US20100092427A1 - Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy - Google Patents

Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy Download PDF

Info

Publication number: US20100092427A1
Authority: US; United States
Prior art keywords: azido; dideoxy; alkyl; fluoro; hiv
Prior art date: 2006-07-19
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.): Abandoned

Application number

US12/309,017

Other languages

English (en)

Inventor

Vasu Nair

Byung I. Seo

Vinod R. Uchil

Guochen Chi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Georgia Research Foundation Inc UGARF

Original Assignee

University of Georgia Research Foundation Inc UGARF

Priority date (The priority date 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 date listed.)

2006-07-19

Filing date

2007-07-13

Publication date

2010-04-15

2007-07-13 Application filed by University of Georgia Research Foundation Inc UGARF filed Critical University of Georgia Research Foundation Inc UGARF

2007-07-13 Priority to US12/309,017 priority Critical patent/US20100092427A1/en

2010-04-15 Publication of US20100092427A1 publication Critical patent/US20100092427A1/en

Status Abandoned legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title abstract description 43
239000002253 acid Substances 0.000 title abstract description 20
150000007513 acids Chemical class 0.000 title abstract description 12
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title abstract description 10
230000010076 replication Effects 0.000 title abstract description 7
238000002648 combination therapy Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 116
208000031886 HIV Infections Diseases 0.000 claims abstract description 106
208000030507 AIDS Diseases 0.000 claims abstract description 98
-1 vaccines Substances 0.000 claims abstract description 47
238000000034 method Methods 0.000 claims abstract description 39
108010002459 HIV Integrase Proteins 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 24
208000015181 infectious disease Diseases 0.000 claims abstract description 18
239000003795 chemical substances by application Substances 0.000 claims abstract description 15
230000036436 anti-hiv Effects 0.000 claims abstract description 13
239000003443 antiviral agent Substances 0.000 claims abstract description 13
239000003937 drug carrier Substances 0.000 claims abstract description 12
239000002259 anti human immunodeficiency virus agent Substances 0.000 claims abstract description 10
229940124411 anti-hiv antiviral agent Drugs 0.000 claims abstract description 10
239000002955 immunomodulating agent Substances 0.000 claims abstract description 8
229940121354 immunomodulator Drugs 0.000 claims abstract description 8
208000037357 HIV infectious disease Diseases 0.000 claims description 94
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 94
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 description 61
WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 55
229960002555 zidovudine Drugs 0.000 claims description 50
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 45
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 description 42
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 38
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 38
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 description 38
APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 36
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 33
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 32
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 28
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 27
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 27
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 description 27
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 description 26
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 description 25
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 description 25
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
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 description 25
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 description 24
108010019625 Atazanavir Sulfate Proteins 0.000 claims description 23
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 description 23
MLBVMOWEQCZNCC-OEMFJLHTSA-N fosamprenavir Chemical compound 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 MLBVMOWEQCZNCC-OEMFJLHTSA-N 0.000 claims description 23
UXCAQJAQSWSNPQ-XLPZGREQSA-N Alovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](F)C1 UXCAQJAQSWSNPQ-XLPZGREQSA-N 0.000 claims description 22
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 22
RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims description 22
WMHSRBZIJNQHKT-FFKFEZPRSA-N abacavir sulfate Chemical compound OS(O)(=O)=O.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1.C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 WMHSRBZIJNQHKT-FFKFEZPRSA-N 0.000 claims description 22
GCQYYIHYQMVWLT-HQNLTJAPSA-N Sorivudine Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 GCQYYIHYQMVWLT-HQNLTJAPSA-N 0.000 claims description 21
RYMCFYKJDVMSIR-RNFRBKRXSA-N apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 claims description 21
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 description 21
239000002777 nucleoside Substances 0.000 claims description 21
GWFOVSGRNGAGDL-FSDSQADBSA-N 2-amino-9-[(1r,2r,3s)-2,3-bis(hydroxymethyl)cyclobutyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1C[C@H](CO)[C@H]1CO GWFOVSGRNGAGDL-FSDSQADBSA-N 0.000 claims description 20
MLILORUFDVLTSP-UHFFFAOYSA-N emivirine Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1C(C)C MLILORUFDVLTSP-UHFFFAOYSA-N 0.000 claims description 20
229960003142 fosamprenavir Drugs 0.000 claims description 20
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 description 19
125000001072 heteroaryl group Chemical group 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
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 description 19
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 description 19
239000008194 pharmaceutical composition Substances 0.000 claims description 19
229960000523 zalcitabine Drugs 0.000 claims description 19
229930024421 Adenine Natural products 0.000 claims description 18
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 18
108010074604 Epoetin Alfa Proteins 0.000 claims description 18
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 description 18
229960000643 adenine Drugs 0.000 claims description 18
229960003942 amphotericin b Drugs 0.000 claims description 18
JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims description 18
229960001852 saquinavir Drugs 0.000 claims description 18
CNPVJJQCETWNEU-CYFREDJKSA-N (4,6-dimethyl-5-pyrimidinyl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone Chemical compound N([C@@H](COC)C=1C=CC(=CC=1)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C CNPVJJQCETWNEU-CYFREDJKSA-N 0.000 claims description 17
JORVRJNILJXMMG-OLNQLETPSA-N brecanavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C2OCOC2=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C(C=C1)=CC=C1OCC1=CSC(C)=N1 JORVRJNILJXMMG-OLNQLETPSA-N 0.000 claims description 17
IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 claims description 17
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 17
ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 17
229960000311 ritonavir Drugs 0.000 claims description 17
229960001355 tenofovir disoproxil Drugs 0.000 claims description 17
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 description 16
108010032976 Enfuvirtide Proteins 0.000 claims description 16
108010002350 Interleukin-2 Proteins 0.000 claims description 16
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 description 16
229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 16
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 description 16
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 16
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 description 16
229960002656 didanosine Drugs 0.000 claims description 16
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 16
239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
CWVMWSZEMZOUPC-JUAXIXHSSA-N (3s,5s,8r,9s,10s,13s,14s,16r)-16-bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C([C@H](Br)C4)=O)[C@@H]4[C@@H]3CC[C@H]21 CWVMWSZEMZOUPC-JUAXIXHSSA-N 0.000 claims description 15
OOLUVSIJOMLOCB-UHFFFAOYSA-N 1633-22-3 Chemical compound C1CC(C=C2)=CC=C2CCC2=CC=C1C=C2 OOLUVSIJOMLOCB-UHFFFAOYSA-N 0.000 claims description 15
ASOMNDIOOKDVDC-UHFFFAOYSA-N 1h-indol-2-yl-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 ASOMNDIOOKDVDC-UHFFFAOYSA-N 0.000 claims description 15
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 description 15
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 description 15
JVPFDOXMGPHRJG-BAJZRUMYSA-N [(2s,4r,5r)-5-(6-aminopurin-9-yl)-4-azidooxolan-2-yl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@H]1N=[N+]=[N-] JVPFDOXMGPHRJG-BAJZRUMYSA-N 0.000 claims description 15
229960004748 abacavir Drugs 0.000 claims description 15
229960001830 amprenavir Drugs 0.000 claims description 15
229960000838 tipranavir Drugs 0.000 claims description 15
WKVDSZYIGHLONN-RRKCRQDMSA-N 5-chloro-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](F)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 WKVDSZYIGHLONN-RRKCRQDMSA-N 0.000 claims description 14
229960003205 adefovir dipivoxil Drugs 0.000 claims description 14
229940001018 emtriva Drugs 0.000 claims description 14
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 description 13
OABUIHOVHQHUAO-NTSWFWBYSA-N [(2s,5r)-5-(2,6-diaminopurin-9-yl)oxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CC[C@@H](CO)O1 OABUIHOVHQHUAO-NTSWFWBYSA-N 0.000 claims description 13
229960003804 efavirenz Drugs 0.000 claims description 13
RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 claims description 13
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
XSSYCIGJYCVRRK-RQJHMYQMSA-N (-)-carbovir Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1C[C@H](CO)C=C1 XSSYCIGJYCVRRK-RQJHMYQMSA-N 0.000 claims description 12
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 claims description 12
GWNOTCOIYUNTQP-FQLXRVMXSA-N 4-[4-[[(3r)-1-butyl-3-[(r)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoic acid Chemical compound N([C@@H](C(=O)N1CCCC)[C@H](O)C2CCCCC2)C(=O)C1(CC1)CCN1CC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C=C1 GWNOTCOIYUNTQP-FQLXRVMXSA-N 0.000 claims description 12
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 description 12
102000002265 Human Growth Hormone Human genes 0.000 claims description 12
108010000521 Human Growth Hormone Proteins 0.000 claims description 12
239000000854 Human Growth Hormone Substances 0.000 claims description 12
WPVFJKSGQUFQAP-GKAPJAKFSA-N Valcyte Chemical compound N1C(N)=NC(=O)C2=C1N(COC(CO)COC(=O)[C@@H](N)C(C)C)C=N2 WPVFJKSGQUFQAP-GKAPJAKFSA-N 0.000 claims description 12
108700025316 aldesleukin Proteins 0.000 claims description 12
QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 claims description 12
LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical compound OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 claims description 12
229960000366 emtricitabine Drugs 0.000 claims description 12
QDGZDCVAUDNJFG-FXQIFTODSA-N entecavir (anhydrous) Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)C1=C QDGZDCVAUDNJFG-FXQIFTODSA-N 0.000 claims description 12
229960001936 indinavir Drugs 0.000 claims description 12
229960000884 nelfinavir Drugs 0.000 claims description 12
229960000689 nevirapine Drugs 0.000 claims description 12
XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 12
NIDRYBLTWYFCFV-FMTVUPSXSA-N (+)-calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 claims description 11
QPVWMQXBTCSLCB-BYAJYZPISA-N (2s)-n-[(2s,3s,4r,5s)-3,4-dihydroxy-5-[[(2s)-3-methyl-2-[[methyl(pyridin-2-ylmethyl)carbamoyl]amino]butanoyl]amino]-1,6-diphenylhexan-2-yl]-3-methyl-2-[[methyl(pyridin-2-ylmethyl)carbamoyl]amino]butanamide Chemical compound N([C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)N(C)CC=1N=CC=CC=1)C(C)C)C(=O)N(C)CC1=CC=CC=N1 QPVWMQXBTCSLCB-BYAJYZPISA-N 0.000 claims description 11
CFFCZKKWUJQDFW-LZDJJOMISA-N (e)-3-[3-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]prop-2-enal Chemical compound O=C1N(\C=C\C=O)C(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 CFFCZKKWUJQDFW-LZDJJOMISA-N 0.000 claims description 11
108060003951 Immunoglobulin Proteins 0.000 claims description 11
GLWHPRRGGYLLRV-XLPZGREQSA-N [[(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](N=[N+]=[N-])C1 GLWHPRRGGYLLRV-XLPZGREQSA-N 0.000 claims description 11
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 11
229950007936 apricitabine Drugs 0.000 claims description 11
229960003277 atazanavir Drugs 0.000 claims description 11
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 11
229950009079 brecanavir Drugs 0.000 claims description 11
NIDRYBLTWYFCFV-UHFFFAOYSA-N calanolide F Natural products C1=CC(C)(C)OC2=C1C(OC(C)C(C)C1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-UHFFFAOYSA-N 0.000 claims description 11
229940014461 combivir Drugs 0.000 claims description 11
229960005107 darunavir Drugs 0.000 claims description 11
102000018358 immunoglobulin Human genes 0.000 claims description 11
IMTIXJBINQBHFH-JETAQZOISA-N ingenol triacetate Chemical compound C1=C(COC(C)=O)[C@@H](OC(C)=O)[C@]2(O)[C@@H](OC(C)=O)C(C)=C[C@]32[C@H](C)C[C@H]2C(C)(C)[C@H]2[C@H]1C3=O IMTIXJBINQBHFH-JETAQZOISA-N 0.000 claims description 11
CJPLEFFCVDQQFZ-UHFFFAOYSA-N loviride Chemical compound CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-UHFFFAOYSA-N 0.000 claims description 11
RXBWRFDZXRAEJT-SZNOJMITSA-N palinavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)C(C)C)[C@H](O)CN1[C@@H](C[C@@H](CC1)OCC=1C=CN=CC=1)C(=O)NC(C)(C)C)C1=CC=CC=C1 RXBWRFDZXRAEJT-SZNOJMITSA-N 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
229950009860 vicriviroc Drugs 0.000 claims description 11
108010036239 CD4-IgG(2) Proteins 0.000 claims description 10
SGOIRFVFHAKUTI-LURJTMIESA-N [(2s)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid Chemical compound N1=CN=C2N(C[C@H](C)OCP(O)(O)=O)C=NC2=C1N SGOIRFVFHAKUTI-LURJTMIESA-N 0.000 claims description 10
XUUPZVLCORYPPM-BFHYXJOUSA-N [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 1-methyl-4h-pyridine-3-carboxylate Chemical compound CN1C=CCC(C(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C(NC(=O)C(C)=C2)=O)N=[N+]=[N-])=C1 XUUPZVLCORYPPM-BFHYXJOUSA-N 0.000 claims description 10
229960000531 abacavir sulfate Drugs 0.000 claims description 10
239000000654 additive Substances 0.000 claims description 10
230000000996 additive effect Effects 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
229950004424 alovudine Drugs 0.000 claims description 10
229950005846 amdoxovir Drugs 0.000 claims description 10
AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 10
229940047766 co-trimoxazole Drugs 0.000 claims description 10
108060002021 cyanovirin N Proteins 0.000 claims description 10
229960005319 delavirdine Drugs 0.000 claims description 10
229960005420 etoposide Drugs 0.000 claims description 10
229960001627 lamivudine Drugs 0.000 claims description 10
AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 10
GMLBVLXDRNJFGR-MOUTVQLLSA-N michellamine c Chemical compound C[C@H]1N[C@H](C)CC2=C1C(O)=CC(O)=C2C1=C2C=C(C)C=C(OC)C2=C(O)C(C=2C(=C3C(OC)=CC(C)=CC3=C(C=3C=4C[C@@H](C)N[C@H](C)C=4C(O)=CC=3O)C=2)O)=C1 GMLBVLXDRNJFGR-MOUTVQLLSA-N 0.000 claims description 10
229940072250 norvir Drugs 0.000 claims description 10
229940107904 reyataz Drugs 0.000 claims description 10
229960000329 ribavirin Drugs 0.000 claims description 10
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 10
229960004556 tenofovir Drugs 0.000 claims description 10
229960004693 tenofovir disoproxil fumarate Drugs 0.000 claims description 10
BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 claims description 10
