JP2015526448A5 - - Google Patents
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- JP2015526448A5 JP2015526448A5 JP2015527761A JP2015527761A JP2015526448A5 JP 2015526448 A5 JP2015526448 A5 JP 2015526448A5 JP 2015527761 A JP2015527761 A JP 2015527761A JP 2015527761 A JP2015527761 A JP 2015527761A JP 2015526448 A5 JP2015526448 A5 JP 2015526448A5
- Authority
- JP
- Japan
- Prior art keywords
- independently
- alkyl
- boc
- ethyl
- propyl
- 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
- -1 Boc-NH-alkyl Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 22
- 125000001425 triazolyl group Chemical group 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 125000002720 diazolyl group Chemical group 0.000 claims description 12
- 208000002672 hepatitis B Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 12
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004306 triazinyl group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 10
- 230000003612 virological effect Effects 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 102100040018 Interferon alpha-2 Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 claims description 2
- 108010019182 Alloferon Proteins 0.000 claims description 2
- 108700024845 Hepatitis B virus P Proteins 0.000 claims description 2
- 101000959820 Homo sapiens Interferon alpha-1/13 Proteins 0.000 claims description 2
- 102100040019 Interferon alpha-1/13 Human genes 0.000 claims description 2
- 108010078049 Interferon alpha-2 Proteins 0.000 claims description 2
- 108010005716 Interferon beta-1a Proteins 0.000 claims description 2
- 108010047761 Interferon-alpha Proteins 0.000 claims description 2
- 102000006992 Interferon-alpha Human genes 0.000 claims description 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims description 2
- 108010002350 Interleukin-2 Proteins 0.000 claims description 2
- 102000000588 Interleukin-2 Human genes 0.000 claims description 2
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims description 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 2
- 229920002305 Schizophyllan Polymers 0.000 claims description 2
- YQNQNVDNTFHQSW-UHFFFAOYSA-N acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 YQNQNVDNTFHQSW-UHFFFAOYSA-N 0.000 claims description 2
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 2
- 229960003205 adefovir dipivoxil Drugs 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229960005338 clevudine Drugs 0.000 claims description 2
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 claims description 2
- 239000013256 coordination polymer Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229960000980 entecavir Drugs 0.000 claims description 2
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 claims description 2
- 229960004396 famciclovir Drugs 0.000 claims description 2
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 108010050151 hepatitis B hyperimmune globulin Proteins 0.000 claims description 2
- SPSXSWRZQFPVTJ-ZQQKUFEYSA-N hepatitis b vaccine Chemical compound C([C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CCSC)C(=O)N[C@@H](CC1N=CN=C1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)OC(=O)CNC(=O)CNC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@@H](N)CCCNC(N)=N)C1=CC=CC=C1 SPSXSWRZQFPVTJ-ZQQKUFEYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 230000002584 immunomodulator Effects 0.000 claims description 2
- 229960004461 interferon beta-1a Drugs 0.000 claims description 2
- 229960001627 lamivudine Drugs 0.000 claims description 2
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 2
- 229960001614 levamisole Drugs 0.000 claims description 2
- 229950010248 loretin Drugs 0.000 claims description 2
- ZBJWWKFMHOAPNS-UHFFFAOYSA-N loretin Chemical compound C1=CN=C2C(O)=C(I)C=C(S(O)(=O)=O)C2=C1 ZBJWWKFMHOAPNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229960002480 nitazoxanide Drugs 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229960000329 ribavirin Drugs 0.000 claims description 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229960004556 tenofovir Drugs 0.000 claims description 2
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 0 CC(C)(*)Cc1cc(C2N=C(*)NC(C*)=C2C(O*)=O)ccc1 Chemical compound CC(C)(*)Cc1cc(C2N=C(*)NC(C*)=C2C(O*)=O)ccc1 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- DQNOFLNLZQNVKP-QRWMCTBCSA-N CC1(C)OCCN(CC(NC(c2ncc[s]2)=NC2c(c(Cl)c3)ccc3F)=C2C(OC)=O)[C@@H]1C(O)=O Chemical compound CC1(C)OCCN(CC(NC(c2ncc[s]2)=NC2c(c(Cl)c3)ccc3F)=C2C(OC)=O)[C@@H]1C(O)=O DQNOFLNLZQNVKP-QRWMCTBCSA-N 0.000 description 1
- OFSKLFARLHTLCF-MUMRKEEXSA-N CCOC(C1=C(CN(CCOC2(C)C)[C@@H]2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2(C)C)[C@@H]2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Br)c1)ccc1F)=O OFSKLFARLHTLCF-MUMRKEEXSA-N 0.000 description 1
