HRP20201780T1 - Prolijekovi inhibitora hiv reverzne transkriptaze - Google Patents
Prolijekovi inhibitora hiv reverzne transkriptaze Download PDFInfo
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- HRP20201780T1 HRP20201780T1 HRP20201780TT HRP20201780T HRP20201780T1 HR P20201780 T1 HRP20201780 T1 HR P20201780T1 HR P20201780T T HRP20201780T T HR P20201780TT HR P20201780 T HRP20201780 T HR P20201780T HR P20201780 T1 HRP20201780 T1 HR P20201780T1
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- Croatia
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- compound according
- hiv
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- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title claims 2
- 229940002612 prodrug Drugs 0.000 title 1
- 239000000651 prodrug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims 5
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 229960002555 zidovudine Drugs 0.000 claims 4
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims 3
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims 3
- 229960002656 didanosine Drugs 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 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 3
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims 3
- ZIAOVIPSKUPPQW-UHFFFAOYSA-N 3-chloro-5-[1-[(4-methyl-5-oxo-1h-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile Chemical compound N1C(=O)N(C)C(CN2C(C(OC=3C=C(C=C(Cl)C=3)C#N)=C(C=C2)C(F)(F)F)=O)=N1 ZIAOVIPSKUPPQW-UHFFFAOYSA-N 0.000 claims 2
- VERWQPYQDXWOGT-LVJNJWHOSA-N 4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;[[(2r)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VERWQPYQDXWOGT-LVJNJWHOSA-N 0.000 claims 2
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims 2
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims 2
- UGWQMIXVUBLMAH-IVVFTGHFSA-N [(1s,4r)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol;4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 UGWQMIXVUBLMAH-IVVFTGHFSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229960003804 efavirenz Drugs 0.000 claims 2
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229960002049 etravirine Drugs 0.000 claims 2
- PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims 2
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 2
- IKKXOSBHLYMWAE-QRPMWFLTSA-N islatravir Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@H]1C[C@H](O)[C@](CO)(C#C)O1 IKKXOSBHLYMWAE-QRPMWFLTSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 229960004742 raltegravir Drugs 0.000 claims 2
- CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 229960000523 zalcitabine Drugs 0.000 claims 2
- LHCOVOKZWQYODM-CPEOKENHSA-N 4-amino-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1.O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 LHCOVOKZWQYODM-CPEOKENHSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 claims 1
- 108010019625 Atazanavir Sulfate Proteins 0.000 claims 1
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims 1
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims 1
- 108010032976 Enfuvirtide Proteins 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims 1
- 229940126252 HIV maturation inhibitor Drugs 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 claims 1
- OFFWOVJBSQMVPI-RMLGOCCBSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O.N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 OFFWOVJBSQMVPI-RMLGOCCBSA-N 0.000 claims 1
- LZZSYGOSMIXTGF-UHFFFAOYSA-N P(=O)(OCN1N=C(C=C(C1=O)C(F)(F)F)CN1C=NC(=C(C1=O)OC1=CC(=CC(=C1)C#N)Cl)C(F)(F)F)(O)O Chemical compound P(=O)(OCN1N=C(C=C(C1=O)C(F)(F)F)CN1C=NC(=C(C1=O)OC1=CC(=CC(=C1)C#N)Cl)C(F)(F)F)(O)O LZZSYGOSMIXTGF-UHFFFAOYSA-N 0.000 claims 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims 1
- SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 claims 1
- SCTJKHUUZLXJIP-RUZDIDTESA-N [(2r)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(3-hexadecoxypropoxy)phosphinic acid Chemical compound N1=CN=C2N(C[C@@H](C)OCP(O)(=O)OCCCOCCCCCCCCCCCCCCCC)C=NC2=C1N SCTJKHUUZLXJIP-RUZDIDTESA-N 0.000 claims 1
- 229960004748 abacavir Drugs 0.000 claims 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims 1
