSURYHHMNFJXFL-UHFFFAOYSA-N 0.000 claims 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- FMQREKDKPXNMGS-UHFFFAOYSA-N N12N=C(CC)N=C2C2=CC(Cl)=CN=C2N=C1N1CCN(C)CC1 Chemical compound N12N=C(CC)N=C2C2=CC(Cl)=CN=C2N=C1N1CCN(C)CC1 FMQREKDKPXNMGS-UHFFFAOYSA-N 0.000 claims 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 claims 1
- 208000000592 Nasal Polyps Diseases 0.000 claims 1
- 206010052437 Nasal discomfort Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 1
- 208000031737 Tissue Adhesions Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 206010064948 Viral rhinitis Diseases 0.000 claims 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 claims 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims 1
- QLOWGDIISXJREF-UHFFFAOYSA-N [1,2,4]triazolo[1,5-c]pyrimidine Chemical compound C1=CN=CN2N=CN=C21 QLOWGDIISXJREF-UHFFFAOYSA-N 0.000 claims 1
- OGBRCKYXKKEVAL-UHFFFAOYSA-N [1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-yl]-methylcarbamic acid Chemical compound C1C(N(C)C(O)=O)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 OGBRCKYXKKEVAL-UHFFFAOYSA-N 0.000 claims 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 claims 1
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 238000006254 arylation reaction Methods 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 208000030949 chronic idiopathic urticaria Diseases 0.000 claims 1
- 206010072757 chronic spontaneous urticaria Diseases 0.000 claims 1
- 208000024376 chronic urticaria Diseases 0.000 claims 1
- 206010009887 colitis Diseases 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 229940126543 compound 14 Drugs 0.000 claims 1
- 229940125758 compound 15 Drugs 0.000 claims 1
- 229940126142 compound 16 Drugs 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229940125810 compound 20 Drugs 0.000 claims 1
- 229940126086 compound 21 Drugs 0.000 claims 1
- 229940126208 compound 22 Drugs 0.000 claims 1
- 229940125833 compound 23 Drugs 0.000 claims 1
- 229940125961 compound 24 Drugs 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 229940125851 compound 27 Drugs 0.000 claims 1
- 229940127204 compound 29 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229940125877 compound 31 Drugs 0.000 claims 1
- 229940125878 compound 36 Drugs 0.000 claims 1
- 229940125807 compound 37 Drugs 0.000 claims 1
- 229940127573 compound 38 Drugs 0.000 claims 1
- 229940126540 compound 41 Drugs 0.000 claims 1
- 229940125936 compound 42 Drugs 0.000 claims 1
- 229940125844 compound 46 Drugs 0.000 claims 1
- 229940127271 compound 49 Drugs 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 229940126545 compound 53 Drugs 0.000 claims 1
- 229940127113 compound 57 Drugs 0.000 claims 1
- 229940125900 compound 59 Drugs 0.000 claims 1
- 229940126179 compound 72 Drugs 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 claims 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000000640 hydroxylating effect Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 claims 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 208000037916 non-allergic rhinitis Diseases 0.000 claims 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims 1
- 230000003349 osteoarthritic effect Effects 0.000 claims 1
- 208000027753 pain disease Diseases 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 208000027491 vestibular disease Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20110100369 | 2011-09-30 | ||