229940052255 ziagen Drugs 0.000 claims description 10
HDMHBHNRWDNNCD-UHFFFAOYSA-N 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine Chemical compound OCCOCN1C(=O)NC(=O)C(C)=C1SC1=CC=CC=C1 HDMHBHNRWDNNCD-UHFFFAOYSA-N 0.000 claims description 9
ZGTVUJJJVGOODR-RRKCRQDMSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-chloropyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 ZGTVUJJJVGOODR-RRKCRQDMSA-N 0.000 claims description 9
WZGBNAXNHRMYLG-ZXFLCMHBSA-N 4-amino-1-[(2r,4r,5s)-4,5-bis(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](CO)C1 WZGBNAXNHRMYLG-ZXFLCMHBSA-N 0.000 claims description 9
HSBKFSPNDWWPSL-CAHLUQPWSA-N 4-amino-5-fluoro-1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1C=C[C@@H](CO)O1 HSBKFSPNDWWPSL-CAHLUQPWSA-N 0.000 claims description 9
ZNFFMCYSMBXZQU-NSHDSACASA-N 5-chloro-8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2h-2,7,9a-triaza-benzo[cd]azulene-1-thione Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=C(Cl)C1=C32 ZNFFMCYSMBXZQU-NSHDSACASA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 9
229960004525 lopinavir Drugs 0.000 claims description 9
BUYBIVUAJHJDTC-UHFFFAOYSA-N n-[2-[4-[[3-(tert-butylamino)pyridin-2-yl]-ethylamino]piperidine-1-carbonyl]-1h-indol-5-yl]methanesulfonamide Chemical compound C1CN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CCC1N(CC)C1=NC=CC=C1NC(C)(C)C BUYBIVUAJHJDTC-UHFFFAOYSA-N 0.000 claims description 9
239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 9
229950009279 sorivudine Drugs 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
229940111527 trizivir Drugs 0.000 claims description 9
NIDRYBLTWYFCFV-SEDUGSJDSA-N (+)-calanolide b Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-SEDUGSJDSA-N 0.000 claims description 8
YWJCZGDVJQLZET-GGHFOJMISA-N (2r,3s,4r,5r)-2-[[[(z)-4-aminobut-2-enyl]-methylamino]methyl]-5-(6-aminopurin-9-yl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CN(C\C=C/CN)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 YWJCZGDVJQLZET-GGHFOJMISA-N 0.000 claims description 8
JNBVLGDICHLLTN-DZUOILHNSA-N (2s)-2-acetamido-n-[(2s,3s)-4-[[[(2s)-2-acetamido-3-methylbutanoyl]amino]-(cyclohexylmethyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(C)=O)C(C)C)[C@@H](O)CN(CC1CCCCC1)NC(=O)[C@@H](NC(C)=O)C(C)C)C1=CC=CC=C1 JNBVLGDICHLLTN-DZUOILHNSA-N 0.000 claims description 8
WYCLUAUPFCMDTI-KZMNDDLNSA-N (3ar,6s,7as)-n-tert-butyl-5-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,3a,4,6,7,7a-hexahydro-2h-thieno[3,2-c]pyridine-6-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2SCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 WYCLUAUPFCMDTI-KZMNDDLNSA-N 0.000 claims description 8
CRSXNVVRUNDJIA-ZCFIWIBFSA-N (3r)-3,6-diamino-n-(aminomethyl)hexanamide Chemical compound NCCC[C@@H](N)CC(=O)NCN CRSXNVVRUNDJIA-ZCFIWIBFSA-N 0.000 claims description 8
FDCWKQRNKFBQAS-HYULELHQSA-N (3r,5r)-3,5-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4-hydroxy-1-(2-methoxy-2-oxoacetyl)oxycyclohexane-1-carboxylic acid Chemical compound O([C@@H]1CC(C[C@H](C1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)(OC(=O)C(=O)OC)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 FDCWKQRNKFBQAS-HYULELHQSA-N 0.000 claims description 8
XCVGQMUMMDXKCY-WZJLIZBTSA-N (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one Chemical compound C1=CC(CO)=CC=C1CN1C(=O)N(CC=2C=CC(CO)=CC=2)[C@H](CC=2C=CC=CC=2)[C@H](O)[C@@H](O)[C@H]1CC1=CC=CC=C1 XCVGQMUMMDXKCY-WZJLIZBTSA-N 0.000 claims description 8
GBMQKZSGGJRJQY-UHFFFAOYSA-N 1-(2-hydroxyethoxymethyl)-5-methyl-6-(3-methylphenyl)sulfanylpyrimidine-2,4-dione Chemical compound CC1=CC=CC(SC=2N(C(=O)NC(=O)C=2C)COCCO)=C1 GBMQKZSGGJRJQY-UHFFFAOYSA-N 0.000 claims description 8
VXIBYIHJONGOIE-UHFFFAOYSA-N 1-(2-hydroxyethoxymethyl)-5-methyl-6-phenylsulfanyl-2-sulfanylidenepyrimidin-4-one Chemical compound OCCOCN1C(=S)NC(=O)C(C)=C1SC1=CC=CC=C1 VXIBYIHJONGOIE-UHFFFAOYSA-N 0.000 claims description 8
FKHGYIRFPRYMOH-UBKIQSJTSA-N 1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound C1[C@H](F)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 FKHGYIRFPRYMOH-UBKIQSJTSA-N 0.000 claims description 8
RHBTTWULFWNOBZ-XLPZGREQSA-N 1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound O=C1NC(=S)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](F)C1 RHBTTWULFWNOBZ-XLPZGREQSA-N 0.000 claims description 8
BKIUEHLYJFLWPK-SHYZEUOFSA-N 1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](F)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 BKIUEHLYJFLWPK-SHYZEUOFSA-N 0.000 claims description 8
FDCWKQRNKFBQAS-UHFFFAOYSA-N 1-methoxyoxalyl-3,5-dicaffeoylquinic acid Natural products OC1C(OC(=O)C=CC=2C=C(O)C(O)=CC=2)CC(OC(=O)C(=O)OC)(C(O)=O)CC1OC(=O)C=CC1=CC=C(O)C(O)=C1 FDCWKQRNKFBQAS-UHFFFAOYSA-N 0.000 claims description 8
GHYVQWKIJDRIPJ-XLPZGREQSA-N 106060-85-9 Chemical compound C1OC2=NC(=O)C(C)=CN2[C@H]2C[C@H](N=[N+]=[N-])[C@@H]1O2 GHYVQWKIJDRIPJ-XLPZGREQSA-N 0.000 claims description 8
FJEFHLWFBLZMJP-SHYZEUOFSA-N 120826-45-1 Chemical compound C1OC2=NC(=O)C=CN2[C@H]2C[C@H](N=[N+]=[N-])[C@@H]1O2 FJEFHLWFBLZMJP-SHYZEUOFSA-N 0.000 claims description 8
RTJUXLYUUDBAJN-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1C[C@H](F)[C@@H](CO)O1 RTJUXLYUUDBAJN-KVQBGUIXSA-N 0.000 claims description 8
FZYYPNOHKXTKLI-NTSWFWBYSA-N 2-amino-9-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)C=C1 FZYYPNOHKXTKLI-NTSWFWBYSA-N 0.000 claims description 8
HEMNVSCJOZIBEQ-UHFFFAOYSA-N 2-amino-n-[4-chloro-2-(1h-pyrrole-2-carbonyl)phenyl]acetamide Chemical compound NCC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CN1 HEMNVSCJOZIBEQ-UHFFFAOYSA-N 0.000 claims description 8
KRZBCHWVBQOTNZ-PSEXTPKNSA-N 3,5-di-O-caffeoyl quinic acid Chemical compound O([C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-PSEXTPKNSA-N 0.000 claims description 8
CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 claims description 8
HNSUDSIHCJEYQG-SHYZEUOFSA-N 4-amino-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](F)C1 HNSUDSIHCJEYQG-SHYZEUOFSA-N 0.000 claims description 8
KZWNMZZXEWOPAS-RRKCRQDMSA-N 4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-chloropyrimidin-2-one Chemical compound C1=C(Cl)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 KZWNMZZXEWOPAS-RRKCRQDMSA-N 0.000 claims description 8
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 description 8
DKTULUNJRRRNTA-RRKCRQDMSA-N 4-amino-5-chloro-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(Cl)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](F)C1 DKTULUNJRRRNTA-RRKCRQDMSA-N 0.000 claims description 8
IADVHAUOJNFDIQ-DTWKUNHWSA-N 4-amino-5-ethyl-1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C(CC)=CN1[C@@H]1O[C@H](CO)CC1 IADVHAUOJNFDIQ-DTWKUNHWSA-N 0.000 claims description 8
WZRJTRPJURQBRM-UHFFFAOYSA-N 4-amino-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 WZRJTRPJURQBRM-UHFFFAOYSA-N 0.000 claims description 8
BWBBMKFAGMRESB-RRKCRQDMSA-N 5-bromo-1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](F)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 BWBBMKFAGMRESB-RRKCRQDMSA-N 0.000 claims description 8
LEAKQIXYSHIHCW-UHFFFAOYSA-N 7-chloro-N-methyl-5-(1H-pyrrol-2-yl)-3H-1,4-benzodiazepin-2-amine Chemical compound N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CN1 LEAKQIXYSHIHCW-UHFFFAOYSA-N 0.000 claims description 8
DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 claims description 8
IJDNMADFCZSLQD-UPMPAGDASA-N Conocurvone Chemical compound O1[C@](C)(CCC=C(C)C)C=CC2=C1C=CC(C1=O)=C2C(=O)C(O)=C1C(C(=O)C=1C=2C=C[C@@](C)(CCC=C(C)C)OC=2C=CC=1C1=O)=C1C1=C(O)C(=O)C2=C(C=C[C@](CCC=C(C)C)(C)O3)C3=CC=C2C1=O IJDNMADFCZSLQD-UPMPAGDASA-N 0.000 claims description 8
LXBIFEVIBLOUGU-UHFFFAOYSA-N Deoxymannojirimycin Natural products OCC1NCC(O)C(O)C1O LXBIFEVIBLOUGU-UHFFFAOYSA-N 0.000 claims description 8
108010050904 Interferons Proteins 0.000 claims description 8
102000014150 Interferons Human genes 0.000 claims description 8
XWNMORIHKRROGW-UHFFFAOYSA-N Ro 5-3335 Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CN1 XWNMORIHKRROGW-UHFFFAOYSA-N 0.000 claims description 8
VWQYIIIPRYCMSY-KVQBGUIXSA-N [(2r,3s,5r)-5-(2,6-diaminopurin-9-yl)-3-fluorooxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1C[C@H](F)[C@@H](CO)O1 VWQYIIIPRYCMSY-KVQBGUIXSA-N 0.000 claims description 8
QVRGWJZTKCMSIW-NTSWFWBYSA-N [(2s,5r)-5-(2,6-diaminopurin-9-yl)-2,5-dihydrofuran-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)C=C1 QVRGWJZTKCMSIW-NTSWFWBYSA-N 0.000 claims description 8
JFUOUIPRAAGUGF-NKWVEPMBSA-N [(2s,5r)-5-(6-aminopurin-9-yl)-2,5-dihydrofuran-2-yl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C=C1 JFUOUIPRAAGUGF-NKWVEPMBSA-N 0.000 claims description 8
UCPOMLWZWRTIAA-UHFFFAOYSA-N [4-[3-(ethylamino)pyridin-2-yl]piperazin-1-yl]-(5-methoxy-1h-indol-2-yl)methanone Chemical compound CCNC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(OC)C=C3C=2)CC1 UCPOMLWZWRTIAA-UHFFFAOYSA-N 0.000 claims description 8
IKIIZLYTISPENI-ZFORQUDYSA-N baicalin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IKIIZLYTISPENI-ZFORQUDYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 8
PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 claims description 8
229960002062 enfuvirtide Drugs 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
229960005102 foscarnet Drugs 0.000 claims description 8
229940079322 interferon Drugs 0.000 claims description 8
MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 claims description 8
CKNAQFVBEHDJQV-UHFFFAOYSA-N oltipraz Chemical compound S1SC(=S)C(C)=C1C1=CN=CC=N1 CKNAQFVBEHDJQV-UHFFFAOYSA-N 0.000 claims description 8
YIQPUIGJQJDJOS-UHFFFAOYSA-N plerixafor Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CN1CCCNCCNCCCNCC1 YIQPUIGJQJDJOS-UHFFFAOYSA-N 0.000 claims description 8
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 8
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 8
229960003604 testosterone Drugs 0.000 claims description 8
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 8
VGJJGVNGFKVNSV-NUHKNMDZSA-N (3s,4as,8as)-n-tert-butyl-2-[(2r,3s)-3-[[(2s)-3-(4-fluorophenyl)sulfonyl-2-(methanesulfonamido)propanoyl]amino]-2-hydroxy-4-phenylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinoline-3-carboxamide 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](CS(=O)(=O)C=1C=CC(F)=CC=1)NS(C)(=O)=O)C1=CC=CC=C1 VGJJGVNGFKVNSV-NUHKNMDZSA-N 0.000 claims description 7
GKNMUCPEXSCGKC-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 GKNMUCPEXSCGKC-UHFFFAOYSA-N 0.000 claims description 7
SUUIYCJSXUMURT-DJLDLDEBSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-ethylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(CC)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 SUUIYCJSXUMURT-DJLDLDEBSA-N 0.000 claims description 7
BDKVACCVHNPPIG-UHFFFAOYSA-N 1-[10-hydroxy-11-(octylamino)undecyl]-3,7-dimethylpurine-2,6-dione Chemical compound O=C1N(CCCCCCCCCC(O)CNCCCCCCCC)C(=O)N(C)C2=C1N(C)C=N2 BDKVACCVHNPPIG-UHFFFAOYSA-N 0.000 claims description 7
MTLZEBXFKNNOHO-UHFFFAOYSA-N 1-[5-[[[2-[[[2-[[[2-[[[2-[[[2-[[[2-[[[5-(2-amino-6-oxo-1h-purin-9-yl)-2-[[[5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[2-[[[5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[2-[[[5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethy Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(S)(=O)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)OC2C(OC(C2)N2C(N=C(N)C=C2)=O)CO)C(O)C1 MTLZEBXFKNNOHO-UHFFFAOYSA-N 0.000 claims description 7
MACMXKSWRALLJO-RRKCRQDMSA-N 2-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-1,2,4-triazine-3,5-dione Chemical compound O=C1NC(=O)C(C)=NN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 MACMXKSWRALLJO-RRKCRQDMSA-N 0.000 claims description 7
AIDDFYOGNWXFIU-UHFFFAOYSA-N 4-(1,5-dibenzyl-2-oxopyridin-3-yl)-4-hydroxy-2-oxobut-3-enoic acid Chemical compound C=1N(CC=2C=CC=CC=2)C(=O)C(C(O)=CC(=O)C(=O)O)=CC=1CC1=CC=CC=C1 AIDDFYOGNWXFIU-UHFFFAOYSA-N 0.000 claims description 7
XQSPYNMVSIKCOC-RITPCOANSA-N 4-amino-5-fluoro-1-[(2s,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)SC1 XQSPYNMVSIKCOC-RITPCOANSA-N 0.000 claims description 7
ZHDAIMVFDVNKKA-UHFFFAOYSA-N C1=C(CC=2C=CC=CC=2)C(=O)C(C(=O)C=C(O)C(=O)O)=CN1CC1=CC=CC=C1 Chemical compound C1=C(CC=2C=CC=CC=2)C(=O)C(C(=O)C=C(O)C(=O)O)=CN1CC1=CC=CC=C1 ZHDAIMVFDVNKKA-UHFFFAOYSA-N 0.000 claims description 7
NIDRYBLTWYFCFV-IUUKEHGRSA-N Calanolide A Natural products C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-IUUKEHGRSA-N 0.000 claims description 7
IMTIXJBINQBHFH-UHFFFAOYSA-N Ingenol triacetate Natural products C1=C(COC(C)=O)C(OC(C)=O)C2(O)C(OC(C)=O)C(C)=CC32C(C)CC2C(C)(C)C2C1C3=O IMTIXJBINQBHFH-UHFFFAOYSA-N 0.000 claims description 7
108010078049 Interferon alpha-2 Proteins 0.000 claims description 7
229910019142 PO4 Inorganic materials 0.000 claims description 7
229930012538 Paclitaxel Natural products 0.000 claims description 7
HTJGLYIJVSDQAE-VWNXEWBOSA-N [(1s,6s,7s,8r,8ar)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate Chemical compound O[C@H]1[C@H](O)[C@@H](OC(=O)CCC)CN2CC[C@H](O)[C@@H]21 HTJGLYIJVSDQAE-VWNXEWBOSA-N 0.000 claims description 7
HYFBPEGMDSQUBT-NKWVEPMBSA-N [(2s,5r)-5-(6-chloropurin-9-yl)oxolan-2-yl]methanol Chemical compound O1[C@H](CO)CC[C@@H]1N1C2=NC=NC(Cl)=C2N=C1 HYFBPEGMDSQUBT-NKWVEPMBSA-N 0.000 claims description 7
229960005475 antiinfective agent Drugs 0.000 claims description 7
XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 claims description 7
YJEJKUQEXFSVCJ-WRFMNRASSA-N bevirimat Chemical compound C1C[C@H](OC(=O)CC(C)(C)C(O)=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C YJEJKUQEXFSVCJ-WRFMNRASSA-N 0.000 claims description 7
229950002892 bevirimat Drugs 0.000 claims description 7
YQXCVAGCMNFUMQ-UHFFFAOYSA-N capravirine Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC1=C(C(C)C)N=C(COC(N)=O)N1CC1=CC=NC=C1 YQXCVAGCMNFUMQ-UHFFFAOYSA-N 0.000 claims description 7
CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 7
229960000633 dextran sulfate Drugs 0.000 claims description 7
229960002049 etravirine Drugs 0.000 claims description 7
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 description 7
229960004884 fluconazole Drugs 0.000 claims description 7
229940099052 fuzeon Drugs 0.000 claims description 7
MECRKILGNPUEFQ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine Chemical compound NCCON MECRKILGNPUEFQ-UHFFFAOYSA-N 0.000 claims description 7
229960001592 paclitaxel Drugs 0.000 claims description 7
229950006460 palinavir Drugs 0.000 claims description 7
YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 claims description 7
239000010452 phosphate Substances 0.000 claims description 7
WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 claims description 7
229940064914 retrovir Drugs 0.000 claims description 7
JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 claims description 7
SGOIRFVFHAKUTI-ZCFIWIBFSA-N tenofovir (anhydrous) Chemical compound N1=CN=C2N(C[C@@H](C)OCP(O)(O)=O)C=NC2=C1N SGOIRFVFHAKUTI-ZCFIWIBFSA-N 0.000 claims description 7
NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 claims description 7
229960001099 trimetrexate Drugs 0.000 claims description 7
229940100050 virazole Drugs 0.000 claims description 7
CJPLEFFCVDQQFZ-INIZCTEOSA-N α-(2,6-dichlorophenyl)-α-(2-acetyl-5-methylanilino)acetamide Chemical compound CC(=O)C1=CC=C(C)C=C1N[C@H](C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-INIZCTEOSA-N 0.000 claims description 7
DBPMWRYLTBNCCE-UHFFFAOYSA-N 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1h-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione Chemical compound C1=2C(OC)=CN=C(OC)C=2NC=C1C(=O)C(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 DBPMWRYLTBNCCE-UHFFFAOYSA-N 0.000 claims description 6
OKGPFTLYBPQBIX-CQSZACIVSA-N 1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-2-(4-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)ethane-1,2-dione Chemical compound C1=2C(OC)=CC=NC=2NC=C1C(=O)C(=O)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 OKGPFTLYBPQBIX-CQSZACIVSA-N 0.000 claims description 6
VKYMRXNXDPKKRV-RRKCRQDMSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-bromopyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 VKYMRXNXDPKKRV-RRKCRQDMSA-N 0.000 claims description 6