- IAEWKMLDZVNIPH-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)N(C)C(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)N(C)C(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O IAEWKMLDZVNIPH-UHFFFAOYSA-N 0.000 description 1
- QFWBYXBJOVCVOD-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2ncc(F)[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2ncc(F)[s]2)=NC1c(c(Br)c1)ccc1F)=O QFWBYXBJOVCVOD-UHFFFAOYSA-N 0.000 description 1
- UUPVEIPMBAVNBK-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Br)c1)ccc1F)=O UUPVEIPMBAVNBK-UHFFFAOYSA-N 0.000 description 1
- BBLVJWYJXCCUSY-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2ncc[s]2)=NC1c1ccccc1[N+]([O-])=O)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2ncc[s]2)=NC1c1ccccc1[N+]([O-])=O)=O BBLVJWYJXCCUSY-UHFFFAOYSA-N 0.000 description 1
- WKAYRCYSFWNGBI-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(Br)c1)ccc1F)=O WKAYRCYSFWNGBI-UHFFFAOYSA-N 0.000 description 1
- MJBINAGELGCSNH-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(Cl)c1)ccc1Cl)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(Cl)c1)ccc1Cl)=O MJBINAGELGCSNH-UHFFFAOYSA-N 0.000 description 1
- GMABFVNXNBYLRG-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(Cl)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(Cl)c1)ccc1F)=O GMABFVNXNBYLRG-UHFFFAOYSA-N 0.000 description 1
- PSWVQHQRNNQNMR-UHFFFAOYSA-N CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(F)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)C2C(O)=O)NC(c2nnc[s]2)=NC1c(c(F)c1)ccc1F)=O PSWVQHQRNNQNMR-UHFFFAOYSA-N 0.000 description 1
- XHQARFVMKXBHEP-YMXDCFFPSA-N CCOC(C1=C(CN(CCOC2)[C@@H]2C(O)=O)NC(c2nc(CC(NC)=O)c[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)[C@@H]2C(O)=O)NC(c2nc(CC(NC)=O)c[s]2)=NC1c(c(Br)c1)ccc1F)=O XHQARFVMKXBHEP-YMXDCFFPSA-N 0.000 description 1
- HWQOEBDZYHAIJZ-YMXDCFFPSA-N CCOC(C1=C(CN(CCOC2)[C@@H]2C(O)=O)NC(c2nc(CC(OC)=O)c[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCOC2)[C@@H]2C(O)=O)NC(c2nc(CC(OC)=O)c[s]2)=NC1c(c(Br)c1)ccc1F)=O HWQOEBDZYHAIJZ-YMXDCFFPSA-N 0.000 description 1
- WBKTURKJTYJXFU-UHFFFAOYSA-N CCOC(C1=C(CN2C(CCC(O)=O)COCC2)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN2C(CCC(O)=O)COCC2)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O WBKTURKJTYJXFU-UHFFFAOYSA-N 0.000 description 1
- DKIVMEDHCYQDRF-UHFFFAOYSA-N CCOC(C1=C(CN2CC(CC(O)=O)OCC2)NC(c2ncc[s]2)=NC1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN2CC(CC(O)=O)OCC2)NC(c2ncc[s]2)=NC1c(c(Br)c1)ccc1F)=O DKIVMEDHCYQDRF-UHFFFAOYSA-N 0.000 description 1
- LQEFLXVHBFVRBL-UHFFFAOYSA-N CCOC(C1=C(CN2CC(CC(O)=O)OCC2)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN2CC(CC(O)=O)OCC2)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O LQEFLXVHBFVRBL-UHFFFAOYSA-N 0.000 description 1
- CUAAEOFQFPMMKH-YTZBPGPESA-N CCOC(C1=C(CN2[C@H](COC(C(C(C)C)N)=O)COCC2)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1Cl)=O Chemical compound CCOC(C1=C(CN2[C@H](COC(C(C(C)C)N)=O)COCC2)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1Cl)=O CUAAEOFQFPMMKH-YTZBPGPESA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 1
- 229950002828 propagermanium Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210303033 | 2012-08-24 | ||
| CN201210303033.4 | 2012-08-24 | ||
| CN201310116949 | 2013-04-03 | ||
| CN201310116949.3 | 2013-04-03 | ||
| PCT/CN2013/001001 WO2014029193A1 (en) | 2012-08-24 | 2013-08-23 | Dihydropyrimidine compounds and their application in pharmaceuticals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015526448A JP2015526448A (ja) | 2015-09-10 |
| JP2015526448A5 true JP2015526448A5 (https=) | 2016-10-06 |
| JP6263533B2 JP6263533B2 (ja) | 2018-01-17 |
Family
ID=50149385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015527761A Active JP6263533B2 (ja) | 2012-08-24 | 2013-08-23 | ジヒドロピリミジン化合物及び医薬におけるその適用 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US9340538B2 (https=) |
| EP (1) | EP2888241B1 (https=) |
| JP (1) | JP6263533B2 (https=) |
| KR (1) | KR102148678B1 (https=) |
| CN (2) | CN103626752B (https=) |
| AU (1) | AU2013305390C1 (https=) |
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-
2013
- 2013-08-23 CN CN201310373003.5A patent/CN103626752B/zh active Active
- 2013-08-23 KR KR1020147036508A patent/KR102148678B1/ko active Active
- 2013-08-23 JP JP2015527761A patent/JP6263533B2/ja active Active
- 2013-08-23 EP EP13830553.7A patent/EP2888241B1/en active Active
- 2013-08-23 HU HUE13830553A patent/HUE034919T2/en unknown
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- 2013-08-23 US US14/416,061 patent/US9340538B2/en active Active
- 2013-08-23 BR BR112015002858A patent/BR112015002858A2/pt active Search and Examination
- 2013-08-23 WO PCT/CN2013/001001 patent/WO2014029193A1/en not_active Ceased
- 2013-08-23 ES ES13830553.7T patent/ES2640049T3/es active Active
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