- 229960001830 amprenavir Drugs 0.000 claims 1
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 229960003277 atazanavir Drugs 0.000 claims 1
- AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims 1
- PMDQGYMGQKTCSX-HQROKSDRSA-L calcium;[(2r,3s)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3s)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphate Chemical compound [Ca+2].C([C@@H]([C@H](OP([O-])([O-])=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 PMDQGYMGQKTCSX-HQROKSDRSA-L 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 229960005107 darunavir Drugs 0.000 claims 1
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims 1
- 229960002542 dolutegravir Drugs 0.000 claims 1
- RHWKPHLQXYSBKR-BMIGLBTASA-N dolutegravir Chemical compound C([C@@H]1OCC[C@H](N1C(=O)C1=C(O)C2=O)C)N1C=C2C(=O)NCC1=CC=C(F)C=C1F RHWKPHLQXYSBKR-BMIGLBTASA-N 0.000 claims 1
- 229950003141 doravirine Drugs 0.000 claims 1
- 229960003586 elvitegravir Drugs 0.000 claims 1
- JUZYLCPPVHEVSV-LJQANCHMSA-N elvitegravir Chemical compound COC1=CC=2N([C@H](CO)C(C)C)C=C(C(O)=O)C(=O)C=2C=C1CC1=CC=CC(Cl)=C1F JUZYLCPPVHEVSV-LJQANCHMSA-N 0.000 claims 1
- 229960000366 emtricitabine Drugs 0.000 claims 1
- 229960002062 enfuvirtide Drugs 0.000 claims 1
- PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 claims 1
- LLYJISDUHFXOHK-GOCONZMPSA-N ferroptocide Chemical compound C[C@@H]1CC[C@@]23C[C@@H](C(=O)[C@]2([C@@]1([C@@H](C[C@H]([C@@H]3C)C4=CCN5C(=O)N(C(=O)N5C4)C6=CC=CC=C6)OC(=O)CCl)C)O)O LLYJISDUHFXOHK-GOCONZMPSA-N 0.000 claims 1
- 229960002933 fosamprenavir calcium Drugs 0.000 claims 1
- -1 hexadecyloxypropyl Chemical group 0.000 claims 1
- 239000003084 hiv integrase inhibitor Substances 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 229960001936 indinavir Drugs 0.000 claims 1
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229960001627 lamivudine Drugs 0.000 claims 1
- 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 1
- 229960004525 lopinavir Drugs 0.000 claims 1
- 229960004710 maraviroc Drugs 0.000 claims 1
- GSNHKUDZZFZSJB-QYOOZWMWSA-N maraviroc Chemical compound CC(C)C1=NN=C(C)N1[C@@H]1C[C@H](N2CC[C@H](NC(=O)C3CCC(F)(F)CC3)C=3C=CC=CC=3)CC[C@H]2C1 GSNHKUDZZFZSJB-QYOOZWMWSA-N 0.000 claims 1
- KHASNRBNVBIREH-IZEXYCQBSA-N methyl n-[(2s)-1-[[(5s)-5-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-6-phosphonooxyhexyl]amino]-1-oxo-3,3-diphenylpropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C([C@H](NC(=O)OC)C(=O)NCCCC[C@@H](COP(O)(O)=O)N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C1=CC=CC=C1 KHASNRBNVBIREH-IZEXYCQBSA-N 0.000 claims 1
- 229960000884 nelfinavir Drugs 0.000 claims 1
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims 1
- 229960000689 nevirapine Drugs 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 229960002814 rilpivirine Drugs 0.000 claims 1
- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 claims 1
- 229960000311 ritonavir Drugs 0.000 claims 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims 1
- 229960001852 saquinavir Drugs 0.000 claims 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims 1
- 229960001203 stavudine Drugs 0.000 claims 1
- 229960004556 tenofovir Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 229960000838 tipranavir Drugs 0.000 claims 1
- SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
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- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Claims (19)
1. Spoj strukturne formule I ili njegova farmaceutski prihvatljiva sol:
[image]
naznačeno time što
R1 je
[image]
ili
[image]
R2 je halo ili -C1-3alkil supstituiran sa 1 do 3 -F;
R3 je (a) halo, (b) -C1-3alkil supstituiran sa 1 do 3 -F, ili (3) fenil supstituiran sa halo; i
R4 je
[image]
2. Spoj prema patentnom zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen time što R1 je
[image]
3. Spoj prema patentnom zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen time što R1 je
[image]
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, ili njegova farmaceutski prihvatljiva sol, naznačen time što R2 je metil supstituiran sa 1, 2 ili 3 -F; ili etil supstituiran sa 1, 2 ili 3 -F.