RKFULXUNGOGTPS-RRKCRQDMSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 RKFULXUNGOGTPS-RRKCRQDMSA-N 0.000 claims description 6
ZSNNBSPEFVIUDS-SHYZEUOFSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 ZSNNBSPEFVIUDS-SHYZEUOFSA-N 0.000 claims description 6
IHZVFZOUXUNSPQ-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenyl)sulfonylbenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1[N+]([O-])=O IHZVFZOUXUNSPQ-UHFFFAOYSA-N 0.000 claims description 6
AZEXNJIEBDRVJS-OSHOESKRSA-N 12-deoxyphorbol-13-(3E,5E-decadienoate) Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)C2)C(CO)=C[C@H]1[C@H]1[C@]2(OC(=O)C/C=C/C=C/CCCC)C1(C)C AZEXNJIEBDRVJS-OSHOESKRSA-N 0.000 claims description 6
WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 claims description 6
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims description 6
YXHFBWBUFITUKL-UHFFFAOYSA-N 3-acetyl-1,5-dibenzylpyridin-4-one Chemical compound C1=C(CC=2C=CC=CC=2)C(=O)C(C(=O)C)=CN1CC1=CC=CC=C1 YXHFBWBUFITUKL-UHFFFAOYSA-N 0.000 claims description 6
GSNHKUDZZFZSJB-HLMSNRGBSA-N 4,4-Difluoro-N-[(1S)-3-[(1R,5S)-3-[3-methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboximidic acid Chemical compound CC(C)C1=NN=C(C)N1C1C[C@H](N2CC[C@H](NC(=O)C3CCC(F)(F)CC3)C=3C=CC=CC=3)CC[C@H]2C1 GSNHKUDZZFZSJB-HLMSNRGBSA-N 0.000 claims description 6
GZSDAHQGNUAEBC-XLPZGREQSA-N 4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one Chemical compound O=C1N=C(N)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 GZSDAHQGNUAEBC-XLPZGREQSA-N 0.000 claims description 6
YIEFKLOVIROQIL-SHYZEUOFSA-N 4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 YIEFKLOVIROQIL-SHYZEUOFSA-N 0.000 claims description 6
HSBKFSPNDWWPSL-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1C=C[C@H](CO)O1 HSBKFSPNDWWPSL-VDTYLAMSSA-N 0.000 claims description 6
DQOGWKZQQBYYMW-LQGIGNHCSA-N 5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline-2,4-diamine;(2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O.COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 DQOGWKZQQBYYMW-LQGIGNHCSA-N 0.000 claims description 6
WVLHHLRVNDMIAR-IBGZPJMESA-N AMD 070 Chemical compound C1CCC2=CC=CN=C2[C@H]1N(CCCCN)CC1=NC2=CC=CC=C2N1 WVLHHLRVNDMIAR-IBGZPJMESA-N 0.000 claims description 6
APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
CYQFCXCEBYINGO-DLBZAZTESA-N Dronabinol Natural products C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@H]21 CYQFCXCEBYINGO-DLBZAZTESA-N 0.000 claims description 6
102000018997 Growth Hormone Human genes 0.000 claims description 6
108010051696 Growth Hormone Proteins 0.000 claims description 6
NJBBLOIWMSYVCQ-VZTVMPNDSA-N Kynostatin 272 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 NJBBLOIWMSYVCQ-VZTVMPNDSA-N 0.000 claims description 6
108010071384 Peptide T Proteins 0.000 claims description 6
CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
IBHARWXWOCPXCR-WELGVCPWSA-N [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2-decoxy-3-dodecylsulfanylpropyl) hydrogen phosphate Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](COP(O)(=O)OCC(CSCCCCCCCCCCCC)OCCCCCCCCCC)O[C@H]1N1C(=O)NC(=O)C(C)=C1 IBHARWXWOCPXCR-WELGVCPWSA-N 0.000 claims description 6
DOEIDNFVZPMPSN-DTWKUNHWSA-N [(2s,5r)-5-[6-(dimethylamino)purin-9-yl]oxolan-2-yl]methanol Chemical compound C1=NC=2C(N(C)C)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 DOEIDNFVZPMPSN-DTWKUNHWSA-N 0.000 claims description 6
229960004150 aciclovir Drugs 0.000 claims description 6
229960005310 aldesleukin Drugs 0.000 claims description 6
229940098178 ambisome Drugs 0.000 claims description 6
229940059312 androderm Drugs 0.000 claims description 6
229940062331 androgel Drugs 0.000 claims description 6
229950006356 aplaviroc Drugs 0.000 claims description 6
229940030139 aptivus Drugs 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
229940098166 bactrim Drugs 0.000 claims description 6
229940002637 baraclude Drugs 0.000 claims description 6
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 description 6
239000000679 carrageenan Substances 0.000 claims description 6
229920001525 carrageenan Polymers 0.000 claims description 6
235000010418 carrageenan Nutrition 0.000 claims description 6
229940113118 carrageenan Drugs 0.000 claims description 6
239000001913 cellulose Substances 0.000 claims description 6
229920002678 cellulose Polymers 0.000 claims description 6
229940088900 crixivan Drugs 0.000 claims description 6
229940087451 cytovene Drugs 0.000 claims description 6
NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 6
229940063123 diflucan Drugs 0.000 claims description 6
229940115080 doxil Drugs 0.000 claims description 6
229960004679 doxorubicin Drugs 0.000 claims description 6
229960004242 dronabinol Drugs 0.000 claims description 6
229960003586 elvitegravir Drugs 0.000 claims description 6
229950006528 elvucitabine Drugs 0.000 claims description 6
229960000980 entecavir Drugs 0.000 claims description 6
229940072253 epivir Drugs 0.000 claims description 6
229960003388 epoetin alfa Drugs 0.000 claims description 6
229940089118 epogen Drugs 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229960002963 ganciclovir Drugs 0.000 claims description 6
239000000122 growth hormone Substances 0.000 claims description 6
229950010245 ibalizumab Drugs 0.000 claims description 6
239000002850 integrase inhibitor Substances 0.000 claims description 6
229940124524 integrase inhibitor Drugs 0.000 claims description 6
238000001990 intravenous administration Methods 0.000 claims description 6
229940065638 intron a Drugs 0.000 claims description 6
229940088976 invirase Drugs 0.000 claims description 6
229960003350 isoniazid Drugs 0.000 claims description 6
229940112586 kaletra Drugs 0.000 claims description 6
229940113354 lexiva Drugs 0.000 claims description 6
235000019136 lipoic acid Nutrition 0.000 claims description 6
KBEMFSMODRNJHE-JFWOZONXSA-N lodenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@@H]1F KBEMFSMODRNJHE-JFWOZONXSA-N 0.000 claims description 6
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 description 6
229960004710 maraviroc Drugs 0.000 claims description 6
229940101014 nebupent Drugs 0.000 claims description 6
229940063708 neutrexin Drugs 0.000 claims description 6
229940029359 procrit Drugs 0.000 claims description 6
229940087463 proleukin Drugs 0.000 claims description 6
229960004742 raltegravir Drugs 0.000 claims description 6
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 description 6
229940063627 rescriptor Drugs 0.000 claims description 6
229960000885 rifabutin Drugs 0.000 claims description 6
229940063639 rifadin Drugs 0.000 claims description 6
229960001225 rifampicin Drugs 0.000 claims description 6
229940049560 rimactane Drugs 0.000 claims description 6
102200046712 rs752492870 Human genes 0.000 claims description 6
229960004532 somatropin Drugs 0.000 claims description 6
229940054565 sustiva Drugs 0.000 claims description 6
229960002663 thioctic acid Drugs 0.000 claims description 6
229940035307 toposar Drugs 0.000 claims description 6
229940010343 valcyte Drugs 0.000 claims description 6
229960002149 valganciclovir Drugs 0.000 claims description 6
MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims description 6
229960000604 valproic acid Drugs 0.000 claims description 6
229940023080 viracept Drugs 0.000 claims description 6
229940098802 viramune Drugs 0.000 claims description 6
229940087450 zerit Drugs 0.000 claims description 6
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 6
NQWVSMVXKMHKTF-JKSUJKDBSA-N (-)-Arctigenin Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1[C@@H](CC=2C=C(OC)C(O)=CC=2)C(=O)OC1 NQWVSMVXKMHKTF-JKSUJKDBSA-N 0.000 claims description 5
LOOAUVYUIGMRGU-VAOFZXAKSA-N (2r,3s,5r)-3-hydroxy-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolane-2-carbonitrile Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@@](CO)(C#N)[C@@H](O)C1 LOOAUVYUIGMRGU-VAOFZXAKSA-N 0.000 claims description 5
LFYJIPVHOHZXNZ-BAJZRUMYSA-N (2r,3s,5r)-5-(6-aminopurin-9-yl)-2-azido-2-(hydroxymethyl)oxolan-3-ol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](O)[C@](CO)(N=[N+]=[N-])O1 LFYJIPVHOHZXNZ-BAJZRUMYSA-N 0.000 claims description 5
UFSMRNQSQSGJII-QYRZKEDASA-N (2s)-n-[(2s,3s)-4-[(4r)-4-(tert-butylcarbamoyl)-5,5-dimethyl-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl]-2-[(2-naphthalen-1-yloxyacetyl)amino]butanediamide Chemical compound C1SC(C)(C)[C@@H](C(=O)NC(C)(C)C)N1C(=O)[C@@H](O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)COC=1C2=CC=CC=C2C=CC=1)CC1=CC=CC=C1 UFSMRNQSQSGJII-QYRZKEDASA-N 0.000 claims description 5
AHWCYDXQIXZVRK-RPQLRNILSA-N (4r)-n-tert-butyl-3-[(2s,3s)-2-hydroxy-3-[[(2r)-2-[(2-isoquinolin-5-yloxyacetyl)amino]-3-methylsulfanylpropanoyl]amino]-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](C(C)(C)SC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 AHWCYDXQIXZVRK-RPQLRNILSA-N 0.000 claims description 5
HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 claims description 5
GWKIPRVERALPRD-ZDUSSCGKSA-N (s)-4-isopropoxycarbonyl-6-methoxy-3-methylthiomethyl-3,4-dihydroquinoxalin-2(1h)-thione Chemical compound N1C(=S)[C@H](CSC)N(C(=O)OC(C)C)C2=CC(OC)=CC=C21 GWKIPRVERALPRD-ZDUSSCGKSA-N 0.000 claims description 5
AMLBAOPYPUXEQF-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-1,3-dihydro-[1,3]thiazolo[3,4-a]benzimidazole Chemical compound FC1=CC=CC(F)=C1C1N2C3=CC=CC=C3N=C2CS1 AMLBAOPYPUXEQF-UHFFFAOYSA-N 0.000 claims description 5
HOCFDYZWQYGULA-UHFFFAOYSA-N 1-(5-bromopyridin-2-yl)-3-(2-pyridin-2-ylethyl)thiourea Chemical compound N1=CC(Br)=CC=C1NC(=S)NCCC1=CC=CC=N1 HOCFDYZWQYGULA-UHFFFAOYSA-N 0.000 claims description 5
HOSVVXRRMIIWHJ-CCGCGBOQSA-N 1-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-chloropyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@](CO)(N=[N+]=[N-])O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 HOSVVXRRMIIWHJ-CCGCGBOQSA-N 0.000 claims description 5
UALCCFUZBGNAPH-XLPZGREQSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)-5-methylpyrimidin-2-one Chemical compound O=C1N=C(NO)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 UALCCFUZBGNAPH-XLPZGREQSA-N 0.000 claims description 5
SGKHUXSYWIWHBC-NBEYISGCSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(dimethylamino)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(N(C)C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 SGKHUXSYWIWHBC-NBEYISGCSA-N 0.000 claims description 5
XYEDCFNUBBAPAM-UIISKDMLSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(methylamino)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(NC)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 XYEDCFNUBBAPAM-UIISKDMLSA-N 0.000 claims description 5
LYWDBOUHROZMIU-RRKCRQDMSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 LYWDBOUHROZMIU-RRKCRQDMSA-N 0.000 claims description 5
AXXNSKSOBHVEGQ-UBKIQSJTSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-hydroxypyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(O)=C1 AXXNSKSOBHVEGQ-UBKIQSJTSA-N 0.000 claims description 5
SGSGYWXHZVOHIO-VQBKXICFSA-N 1-[(2r,4s,5s)-4-azido-5-[[[(2r,3r,5s)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-methylphosphoryl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(C)(=O)OC[C@H]2[C@@H](C[C@H](O2)N2C(NC(=O)C(C)=C2)=O)N=[N+]=[N-])[C@@H](N=[N+]=[N-])C1 SGSGYWXHZVOHIO-VQBKXICFSA-N 0.000 claims description 5
VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 5
ZBUCRYGAWXPNSN-NBEYISGCSA-N 2-[1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]oxyacetonitrile Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(OCC#N)=C1 ZBUCRYGAWXPNSN-NBEYISGCSA-N 0.000 claims description 5
LGLGKVCCXSGELG-XLPZGREQSA-N 2-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-4-one Chemical compound NC1=NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 LGLGKVCCXSGELG-XLPZGREQSA-N 0.000 claims description 5
HETOJIJPBJGZFJ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1C[C@H](N=[N+]=[N-])[C@@H](CO)O1 HETOJIJPBJGZFJ-KVQBGUIXSA-N 0.000 claims description 5
JECSVLDNKUJUJT-MTQIGAJGSA-N 4-amino-1-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@@](CO)(N=[N+]=[N-])[C@@H](O)C1 JECSVLDNKUJUJT-MTQIGAJGSA-N 0.000 claims description 5
WPVOAMIAPQZNOC-RRKCRQDMSA-N 4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 WPVOAMIAPQZNOC-RRKCRQDMSA-N 0.000 claims description 5
QBEIABZPRBJOFU-CAHLUQPWSA-N 4-amino-5-fluoro-1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)CC1 QBEIABZPRBJOFU-CAHLUQPWSA-N 0.000 claims description 5
GBKMCUTZIIKOCB-RRKCRQDMSA-N 5-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(N)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 GBKMCUTZIIKOCB-RRKCRQDMSA-N 0.000 claims description 5
NFYXXBIRONUIPP-UHFFFAOYSA-N 5-ethyl-1-(phenylmethoxymethyl)-6-pyridin-2-ylsulfanylpyrimidine-2,4-dione Chemical compound C=1C=CC=CC=1COCN1C(=O)NC(=O)C(CC)=C1SC1=CC=CC=N1 NFYXXBIRONUIPP-UHFFFAOYSA-N 0.000 claims description 5
TYQPBHYPIRLWKU-NKWVEPMBSA-N 9-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3h-purin-6-one Chemical compound C1=C[C@@H](CO)O[C@H]1N1C(NC=NC2=O)=C2N=C1 TYQPBHYPIRLWKU-NKWVEPMBSA-N 0.000 claims description 5
102100039864 ATPase family AAA domain-containing protein 2 Human genes 0.000 claims description 5
YYGRXNOXOVZIKE-UHFFFAOYSA-N Arctigenin Natural products COC1CCC(CC2COC(=O)C2CC3CCC(O)C(C3)OC)CC1OC YYGRXNOXOVZIKE-UHFFFAOYSA-N 0.000 claims description 5
PUSFZTXXJJTAMV-UHFFFAOYSA-N C=1N(CC=2C=CC=CC=2)C(=O)C(C(=O)C=C(O)C(=O)OC)=CC=1CC1=CC=CC=C1 Chemical compound C=1N(CC=2C=CC=CC=2)C(=O)C(C(=O)C=C(O)C(=O)OC)=CC=1CC1=CC=CC=C1 PUSFZTXXJJTAMV-UHFFFAOYSA-N 0.000 claims description 5
229920002558 Curdlan Polymers 0.000 claims description 5
239000001879 Curdlan Substances 0.000 claims description 5
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
108010036949 Cyclosporine Proteins 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
OIFFJDGSLVHPCW-UHFFFAOYSA-N Guayarol Natural products COc1ccc(CC2C(Cc3ccc(O)c(O)c3)COC2=O)cc1OC OIFFJDGSLVHPCW-UHFFFAOYSA-N 0.000 claims description 5
101000887284 Homo sapiens ATPase family AAA domain-containing protein 2 Proteins 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
XCVUOCMQYKSJJR-IGRGDXOOSA-N Kni 102 Chemical compound CC(C)(C)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 XCVUOCMQYKSJJR-IGRGDXOOSA-N 0.000 claims description 5
NQWVSMVXKMHKTF-UHFFFAOYSA-N L-Arctigenin Natural products C1=C(OC)C(OC)=CC=C1CC1C(CC=2C=C(OC)C(O)=CC=2)C(=O)OC1 NQWVSMVXKMHKTF-UHFFFAOYSA-N 0.000 claims description 5
ZILOOGIOHVCEKS-HZFUHODCSA-N Telinavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)C(=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 ZILOOGIOHVCEKS-HZFUHODCSA-N 0.000 claims description 5
IPNBHSCJCMEBFX-UHFFFAOYSA-N Thiangazole Natural products O1C(C)=C(C(=O)NC)N=C1C1(C)N=C(C2(C)N=C(SC2)C2(C)N=C(C=CC=3C=CC=CC=3)SC2)SC1 IPNBHSCJCMEBFX-UHFFFAOYSA-N 0.000 claims description 5
PYJIWOQTJHPDAK-BWZBUEFSSA-N [(1s,2r,3r)-3-(6-aminopurin-9-yl)-2-(hydroxymethyl)cyclobutyl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1C[C@H](CO)[C@H]1CO PYJIWOQTJHPDAK-BWZBUEFSSA-N 0.000 claims description 5
ZZOQOCAXOCFBLH-GTTJKFTRSA-N [(2s,5r)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-cyanoethyl phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(=O)(OCCC#N)OC[C@H]2O[C@H](CC2)N2C3=NC=NC(N)=C3N=C2)[C@@H](N=[N+]=[N-])C1 ZZOQOCAXOCFBLH-GTTJKFTRSA-N 0.000 claims description 5
ODPGJSIBNBRBDT-JGVFFNPUSA-N [(2s,5r)-5-[6-(methylamino)purin-9-yl]oxolan-2-yl]methanol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 ODPGJSIBNBRBDT-JGVFFNPUSA-N 0.000 claims description 5
ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 claims description 5
MRIVVOQRLBCTOK-SHYZEUOFSA-N [1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl] thiocyanate Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(SC#N)=C1 MRIVVOQRLBCTOK-SHYZEUOFSA-N 0.000 claims description 5
229940030360 abacavir / lamivudine Drugs 0.000 claims description 5
229940114030 abacavir / lamivudine / zidovudine Drugs 0.000 claims description 5
239000008186 active pharmaceutical agent Substances 0.000 claims description 5
