JP2014531458A5 - - Google Patents
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- 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
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- 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
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| CN112010772A (zh) * | 2016-01-26 | 2020-12-01 | 赵鸣 | 5-氨基酮戊酸及其衍生物的盐化合物和应用 |
| KR20190025943A (ko) | 2016-07-01 | 2019-03-12 | 쥐원 쎄라퓨틱스, 인크. | 피리미딘-기재 항증식제 |
| KR102635931B1 (ko) * | 2016-12-14 | 2024-02-13 | 에스케이바이오팜 주식회사 | 가려움증의 예방, 경감 또는 치료를 위한 카바메이트 화합물의 용도 |
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| 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 |
| CN119968370A (zh) * | 2022-09-29 | 2025-05-09 | Jw制药公司 | 用于制备1-(8-溴吡啶并[2,3-e][1,2,4]三唑并[4,3-a]吡嗪-4-基)-n-甲基氮杂环丁烷-3-胺的盐和结晶形式的方法和新结晶形式 |
| 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 |
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- 2012-09-28 RS RS20181171A patent/RS57854B1/sr unknown
- 2012-09-28 ES ES12834688.9T patent/ES2687693T3/es active Active
- 2012-09-28 TW TW101135774A patent/TWI551600B/zh active
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- 2012-09-28 JP JP2014533218A patent/JP6031107B2/ja active Active
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