| KR10-2011-0100369 | 2011-09-30 | ||
| KR10-2012-0033444 | 2012-03-30 | ||
| KR20120033444 | 2012-03-30 | ||
| PCT/KR2012/007965 WO2013048214A2 (en) | 2011-09-30 | 2012-09-28 | Novel heterocyclic derivatives and their uses |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014531458A JP2014531458A (ja) | 2014-11-27 |
| JP2014531458A5 true JP2014531458A5 (OSRAM) | 2015-08-27 |
| JP6031107B2 JP6031107B2 (ja) | 2016-11-24 |
Family
ID=47996667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014533218A Active JP6031107B2 (ja) | 2011-09-30 | 2012-09-28 | 新規な複素環誘導体及びその用途 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US9586959B2 (OSRAM) |
| EP (2) | EP3461825B1 (OSRAM) |
| JP (1) | JP6031107B2 (OSRAM) |
| KR (1) | KR101800749B1 (OSRAM) |
| CN (1) | CN103889986B (OSRAM) |
| AR (1) | AR088085A1 (OSRAM) |
| AU (1) | AU2012316912B9 (OSRAM) |
| BR (1) | BR112014007645A2 (OSRAM) |
| CA (1) | CA2848154C (OSRAM) |
| CY (1) | CY1121292T1 (OSRAM) |
| DK (2) | DK2760865T3 (OSRAM) |
| ES (2) | ES2687693T3 (OSRAM) |
| FI (1) | FI3461825T3 (OSRAM) |
| HR (2) | HRP20181310T1 (OSRAM) |
| HU (2) | HUE062842T2 (OSRAM) |
| LT (2) | LT3461825T (OSRAM) |
| MX (1) | MX355795B (OSRAM) |
| PL (2) | PL3461825T3 (OSRAM) |
| PT (2) | PT2760865T (OSRAM) |
| RS (2) | RS57854B1 (OSRAM) |
| RU (1) | RU2628074C2 (OSRAM) |
| SG (1) | SG11201400484RA (OSRAM) |
| SI (2) | SI2760865T1 (OSRAM) |
| TR (1) | TR201814710T4 (OSRAM) |
| TW (1) | TWI551600B (OSRAM) |
| WO (1) | WO2013048214A2 (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015000715A1 (en) | 2013-07-02 | 2015-01-08 | Syngenta Participations Ag | Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents |
| CN103435561B (zh) * | 2013-08-19 | 2016-08-10 | 上海交通大学 | 一种新型d-氨基酸氧化酶抑制剂及其制备和应用 |
| CN104016909B (zh) * | 2014-04-03 | 2016-04-20 | 定陶县友帮化工有限公司 | 一种2-氨基-3-溴-5-氯吡啶的合成方法 |
| CN104016911A (zh) * | 2014-04-03 | 2014-09-03 | 定陶县友帮化工有限公司 | 一种2-氨基-3,5-二溴吡啶的合成方法 |
| CN106187793A (zh) * | 2016-01-26 | 2016-12-07 | 赵鸣 | 5‑氨基酮戊酸及其衍生物的盐化合物和应用 |
| WO2018005860A1 (en) | 2016-07-01 | 2018-01-04 | G1 Therapeutics, Inc. | Pyrimidine-based antiproliferative agents |
| US10905675B2 (en) | 2016-12-14 | 2021-02-02 | Sk Biopharmaceuticals Co., Ltd. | Use of carbamate compound for prevention, alleviation or treatment of pruritus |
| US11028090B2 (en) | 2017-01-26 | 2021-06-08 | Dong Wha Pharm. Co., Ltd. | [1,2,4]Triazolo[4,3-a]quinoxaline derivative, method for preparing same, and pharmaceutical composition for preventing or treating BET protein-related diseases, containing same as active ingredient |
| US11365196B2 (en) | 2017-02-27 | 2022-06-21 | Betta Pharmaceuticals Co., Ltd. | FGFR inhibitor and application thereof |
| TW202021969A (zh) * | 2018-05-31 | 2020-06-16 | 南韓商Ｃ＆Ｃ新藥研究所 | 雜環衍生物及其用途 |
| GB2575490A (en) * | 2018-07-12 | 2020-01-15 | Recordati Ind Chimica E Farmaceutica Spa | P2X3 receptor antagonists |
| US11718622B2 (en) | 2020-03-16 | 2023-08-08 | Exelixis Inc. | Heterocyclic adenosine receptor antagonists |
| EP4652997A2 (en) | 2020-05-19 | 2025-11-26 | Pharmacosmos Holding A/s | Cyclin-dependent kinase inhibiting compounds for the treatment of medical disorders |
| EP4067357A1 (en) * | 2021-03-30 | 2022-10-05 | JW Pharmaceutical Corporation | Novel crystalline form of 1-(8-bromopyrido[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)-n-methylazetidin-3-amine hydrogen sulfate monohydrate |