229940009456 adriamycin Drugs 0.000 claims description 5
229940068561 atripla Drugs 0.000 claims description 5
GIXWDMTZECRIJT-UHFFFAOYSA-N aurintricarboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=CC1=C(C=1C=C(C(O)=CC=1)C(O)=O)C1=CC=C(O)C(C(O)=O)=C1 GIXWDMTZECRIJT-UHFFFAOYSA-N 0.000 claims description 5
229960004099 azithromycin Drugs 0.000 claims description 5
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
229940087430 biaxin Drugs 0.000 claims description 5
229960002626 clarithromycin Drugs 0.000 claims description 5
229940055354 copegus Drugs 0.000 claims description 5
235000019316 curdlan Nutrition 0.000 claims description 5
229940078035 curdlan Drugs 0.000 claims description 5
229940094111 depo-testosterone Drugs 0.000 claims description 5
229940019131 epzicom Drugs 0.000 claims description 5
229940097709 hepsera Drugs 0.000 claims description 5
BXENDTPSKAICGV-UHFFFAOYSA-N inophyllum-P Natural products C=1C(=O)OC2=C3C(O)C(C)C(C)OC3=C3C=CC(C)(C)OC3=C2C=1C1=CC=CC=C1 BXENDTPSKAICGV-UHFFFAOYSA-N 0.000 claims description 5
229960004130 itraconazole Drugs 0.000 claims description 5
108010075606 kynostatin 272 Proteins 0.000 claims description 5
229940033984 lamivudine / zidovudine Drugs 0.000 claims description 5
229940113983 lopinavir / ritonavir Drugs 0.000 claims description 5
NWFYESYCEQICQP-UHFFFAOYSA-N methylmatairesinol Natural products C1=C(OC)C(OC)=CC=C1CC1C(=O)OCC1CC1=CC=C(O)C(OC)=C1 NWFYESYCEQICQP-UHFFFAOYSA-N 0.000 claims description 5
IPNBHSCJCMEBFX-WMXIMKIMSA-N n,5-dimethyl-2-[(4r)-4-methyl-2-[(4s)-4-methyl-2-[(4s)-4-methyl-2-[(e)-2-phenylethenyl]-5h-1,3-thiazol-4-yl]-5h-1,3-thiazol-4-yl]-5h-1,3-thiazol-4-yl]-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=C(C(=O)NC)N=C1[C@@]1(C)N=C([C@@]2(C)N=C(SC2)[C@@]2(C)N=C(\C=C\C=3C=CC=CC=3)SC2)SC1 IPNBHSCJCMEBFX-WMXIMKIMSA-N 0.000 claims description 5
NRVIEWRSGDDWHP-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-1-[4-[[(2-chlorophenyl)methylamino]methyl]cyclohexyl]methanamine;hydron;dichloride Chemical compound Cl.Cl.ClC1=CC=CC=C1CNCC1CCC(CNCC=2C(=CC=CC=2)Cl)CC1 NRVIEWRSGDDWHP-UHFFFAOYSA-N 0.000 claims description 5
RPJPZDVUUKWPGT-FOIHOXPVSA-N nim811 Chemical compound CC[C@H](C)[C@@H]1N(C)C(=O)CN(C)C(=O)[C@H](CC)NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC1=O RPJPZDVUUKWPGT-FOIHOXPVSA-N 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
229940068586 prezista Drugs 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
229960001203 stavudine Drugs 0.000 claims description 5
XETIIHXJGVJJAT-NODMNJIGSA-N tert-butyl n-[(e,2s,3s,5r)-5-[[1-(1h-benzimidazol-2-ylmethylamino)-3-methyl-1-oxopentan-2-yl]carbamoyl]-3-hydroxy-1,8-diphenyloct-7-en-2-yl]carbamate Chemical compound C([C@@H](C(=O)NC(C(C)CC)C(=O)NCC=1NC2=CC=CC=C2N=1)C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OC(C)(C)C)\C=C\C1=CC=CC=C1 XETIIHXJGVJJAT-NODMNJIGSA-N 0.000 claims description 5
229940008349 truvada Drugs 0.000 claims description 5
229940053728 vitrasert Drugs 0.000 claims description 5
229940072251 zithromax Drugs 0.000 claims description 5
229940107931 zovirax Drugs 0.000 claims description 5
KRZBCHWVBQOTNZ-UHFFFAOYSA-N (-) 3,5-dicaffeoyl-muco-quinic acid Natural products OC1C(OC(=O)C=CC=2C=C(O)C(O)=CC=2)CC(O)(C(O)=O)CC1OC(=O)C=CC1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-UHFFFAOYSA-N 0.000 claims description 4
LGLVVVCSQBZONM-HCCLCSBVSA-N (2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentano Chemical compound NC(N)=NCCC[C@@H](NC(=O)C)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(N)=O LGLVVVCSQBZONM-HCCLCSBVSA-N 0.000 claims description 4
PHIRWRJXMDCHJF-GBYUNDSOSA-N (2s)-1-[(2r)-2-[[(2r)-6-amino-2-[[(2r)-6-amino-2-[[2-[[2-[[2-[[2-[[2-(6-aminohexylamino)acetyl]-[3-(diaminomethylideneamino)propyl]amino]acetyl]-[3-(diaminomethylideneamino)propyl]amino]acetyl]-benzylamino]acetyl]-[3-(diaminomethylideneamino)propyl]amino] Chemical compound O=C([C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCCN)NC(=O)[C@@H](CCCCN)NC(=O)CN(CCCN=C(N)N)C(=O)CN(C(=O)CN(CCCN=C(N)N)C(=O)CN(CCCN=C(N)N)C(=O)CNCCCCCCN)CC=1C=CC=CC=1)N1CCC[C@H]1C(N)=O PHIRWRJXMDCHJF-GBYUNDSOSA-N 0.000 claims description 4
PWAMRQBZIMSSPD-XFTNXAEASA-N (2s)-n-[(2s,3r)-4-[(2s)-2-(tert-butylcarbamoyl)piperidin-1-yl]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide Chemical compound CC(C)(C)NC(=O)[C@@H]1CCCCN1C[C@@H](O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)CC1=CC=CC=C1 PWAMRQBZIMSSPD-XFTNXAEASA-N 0.000 claims description 4
VACGBZYEDFQOIU-UHFFFAOYSA-N (4-acetamidophenyl) 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(NC(=O)C)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 VACGBZYEDFQOIU-UHFFFAOYSA-N 0.000 claims description 4
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 4
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
108010030583 (melle-4)cyclosporin Proteins 0.000 claims description 4
IGFIJVXZVHIJST-UHFFFAOYSA-N 1-(ethoxymethyl)-5-ethyl-6-phenylselanylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(COCC)C([Se]C=2C=CC=CC=2)=C1CC IGFIJVXZVHIJST-UHFFFAOYSA-N 0.000 claims description 4
CJUYXNGOWAETEX-UHFFFAOYSA-N 1-(ethoxymethyl)-5-ethyl-6-phenylsulfanylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(COCC)C(SC=2C=CC=CC=2)=C1CC CJUYXNGOWAETEX-UHFFFAOYSA-N 0.000 claims description 4
ZNPKSOLUIAAPQI-NYNCVSEMSA-N 1-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@@](CO)(N=[N+]=[N-])[C@@H](O)C1 ZNPKSOLUIAAPQI-NYNCVSEMSA-N 0.000 claims description 4
HQMDKFQJGGNORX-MTQIGAJGSA-N 1-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@](CO)(N=[N+]=[N-])O[C@H]1N1C(=O)NC(=O)C=C1 HQMDKFQJGGNORX-MTQIGAJGSA-N 0.000 claims description 4
YXDSILBXLUFJID-RRKCRQDMSA-N 1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 YXDSILBXLUFJID-RRKCRQDMSA-N 0.000 claims description 4
XKKCQTLDIPIRQD-JGVFFNPUSA-N 1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)CC1 XKKCQTLDIPIRQD-JGVFFNPUSA-N 0.000 claims description 4
MIXHWWCIYLMJQR-XCBNKYQSSA-N 1-[(2r,5s)-5-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@@](CO)(N=[N+]=[N-])CC1 MIXHWWCIYLMJQR-XCBNKYQSSA-N 0.000 claims description 4
MPCCEBBDYNZILE-UHFFFAOYSA-N 1-[3-acetyl-5-[(2-amino-1,6-dimethylpyrimidin-4-ylidene)amino]phenyl]ethanone;hydrochloride Chemical compound Cl.CC(=O)C1=CC(C(=O)C)=CC(N=C2N=C(N)N(C)C(C)=C2)=C1 MPCCEBBDYNZILE-UHFFFAOYSA-N 0.000 claims description 4
UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 4
NZANGQBKHOWGDW-LBACSGLVSA-N 2-amino-9-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1C[C@H](O)[C@](CO)(N=[N+]=[N-])O1 NZANGQBKHOWGDW-LBACSGLVSA-N 0.000 claims description 4
OCLZPNCLRLDXJC-NTSWFWBYSA-N 2-amino-9-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](CO)O1 OCLZPNCLRLDXJC-NTSWFWBYSA-N 0.000 claims description 4
MVCIFQBXXSMTQD-UHFFFAOYSA-N 3,5-dicaffeoylquinic acid Natural products Cc1ccc(C=CC(=O)OC2CC(O)(CC(OC(=O)C=Cc3ccc(O)c(O)c3)C2O)C(=O)O)cc1C MVCIFQBXXSMTQD-UHFFFAOYSA-N 0.000 claims description 4
MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 claims description 4
YGSNHAHYDLJAOD-YLWLKBPMSA-N 4-amino-1-[(2r,5s)-3-hydroxy-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1C(O)=C[C@@H](CO)O1 YGSNHAHYDLJAOD-YLWLKBPMSA-N 0.000 claims description 4
RYMCFYKJDVMSIR-BQBZGAKWSA-N 4-amino-1-[(2s,4s)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1S[C@@H](CO)OC1 RYMCFYKJDVMSIR-BQBZGAKWSA-N 0.000 claims description 4
XQSPYNMVSIKCOC-PHDIDXHHSA-N 4-amino-5-fluoro-1-[(2r,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-PHDIDXHHSA-N 0.000 claims description 4
PANPMNGUWWTDHB-WDSKDSINSA-N 4-amino-5-fluoro-1-[(2s,4s)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1S[C@@H](CO)OC1 PANPMNGUWWTDHB-WDSKDSINSA-N 0.000 claims description 4
SEAXPFZOFZLHLQ-UHFFFAOYSA-N 5-chloro-3-phenylsulfanyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1SC1=CC=CC=C1 SEAXPFZOFZLHLQ-UHFFFAOYSA-N 0.000 claims description 4
LNEPZLRCYLNOIU-UHFFFAOYSA-N 6-[(3,5-dimethylphenyl)methyl]-1-(ethoxymethyl)-5-ethylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=C(C)C=C(C)C=2)=C1CC LNEPZLRCYLNOIU-UHFFFAOYSA-N 0.000 claims description 4
ZPMSFPSRIQLYQI-UHFFFAOYSA-N 6-benzyl-1-(ethoxymethyl)-5-ethylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1CC ZPMSFPSRIQLYQI-UHFFFAOYSA-N 0.000 claims description 4
IXYDFPDGIIMFGM-BAJZRUMYSA-N 9-[(2r,4s,5r)-5-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1[C@H](O)[C@](CO)(N=[N+]=[N-])O[C@H]1N1C(NC=NC2=O)=C2N=C1 IXYDFPDGIIMFGM-BAJZRUMYSA-N 0.000 claims description 4
SSIBMWPFXYSVEK-CUPIEXAXSA-N A 80987 Chemical compound N([C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=NC=CC=1)C(=O)OCC1=CC=CC=N1 SSIBMWPFXYSVEK-CUPIEXAXSA-N 0.000 claims description 4
239000004156 Azodicarbonamide Substances 0.000 claims description 4
WVPSCZBMYQIZMS-QNRWOPMTSA-N BILA 2185BS Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H](CC1)SC=1C=CN=CC=1)C(=O)NC(C)(C)C)CC1=CC=CC=C1 WVPSCZBMYQIZMS-QNRWOPMTSA-N 0.000 claims description 4
OCOMYWBZKIPFJL-UHFFFAOYSA-N C1=C(CC=2C=CC=CC=2)C(=O)C(C(=O)C=C(O)C(=O)OC)=CN1CC1=CC=CC=C1 Chemical compound C1=C(CC=2C=CC=CC=2)C(=O)C(C(=O)C=C(O)C(=O)OC)=CN1CC1=CC=CC=C1 OCOMYWBZKIPFJL-UHFFFAOYSA-N 0.000 claims description 4
108010038168 CGP 64222 Proteins 0.000 claims description 4
JDVVGAQPNNXQDW-WCMLQCRESA-N Castanospermine Natural products O[C@H]1[C@@H](O)[C@H]2[C@@H](O)CCN2C[C@H]1O JDVVGAQPNNXQDW-WCMLQCRESA-N 0.000 claims description 4
JDVVGAQPNNXQDW-TVNFTVLESA-N Castinospermine Chemical compound C1[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-TVNFTVLESA-N 0.000 claims description 4
IJDNMADFCZSLQD-UHFFFAOYSA-N Conocurvone Natural products CC(C)=CCCC1(C)Oc2ccc3C(=O)C(=C(O)C(=O)c3c2C=C1)C1=C(C(=O)c2c(ccc3OC(C)(CCC=C(C)C)C=Cc23)C1=O)C1=C(O)C(=O)c2c(ccc3OC(C)(CCC=C(C)C)C=Cc23)C1=O IJDNMADFCZSLQD-UHFFFAOYSA-N 0.000 claims description 4
229930105110 Cyclosporin A Natural products 0.000 claims description 4
101001128694 Homo sapiens Neuroendocrine convertase 1 Proteins 0.000 claims description 4
101000828971 Homo sapiens Signal peptidase complex subunit 3 Proteins 0.000 claims description 4
101000979222 Hydra vulgaris PC3-like endoprotease variant A Proteins 0.000 claims description 4
101000979221 Hydra vulgaris PC3-like endoprotease variant B Proteins 0.000 claims description 4
108010000668 KNI 102 Proteins 0.000 claims description 4
108010056642 N-alpha-acetyl-nona-D-arginine amide acetate Proteins 0.000 claims description 4
IPQKDIRUZHOIOM-UHFFFAOYSA-N Oroxin A Natural products OC1C(O)C(O)C(CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IPQKDIRUZHOIOM-UHFFFAOYSA-N 0.000 claims description 4
102100023789 Signal peptidase complex subunit 3 Human genes 0.000 claims description 4
241000251131 Sphyrna Species 0.000 claims description 4
LWEKFDHXJHJYGB-RXMQYKEDSA-N [(2r)-1-(2,6-diaminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid Chemical compound N1=C(N)N=C2N(C[C@@H](C)OCP(O)(O)=O)C=NC2=C1N LWEKFDHXJHJYGB-RXMQYKEDSA-N 0.000 claims description 4
ZYXJGWBYPOHODT-JCHHYUSOSA-N [(2r,3r)-1,1-dioxo-2-propan-2-ylthiolan-3-yl] n-[(2r,3r)-4-[(3ar,6s,7as)-6-(tert-butylcarbamoyl)-3,3a,4,6,7,7a-hexahydro-2h-thieno[3,2-c]pyridin-5-yl]-3-hydroxy-1-phenylsulfanylbutan-2-yl]carbamate Chemical compound C1CS(=O)(=O)[C@H](C(C)C)[C@@H]1OC(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2SCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 ZYXJGWBYPOHODT-JCHHYUSOSA-N 0.000 claims description 4
XURFYCWNUGWGDL-VQJWOFKYSA-N [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2s,5r)-5-(6-oxo-3h-purin-9-yl)oxolan-2-yl]methyl hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OC[C@H]2O[C@H](CC2)N2C3=C(C(N=CN3)=O)N=C2)[C@@H](N=[N+]=[N-])C1 XURFYCWNUGWGDL-VQJWOFKYSA-N 0.000 claims description 4
UFWRXJDSXCFZFA-JGVFFNPUSA-N [(2s,5r)-5-(6-methylsulfanylpurin-9-yl)oxolan-2-yl]methanol Chemical compound C1=NC=2C(SC)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 UFWRXJDSXCFZFA-JGVFFNPUSA-N 0.000 claims description 4
NWYIHZNMQZMTPL-DTWKUNHWSA-N [(2s,5r)-5-[6-(ethylamino)purin-9-yl]oxolan-2-yl]methanol Chemical compound C1=NC=2C(NCC)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 NWYIHZNMQZMTPL-DTWKUNHWSA-N 0.000 claims description 4
KZUGHQWNFSZLLP-UHFFFAOYSA-N [1-(2-amino-6-oxo-3h-purin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid Chemical compound N1C(N)=NC(=O)C2=C1N(CC(CF)OCP(O)(O)=O)C=N2 KZUGHQWNFSZLLP-UHFFFAOYSA-N 0.000 claims description 4
BFZJTDBFUROXJA-UHFFFAOYSA-N [1-(6-aminopurin-9-yl)-3-fluoropropan-2-yl]oxymethylphosphonic acid Chemical compound NC1=NC=NC2=C1N=CN2CC(CF)OCP(O)(O)=O BFZJTDBFUROXJA-UHFFFAOYSA-N 0.000 claims description 4
KBEMFSMODRNJHE-UHFFFAOYSA-N [5-(6-aminopurin-9-yl)-4-fluorooxolan-2-yl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1C1OC(CO)CC1F KBEMFSMODRNJHE-UHFFFAOYSA-N 0.000 claims description 4
229960001997 adefovir Drugs 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
229950006463 atevirdine Drugs 0.000 claims description 4
235000019399 azodicarbonamide Nutrition 0.000 claims description 4
AQHDANHUMGXSJZ-UHFFFAOYSA-N baicalin Natural products OC1C(O)C(C(O)CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 AQHDANHUMGXSJZ-UHFFFAOYSA-N 0.000 claims description 4
229960003321 baicalin Drugs 0.000 claims description 4
TZRRVSCDIPHXHN-RRUVMKMCSA-N benzyl n-[(2s)-1-[[(2s,3r,4r,5s)-3,4-dihydroxy-5-[[(2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-1,6-diphenylhexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound N([C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@@H](O)[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)OCC=1C=CC=CC=1)C(C)C)C(=O)OCC1=CC=CC=C1 TZRRVSCDIPHXHN-RRUVMKMCSA-N 0.000 claims description 4
TZRRVSCDIPHXHN-UNHORJANSA-N benzyl n-[(2s)-1-[[(2s,3s,4s,5s)-3,4-dihydroxy-5-[[(2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-1,6-diphenylhexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound N([C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)[C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)OCC=1C=CC=CC=1)C(C)C)C(=O)OCC1=CC=CC=C1 TZRRVSCDIPHXHN-UNHORJANSA-N 0.000 claims description 4
229950008230 capravirine Drugs 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229950003414 celgosivir Drugs 0.000 claims description 4
GPNLPYGUGHPGKX-FBHZOYHQSA-J chembl296274 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)C1=CC(O)=CC(O)=C1N=NC(C=C1S([O-])(=O)=O)=CC=C1\C=C\C1=CC=C(N=NC=2C(=CC(O)=CC=2O)C([O-])=O)C=C1S([O-])(=O)=O GPNLPYGUGHPGKX-FBHZOYHQSA-J 0.000 claims description 4
229960001265 ciclosporin Drugs 0.000 claims description 4
229940104302 cytosine Drugs 0.000 claims description 4
MSJQCBORNZDNDU-UHFFFAOYSA-D decasodium 3-methoxy-6-[2-(6-methoxy-4,5-disulfonatooxyoxan-3-yl)oxy-5-[5-(5-methoxy-3,4-disulfonatooxyoxan-2-yl)oxy-3,4-disulfonatooxyoxan-2-yl]oxy-4-sulfonatooxyoxan-3-yl]oxy-4,5-disulfonatooxyoxane-2-carboxylate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].COC1COC(OC2COC(OC3COC(OC4COC(OC)C(OS([O-])(=O)=O)C4OS([O-])(=O)=O)C(OC4OC(C(OC)C(OS([O-])(=O)=O)C4OS([O-])(=O)=O)C([O-])=O)C3OS([O-])(=O)=O)C(OS([O-])(=O)=O)C2OS([O-])(=O)=O)C(OS([O-])(=O)=O)C1OS([O-])(=O)=O MSJQCBORNZDNDU-UHFFFAOYSA-D 0.000 claims description 4
229940043249 elmiron Drugs 0.000 claims description 4
229950002002 emivirine Drugs 0.000 claims description 4
229940108452 foscavir Drugs 0.000 claims description 4
GFTDIFRKHSPLIX-VNLWOOSYSA-N harziphilone Chemical compound C([C@@H](O)[C@@](C)(O)C1=O)C2=C1COC(/C=C/C=C/C)=C2 GFTDIFRKHSPLIX-VNLWOOSYSA-N 0.000 claims description 4
NUBQKPWHXMGDLP-BDEHJDMKSA-N indinavir sulfate Chemical compound OS(O)(=O)=O.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 NUBQKPWHXMGDLP-BDEHJDMKSA-N 0.000 claims description 4
BXENDTPSKAICGV-LKBUQDJMSA-N inophyllum-b Chemical compound O([C@@H]([C@H]([C@H](O)C1=C2OC(=O)C=3)C)C)C1=C1C=CC(C)(C)OC1=C2C=3C1=CC=CC=C1 BXENDTPSKAICGV-LKBUQDJMSA-N 0.000 claims description 4
108010074280 kynostatin 227 Proteins 0.000 claims description 4
229950004697 lasinavir Drugs 0.000 claims description 4
229950006243 loviride Drugs 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