5. Spoj prema patentnom zahtjevu 4, ili njegova farmaceutski prihvatljiva sol, naznačen time što R2 je -CHF2, -CF3 ili -CF2CH3.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, ili njegova farmaceutski prihvatljiva sol, naznačen time što R3 je -F; -Cl; metil supstituiran sa 1, 2 ili 3 -F; etil supstituiran sa 1, 2 ili 3 -F; ili fenil supstituiran sa -F.
7. Spoj prema patentnom zahtjevu 6, ili njegova farmaceutski prihvatljiva sol, naznačen time što R3 je - Cl, -CHF2, -CF3, -CF2CH3 ili fenil supstituiran sa -F.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, ili njegova farmaceutski prihvatljiva sol, naznačen time što R4 je:
[image]
ili
[image]
gdje su X+ i X2+ pozitivni protu-ioni.
9. Spoj prema patentnom zahtjevu 8, naznačen time što pozitivni protu-ioni su K+, Na+ ili NH4+.
10. Spoj prema patentnom zahtjevu 1 koji je:
[image]
[image]
ili njegova farmaceutski prihvatljiva sol.
11. Spoj prema patentnom zahtjevu 1 koji je:
(3-((5-(3-hloro-5-cijanofenoksi)-6-okso-4-(trifluorometil)pirimidin-1(6H)-il)metil)-6-okso-5-(trifluorometil)piridazin-1(6H)-il)metil fosfat
[image]
ili njegova farmaceutski prihvatljiva sol.
12. Farmaceutski pripravak koji sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 11 ili njegovu farmaceutski prihvatljivu sol i farmaceutski prihvatljiv nosač.
13. Farmaceutski pripravak koji sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 11, ili njegovu farmaceutski prihvatljivu sol i farmaceutski prihvatljiv nosač i dodatno sadrži efikasnu količinu anti-HIV sredstva izabranog od anti-HIV antivirusnog sredstva, imunomodulatora ili anti-infektivnog sredstva.
14. Farmaceutski pripravak prema patentnom zahtjevu 13, naznačen time što anti-HIV antivirusno sredstvo je inhibitor HIV proteaze, inhibitor HIV reverzne transkriptaze, inhibitor HIV integraze, inhibitor fuzije HIV-a, inhibitor ulaska HIV-a ili inhibitor sazrijevanja HIV-a.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol za uporabu u terapiji.
16. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11 ili njegova farmaceutski prihvatljiva sol za uporabu u inhibiciji replikacije HIV-a.
17. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11 ili njegova farmaceutski prihvatljiva sol za uporabu u liječenju ili profilaksi infekcije HIV-om ili za uporabu u liječenju profilaksi ili odlaganju početka SIDA-e.
