PT1560827E

PT1560827E - Agentes anti-infecciosos

Agentes anti-infecciosos Download PDF

Info

Publication number: PT1560827E
Authority: PT; Portugal
Prior art keywords: alkyl; group; heteroaryl; heterocycle; alkenyl
Prior art date: 2002-11-01

Application number

PT03768559T

Other languages

English (en)

Portuguese (pt)

Inventor

Dale J Kempf

John K Pratt

David A Betebenner

Pamela L Donner

Brian E Green

Keith F Mcdaniel

Clarence J Maring

Vincent S Stoll

Rong Zhang

Original Assignee

Abbott Lab

Priority date

2002-11-01

Filing date

2003-10-31

Publication date

2011-03-17

2002-11-01 Priority claimed from US10/285,714 external-priority patent/US20040097492A1/en

2003-07-23 Priority claimed from US10/625,121 external-priority patent/US20040162285A1/en

2003-10-06 Priority claimed from US10/679,881 external-priority patent/US20050075331A1/en

2003-10-31 Application filed by Abbott Lab filed Critical Abbott Lab

2011-03-17 Publication of PT1560827E publication Critical patent/PT1560827E/pt

Links

229960005475 antiinfective agent Drugs 0.000 title description 4
239000004599 antimicrobial Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 524
241000711549 Hepacivirus C Species 0.000 claims abstract description 96
208000015181 infectious disease Diseases 0.000 claims abstract description 84
239000000203 mixture Substances 0.000 claims abstract description 83
230000002401 inhibitory effect Effects 0.000 claims abstract description 26
230000029812 viral genome replication Effects 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims description 560
125000001072 heteroaryl group Chemical group 0.000 claims description 175
125000000623 heterocyclic group Chemical group 0.000 claims description 174
125000003342 alkenyl group Chemical group 0.000 claims description 170
-1 cycloalkenylalkyl Chemical group 0.000 claims description 149
125000003118 aryl group Chemical group 0.000 claims description 147
125000000304 alkynyl group Chemical group 0.000 claims description 128
125000003710 aryl alkyl group Chemical group 0.000 claims description 119
125000001188 haloalkyl group Chemical group 0.000 claims description 111
239000003795 chemical substances by application Substances 0.000 claims description 109
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 108
125000000753 cycloalkyl group Chemical group 0.000 claims description 107
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 103
125000001424 substituent group Chemical group 0.000 claims description 98
125000000392 cycloalkenyl group Chemical group 0.000 claims description 95
125000004093 cyano group Chemical group *C#N 0.000 claims description 93
125000004043 oxo group Chemical group O=* 0.000 claims description 86
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 71
125000004438 haloalkoxy group Chemical group 0.000 claims description 65
239000003443 antiviral agent Substances 0.000 claims description 63
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
239000001257 hydrogen Substances 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 59
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 58
201000010099 disease Diseases 0.000 claims description 57
230000007236 host immunity Effects 0.000 claims description 52
241000725303 Human immunodeficiency virus Species 0.000 claims description 50
150000002431 hydrogen Chemical group 0.000 claims description 48
230000010076 replication Effects 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 41
239000002671 adjuvant Substances 0.000 claims description 38
239000000427 antigen Substances 0.000 claims description 36
108091007433 antigens Proteins 0.000 claims description 36
102000036639 antigens Human genes 0.000 claims description 36
102000004127 Cytokines Human genes 0.000 claims description 35
108090000695 Cytokines Proteins 0.000 claims description 35
108010047761 Interferon-alpha Proteins 0.000 claims description 35
102000006992 Interferon-alpha Human genes 0.000 claims description 35
125000004966 cyanoalkyl group Chemical group 0.000 claims description 35
229960005486 vaccine Drugs 0.000 claims description 35
125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 34
102000003996 Interferon-beta Human genes 0.000 claims description 33
108090000467 Interferon-beta Proteins 0.000 claims description 33
102000008070 Interferon-gamma Human genes 0.000 claims description 33
108010074328 Interferon-gamma Proteins 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
229960003130 interferon gamma Drugs 0.000 claims description 33
229960001388 interferon-beta Drugs 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 33
125000004967 formylalkyl group Chemical group 0.000 claims description 32
125000004971 nitroalkyl group Chemical group 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
208000002672 hepatitis B Diseases 0.000 claims description 27
125000005018 aryl alkenyl group Chemical group 0.000 claims description 26
125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 24
208000024891 symptom Diseases 0.000 claims description 24
241000700605 Viruses Species 0.000 claims description 23
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 23
229910052703 rhodium Inorganic materials 0.000 claims description 23
239000008194 pharmaceutical composition Substances 0.000 claims description 21
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 20
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 19
125000004181 carboxyalkyl group Chemical group 0.000 claims description 19
230000003915 cell function Effects 0.000 claims description 19
125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 19
102000004169 proteins and genes Human genes 0.000 claims description 19
108090000623 proteins and genes Proteins 0.000 claims description 19