IMPWGYVYFQPDFN-SZNOJMITSA-N n-[(2s)-1-[[(2s,3r)-4-[(2s,4r)-2-(tert-butylcarbamoyl)-4-(pyridin-3-ylmethylsulfanyl)piperidin-1-yl]-3-hydroxy-1-phenylbutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]quinoline-2-carboxamide Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1N=C2C=CC=CC2=CC=1)C(C)C)[C@H](O)CN1[C@@H](C[C@@H](CC1)SCC=1C=NC=CC=1)C(=O)NC(C)(C)C)C1=CC=CC=C1 IMPWGYVYFQPDFN-SZNOJMITSA-N 0.000 claims description 4
229920004918 nonoxynol-9 Polymers 0.000 claims description 4
229940087419 nonoxynol-9 Drugs 0.000 claims description 4
229950008687 oltipraz Drugs 0.000 claims description 4
229960002169 plerixafor Drugs 0.000 claims description 4
HKIRXDARVDUJOP-RHIIWVEJSA-N pyridin-2-ylmethyl n-[(2s)-1-[[(2s,3r,4s,5s)-3,4-dihydroxy-5-[[(2s)-3-methyl-2-(pyridin-2-ylmethoxycarbonylamino)butanoyl]amino]-1,6-diphenylhexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound N([C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)OCC=1N=CC=CC=1)C(C)C)C(=O)OCC1=CC=CC=N1 HKIRXDARVDUJOP-RHIIWVEJSA-N 0.000 claims description 4
HKIRXDARVDUJOP-JPRYDEJLSA-N pyridin-2-ylmethyl n-[(2s)-1-[[(2s,3s,4s,5s)-3,4-dihydroxy-5-[[(2s)-3-methyl-2-(pyridin-2-ylmethoxycarbonylamino)butanoyl]amino]-1,6-diphenylhexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound N([C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)[C@H](O)[C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)OCC=1N=CC=CC=1)C(C)C)C(=O)OCC1=CC=CC=N1 HKIRXDARVDUJOP-JPRYDEJLSA-N 0.000 claims description 4
CRROWNPCQUJQGS-MCEBTLFFSA-N pyridin-2-ylmethyl n-[(2s)-1-[[(2s,4s,5s)-4-hydroxy-1,6-diphenyl-5-(1,3-thiazol-5-ylmethoxycarbonylamino)hexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate 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)OCC1=CC=CC=N1 CRROWNPCQUJQGS-MCEBTLFFSA-N 0.000 claims description 4
108091092562 ribozyme Proteins 0.000 claims description 4
229950005820 telinavir Drugs 0.000 claims description 4
FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 claims description 4
KOLLFWOTBZCTDF-XFTNXAEASA-N tert-butyl (2s)-1-[(2r,3s)-3-[[(2s)-4-amino-2-(naphthalene-2-carbonylamino)-4-oxobutanoyl]amino]-2-hydroxy-4-phenylbutyl]pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)[C@@H]1CCCN1C[C@@H](O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)C=1C=C2C=CC=CC2=CC=1)CC1=CC=CC=C1 KOLLFWOTBZCTDF-XFTNXAEASA-N 0.000 claims description 4
OQHZMGOXOOOFEE-SYQUUIDJSA-N tert-butyl n-[(2s,3r)-3-hydroxy-4-[[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]butyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@H](O)CNC[C@@H](O)[C@H](CC=1C=CC(OCC(=O)N2CCOCC2)=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 OQHZMGOXOOOFEE-SYQUUIDJSA-N 0.000 claims description 4
IYLCQJSWFWQHCD-AIIVFDHXSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-5-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]-6-oxo-1-phenylhexan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@@H](O)C[C@@H](CC=1C=CC(OCCN2CCOCC2)=CC=1)C(=O)N[C@H]1C2=CC=CC=C2C[C@H]1O)C1=CC=CC=C1 IYLCQJSWFWQHCD-AIIVFDHXSA-N 0.000 claims description 4
ZJBUCZFZQXPYFC-JOFXVPDFSA-N tert-butyl n-[(2s,3s,5r)-5-benzyl-3-hydroxy-6-[[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-6-oxo-1-phenylhexan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@@H](O)C[C@@H](CC=1C=CC=CC=1)C(=O)N[C@H]1C2=CC=CC=C2C[C@H]1O)C1=CC=CC=C1 ZJBUCZFZQXPYFC-JOFXVPDFSA-N 0.000 claims description 4
229960003433 thalidomide Drugs 0.000 claims description 4
229940113082 thymine Drugs 0.000 claims description 4
229950011282 tivirapine Drugs 0.000 claims description 4
DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 claims description 4
229950000977 trovirdine Drugs 0.000 claims description 4
PANPMNGUWWTDHB-PHDIDXHHSA-N 4-amino-5-fluoro-1-[(2r,4r)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1S[C@H](CO)OC1 PANPMNGUWWTDHB-PHDIDXHHSA-N 0.000 claims description 3
VWGBUXWULYJCCJ-QKGCVVFFSA-N [(2r,5s)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)OC[C@@H]2O[C@@H](CC2)N2C3=NC=NC(N)=C3N=C2)[C@@H](N=[N+]=[N-])C1 VWGBUXWULYJCCJ-QKGCVVFFSA-N 0.000 claims description 3
239000004599 antimicrobial Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000007921 spray Substances 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
230000002584 immunomodulator Effects 0.000 claims description 2
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
VAPNKLKDKUDFHK-UHFFFAOYSA-H suramin sodium Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(S([O-])(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O)C)C=CC=3)C)=CC=C(S([O-])(=O)=O)C2=C1 VAPNKLKDKUDFHK-UHFFFAOYSA-H 0.000 claims description 2
229960000621 suramin sodium Drugs 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
102000000588 Interleukin-2 Human genes 0.000 claims 6
KIQXCFBLXGRXPY-NSCUHMNNSA-N methyl (e)-2,5-diamino-2-(fluoromethyl)pent-3-enoate Chemical compound COC(=O)C(N)(CF)\C=C\CN KIQXCFBLXGRXPY-NSCUHMNNSA-N 0.000 claims 6
NPHYUIHLLMXOFR-LKEWCRSYSA-N 1-[(2r,3r,5s)-3-fluoro-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1[C@H](F)C[C@@H](CO)O1 NPHYUIHLLMXOFR-LKEWCRSYSA-N 0.000 claims 3
NLEPLDKPYLYCSY-UHFFFAOYSA-N 2-fluoroquinoline Chemical class C1=CC=CC2=NC(F)=CC=C21 NLEPLDKPYLYCSY-UHFFFAOYSA-N 0.000 claims 3
125000003342 alkenyl group Chemical group 0.000 claims 3
125000005037 alkyl phenyl group Chemical group 0.000 claims 3
229950003188 isovaleryl diethylamide Drugs 0.000 claims 3
239000006186 oral dosage form Substances 0.000 claims 3
239000006201 parenteral dosage form Substances 0.000 claims 3
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
239000006215 rectal suppository Substances 0.000 claims 2
229940100618 rectal suppository Drugs 0.000 claims 2
YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-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
229950006790 adenosine phosphate Drugs 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 42
102100034343 Integrase Human genes 0.000 abstract description 36
238000011282 treatment Methods 0.000 abstract description 31
108010061833 Integrases Proteins 0.000 abstract description 13
230000005764 inhibitory process Effects 0.000 abstract description 9
229940124597 therapeutic agent Drugs 0.000 abstract description 9
230000002265 prevention Effects 0.000 abstract description 8
239000003242 anti bacterial agent Substances 0.000 abstract description 7
229940088710 antibiotic agent Drugs 0.000 abstract description 7
229940121357 antivirals Drugs 0.000 abstract description 6
229960005486 vaccine Drugs 0.000 abstract description 5
238000011277 treatment modality Methods 0.000 abstract 1
206010001513 AIDS related complex Diseases 0.000 description 66
241000725303 Human immunodeficiency virus Species 0.000 description 50
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
150000003833 nucleoside derivatives Chemical class 0.000 description 18
239000000243 solution Substances 0.000 description 18
201000010099 disease Diseases 0.000 description 17
229940099797 HIV integrase inhibitor Drugs 0.000 description 15
235000019439 ethyl acetate Nutrition 0.000 description 15
229940125777 fusion inhibitor Drugs 0.000 description 15
239000003084 hiv integrase inhibitor Substances 0.000 description 15
239000007787 solid Substances 0.000 description 15
0 C1CCC1.[1*]C.[2*]C.[3*]C.[4*]C.[5*]/C(O)=C/C(C)=O Chemical compound C1CCC1.[1*]C.[2*]C.[3*]C.[4*]C.[5*]/C(O)=C/C(C)=O 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
238000005160 1H NMR spectroscopy Methods 0.000 description 13
208000007766 Kaposi sarcoma Diseases 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
102000004190 Enzymes Human genes 0.000 description 11
108090000790 Enzymes Proteins 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
229910001868 water Inorganic materials 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
102100020873 Interleukin-2 Human genes 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 9
108020005202 Viral DNA Proteins 0.000 description 9
229940079593 drug Drugs 0.000 description 9
150000005299 pyridinones Chemical group 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
108700020129 Human immunodeficiency virus 1 p31 integrase Proteins 0.000 description 8
230000000840 anti-viral effect Effects 0.000 description 8
DFVFTMTWCUHJBL-BQBZGAKWSA-N statine Chemical compound CC(C)C[C@H](N)[C@@H](O)CC(O)=O DFVFTMTWCUHJBL-BQBZGAKWSA-N 0.000 description 8
WNRAGPQTICKJJQ-UHFFFAOYSA-N 1,5-dibenzyl-3-bromopyridin-2-one Chemical compound C=1N(CC=2C=CC=CC=2)C(=O)C(Br)=CC=1CC1=CC=CC=C1 WNRAGPQTICKJJQ-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
241000700605 Viruses Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000002560 therapeutic procedure Methods 0.000 description 7
230000003612 virological effect Effects 0.000 description 7
YGLZLNHYUDXOSU-UHFFFAOYSA-N 5-benzylpyridin-2-amine Chemical compound C1=NC(N)=CC=C1CC1=CC=CC=C1 YGLZLNHYUDXOSU-UHFFFAOYSA-N 0.000 description 6
206010007134 Candida infections Diseases 0.000 description 6
206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 description 6
108020004414 DNA Proteins 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
201000003984 candidiasis Diseases 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
208000001763 cytomegalovirus retinitis Diseases 0.000 description 6
239000000725 suspension Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
UBOOUPJCJJSWRJ-UHFFFAOYSA-N 1,3-dibenzyl-5-bromopyridin-4-one Chemical compound C1=C(CC=2C=CC=CC=2)C(=O)C(Br)=CN1CC1=CC=CC=C1 UBOOUPJCJJSWRJ-UHFFFAOYSA-N 0.000 description 5
QIZVFBCVSLXDHZ-UHFFFAOYSA-N 5-benzyl-3-bromo-1h-pyridin-2-one Chemical compound N1C(=O)C(Br)=CC(CC=2C=CC=CC=2)=C1 QIZVFBCVSLXDHZ-UHFFFAOYSA-N 0.000 description 5
VXOULVVFCZRMKX-UHFFFAOYSA-N 5-benzyl-3-bromopyridin-2-amine Chemical compound C1=C(Br)C(N)=NC=C1CC1=CC=CC=C1 VXOULVVFCZRMKX-UHFFFAOYSA-N 0.000 description 5
241000222122 Candida albicans Species 0.000 description 5
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
239000007832 Na2SO4 Substances 0.000 description 5
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
UNRVNAXWYRMETC-UHFFFAOYSA-N 3,5-dibromo-3h-pyridin-4-one Chemical compound BrC1C=NC=C(Br)C1=O UNRVNAXWYRMETC-UHFFFAOYSA-N 0.000 description 4
DVYUQEBYBNFWMX-UHFFFAOYSA-N 3-benzyl-5-bromo-3h-pyridin-4-one Chemical compound O=C1C(Br)=CN=CC1CC1=CC=CC=C1 DVYUQEBYBNFWMX-UHFFFAOYSA-N 0.000 description 4
QPUZNRACNNACMR-UHFFFAOYSA-N 3-bromo-5-[hydroxy(phenyl)methyl]-3h-pyridin-4-one Chemical compound C=1C=CC=CC=1C(O)C1=CN=CC(Br)C1=O QPUZNRACNNACMR-UHFFFAOYSA-N 0.000 description 4
YSELFBXGHZXEJR-HMAPJEAMSA-N CC(=O)/C(O)=C/C(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O Chemical compound CC(=O)/C(O)=C/C(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O YSELFBXGHZXEJR-HMAPJEAMSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
229940126656 GS-4224 Drugs 0.000 description 4
UTVMTZSDFPYLRX-BKUYFWCQSA-N O=C(/C=C(\O)C(=O)O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O Chemical compound O=C(/C=C(\O)C(=O)O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O UTVMTZSDFPYLRX-BKUYFWCQSA-N 0.000 description 4
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
230000002924 anti-infective effect Effects 0.000 description 4
239000012867 bioactive agent Substances 0.000 description 4
NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
238000007876 drug discovery Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
210000003714 granulocyte Anatomy 0.000 description 4
230000036541 health Effects 0.000 description 4
RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 4
230000003641 microbiacidal effect Effects 0.000 description 4
229940124561 microbicide Drugs 0.000 description 4
239000002855 microbicide agent Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003921 oil Substances 0.000 description 4
108700004029 pol Genes Proteins 0.000 description 4
101150088264 pol gene Proteins 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000035892 strand transfer Effects 0.000 description 4
231100001274 therapeutic index Toxicity 0.000 description 4
LCADVYTXPLBAGB-AUQKUMLUSA-N (2e,4e,6z,8e,10e,14e)-13-hydroxy-n-(1-hydroxypropan-2-yl)-2,10,12,14,16-pentamethyl-18-phenyloctadeca-2,4,6,8,10,14-hexaenamide Chemical compound OCC(C)NC(=O)C(\C)=C\C=C\C=C/C=C/C(/C)=C/C(C)C(O)C(\C)=C\C(C)CCC1=CC=CC=C1 LCADVYTXPLBAGB-AUQKUMLUSA-N 0.000 description 3
XOYXESIZZFUVRD-UVSAJTFZSA-N (2s,3s,4r,5s,6s)-6-[(2r,3r,4r,5s,6r)-6-[(2r,3s,4r,5s,6r)-5-acetamido-6-[(2r,3r,4r,5s,6r)-4-acetyloxy-6-[(2r,3r,4r,5s,6r)-4-acetyloxy-6-[(2r,3r,4r,5s,6s)-4-acetyloxy-5-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-5-hydroxy-2-(hydroxymethyl)oxan-3-yl]ox Chemical compound CC(=O)O[C@@H]1[C@H](O)[C@@H](OC)O[C@H](CO)[C@H]1O[C@@H]1[C@@H](O)[C@@H](OC(C)=O)[C@H](O[C@@H]2[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]3[C@H]([C@@H](O)[C@H](O[C@@H]4[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]5[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]6[C@H]([C@@H](OC(C)=O)[C@H](O[C@@H]7[C@H]([C@@H](OC(C)=O)[C@H](OC)[C@@H](CO)O7)O)[C@@H](CO)O6)O)[C@H](O5)C(O)=O)O)[C@@H](CO)O4)O)[C@@H](CO)O3)NC(C)=O)[C@@H](CO)O2)O)[C@@H](CO)O1 XOYXESIZZFUVRD-UVSAJTFZSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
206010012735 Diarrhoea Diseases 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
208000007514 Herpes zoster Diseases 0.000 description 3
206010025323 Lymphomas Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000208125 Nicotiana Species 0.000 description 3
235000002637 Nicotiana tabacum Nutrition 0.000 description 3
108091005804 Peptidases Proteins 0.000 description 3
239000004365 Protease Substances 0.000 description 3
206010038705 Respiratory moniliasis Diseases 0.000 description 3
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 3
210000001744 T-lymphocyte Anatomy 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
229960005327 acemannan Drugs 0.000 description 3
230000000843 anti-fungal effect Effects 0.000 description 3
230000001355 anti-mycobacterial effect Effects 0.000 description 3
230000000118 anti-neoplastic effect Effects 0.000 description 3
229940121375 antifungal agent Drugs 0.000 description 3
239000003926 antimycobacterial agent Substances 0.000 description 3
238000013459 approach Methods 0.000 description 3
230000008512 biological response Effects 0.000 description 3
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
239000012267 brine Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
238000013461 design Methods 0.000 description 3
208000002672 hepatitis B Diseases 0.000 description 3
230000010354 integration Effects 0.000 description 3
210000002540 macrophage Anatomy 0.000 description 3
230000000813 microbial effect Effects 0.000 description 3
239000003607 modifier Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000002773 nucleotide Substances 0.000 description 3
125000003729 nucleotide group Chemical group 0.000 description 3
230000002093 peripheral effect Effects 0.000 description 3
238000012545 processing Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000004936 stimulating effect Effects 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 3
229960001082 trimethoprim Drugs 0.000 description 3
AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 2
RLXJTRMVNXHNQH-UHFFFAOYSA-N 2-(6-oxo-3h-purin-9-yl)ethoxymethylphosphonic acid Chemical compound N1C=NC(=O)C2=C1N(CCOCP(O)(=O)O)C=N2 RLXJTRMVNXHNQH-UHFFFAOYSA-N 0.000 description 2
HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical class C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 description 2
CTNTUFQBOKZSPI-UHFFFAOYSA-N 4-[(5-methyl-1,2-oxazol-3-yl)methylsulfonyl]aniline;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=CC(CS(=O)(=O)C=2C=CC(N)=CC=2)=N1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 CTNTUFQBOKZSPI-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241001227713 Chiron Species 0.000 description 2
208000006081 Cryptococcal meningitis Diseases 0.000 description 2
YDDUMTOHNYZQPO-RVXRWRFUSA-N Cynarine Chemical compound O([C@@H]1C[C@@](C[C@H]([C@@H]1O)O)(OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDUMTOHNYZQPO-RVXRWRFUSA-N 0.000 description 2
241000701022 Cytomegalovirus Species 0.000 description 2
206010011831 Cytomegalovirus infection Diseases 0.000 description 2
FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 2