18. Farmaceutski pripravak prema patentnom zahtjevu 12 koji dodatno sadrži jedno ili više anti-HIV sredstava izabranih iz sljedeće tablice:
abakavir, ABC
abakavir +lamivudin
abakavir + lamivudin + zidovudin
Amprenavir
Atazanavir
AZT, zidovudin, azidotimidin
Kapravirin
darunavir
ddC, zalcitabin, dideoksicitidin
ddI, didanozin, dideoksiinozin
ddI (gastrorezistentno obložen)
Delavirdin, DLV
dolutegravir
Doravirin, MK-1439
Efavirenc, EFV
efavirenc + emtricitabin + tenofovir DF
EFdA (4'-etinil-2-fluoro-2'-deoksiadenozin)
Elvitegravir
Emtricitabin, FTC
Emtricitabin + tenofovir DF
Emvirin
Enfuvirtid
Gastrorezistentno obložen didanozin
Etravirin, TMC-125
fosamprenavir kalcijum
Indinavir
Lamivudin, 3TC
lamivudin + zidovudin
Lopinavir
lopinavir + ritonavir
Maravirok
Nelfinavir
Nevirapin, NVP
PPL-100 (također poznat kao PL-462) (Ambrilia)
raltegravir, MK-0518
Rilpivirin
Ritonavir
sakvinavir
stavudin, d4T, didehidrodeoksitimidin
tenofovir DF (DF = disoproksil fumarat), TDF
Tenofovir, heksadeciloksipropil (CMX-157)
Tipranavir
Vicrivirok
19. Kombinacija koja sadrži spoj prema bilo kojem od patentnih zahtjeva 1-11, ili njegovu farmaceutski prihvatljivu sol i jedno ili više anti-HIV sredstava izabranih iz tablice u patentnom zahtjevu 18.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461973689P | 2014-04-01 | 2014-04-01 | |
| EP15774282.6A EP3125894B1 (en) | 2014-04-01 | 2015-03-27 | Prodrugs of hiv reverse transcriptase inhibitors |
| PCT/US2015/022868 WO2015153304A1 (en) | 2014-04-01 | 2015-03-27 | Prodrugs of hiv reverse transcriptase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20201780T1 true HRP20201780T1 (hr) | 2021-06-25 |
Family
ID=54241131
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20201780TT HRP20201780T1 (hr) | 2014-04-01 | 2020-11-04 | Prolijekovi inhibitora hiv reverzne transkriptaze |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US10004740B2 (hr) |
| EP (2) | EP3785714A1 (hr) |
| JP (1) | JP6342011B2 (hr) |
| KR (1) | KR102440843B1 (hr) |
| CN (1) | CN106456639B (hr) |
| AU (1) | AU2015241247B2 (hr) |
| BR (1) | BR112016022722B8 (hr) |
| CA (1) | CA2944187C (hr) |
| CY (1) | CY1123582T1 (hr) |
| DK (1) | DK3125894T3 (hr) |
| ES (1) | ES2828951T3 (hr) |
| HR (1) | HRP20201780T1 (hr) |
| HU (1) | HUE051848T2 (hr) |
| LT (1) | LT3125894T (hr) |
| MX (1) | MX2016012915A (hr) |
| PL (1) | PL3125894T3 (hr) |
| PT (1) | PT3125894T (hr) |
| RS (1) | RS61016B1 (hr) |
| RU (1) | RU2693622C2 (hr) |
| SI (1) | SI3125894T1 (hr) |
| WO (1) | WO2015153304A1 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3470B1 (ar) | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| US10004740B2 (en) | 2014-04-01 | 2018-06-26 | Merck Sharp & Dohme Corp. | Prodrugs of HIV reverse transcriptase inhibitors |
| CN106008362B (zh) * | 2016-05-24 | 2018-08-10 | 杰达维（上海）医药科技发展有限公司 | 一种嘧啶衍生物的制备方法 |
| JP7253498B2 (ja) | 2017-12-22 | 2023-04-06 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
| CR20210317A (es) * | 2018-12-18 | 2021-07-14 | Merck Sharp & Dohme | Derivados de pirimidona como agentes citotóxicos selectivos contra células infectadas por vih |