| TW202317568A (zh) | 2021-06-22 | 2023-05-01 | 丹麥商理奧藥品公司 | 1-(8-溴化吡啶并[2,3-e][1,2,4]三唑并[4,3-a]吡嗪-4-基)-n-甲基吖丁啶-3-胺半琥珀酸鹽之新穎結晶形式 |
| TW202423429A (zh) | 2022-09-29 | 2024-06-16 | 韓商Ｊｗ製藥公司 | 1-(8-溴化吡啶并[2,3-e][1,2,4]三唑并[4,3-a]吡嗪-4-基)-n-甲基吖丁啶-3-胺之鹽及結晶形式之製備方法以及新穎的結晶形式 |
| TW202428578A (zh) * | 2022-09-29 | 2024-07-16 | 韓商Ｊｗ製藥公司 | １－（８－溴化吡啶并［２，３－ｅ］［１，２，４］三唑并［４，３－ａ］吡嗪－４－基）－ｎ－甲基吖丁啶－３－胺之新穎結晶型 |
| TW202425977A (zh) * | 2022-09-30 | 2024-07-01 | 韓商Ｊｗ製藥公司 | １－（８－溴化吡啶并［２，３－ｅ］［１，２，４］三唑并［４，３－ａ］吡嗪－４－基）－ｎ－甲基吖丁啶－３－胺單琥珀酸鹽之新穎結晶型 |
| US12122775B1 (en) | 2024-01-16 | 2024-10-22 | King Faisal University | Substituted pyrido[4,3-e]pyrrolo[1,2-a]pyrazines as CK2 inhibitors |
| US12173001B1 (en) | 2024-01-16 | 2024-12-24 | King Faisal University | Pyrido[3,4-e][1,2,4]triazolo[4,3-c]pyrimidines as CK2 inhibitors |
| US12129252B1 (en) | 2024-02-15 | 2024-10-29 | King Faisal University | Pyrrolo[2,3-c][2,6]naphthyridine-8-carboxylic acids as CK2 inhibitors |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4831013A (en) * | 1986-03-20 | 1989-05-16 | Ciba-Geigy Corporation | 2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof |
| US5070086A (en) | 1987-12-23 | 1991-12-03 | Schering Corporation | Imidazo- and pyrimido-quinoline, naphthyridine and pyridopyrazine compounds |
| CN1285834A (zh) * | 1997-11-11 | 2001-02-28 | 小野药品工业株式会社 | 稠合吡嗪化合物 |
| ATE430149T1 (de) * | 1998-03-04 | 2009-05-15 | Bristol Myers Squibb Co | Heterocyclen substituierte imidazopyrazine als protein- tyrosin-kinase-inhibitoren |
| JP2000119271A (ja) | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| JP2000319277A (ja) | 1999-05-11 | 2000-11-21 | Ono Pharmaceut Co Ltd | 縮合ピラジン化合物およびその化合物を有効成分とする薬剤 |
| CA2520251A1 (en) | 2003-03-27 | 2004-10-07 | Pfizer Products Inc. | Substituted 4-amino[1,2,4]triazolo[4,3-a]quinoxalines |
| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| WO2009068246A2 (en) * | 2007-11-30 | 2009-06-04 | Elbion Gmbh | Methods of treating obesity and metabolic disorders |
| KR101208778B1 (ko) * | 2008-03-03 | 2012-12-05 | 노파르티스 아게 | Ｔｌｒ 활성 조정제로서의 화합물 및 조성물 |
| TW201024297A (en) * | 2008-09-10 | 2010-07-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| CN100580335C (zh) * | 2008-09-11 | 2010-01-13 | 艾欧史密斯(中国)热水器有限公司 | 承压式太阳能热水器 |
| AU2009333653B2 (en) * | 2008-12-17 | 2015-09-10 | Merck Patent Gmbh | C-ring modified tricyclic benzonaphthiridinone protein kinase inhibitors and use thereof |
| BRPI1007358A2 (pt) | 2009-01-23 | 2018-03-06 | Takeda Pharmaceutical Company Limited | inibidores de poli (adp-ribose) polimerase (parp) |
| JP5715625B2 (ja) | 2009-07-30 | 2015-05-07 | 武田薬品工業株式会社 | ポリ（ａｄｐ−リボース）ポリメラーゼ（ｐａｒｐ）阻害剤 |
| GB0919423D0 (en) * | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| WO2011060207A1 (en) | 2009-11-16 | 2011-05-19 | Schering Corporation | FUSED TRICYCLIC COMPOUNDS WITH ADENOSINE A2a RECEPTOR ANTAGONIST ACTIVITY |
| TW201204727A (en) * | 2010-03-10 | 2012-02-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
-
2012
- 2012-09-28 CN CN201280051950.6A patent/CN103889986B/zh active Active
- 2012-09-28 FI FIEP18180710.8T patent/FI3461825T3/fi active
- 2012-09-28 PL PL18180710.8T patent/PL3461825T3/pl unknown
- 2012-09-28 MX MX2014003042A patent/MX355795B/es active IP Right Grant
- 2012-09-28 TR TR2018/14710T patent/TR201814710T4/tr unknown