102100031939 Erythropoietin Human genes 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
208000009889 Herpes Simplex Diseases 0.000 description 2
201000002563 Histoplasmosis Diseases 0.000 description 2
241000282412 Homo Species 0.000 description 2
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
108010074328 Interferon-gamma Proteins 0.000 description 2
102000008070 Interferon-gamma Human genes 0.000 description 2
206010027209 Meningitis cryptococcal Diseases 0.000 description 2
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
206010035664 Pneumonia Diseases 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
208000019802 Sexually transmitted disease Diseases 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
102100040247 Tumor necrosis factor Human genes 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
208000007502 anemia Diseases 0.000 description 2
239000003957 anion exchange resin Substances 0.000 description 2
230000000842 anti-protozoal effect Effects 0.000 description 2
230000000692 anti-sense effect Effects 0.000 description 2
239000003904 antiprotozoal agent Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
125000002618 bicyclic heterocycle group Chemical group 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229950009125 cynarine Drugs 0.000 description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
230000002500 effect on skin Effects 0.000 description 2
VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical group NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 2
229960002759 eflornithine Drugs 0.000 description 2
UIPBKZGYQDPIPY-UHFFFAOYSA-N eulicin Chemical compound NC(N)=NCCCCCCCCC(O)C(CCCN)NC(=O)CCCCCCCCN=C(N)N UIPBKZGYQDPIPY-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
229940044627 gamma-interferon Drugs 0.000 description 2
238000001415 gene therapy Methods 0.000 description 2
230000012010 growth Effects 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
YOZNUFWCRFCGIH-BYFNXCQMSA-L hydroxocobalamin Chemical compound O[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O YOZNUFWCRFCGIH-BYFNXCQMSA-L 0.000 description 2
PHOKTTKFQUYZPI-UHFFFAOYSA-N hypericin Natural products Cc1cc(O)c2c3C(=O)C(=Cc4c(O)c5c(O)cc(O)c6c7C(=O)C(=Cc8c(C)c1c2c(c78)c(c34)c56)O)O PHOKTTKFQUYZPI-UHFFFAOYSA-N 0.000 description 2
BTXNYTINYBABQR-UHFFFAOYSA-N hypericin Chemical compound C12=C(O)C=C(O)C(C(C=3C(O)=CC(C)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 BTXNYTINYBABQR-UHFFFAOYSA-N 0.000 description 2
229940005608 hypericin Drugs 0.000 description 2
210000000987 immune system Anatomy 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
238000004255 ion exchange chromatography Methods 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
230000035800 maturation Effects 0.000 description 2
GMLBVLXDRNJFGR-UHFFFAOYSA-N michellanine A Natural products CC1NC(C)CC2=C1C(O)=CC(O)=C2C1=C2C=C(C)C=C(OC)C2=C(O)C(C=2C(=C3C(OC)=CC(C)=CC3=C(C=3C=4CC(C)NC(C)C=4C(O)=CC=3O)C=2)O)=C1 GMLBVLXDRNJFGR-UHFFFAOYSA-N 0.000 description 2
VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 description 2
ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 2
239000007922 nasal spray Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229940042443 other antivirals in atc Drugs 0.000 description 2
YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
235000010603 pastilles Nutrition 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
229960004448 pentamidine Drugs 0.000 description 2
XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 2
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 2
LCADVYTXPLBAGB-GNCBHIOISA-N phenalamide A1 Natural products CC(CO)NC(=O)C(=CC=CC=C/C=C/C(=C/C(C)C(O)C(=CC(C)CCc1ccccc1)C)/C)C LCADVYTXPLBAGB-GNCBHIOISA-N 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
229960002847 prasterone Drugs 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
SSKVDVBQSWQEGJ-UHFFFAOYSA-N pseudohypericin Natural products C12=C(O)C=C(O)C(C(C=3C(O)=CC(O)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 SSKVDVBQSWQEGJ-UHFFFAOYSA-N 0.000 description 2
230000000306 recurrent effect Effects 0.000 description 2
238000012552 review Methods 0.000 description 2
ATEBXHFBFRCZMA-VXTBVIBXSA-N rifabutin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC(=C2N3)C(=O)C=4C(O)=C5C)C)OC)C5=C1C=4C2=NC13CCN(CC(C)C)CC1 ATEBXHFBFRCZMA-VXTBVIBXSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
230000005582 sexual transmission Effects 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
241000894007 species Species 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000013268 sustained release Methods 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
229940125670 thienopyridine Drugs 0.000 description 2
239000002175 thienopyridine Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
201000008827 tuberculosis Diseases 0.000 description 2
ZMCJFJZOSKEMOM-DNKZPPIMSA-N (4,6-dimethylpyrimidin-5-yl)-[4-[(3s)-4-[(1r,2r)-2-ethoxy-5-(trifluoromethyl)-2,3-dihydro-1h-inden-1-yl]-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl]methanone Chemical compound N([C@@H]1C2=CC=C(C=C2C[C@H]1OCC)C(F)(F)F)([C@H](C1)C)CCN1C(CC1)(C)CCN1C(=O)C1=C(C)N=CN=C1C ZMCJFJZOSKEMOM-DNKZPPIMSA-N 0.000 description 1
STLZZYGRXNVQKV-UHFFFAOYSA-N 1-(2-bromoprop-2-enyl)-2-ethylbenzimidazole Chemical compound C1=CC=C2N(CC(Br)=C)C(CC)=NC2=C1 STLZZYGRXNVQKV-UHFFFAOYSA-N 0.000 description 1
ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
UJIBOGAQJRDRES-UHFFFAOYSA-N 1h-pyridin-2-one Chemical group OC1=CC=CC=N1.O=C1C=CC=CN1 UJIBOGAQJRDRES-UHFFFAOYSA-N 0.000 description 1
INQXGZFDGDSRIF-UHFFFAOYSA-N 1h-quinoxaline-2-thione Chemical compound C1=CC=CC2=NC(S)=CN=C21 INQXGZFDGDSRIF-UHFFFAOYSA-N 0.000 description 1
VNIWZCGZPBJWBI-UHFFFAOYSA-N 2-(1,1-dioxothiazinan-2-yl)-n-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound OC=1C(=O)N(C)C(N2S(CCCC2)(=O)=O)=NC=1C(=O)NCC1=CC=C(F)C=C1 VNIWZCGZPBJWBI-UHFFFAOYSA-N 0.000 description 1
XHXFQGAZAVKMFF-UHFFFAOYSA-N 2-(2,6-diaminopurin-9-yl)ethoxymethylphosphonic acid Chemical compound NC1=NC(N)=C2N=CN(CCOCP(O)(O)=O)C2=N1 XHXFQGAZAVKMFF-UHFFFAOYSA-N 0.000 description 1
VFSNCDDPONNCST-UHFFFAOYSA-N 2-(2-aminopurin-9-yl)ethoxymethylphosphonic acid Chemical compound NC1=NC=C2N=CN(CCOCP(O)(O)=O)C2=N1 VFSNCDDPONNCST-UHFFFAOYSA-N 0.000 description 1
RCQMOSJJIVCPJO-UHFFFAOYSA-N 2-(5-methyl-2,4-dioxopyrimidin-1-yl)ethoxymethylphosphonic acid Chemical compound CC1=CN(CCOCP(O)(O)=O)C(=O)NC1=O RCQMOSJJIVCPJO-UHFFFAOYSA-N 0.000 description 1
ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 description 1
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
PQCVYHSKABCYON-UHFFFAOYSA-N 2-oxo-1h-pyridine-3-carboxamide Chemical class NC(=O)C1=CC=CN=C1O PQCVYHSKABCYON-UHFFFAOYSA-N 0.000 description 1
UYEXLMLQBNGMAW-UHFFFAOYSA-N 3-(benzenesulfonyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1S(=O)(=O)C1=CC=CC=C1 UYEXLMLQBNGMAW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
QBEIABZPRBJOFU-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)CC1 QBEIABZPRBJOFU-VDTYLAMSSA-N 0.000 description 1
GJOHLWZHWQUKAU-UHFFFAOYSA-N 5-azaniumylpentan-2-yl-(6-methoxyquinolin-8-yl)azanium;dihydrogen phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 GJOHLWZHWQUKAU-UHFFFAOYSA-N 0.000 description 1
OFVMLCJEDYAOIB-FYWRMAATSA-N 5-ethyl-2-methoxy-3-methyl-6-[2-[(e)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Chemical compound O1C(OC)=C(C)C(=O)C(CC)=C1C1=COC(CC\C(C)=C\C=2C=CC=CC=2)=N1 OFVMLCJEDYAOIB-FYWRMAATSA-N 0.000 description 1
VJXSSYDSOJBUAV-UHFFFAOYSA-N 6-(2,5-dimethoxy-benzyl)-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine Chemical compound COC1=CC=C(OC)C(CC=2C(=C3C(N)=NC(N)=NC3=NC=2)C)=C1 VJXSSYDSOJBUAV-UHFFFAOYSA-N 0.000 description 1
XLSVUDSRCQEFCI-POVHPDDCSA-N 6-[(2r,3r,4r,5s,6r)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexyl [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl carbonate Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OCCCCCCOC(=O)OC[C@@H]1[C@@H](N=[N+]=[N-])C[C@H](N2C(NC(=O)C(C)=C2)=O)O1 XLSVUDSRCQEFCI-POVHPDDCSA-N 0.000 description 1
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
QWLNINWUBHHOLU-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-4-hydroxy-n-(2-hydroxyethyl)-1-methyl-2-oxo-1,5-naphthyridine-3-carboxamide Chemical compound C=1N=C2C(O)=C(C(=O)NCCO)C(=O)N(C)C2=CC=1CC1=CC=C(F)C=C1 QWLNINWUBHHOLU-UHFFFAOYSA-N 0.000 description 1
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
NZVORGQIEFTOQZ-UHFFFAOYSA-N 9-[2-(phosphonomethoxy)ethyl]guanine Chemical compound N1C(N)=NC(=O)C2=C1N(CCOCP(O)(O)=O)C=N2 NZVORGQIEFTOQZ-UHFFFAOYSA-N 0.000 description 1
229940124321 AIDS medicine Drugs 0.000 description 1
101000620356 Actinidia deliciosa Pectinesterase inhibitor Proteins 0.000 description 1
241000427202 Adria Species 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
208000004597 Bacillary angiomatosis Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
201000004569 Blindness Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
208000014644 Brain disease Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
CIUUIPMOFZIWIZ-UHFFFAOYSA-N Bropirimine Chemical compound NC1=NC(O)=C(Br)C(C=2C=CC=CC=2)=N1 CIUUIPMOFZIWIZ-UHFFFAOYSA-N 0.000 description 1
ZMLYTZGCZMSWSK-UHFFFAOYSA-N C.C=C(OCC)[Sn](CCCC)(CCCC)CCCC.ClCC1=CC=CC=C1.NC1=C(Br)C=C(CC2=CC=CC=C2)C=N1.NC1=CC=C(CC2=CC=CC=C2)C=N1.NC1=CC=CC=N1.O.O=C1C(Br)=CC(CC2=CC=CC=C2)=CN1CC1=CC=CC=C1.O=C1NC=C(CC2=CC=CC=C2)C=C1Br Chemical compound C.C=C(OCC)[Sn](CCCC)(CCCC)CCCC.ClCC1=CC=CC=C1.NC1=C(Br)C=C(CC2=CC=CC=C2)C=N1.NC1=CC=C(CC2=CC=CC=C2)C=N1.NC1=CC=CC=N1.O.O=C1C(Br)=CC(CC2=CC=CC=C2)=CN1CC1=CC=CC=C1.O=C1NC=C(CC2=CC=CC=C2)C=C1Br ZMLYTZGCZMSWSK-UHFFFAOYSA-N 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
MSXJGNKHLFPZHK-UHFFFAOYSA-N C=C(OCC)[Sn](CCCC)(CCCC)CCCC.CC(=O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O.CCO.COC(=O)C(=O)OC.ClCCl.O.O=C1C(Br)=CN(CC2=CC=CC=C2)C=C1CC1=CC=CC=C1.O=C1C(Br)=CNC=C1Br.O=C1C(Br)=CNC=C1C(O)C1=CC=CC=C1.O=C1C(Br)=CNC=C1CC1=CC=CC=C1.O=C1C=CNC=C1 Chemical compound C=C(OCC)[Sn](CCCC)(CCCC)CCCC.CC(=O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O.CCO.COC(=O)C(=O)OC.ClCCl.O.O=C1C(Br)=CN(CC2=CC=CC=C2)C=C1CC1=CC=CC=C1.O=C1C(Br)=CNC=C1Br.O=C1C(Br)=CNC=C1C(O)C1=CC=CC=C1.O=C1C(Br)=CNC=C1CC1=CC=CC=C1.O=C1C=CNC=C1 MSXJGNKHLFPZHK-UHFFFAOYSA-N 0.000 description 1
VXENWMIJIQKZKT-UHFFFAOYSA-N CC(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O Chemical compound CC(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O VXENWMIJIQKZKT-UHFFFAOYSA-N 0.000 description 1
FQSNXTLVORIMCP-KYWAJXRTSA-N CC(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O.COC(=O)/C(O)=C/C(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O.COC(=O)C(=O)OC.O=C(/C=C(\O)C(=O)O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O Chemical compound CC(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O.COC(=O)/C(O)=C/C(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O.COC(=O)C(=O)OC.O=C(/C=C(\O)C(=O)O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O FQSNXTLVORIMCP-KYWAJXRTSA-N 0.000 description 1
108010041884 CD4 Immunoadhesins Proteins 0.000 description 1
PUSFZTXXJJTAMV-HMAPJEAMSA-N COC(=O)/C(O)=C/C(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O Chemical compound COC(=O)/C(O)=C/C(=O)C1=CC(CC2=CC=CC=C2)=CN(CC2=CC=CC=C2)C1=O PUSFZTXXJJTAMV-HMAPJEAMSA-N 0.000 description 1
OCOMYWBZKIPFJL-XKZIYDEJSA-N COC(=O)/C(O)=C/C(=O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O Chemical compound COC(=O)/C(O)=C/C(=O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O OCOMYWBZKIPFJL-XKZIYDEJSA-N 0.000 description 1
BVVHCPREVYFNLW-HCZFVGFKSA-N COC(=O)/C(O)=C/C(=O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O.O=C(/C=C(\O)C(=O)O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O Chemical compound COC(=O)/C(O)=C/C(=O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O.O=C(/C=C(\O)C(=O)O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O BVVHCPREVYFNLW-HCZFVGFKSA-N 0.000 description 1
206010006895 Cachexia Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
206010008263 Cervical dysplasia Diseases 0.000 description 1
206010008342 Cervix carcinoma Diseases 0.000 description 1
206010061809 Cervix carcinoma stage 0 Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
241000223205 Coccidioides immitis Species 0.000 description 1
108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
201000007336 Cryptococcosis Diseases 0.000 description 1
241000221204 Cryptococcus neoformans Species 0.000 description 1
208000008953 Cryptosporidiosis Diseases 0.000 description 1
206010011502 Cryptosporidiosis infection Diseases 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
DYEFUKCXAQOFHX-UHFFFAOYSA-N Ebselen Chemical compound [se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 DYEFUKCXAQOFHX-UHFFFAOYSA-N 0.000 description 1
208000032274 Encephalopathy Diseases 0.000 description 1
102100031780 Endonuclease Human genes 0.000 description 1
108010042407 Endonucleases Proteins 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
108090000394 Erythropoietin Proteins 0.000 description 1
102000003951 Erythropoietin Human genes 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
108010010369 HIV Protease Proteins 0.000 description 1
108010078851 HIV Reverse Transcriptase Proteins 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
208000005794 Hairy Leukoplakia Diseases 0.000 description 1
101100005713 Homo sapiens CD4 gene Proteins 0.000 description 1
101000812677 Homo sapiens Nucleotide pyrophosphatase Proteins 0.000 description 1
108010070875 Human Immunodeficiency Virus tat Gene Products Proteins 0.000 description 1
241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
108010054710 IMREG-1 Proteins 0.000 description 1
206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
VEBVPUXQAPLADL-UHFFFAOYSA-N Ingenol Natural products C1=C(CO)C(O)C2(O)C(O)C(C)=CC32C(C)CC2C(C)(C)C2C1C3=O VEBVPUXQAPLADL-UHFFFAOYSA-N 0.000 description 1
108010054698 Interferon Alfa-n3 Proteins 0.000 description 1
108010047761 Interferon-alpha Proteins 0.000 description 1
102000006992 Interferon-alpha Human genes 0.000 description 1
102000003996 Interferon-beta Human genes 0.000 description 1
108090000467 Interferon-beta Proteins 0.000 description 1
241000764238 Isis Species 0.000 description 1
206010023076 Isosporiasis Diseases 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
239000002211 L-ascorbic acid Substances 0.000 description 1
235000000069 L-ascorbic acid Nutrition 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
206010024641 Listeriosis Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
206010025476 Malabsorption Diseases 0.000 description 1
208000004155 Malabsorption Syndromes Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
YFGBQHOOROIVKG-FKBYEOEOSA-N Met-enkephalin Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 YFGBQHOOROIVKG-FKBYEOEOSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
108010042237 Methionine Enkephalin Proteins 0.000 description 1
241000186359 Mycobacterium Species 0.000 description 1
241001502334 Mycobacterium avium complex bacterium Species 0.000 description 1
241000186363 Mycobacterium kansasii Species 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
ONXPDKGXOOORHB-BYPYZUCNSA-N N(5)-methyl-L-glutamine Chemical compound CNC(=O)CC[C@H](N)C(O)=O ONXPDKGXOOORHB-BYPYZUCNSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
102100039306 Nucleotide pyrophosphatase Human genes 0.000 description 1
ZHDAIMVFDVNKKA-MTJSOVHGSA-N O=C(/C=C(\O)C(=O)O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O Chemical compound O=C(/C=C(\O)C(=O)O)C1=CN(CC2=CC=CC=C2)C=C(CC2=CC=CC=C2)C1=O ZHDAIMVFDVNKKA-MTJSOVHGSA-N 0.000 description 1
MXBBVOSRBZCCOD-UHFFFAOYSA-N O=C1C(Br)=CNC=C1Br Chemical compound O=C1C(Br)=CNC=C1Br MXBBVOSRBZCCOD-UHFFFAOYSA-N 0.000 description 1
WFBZHRHOFZNWEO-UHFFFAOYSA-N O=C1C(Br)=CNC=C1C(O)C1=CC=CC=C1 Chemical compound O=C1C(Br)=CNC=C1C(O)C1=CC=CC=C1 WFBZHRHOFZNWEO-UHFFFAOYSA-N 0.000 description 1
NAPLXAROJMQSGK-UHFFFAOYSA-N O=C1C(Br)=CNC=C1CC1=CC=CC=C1 Chemical compound O=C1C(Br)=CNC=C1CC1=CC=CC=C1 NAPLXAROJMQSGK-UHFFFAOYSA-N 0.000 description 1