| BR112021016488A2 (pt) | 2019-02-20 | 2021-10-26 | Sumitomo Chemical Company, Limited | Composto de éter e composição de controle de artrópode nocivo contendo o mesmo |
| KR20220011673A (ko) * | 2019-05-22 | 2022-01-28 | 머크 샤프 앤드 돔 코포레이션 | Hiv 감염된 세포에 대한 선택적 세포독성제로서의 피리디논 유도체 |
| WO2022208370A1 (en) | 2021-03-31 | 2022-10-06 | Pi Industries Ltd. | Fused heterocyclic compounds and their use as pest control agents |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5519021A (en) | 1992-08-07 | 1996-05-21 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
| IT1305313B1 (it) * | 1998-07-17 | 2001-05-04 | Colla Paolo | 3,4 - diidro- 6- benzil-4-oxopirimidine sostituite e relativo processodi produzione e impiego nella terapia delle infezioni da hiv-1. |
| SE9904045D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| AP2065A (en) | 2003-02-07 | 2009-11-26 | Janssen Pharmaceutica Nv | Pyrimidine derivatives for the prevention of HIV infection |
| TW200423930A (en) | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| TW200505441A (en) | 2003-03-24 | 2005-02-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitorsⅠ |
| JP4485520B2 (ja) | 2003-03-24 | 2010-06-23 | エフ．ホフマン−ラ ロシュ アーゲー | 逆転写酵素阻害剤としてのベンジル−ピリダジノン類 |
| EP1699777B1 (en) | 2003-09-08 | 2012-12-12 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7288942B2 (en) * | 2003-10-02 | 2007-10-30 | Naoyuki Sato | Plasma potential measuring method and apparatus, and plasma potential measuring probe |
| CN1934093A (zh) | 2004-01-12 | 2007-03-21 | 吉里德科学公司 | 嘧啶基膦酸酯抗病毒化合物和使用方法 |
| EP1730120A1 (en) | 2004-03-23 | 2006-12-13 | F.Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| US7166738B2 (en) | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
| DK1742908T3 (da) | 2004-04-23 | 2010-01-18 | Hoffmann La Roche | Ikke nukleosid revers transkriptase inhibitorer |
| CA2592092A1 (en) | 2004-12-22 | 2006-06-29 | Pfizer Limited | Nonnucleoside inhibitors of hiv-1 reverse transcriptase |
| AR057455A1 (es) | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
| BRPI0617720A2 (pt) | 2005-10-19 | 2011-08-02 | Hoffmann La Roche | compostos inibidores de nnrt de fenil-acetamida, usos dos referidos compostos e composição farmacêutica que os contém |
| WO2007045572A1 (en) | 2005-10-19 | 2007-04-26 | F. Hoffmann-La Roche Ag | N-phenyl phenylacetamide non-nucleoside reverse transcriptase inihibitors |
| US7803940B2 (en) | 2006-11-24 | 2010-09-28 | Takeda Pharmaceutical Company Limited | Heteromonocyclic compound or a salt thereof having strong antihypertensive action, insulin sensitizing activity and the like production thereof and use thereof for prophylaxis or treatment of cardiovascular diseases, metabolic diseases and/or central nervous system diseases |
| BRPI0719060A2 (pt) | 2006-11-24 | 2014-02-04 | Takeda Pharmaceutical | Composto, prodroga, agente farmacêutico, métodos para inibir um receptor de angiotensina ii e/ou ativar um receptor ativado com proliferador de peroxisoma, e para prevenir ou tratar doenças ou condições, e, uso de um composto |
| TW200831085A (en) | 2006-12-13 | 2008-08-01 | Merck & Co Inc | Non-nucleoside reverse transcriptase inhibitors |