- 2012-09-28 LT LTEP18180710.8T patent/LT3461825T/lt unknown
- 2012-09-28 PT PT12834688T patent/PT2760865T/pt unknown
- 2012-09-28 JP JP2014533218A patent/JP6031107B2/ja active Active
- 2012-09-28 HU HUE18180710A patent/HUE062842T2/hu unknown
- 2012-09-28 AR ARP120103614A patent/AR088085A1/es active IP Right Grant
- 2012-09-28 CA CA2848154A patent/CA2848154C/en active Active
- 2012-09-28 TW TW101135774A patent/TWI551600B/zh active
- 2012-09-28 HR HRP20181310TT patent/HRP20181310T1/hr unknown
- 2012-09-28 EP EP18180710.8A patent/EP3461825B1/en active Active
- 2012-09-28 US US14/347,950 patent/US9586959B2/en active Active
- 2012-09-28 BR BR112014007645A patent/BR112014007645A2/pt not_active Application Discontinuation
- 2012-09-28 HR HRP20230893TT patent/HRP20230893T1/hr unknown
- 2012-09-28 RS RS20181171A patent/RS57854B1/sr unknown
- 2012-09-28 RS RS20230629A patent/RS64575B1/sr unknown
- 2012-09-28 HU HUE12834688A patent/HUE040374T2/hu unknown
- 2012-09-28 DK DK12834688.9T patent/DK2760865T3/en active
- 2012-09-28 DK DK18180710.8T patent/DK3461825T3/da active
- 2012-09-28 ES ES12834688.9T patent/ES2687693T3/es active Active
- 2012-09-28 LT LTEP12834688.9T patent/LT2760865T/lt unknown
- 2012-09-28 RU RU2014115478A patent/RU2628074C2/ru active
- 2012-09-28 WO PCT/KR2012/007965 patent/WO2013048214A2/en not_active Ceased
- 2012-09-28 SG SG11201400484RA patent/SG11201400484RA/en unknown
- 2012-09-28 PT PT181807108T patent/PT3461825T/pt unknown
- 2012-09-28 PL PL12834688T patent/PL2760865T3/pl unknown
- 2012-09-28 AU AU2012316912A patent/AU2012316912B9/en active Active
- 2012-09-28 KR KR1020147010409A patent/KR101800749B1/ko active Active
- 2012-09-28 SI SI201231387T patent/SI2760865T1/sl unknown
- 2012-09-28 SI SI201232039T patent/SI3461825T1/sl unknown
- 2012-09-28 EP EP12834688.9A patent/EP2760865B1/en active Active
- 2012-09-28 ES ES18180710T patent/ES2954303T3/es active Active
-
2018
- 2018-10-09 CY CY20181101040T patent/CY1121292T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014531458A5 (OSRAM) | ||
| RU2014115478A (ru) | Новые гетероциклические производные и их применения | |
| CN116003441B (zh) | 杂芳类衍生物调节剂、其制备方法和应用 | |
| KR102165113B1 (ko) | Ａ2ａ 길항제 성질을 갖는 헤테로비시클로-치환된-[1,2,4]트리아졸로[1,5-ｃ]퀴나졸린-5-아민 화합물 | |
| AU2018201663B2 (en) | Novel tricyclic compounds | |
| KR101499308B1 (ko) | 가용성 구아닐레이트 시클라제 활성화제 | |
| TW575573B (en) | Substituted 6,5-hetero-bicyclic derivatives | |
| KR102021159B1 (ko) | 트리시클릭 헤테로시클릭 화합물 및 jak 저해제 | |
| US20120178915A1 (en) | Pyrimidine derivatives and analogs, preparation method and use thereof | |
| JP2019535664A5 (OSRAM) | ||
| JP2013515729A5 (OSRAM) | ||
| KR20150063028A (ko) | 치환된 티오펜- 및 푸란-융합된 아졸로피리미딘-5-(6h)-온 화합물 | |
| JP2017518326A5 (OSRAM) | ||
| RU2020124116A (ru) | Производные арил-бипиридинамина в качестве ингибиторов фосфатидилинозитолфосфаткиназы | |
| AU2021373162B2 (en) | Pyrazolopyridazinone compound, and pharmaceutical composition and use thereof | |
| Yakovenko et al. | Synthesis of 5-amino-1 H-pyrazolo [4, 3-b] pyridine derivatives and annulation of imidazole and pyrimidine rings thereto | |
| EP1212324A1 (en) | Imidazo-triazine derivatives as ligands for gaba receptors | |
| HK1196820B (en) | Novel heterocyclic derivatives and their uses | |
| HK1196820A (en) | Novel heterocyclic derivatives and their uses | |
| MXPA99002014A (en) | Substituted 6,5-hetero-bicyclic derivatives |