229910052701 rubidium Inorganic materials 0.000 claims description 19
230000008685 targeting Effects 0.000 claims description 19
230000003612 virological effect Effects 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 17
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 16
125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
229910003827 NRaRb Inorganic materials 0.000 claims description 14
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 12
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 12
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000004104 aryloxy group Chemical group 0.000 claims description 10
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 10
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 10
229960001627 lamivudine Drugs 0.000 claims description 10
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 10
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 10
229960004556 tenofovir Drugs 0.000 claims description 10
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 10
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
229960005107 darunavir Drugs 0.000 claims description 6
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 6
125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims description 6
IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims description 6
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 5
108010019625 Atazanavir Sulfate Proteins 0.000 claims description 5
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 5
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 5
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 5
108010032976 Enfuvirtide Proteins 0.000 claims description 5
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 5
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 5
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 5
229960004748 abacavir Drugs 0.000 claims description 5
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 5
229960001997 adefovir Drugs 0.000 claims description 5
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 5
229960001830 amprenavir Drugs 0.000 claims description 5
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 5
229960003277 atazanavir Drugs 0.000 claims description 5
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 5
229960005319 delavirdine Drugs 0.000 claims description 5
229960002656 didanosine Drugs 0.000 claims description 5
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 5
229960003804 efavirenz Drugs 0.000 claims description 5
229960002062 enfuvirtide Drugs 0.000 claims description 5
229960002049 etravirine Drugs 0.000 claims description 5
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 5
229960003142 fosamprenavir Drugs 0.000 claims description 5
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 5
229960001936 indinavir Drugs 0.000 claims description 5
230000005764 inhibitory process Effects 0.000 claims description 5
229960004525 lopinavir Drugs 0.000 claims description 5
229960000884 nelfinavir Drugs 0.000 claims description 5
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 5
229960000689 nevirapine Drugs 0.000 claims description 5
229960001852 saquinavir Drugs 0.000 claims description 5
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 5
229960001203 stavudine Drugs 0.000 claims description 5
ZFEAMMNVDPDEGE-LGRGJMMZSA-N tifuvirtide Chemical compound C([C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)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](CCC(O)=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)C1=CC=C(O)C=C1 ZFEAMMNVDPDEGE-LGRGJMMZSA-N 0.000 claims description 5
229960000523 zalcitabine Drugs 0.000 claims description 5
229960002555 zidovudine Drugs 0.000 claims description 5
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 5
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 4
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 4
230000002265 prevention Effects 0.000 claims description 4
229960000311 ritonavir Drugs 0.000 claims description 4
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 4
229960000838 tipranavir Drugs 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
XTZSQOCPDRDISN-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(1,3-dioxoisoindol-2-yl)quinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(=C(SC)SC)C(=O)N1N1C(=O)C2=CC=CC=C2C1=O XTZSQOCPDRDISN-UHFFFAOYSA-N 0.000 claims description 2
RVSMFGSNSHGPSI-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(cyclobutylamino)quinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(=C(SC)SC)C(=O)N1NC1CCC1 RVSMFGSNSHGPSI-UHFFFAOYSA-N 0.000 claims description 2
JFGJNOCVZLBOHU-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-(cyclopropylmethylamino)quinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(=C(SC)SC)C(=O)N1NCC1CC1 JFGJNOCVZLBOHU-UHFFFAOYSA-N 0.000 claims description 2
SALDWSVHHAJNFX-UHFFFAOYSA-N 3-[bis(methylsulfanyl)methylidene]-1-butyl-1,8-naphthyridine-2,4-dione Chemical compound C1=CN=C2N(CCCC)C(=O)C(=C(SC)SC)C(=O)C2=C1 SALDWSVHHAJNFX-UHFFFAOYSA-N 0.000 claims description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
QBUWSFJEFZOJSZ-UHFFFAOYSA-N N-[[3-(1-benzyl-4-hydroxy-2-oxoquinolin-3-yl)-1,1-dioxo-4H-thieno[2,3-e][1,2,4]thiadiazin-7-yl]methyl]methanesulfonamide Chemical compound N=1S(=O)(=O)C=2C(CNS(=O)(=O)C)=CSC=2NC=1C(C1=O)=C(O)C2=CC=CC=C2N1CC1=CC=CC=C1 QBUWSFJEFZOJSZ-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims description 2
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims description 2
SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 45
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 2
208000031886 HIV Infections Diseases 0.000 claims 1
208000037357 HIV infectious disease Diseases 0.000 claims 1
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