206010030216 Oesophagitis Diseases 0.000 description 1
108091034117 Oligonucleotide Proteins 0.000 description 1
208000001388 Opportunistic Infections Diseases 0.000 description 1
208000007027 Oral Candidiasis Diseases 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
241001631646 Papillomaviridae Species 0.000 description 1
208000029082 Pelvic Inflammatory Disease Diseases 0.000 description 1
235000003823 Petasites japonicus Nutrition 0.000 description 1
240000003296 Petasites japonicus Species 0.000 description 1
OFVMLCJEDYAOIB-UHFFFAOYSA-N Phenoxan Natural products O1C(OC)=C(C)C(=O)C(CC)=C1C1=COC(CCC(C)=CC=2C=CC=CC=2)=N1 OFVMLCJEDYAOIB-UHFFFAOYSA-N 0.000 description 1
208000005384 Pneumocystis Pneumonia Diseases 0.000 description 1
206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 description 1
206010035742 Pneumonitis Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 1
NUQJULCGNZMBEF-UHFFFAOYSA-N Prostratin Natural products COC(=O)C12CC(C)C3(O)C(C=C(CO)CC4(O)C3C=C(C)C4=O)C1C2(C)C NUQJULCGNZMBEF-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
206010038910 Retinitis Diseases 0.000 description 1
108010037442 SPL7013 Proteins 0.000 description 1
206010058878 Salmonella sepsis Diseases 0.000 description 1
206010049677 Salpingo-oophoritis Diseases 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
239000004187 Spiramycin Substances 0.000 description 1
229920002253 Tannate Polymers 0.000 description 1
208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 1
101800001703 Thymopentin Proteins 0.000 description 1
102400000160 Thymopentin Human genes 0.000 description 1
201000005485 Toxoplasmosis Diseases 0.000 description 1
206010054824 Tubo-ovarian abscess Diseases 0.000 description 1
108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
241000287411 Turdidae Species 0.000 description 1
HIINQLBHPIQYHN-JTQLQIEISA-N Tyr-Gly-Gly Chemical compound OC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1 HIINQLBHPIQYHN-JTQLQIEISA-N 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 description 1
208000010399 Wasting Syndrome Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
FMEQWFGAYHJWAO-CVJICSNFSA-N [(1r,2r,4r)-4-(6-aminopurin-9-yl)-2-fluoro-2-(hydroxymethyl)cyclobutyl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1C[C@](F)(CO)[C@H]1CO FMEQWFGAYHJWAO-CVJICSNFSA-N 0.000 description 1
PYJIWOQTJHPDAK-PRJMDXOYSA-N [(1s,2r,3s)-3-(6-aminopurin-9-yl)-2-(hydroxymethyl)cyclobutyl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](CO)[C@H]1CO PYJIWOQTJHPDAK-PRJMDXOYSA-N 0.000 description 1
XGTJCNSZEASLLL-YFKPBYRVSA-N [(2s)-1-(2,6-diaminopurin-9-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid Chemical compound NC1=NC(N)=C2N=CN(C[C@@H](CO)OCP(O)(O)=O)C2=N1 XGTJCNSZEASLLL-YFKPBYRVSA-N 0.000 description 1
FRPXSOOHWNMLPH-LURJTMIESA-N [(2s)-1-(6-aminopurin-9-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid Chemical compound NC1=NC=NC2=C1N=CN2C[C@@H](CO)OCP(O)(O)=O FRPXSOOHWNMLPH-LURJTMIESA-N 0.000 description 1
XDRZJDXXQHFAAE-RRKCRQDMSA-N [(2s,3s,5r)-5-(6-aminopurin-9-yl)-3-azidooxolan-2-yl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](N=[N+]=[N-])[C@@H](CO)O1 XDRZJDXXQHFAAE-RRKCRQDMSA-N 0.000 description 1
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
230000009471 action Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003098 androgen Substances 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
230000003269 anti-cachectic effect Effects 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
238000011225 antiretroviral therapy Methods 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940050390 benzoate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
TZULDDUNYAGRDC-JFKVGHNISA-N benzyl n-[(2s)-1-[[(1r,2s)-1-[(4r,7s)-5,8-dioxo-7-propan-2-yl-12,15-dioxa-3,6,9-triazabicyclo[14.2.2]icosa-1(18),16,19-trien-4-yl]-1-hydroxy-3-phenylpropan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)[C@@H]1C(=O)N[C@H](C(NCCOCCOC2=CC=C(C=C2)CN1)=O)C(C)C)NC(=O)[C@@H](NC(=O)OCC=1C=CC=CC=1)C(C)(C)C)C1=CC=CC=C1 TZULDDUNYAGRDC-JFKVGHNISA-N 0.000 description 1
ZPLNKSVNSSPDBX-BMYMHALSSA-N benzyl n-[(2s)-1-[[(2s,3r,4r)-5-[[(2s)-1-(1h-benzimidazol-2-ylmethylamino)-3-methyl-1-oxobutan-2-yl]amino]-4-[(4-bromophenyl)methylamino]-3-hydroxy-5-oxo-1-phenylpentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound N([C@@H](C(=O)N[C@@H](C(C)C)C(=O)NCC=1NC2=CC=CC=C2N=1)[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)OCC=1C=CC=CC=1)C(C)C)CC1=CC=C(Br)C=C1 ZPLNKSVNSSPDBX-BMYMHALSSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
229920001222 biopolymer Polymers 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000001815 biotherapy Methods 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
229950009494 bropirimine Drugs 0.000 description 1
HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000010376 calcium ascorbate Nutrition 0.000 description 1
229940047036 calcium ascorbate Drugs 0.000 description 1
239000011692 calcium ascorbate Substances 0.000 description 1
BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000004970 cd4 cell Anatomy 0.000 description 1
210000003855 cell nucleus Anatomy 0.000 description 1
PNDKCRDVVKJPKG-WHERJAGFSA-N cenicriviroc Chemical compound C1=CC(OCCOCCCC)=CC=C1C1=CC=C(N(CC(C)C)CCC\C(=C/2)C(=O)NC=3C=CC(=CC=3)[S@@](=O)CC=3N(C=NC=3)CCC)C\2=C1 PNDKCRDVVKJPKG-WHERJAGFSA-N 0.000 description 1
201000010881 cervical cancer Diseases 0.000 description 1
AZFBLLCNOQPJGJ-DVAZEERGSA-N chembl1332607 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)N2)C)OC)C(C(=C3O)C)=C1C(C1=N4)=C3C(O)=C2C1=NC14CCN(CC(C)C)CC1 AZFBLLCNOQPJGJ-DVAZEERGSA-N 0.000 description 1
VSDWMCJBOALEDE-WXFUMESZSA-N chembl501944 Chemical compound C1=C(C)C=C(OC)C2=C(O)C(C=3C=C(C4=CC(C)=CC(OC)=C4C=3O)C3=C(O)C=C(C=4C(C)=N[C@H](C)CC=43)OC)=CC(C=3C=4C[C@@H](C)N[C@H](C)C=4C(O)=CC=3O)=C21 VSDWMCJBOALEDE-WXFUMESZSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
YDDGKXBLOXEEMN-IABMMNSOSA-N chicoric acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-IABMMNSOSA-N 0.000 description 1
VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
229960002023 chloroprocaine Drugs 0.000 description 1
235000019365 chlortetracycline Nutrition 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
239000013611 chromosomal DNA Substances 0.000 description 1
210000000349 chromosome Anatomy 0.000 description 1
229960000724 cidofovir Drugs 0.000 description 1
229940090805 clavulanate Drugs 0.000 description 1
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
229960002227 clindamycin Drugs 0.000 description 1
238000011260 co-administration Methods 0.000 description 1
201000003486 coccidioidomycosis Diseases 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007771 core particle Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
201000008167 cystoisosporiasis Diseases 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
YDDGKXBLOXEEMN-WOJBJXKFSA-N dicaffeoyl-L-tartaric acid Natural products O([C@@H](C(=O)O)[C@@H](OC(=O)C=CC=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)C=CC1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-WOJBJXKFSA-N 0.000 description 1
ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
229960000735 docosanol Drugs 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
229950010033 ebselen Drugs 0.000 description 1
229940009662 edetate Drugs 0.000 description 1
229940105423 erythropoietin Drugs 0.000 description 1
208000006881 esophagitis Diseases 0.000 description 1
229950000206 estolate Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
229960000752 etoposide phosphate Drugs 0.000 description 1
LIQODXNTTZAGID-OCBXBXKTSA-N etoposide phosphate Chemical compound COC1=C(OP(O)(O)=O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 LIQODXNTTZAGID-OCBXBXKTSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
229960004396 famciclovir Drugs 0.000 description 1
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 description 1
239000012847 fine chemical Substances 0.000 description 1
UOPRBHLVKJBASE-XVSBCJMYSA-N fleephilone Chemical compound C1=C2C(=O)C(C)(OC(=O)CC(C)O)C(=O)C=C2C2=C(/C=C/C=C/C)O[C@@H]3[C@@H]2N1CC[C@@H]3O UOPRBHLVKJBASE-XVSBCJMYSA-N 0.000 description 1
229940124307 fluoroquinolone Drugs 0.000 description 1
DLKYYJFLRUUGHJ-SSJCJZGYSA-A fomivirsen sodium Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP([S-])(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP([O-])(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)[C@@H](OP([O-])(=S)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP([O-])(=S)OC[C@@H]2[C@H](C[C@@H](O2)N2C(N=C(N)C=C2)=O)OP([O-])(=S)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DLKYYJFLRUUGHJ-SSJCJZGYSA-A 0.000 description 1
229950011117 fozivudine tidoxil Drugs 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000004927 fusion Effects 0.000 description 1
210000004392 genitalia Anatomy 0.000 description 1
102000018146 globin Human genes 0.000 description 1
108060003196 globin Proteins 0.000 description 1
229960001731 gluceptate Drugs 0.000 description 1
KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229940049906 glutamate Drugs 0.000 description 1
QIADQCOYEFCREQ-UHFFFAOYSA-N hept-6-yne-2,5-diamine Chemical compound CC(N)CCC(N)C#C QIADQCOYEFCREQ-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
229940096120 hydrea Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
229960001103 hydroxocobalamin Drugs 0.000 description 1
235000004867 hydroxocobalamin Nutrition 0.000 description 1
239000011704 hydroxocobalamin Substances 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
239000012729 immediate-release (IR) formulation Substances 0.000 description 1
230000028993 immune response Effects 0.000 description 1
229960001438 immunostimulant agent Drugs 0.000 description 1
239000003022 immunostimulating agent Substances 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
230000001024 immunotherapeutic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
VEBVPUXQAPLADL-POYOOMFHSA-N ingenol Chemical compound C1=C(CO)[C@@H](O)[C@]2(O)[C@@H](O)C(C)=C[C@]32[C@H](C)C[C@H]2C(C)(C)[C@H]2[C@H]1C3=O VEBVPUXQAPLADL-POYOOMFHSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
BXENDTPSKAICGV-ZMOMAAQPSA-N inophyllum p Chemical compound O([C@@H]([C@H]([C@@H](O)C1=C2OC(=O)C=3)C)C)C1=C1C=CC(C)(C)OC1=C2C=3C1=CC=CC=C1 BXENDTPSKAICGV-ZMOMAAQPSA-N 0.000 description 1
238000012739 integrated shape imaging system Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229960003521 interferon alfa-2a Drugs 0.000 description 1
229960001388 interferon-beta Drugs 0.000 description 1
230000009545 invasion Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
VHVPQPYKVGDNFY-ZPGVKDDISA-N itraconazole Chemical compound O=C1N(C(C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-ZPGVKDDISA-N 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
229940121292 leronlimab Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
210000001853 liver microsome Anatomy 0.000 description 1
229950005339 lobucavir Drugs 0.000 description 1
208000018769 loss of vision Diseases 0.000 description 1
231100000864 loss of vision Toxicity 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
229940099262 marinol Drugs 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229940090004 megace Drugs 0.000 description 1
229960001786 megestrol Drugs 0.000 description 1
229960004296 megestrol acetate Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
CMJNUODSZAGDEG-WBASAELKSA-N methyl (2r)-2-[(2r,4s)-4-[2-[[(2r,4s)-2-[(1r)-2-methoxy-2-oxo-1-[(2-phenylacetyl)amino]ethyl]-5,5-dimethyl-1,3-thiazolidine-4-carbonyl]amino]ethylcarbamoyl]-5,5-dimethyl-1,3-thiazolidin-2-yl]-2-[(2-phenylacetyl)amino]acetate Chemical compound N([C@H](C(=O)OC)[C@H]1SC(C)(C)[C@H](C(=O)NCCNC(=O)[C@H]2C(S[C@@H](N2)[C@H](NC(=O)CC=2C=CC=CC=2)C(=O)OC)(C)C)N1)C(=O)CC1=CC=CC=C1 CMJNUODSZAGDEG-WBASAELKSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 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 description 1
LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
JMUHBNWAORSSBD-WKYWBUFDSA-N mifamurtide Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCNC(=O)[C@H](C)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O JMUHBNWAORSSBD-WKYWBUFDSA-N 0.000 description 1
229960005225 mifamurtide Drugs 0.000 description 1
229960003248 mifepristone Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002062 molecular scaffold Substances 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
NLDVPINGTPMESH-UHFFFAOYSA-N n-[2-[4-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl]propan-2-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide;potassium Chemical class [K].O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C NLDVPINGTPMESH-UHFFFAOYSA-N 0.000 description 1
BQEDCCWCORCFJD-UHFFFAOYSA-N n-hydroxy-1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical class C1=CC=C2NC(C(=O)NO)=CC2=N1 BQEDCCWCORCFJD-UHFFFAOYSA-N 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
210000004940 nucleus Anatomy 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
229960000988 nystatin Drugs 0.000 description 1
VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
229940039748 oxalate Drugs 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229940002988 pegasys Drugs 0.000 description 1
108010092853 peginterferon alfa-2a Proteins 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229960001624 pentamidine isethionate Drugs 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
201000003450 persistent generalized lymphadenopathy Diseases 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
229950001030 piritrexim Drugs 0.000 description 1
201000000317 pneumocystosis Diseases 0.000 description 1
229920001432 poly(L-lactide) Polymers 0.000 description 1
229940095679 poly-dex Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229960005179 primaquine Drugs 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 description 1
BOJKFRKNLSCGHY-HXGSDTCMSA-N prostratin Chemical compound C1=C(CO)C[C@]2(O)C(=O)C(C)=C[C@H]2[C@@]2(O)[C@H](C)C[C@@]3(OC(C)=O)C(C)(C)[C@H]3[C@@H]21 BOJKFRKNLSCGHY-HXGSDTCMSA-N 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
125000004219 purine nucleobase group Chemical group 0.000 description 1
ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
108700018720 recombinant interferon alpha 2b-like Proteins 0.000 description 1
108010043277 recombinant soluble CD4 Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000008439 repair process Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000010839 reverse transcription Methods 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229940063122 sandimmune Drugs 0.000 description 1
238000007423 screening assay Methods 0.000 description 1
229940048278 septra Drugs 0.000 description 1
230000009919 sequestration Effects 0.000 description 1
229940117012 serostim Drugs 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229960001294 spiramycin Drugs 0.000 description 1
235000019372 spiramycin Nutrition 0.000 description 1
229930191512 spiramycin Natural products 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229960005404 sulfamethoxazole Drugs 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000008685 targeting Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
JFVZFKDSXNQEJW-CQSZACIVSA-N tenofovir disoproxil Chemical compound N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N JFVZFKDSXNQEJW-CQSZACIVSA-N 0.000 description 1
229950002757 teoclate Drugs 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
229960004517 thymopentin Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
WARKYKQCOXTIAO-UHFFFAOYSA-N tributyl(2-ethoxyethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C/OCC WARKYKQCOXTIAO-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
229940093257 valacyclovir Drugs 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229940111505 videx ec Drugs 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
230000004393 visual impairment Effects 0.000 description 1
229920001221 xylan Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4