| US8404253B2 (en) | 2006-12-28 | 2013-03-26 | Newport Laboratories, Inc. | Modified live (JMSO strain) Haemophilus parasuis vaccine |
| DE102007032507A1 (de) * | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| RU2010125220A (ru) * | 2007-11-20 | 2011-12-27 | Мерк Шарп Энд Домэ Корп. (Us) | Ненуклеозидные ингибиторы обратной транскриптазы |
| CN101918372B (zh) | 2008-01-08 | 2014-03-26 | 默沙东公司 | 用于制备n-取代的羟基嘧啶酮羧酰胺类化合物的方法 |
| MX2012011379A (es) | 2010-03-30 | 2012-11-30 | Merck Canada Inc | Inhibidores no nucleosidicos de la transcriptasa inversa. |
| US20130040914A1 (en) | 2010-04-08 | 2013-02-14 | Samson M. Jolly | Prodrugs of an hiv reverse transcriptase inhibitor |
| JO3470B1 (ar) * | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| US10004740B2 (en) | 2014-04-01 | 2018-06-26 | Merck Sharp & Dohme Corp. | Prodrugs of HIV reverse transcriptase inhibitors |
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- 2015-03-27 US US15/300,405 patent/US10004740B2/en active Active
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- 2015-03-27 HU HUE15774282A patent/HUE051848T2/hu unknown
- 2015-03-27 MX MX2016012915A patent/MX2016012915A/es active IP Right Grant
- 2015-03-27 BR BR112016022722A patent/BR112016022722B8/pt active IP Right Grant
- 2015-03-27 EP EP15774282.6A patent/EP3125894B1/en active Active
- 2015-03-27 KR KR1020167030064A patent/KR102440843B1/ko active IP Right Grant
- 2015-03-27 RS RS20201323A patent/RS61016B1/sr unknown
- 2015-03-27 PT PT157742826T patent/PT3125894T/pt unknown
- 2015-03-27 WO PCT/US2015/022868 patent/WO2015153304A1/en active Application Filing
- 2015-03-27 AU AU2015241247A patent/AU2015241247B2/en active Active
- 2015-03-27 RU RU2016142611A patent/RU2693622C2/ru active
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Also Published As
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|---|---|
| CY1123582T1 (el) | 2022-03-24 |
| CN106456639A (zh) | 2017-02-22 |
| ES2828951T3 (es) | 2021-05-28 |
| US20170173015A1 (en) | 2017-06-22 |
| CA2944187C (en) | 2018-06-19 |
| PT3125894T (pt) | 2020-11-05 |
| JP2017512802A (ja) | 2017-05-25 |
| KR20160133000A (ko) | 2016-11-21 |
| DK3125894T3 (da) | 2020-11-16 |
| AU2015241247A1 (en) | 2016-10-06 |
| US10004740B2 (en) | 2018-06-26 |
| BR112016022722A2 (pt) | 2017-10-31 |
| BR112016022722B1 (pt) | 2023-03-07 |
| RU2016142611A3 (hr) | 2018-12-26 |
| EP3125894A1 (en) | 2017-02-08 |
| WO2015153304A1 (en) | 2015-10-08 |
| LT3125894T (lt) | 2020-12-10 |
| SI3125894T1 (sl) | 2020-12-31 |
| RU2693622C2 (ru) | 2019-07-03 |
| MX2016012915A (es) | 2016-12-07 |
| EP3125894A4 (en) | 2017-12-13 |
| JP6342011B2 (ja) | 2018-06-13 |
| EP3125894B1 (en) | 2020-09-09 |
| CN106456639B (zh) | 2019-05-10 |
| RU2016142611A (ru) | 2018-05-03 |
| HUE051848T2 (hu) | 2021-03-29 |
| EP3785714A1 (en) | 2021-03-03 |
| CA2944187A1 (en) | 2015-10-08 |
| AU2015241247B2 (en) | 2017-09-14 |
| BR112016022722B8 (pt) | 2023-11-21 |
| KR102440843B1 (ko) | 2022-09-29 |
| PL3125894T3 (pl) | 2021-02-08 |
| RS61016B1 (sr) | 2020-12-31 |
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