Definitions

a Category 1 HIV infection is characterized by the patient or subject being HIV positive, asymptomatic (no symptoms) and having never had fewer than 500 CD4 cells. If the patient has had any of the AIDS-defining diseases listed for categories 2 (ARC) or 3 (AIDS), then the patient is not in this category. If the patient's t-cell count has ever dropped below 500, that patient is considered either Category 2 (ARC) or Category 3 (AIDS).
a Category 2 (ARC) infection is characterized by the following criteria: The patient's T-cells have dropped below 500 but never below 200, and that patient has never had any Category 3 diseases (as set forth below) but have had at least one of the following defining illnesses—
R 1 and R 2 are independently benzyl groups or independently substituted benzyl groups with 1 to 3 substituents on the phenyl rings selected from fluorine, chlorine, C 1-4 alkyl, C 2-4 alkenyl, methoxy; wherein R 3 is H, C 1-3 alkyl, C 2-3 alkenyl, fluorine, chlorine, methoxy; wherein R 4 is H, F, Cl, OH wherein R 5 is CO 2 H or P(O)(OH) 2 or a pharmaceutically acceptable salt thereof.

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Virology (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

US12/309,017 2006-07-19 2007-07-13 Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy Abandoned US20100092427A1 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US12/309,017 US20100092427A1 (en)	2006-07-19	2007-07-13	Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US83199006P	2006-07-19	2006-07-19
US92019707P	2007-03-27	2007-03-27
US92019607P	2007-03-27	2007-03-27
US12/309,017 US20100092427A1 (en)	2006-07-19	2007-07-13	Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy
PCT/US2007/015981 WO2008010953A2 (en)	2006-07-19	2007-07-13	Pyridinone diketo acids: inhibitors of hiv replication in combination therapy

Publications (1)

Publication Number	Publication Date
US20100092427A1 true US20100092427A1 (en)	2010-04-15

Family

ID=38957288

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
US12/309,017 Abandoned US20100092427A1 (en)	2006-07-19	2007-07-13	Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy
US11/827,959 Expired - Fee Related US7888375B2 (en)	2006-07-19	2007-07-13	Pyridinone diketo acids: inhibitors of HIV replication

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
US11/827,959 Expired - Fee Related US7888375B2 (en)	2006-07-19	2007-07-13	Pyridinone diketo acids: inhibitors of HIV replication

Country Status (7)

Country	Link
US (2)	US20100092427A1 (es)
EP (1)	EP2046328A4 (es)
JP (1)	JP2009543865A (es)
AU (1)	AU2007275805A1 (es)
CA (1)	CA2657034A1 (es)
MX (1)	MX2009000661A (es)
WO (1)	WO2008010953A2 (es)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20100092427A1 (en) *	2006-07-19	2010-04-15	The University Of Georgia Research Foundation	Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy
CA3034994A1 (en)	2008-06-03	2009-12-10	Intermune, Inc.	Substituted aryl-2 pyridone compounds and use thereof for treating inflammatory and fibrotic disorders
JP2009295695A (ja) *	2008-06-03	2009-12-17	Sumco Corp	半導体薄膜付基板およびその製造方法
MX2012006485A (es) *	2009-12-07	2012-08-23	Univ Georgia	Piridinon hidroxiclicopentil carboxamidas: inhibidores de la integrasa del vih con aplicaciones terapeuticas.
US9085605B2 (en) *	2010-05-27	2015-07-21	Shenzhen Salubris Pharmaceuticals Co., Ltd.	Chemical synthesis and anti-tumor and anti-metastatic effects of dual functional conjugate
JO2998B1 (ar)	2010-06-04	2016-09-05	Amgen Inc	مشتقات بيبيريدينون كمثبطات mdm2 لعلاج السرطان
JP6093770B2 (ja)	2011-09-27	2017-03-08	アムジエン・インコーポレーテツド	癌の治療のためのｍｄｍ２阻害剤としての複素環化合物
ES3018133T3 (en)	2011-11-30	2025-05-14	Univ Emory	Jak inhibitors for use in the prevention or treatment of a viral disease caused by a coronaviridae
WO2013148174A1 (en) *	2012-03-31	2013-10-03	University Of Georgia Research Foundation, Inc.	New anti-mycobacterial drugs against tuberculosis
AR092742A1 (es)	2012-10-02	2015-04-29	Intermune Inc	Piridinonas antifibroticas
AP2015008510A0 (en)	2012-12-21	2015-06-30	Gilead Sciences Inc	Polycyclic-carbamoylpyridone compounds and their pharmaceutical use
US11407721B2 (en)	2013-02-19	2022-08-09	Amgen Inc.	CIS-morpholinone and other compounds as MDM2 inhibitors for the treatment of cancer
WO2014134201A1 (en)	2013-02-28	2014-09-04	Amgen Inc.	A benzoic acid derivative mdm2 inhibitor for the treatment of cancer
MX374513B (es)	2013-03-14	2025-03-06	Amgen Inc	Compuestos de morfolinona de ácido heteroarilo como inhibidores mdm2 para el tratamiento de cáncer.
JOP20200296A1 (ar)	2013-06-10	2017-06-16	Amgen Inc	عمليات صنع وأشكال بلورية من mdm2 مثبط
PL3252058T3 (pl)	2013-07-12	2021-07-19	Gilead Sciences, Inc.	Policykliczne związki karbamoilopirydonowe i ich zastosowanie do leczenia infekcji hiv
NO2865735T3 (es)	2013-07-12	2018-07-21
CA2943363A1 (en)	2014-04-02	2015-10-08	Intermune, Inc.	Anti-fibrotic pyridinones
TWI677489B (zh)	2014-06-20	2019-11-21	美商基利科學股份有限公司	多環型胺甲醯基吡啶酮化合物之合成
TW201613936A (en)	2014-06-20	2016-04-16	Gilead Sciences Inc	Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
NO2717902T3 (es)	2014-06-20	2018-06-23
CA2960436C (en)	2014-09-16	2021-01-05	Gilead Sciences, Inc.	Solid forms of a toll-like receptor modulator
CN104387376B (zh) *	2014-10-30	2017-01-18	广东东阳光药业有限公司	吡啶酮类化合物及其组合物和用途
TWI738321B (zh)	2014-12-23	2021-09-01	美商基利科學股份有限公司	多環胺甲醯基吡啶酮化合物及其醫藥用途
ES2718410T3 (es)	2015-04-02	2019-07-01	Gilead Sciences Inc	Compuestos de carbamoilpiridonas policíclicos y su utilización farmacéutica
JP6767011B2 (ja) *	2015-09-18	2020-10-14	ヤマサ醤油株式会社	抗ｄｎａウィルス活性などの生理活性を有するヌクレオシド誘導体
CN114685491B (zh) *	2020-12-31	2024-01-12	清华大学	吡啶-2-胺衍生物及其药物组合物和用途

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6492423B1 (en) *	1998-07-27	2002-12-10	Istituto Di Ricerche Di Biologia Molecolare Pangeletti Spa	Diketoacid-derivatives as inhibitors of polymerases
US20080020010A1 (en) *	2006-07-19	2008-01-24	The University Of Georgia Research Foundation, Inc.	Pyridinone diketo acids: inhibitors of HIV replication

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1291571A (en)	1969-03-29	1972-10-04	Fisons Pharmaceuticals Ltd	Aza chromone-2-carboxylic acids
AU757409B2 (en)	1998-06-03	2003-02-20	Merck & Co., Inc.	Hiv integrase inhibitors
EP1082121A4 (en)	1998-06-03	2003-02-05	Merck & Co Inc	HIV integrase
JP2002516858A (ja)	1998-06-03	2002-06-11	メルクエンドカムパニーインコーポレーテッド	Ｈｉｖインテグラーゼ阻害薬
CA2353961A1 (en)	1998-12-25	2000-07-06	Shionogi & Co., Ltd.	Heteroaromatic derivatives having an inhibitory activity against hiv integrase
EP1196384A4 (en)	1999-06-25	2002-10-23	Merck & Co Inc	1- (AROMATIC OR HETEROAROMATICALLY SUBSTITUTED) -3- (HETEROAROMATICALLY SUBSTITUTED) -1,3-PROPANDIONS AND THEIR APPLICATIONS
US20030171406A1 (en)	2000-06-13	2003-09-11	Akihiko Sato	Medicinal compositions containing propenone derivatives
WO2002030426A1 (en)	2000-10-12	2002-04-18	Merck & Co., Inc.	Aza- and polyaza-naphthalenyl-carboxamides useful as hiv integrase inhibitors
HRP20040373B1 (en)	2001-10-26	2012-09-30	Instituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A.	N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase
EP3406596A1 (en)	2002-11-20	2018-11-28	Japan Tobacco Inc.	4-oxoquinoline compound and use thereof as hiv integrase inhibitor
US7776883B2 (en)	2004-03-10	2010-08-17	The United States Of America As Represented By The Department Of Health And Human Services	Quinolin-4-ones as inhibitors of retroviral integrase for the treatment of HIV, AIDS and AIDS related complex (ARC)
US7459562B2 (en)	2004-04-23	2008-12-02	Bristol-Myers Squibb Company	Monocyclic heterocycles as kinase inhibitors
US7115601B2 (en)	2004-05-18	2006-10-03	Bristol-Myers Squibb Company	HIV integrase inhibitors
WO2005113509A1 (en)	2004-05-20	2005-12-01	Japan Tobacco Inc.	Novel 4-oxoquinoline compound and use thereof as hiv integrase inhibitor
US7157447B2 (en)	2004-05-28	2007-01-02	Bristol-Myers Squibb Company	Bicyclic heterocycles as HIV integrase inhibitors
US7176196B2 (en)	2004-05-28	2007-02-13	Bristol-Myers Squibb Company	Bicyclic heterocycles as HIV integrase inhibitors
US20070232644A1 (en)	2004-09-07	2007-10-04	Pfizer Inc.	Inhibitors of the Hiv Integrase Enzyme
CN101014572B (zh)	2004-09-15	2011-07-06	盐野义制药株式会社	具有hiv整合酶抑制活性的氨基甲酰基吡啶酮衍生物
US7745459B2 (en)	2004-09-21	2010-06-29	Japan Tobacco Inc.	Quinolizinone compound and use thereof as HIV integrase inhibitor
WO2006033422A1 (ja)	2004-09-21	2006-03-30	Japan Tobacco Inc.	キノリジノン化合物、およびそのｈｉｖインテグラーゼ阻害剤としての利用
UA87884C2 (uk)	2004-12-03	2009-08-25	Мерк Энд Ко., Инк.	Безводна кристалічна калієва сіль інгібітора віл-інтегрази
US7250421B2 (en)	2005-01-31	2007-07-31	University Of Georgia Research Foundation, Inc.	Diketo acids with nucleobase scaffolds: anti-HIV replication inhibitors targeted at HIV integrase

2007
- 2007-07-13 US US12/309,017 patent/US20100092427A1/en not_active Abandoned
- 2007-07-13 US US11/827,959 patent/US7888375B2/en not_active Expired - Fee Related
- 2007-07-13 JP JP2009520774A patent/JP2009543865A/ja not_active Withdrawn
- 2007-07-13 CA CA002657034A patent/CA2657034A1/en not_active Abandoned
- 2007-07-13 WO PCT/US2007/015981 patent/WO2008010953A2/en not_active Ceased
- 2007-07-13 MX MX2009000661A patent/MX2009000661A/es not_active Application Discontinuation
- 2007-07-13 AU AU2007275805A patent/AU2007275805A1/en not_active Abandoned
- 2007-07-13 EP EP07810432A patent/EP2046328A4/en not_active Withdrawn

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6492423B1 (en) *	1998-07-27	2002-12-10	Istituto Di Ricerche Di Biologia Molecolare Pangeletti Spa	Diketoacid-derivatives as inhibitors of polymerases
US20080020010A1 (en) *	2006-07-19	2008-01-24	The University Of Georgia Research Foundation, Inc.	Pyridinone diketo acids: inhibitors of HIV replication
US7888375B2 (en) *	2006-07-19	2011-02-15	The University Of Georgia Research Foundation, Inc	Pyridinone diketo acids: inhibitors of HIV replication

Also Published As

Publication number	Publication date
MX2009000661A (es)	2009-03-27
WO2008010953A3 (en)	2008-05-08
JP2009543865A (ja)	2009-12-10
WO2008010953A2 (en)	2008-01-24
EP2046328A2 (en)	2009-04-15
AU2007275805A1 (en)	2008-01-24
CA2657034A1 (en)	2008-01-24
US7888375B2 (en)	2011-02-15
EP2046328A4 (en)	2009-10-28
US20080020010A1 (en)	2008-01-24

Publication	Publication Date	Title
US20100092427A1 (en)	2010-04-15	Pyridinone Diketo Acids: Inhibitors of HIV Replication in Combination Therapy
US8703801B2 (en)	2014-04-22	Pyridinone hydroxycyclopentyl carboxamides: HIV integrase inhibitors with therapeutic applications
US8742123B2 (en)	2014-06-03	HIV integrase inhibitors from pyridoxine
US7569573B2 (en)	2009-08-04	Diketo acids with nucleobase scaffolds: anti-HIV replication inhibitors targeted at HIV integrase
WO2007106450A2 (en)	2007-09-20	Diketo acids with nucleobase scaffolds: anti-hiv replication inhibitors targeted at hiv integrase in combination therapy
CA2397665A1 (en)	2001-07-26	Alpha v integrin receptor antagonists
US20170304239A1 (en)	2017-10-26	Inhibitors of human immunodeficiency virus replication
JP2013512957A5 (es)	2014-01-16
CN101516369A (zh)	2009-08-26	吡啶酮二酮酸：用于组合治疗的hiv复制抑制剂
US9650360B2 (en)	2017-05-16	Anti-mycobacterial drugs against tuberculosis
US8664248B2 (en)	2014-03-04	Derivatives of pyridoxine for inhibiting HIV integrase
HK1130201A (en)	2009-12-24	Pyridinone diketo acids: inhibitors of hiv replication in combination therapy
US10221208B2 (en)	2019-03-05	Methods of producing an HIV maturation inhibitor
HK1174331A (en)	2013-06-07	Pyridinone hydroxycyclopentyl carboxamides: hiv integrase inhibitors with therapeutic applications

Legal Events

Date	Code	Title	Description
2012-07-31	STCB	Information on status: application discontinuation	Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION