HRP960070A2 - Use of quinoxaline and protease inhibitors in a composition for the treatment of aids and/or hiv infections - Google Patents
Use of quinoxaline and protease inhibitors in a composition for the treatment of aids and/or hiv infections Download PDFInfo
- Publication number
- HRP960070A2 HRP960070A2 HR19506742.8A HRP960070A HRP960070A2 HR P960070 A2 HRP960070 A2 HR P960070A2 HR P960070 A HRP960070 A HR P960070A HR P960070 A2 HRP960070 A2 HR P960070A2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- alkyl
- hydroxy
- alkoxy
- chlorine
- Prior art date
Links
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title claims description 15
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title claims description 13
- 238000011282 treatment Methods 0.000 title description 16
- 208000031886 HIV Infections Diseases 0.000 title description 10
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title description 6
- 239000000203 mixture Substances 0.000 title description 3
- -1 trifluoromethoxy, hydroxy Chemical group 0.000 claims description 352
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 126
- 239000000460 chlorine Substances 0.000 claims description 126
- 229910052801 chlorine Inorganic materials 0.000 claims description 126
- 229910052731 fluorine Inorganic materials 0.000 claims description 126
- 239000011737 fluorine Substances 0.000 claims description 126
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 101
- 125000001153 fluoro group Chemical group F* 0.000 claims description 100
- 125000004043 oxo group Chemical group O=* 0.000 claims description 96
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 50
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 50
- 229910052794 bromium Inorganic materials 0.000 claims description 50
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 39
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 24
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 24
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 16
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 150000003252 quinoxalines Chemical class 0.000 claims description 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- WTDPAKYOVVTLLX-XGKFQTDJSA-N 1,3-thiazol-5-ylmethyl n-[(2s,3s,5s)-3-hydroxy-5-[[(2s)-3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-oxazol-4-yl)methyl]carbamoyl]amino]butanoyl]amino]-1,6-diphenylhexan-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)N(C)CC1=COC(C(C)C)=N1 WTDPAKYOVVTLLX-XGKFQTDJSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- QAGMBTAACMQRSS-MTULOOOASA-N [(2r,3s)-3,5-diacetyloxyoxolan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1OC(OC(C)=O)C[C@@H]1OC(C)=O QAGMBTAACMQRSS-MTULOOOASA-N 0.000 claims description 4
- AHDUVPQPGGNRDS-UHFFFAOYSA-N [4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamic acid Chemical compound C=1C=C(N)C=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(O)=O)CC1=CC=CC=C1 AHDUVPQPGGNRDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 229960000310 isoleucine Drugs 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
- 229960001852 saquinavir Drugs 0.000 claims description 4
- 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 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 239000011669 selenium Chemical group 0.000 claims description 4
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 3
- AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 3
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 2
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002829 nitrogen Chemical class 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 3
- AEABQBMUYZBBCW-UHFFFAOYSA-N pentanamide Chemical compound CC[CH]CC(N)=O AEABQBMUYZBBCW-UHFFFAOYSA-N 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 15
- 208000030507 AIDS Diseases 0.000 description 14
- 239000000126 substance Substances 0.000 description 10
- 241000700605 Viruses Species 0.000 description 9
- 230000002195 synergetic effect Effects 0.000 description 9
- 206010001513 AIDS related complex Diseases 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000011321 prophylaxis Methods 0.000 description 5
- 230000001629 suppression Effects 0.000 description 5
- 230000003612 virological effect Effects 0.000 description 5
- 241001494479 Pecora Species 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 241001430294 unidentified retrovirus Species 0.000 description 4
- 241000283707 Capra Species 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 125000001942 asparaginyl group Chemical group 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
- 241000701022 Cytomegalovirus Species 0.000 description 2
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 2
- 241000713800 Feline immunodeficiency virus Species 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 2
- 241000713311 Simian immunodeficiency virus Species 0.000 description 2
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 2
- 125000002252 acyl group Chemical class 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 229960002555 zidovudine Drugs 0.000 description 2
- NJBBLOIWMSYVCQ-OKHMJZBSSA-N (4r)-n-tert-butyl-3-[2-hydroxy-3-[[(2r)-2-[(2-isoquinolin-5-yloxyacetyl)amino]-3-methylsulfanylpropanoyl]amino]-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide Chemical compound O=C([C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)NC(C(O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)CC1=CC=CC=C1 NJBBLOIWMSYVCQ-OKHMJZBSSA-N 0.000 description 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- 125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 150000008078 2H-1,4-diazepin-2-ones Chemical class 0.000 description 1
- HWNXBSPMIWHNTD-XVFCMESISA-N 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-imino-1,3-thiazin-2-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)SC(=N)C=C1 HWNXBSPMIWHNTD-XVFCMESISA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 241000713756 Caprine arthritis encephalitis virus Species 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 241000353621 Eilat virus Species 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 241000714165 Feline leukemia virus Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010369 HIV Protease Proteins 0.000 description 1
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 208000005599 HTLV-I Infections Diseases 0.000 description 1
- 208000007687 HTLV-II Infections Diseases 0.000 description 1
- 241000598436 Human T-cell lymphotropic virus Species 0.000 description 1
- 206010020460 Human T-cell lymphotropic virus type I infection Diseases 0.000 description 1
- 241000714260 Human T-lymphotropic virus 1 Species 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 102000000588 Interleukin-2 Human genes 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 241000711902 Pneumovirus Species 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010038997 Retroviral infections Diseases 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229960002656 didanosine Drugs 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
- 229960002963 ganciclovir Drugs 0.000 description 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 108010075606 kynostatin 272 Proteins 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000380 osteotoxicity Toxicity 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 230000033041 viral attachment to host cell Effects 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
-
- 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
-
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19506742A DE19506742A1 (de) | 1995-02-27 | 1995-02-27 | Verwendung von Chinoxalinen in Kombination mit Protease-Inhibitoren als Arzneimittel zur Behandlung von AIDS und/oder HIV-Infektionen |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP960070A2 true HRP960070A2 (en) | 1997-10-31 |
Family
ID=7755115
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR19506742.8A HRP960070A2 (en) | 1995-02-27 | 1996-02-13 | Use of quinoxaline and protease inhibitors in a composition for the treatment of aids and/or hiv infections |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP0728481A3 (fi) |
JP (1) | JPH08245392A (fi) |
KR (1) | KR960030951A (fi) |
CN (1) | CN1141196A (fi) |
AR (1) | AR003923A1 (fi) |
AU (1) | AU710158B2 (fi) |
BR (1) | BR9600809A (fi) |
CA (1) | CA2170222A1 (fi) |
CZ (1) | CZ57896A3 (fi) |
DE (1) | DE19506742A1 (fi) |
FI (1) | FI960850A (fi) |
HR (1) | HRP960070A2 (fi) |
HU (1) | HUP9600455A3 (fi) |
IL (1) | IL117247A (fi) |
NO (1) | NO960775L (fi) |
NZ (1) | NZ286058A (fi) |
PL (1) | PL312908A1 (fi) |
SK (1) | SK25196A3 (fi) |
ZA (1) | ZA961516B (fi) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2270546A1 (en) * | 1996-11-08 | 1998-05-22 | Japan Energy Corporation | Aids remedy |
DE19703131A1 (de) * | 1997-01-29 | 1998-07-30 | Bayer Ag | Verwendung von Chinoxalin in Dreier-Kombination mit Protease-Inhibitoren und Reverse Transkriptaseinhibitoren als Arzneimittel zur Behandlung von AIDS und/oder HIV-Infektionen |
US6635626B1 (en) | 1997-08-25 | 2003-10-21 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
US6235740B1 (en) | 1997-08-25 | 2001-05-22 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
US6436989B1 (en) | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
WO1999045009A1 (en) * | 1998-03-04 | 1999-09-10 | Bristol-Myers Squibb Company | Heterocyclo-substituted imidazopyrazine protein tyrosine kinase inhibitors |
AU6329599A (en) * | 1998-09-28 | 2000-04-17 | Glaxo Group Limited | Antiviral combinations comprising (s)-2-ethyl -7-fluoro -3-oxo-3, 4-dihydro -2h-quinoxaline -1-carboxylic acid isopropyl ester |
GB9911887D0 (en) * | 1999-05-21 | 1999-07-21 | Glaxo Group Ltd | Methods and medicaments for post exposure prophylaxis of an hiv infection |
DE10013318A1 (de) * | 2000-03-17 | 2001-09-20 | Merck Patent Gmbh | Formulierung enthaltend Chinoxalinderivate |
CA2506415A1 (en) | 2002-11-19 | 2004-06-03 | Achillion Pharmaceuticals, Inc. | Substituted aryl thioureas and releated compounds; inhibitors of viral replication |
TW200600492A (en) | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
US7351709B2 (en) | 2004-06-09 | 2008-04-01 | Wyeth | Estrogen receptor ligands |
JP2016504990A (ja) * | 2012-12-20 | 2016-02-18 | バイエル ファーマ アクチエンゲゼルシャフト | Betタンパク質抑制性ジヒドロピリドピラジノン |
DE102017005089A1 (de) | 2016-05-30 | 2017-11-30 | Bayer Pharma Aktiengesellschaft | Substitulerte 3,4-Dihydrochinoxalin-2(1H)-one |
DE102017005091A1 (de) | 2016-05-30 | 2017-11-30 | Bayer Pharma Aktiengesellschaft | Substituierte 3,4-Dihydropyrido[2,3-b]pyrazin-2(1H)-one |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2164639T3 (es) * | 1991-04-15 | 2002-03-01 | Aventis Pharma Gmbh | Quinoxalinas, procedimiento para su preparacion y su empleo. |
-
1995
- 1995-02-27 DE DE19506742A patent/DE19506742A1/de not_active Withdrawn
-
1996
- 1996-02-13 HR HR19506742.8A patent/HRP960070A2/hr not_active Application Discontinuation
- 1996-02-14 AR ARP960101379A patent/AR003923A1/es unknown
- 1996-02-14 EP EP96102129A patent/EP0728481A3/de not_active Withdrawn
- 1996-02-20 AU AU45615/96A patent/AU710158B2/en not_active Ceased
- 1996-02-23 NZ NZ286058A patent/NZ286058A/en unknown
- 1996-02-23 PL PL96312908A patent/PL312908A1/xx unknown
- 1996-02-23 IL IL11724796A patent/IL117247A/xx active IP Right Grant
- 1996-02-23 CA CA002170222A patent/CA2170222A1/en not_active Abandoned
- 1996-02-23 FI FI960850A patent/FI960850A/fi unknown
- 1996-02-23 JP JP8060286A patent/JPH08245392A/ja active Pending
- 1996-02-26 HU HU9600455A patent/HUP9600455A3/hu unknown
- 1996-02-26 ZA ZA961516A patent/ZA961516B/xx unknown
- 1996-02-26 SK SK251-96A patent/SK25196A3/sk unknown
- 1996-02-26 KR KR1019960004623A patent/KR960030951A/ko not_active Application Discontinuation
- 1996-02-26 BR BR9600809A patent/BR9600809A/pt active Search and Examination
- 1996-02-26 NO NO960775A patent/NO960775L/no not_active Application Discontinuation
- 1996-02-26 CZ CZ96578A patent/CZ57896A3/cs unknown
- 1996-02-27 CN CN96102709A patent/CN1141196A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
AR003923A1 (es) | 1998-09-30 |
IL117247A0 (en) | 1996-06-18 |
NO960775L (no) | 1996-08-28 |
IL117247A (en) | 2000-10-31 |
CZ57896A3 (en) | 1996-09-11 |
HUP9600455A2 (en) | 1996-12-30 |
AU710158B2 (en) | 1999-09-16 |
CA2170222A1 (en) | 1996-08-28 |
AU4561596A (en) | 1996-09-05 |
HUP9600455A3 (en) | 1998-04-28 |
CN1141196A (zh) | 1997-01-29 |
KR960030951A (ko) | 1996-09-17 |
FI960850A0 (fi) | 1996-02-23 |
FI960850A (fi) | 1996-08-28 |
DE19506742A1 (de) | 1996-08-29 |
SK25196A3 (en) | 1997-05-07 |
ZA961516B (en) | 1996-09-03 |
PL312908A1 (en) | 1996-09-02 |
BR9600809A (pt) | 1997-12-23 |
EP0728481A2 (de) | 1996-08-28 |
HU9600455D0 (en) | 1996-04-29 |
EP0728481A3 (de) | 1998-07-08 |
JPH08245392A (ja) | 1996-09-24 |
NO960775D0 (no) | 1996-02-26 |
NZ286058A (en) | 1998-09-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Liu et al. | Cathepsin L-selective inhibitors: A potentially promising treatment for COVID-19 patients | |
US11065227B2 (en) | Use of cannabinoids in the treatment of multiple myeloma | |
HRP960070A2 (en) | Use of quinoxaline and protease inhibitors in a composition for the treatment of aids and/or hiv infections | |
US20180104270A1 (en) | Compositions and methods for treating disease states associated with activated t cells and/or b cells | |
EP3062809B1 (en) | A cxcr4 peptide inhibitor for use in treating acute myeloid leukemia with a flt3 mutation | |
US20100324034A1 (en) | Methods of Using SAHA for Treating HIV Infection | |
CA2278773A1 (en) | Quinoxaline in triple combination with protease inhibitors and reverse transcriptase inhibitors as medicines for treating aids | |
WO2016069854A1 (en) | Enhancing the anti-tumor, anti-viral, and anti-protozoan effects of 2-amino-n-[4-[5-phenanthren-2-yl-3-(trifluoromethyl)pyrazol-1-yl] phenyl]acetamide (osu-03012) and other pharmaceutical drugs | |
US20160082071A1 (en) | Methods of treating myeloid leukemia | |
Schneider et al. | A new model for post-integration latency in macroglial cells to study HIV-1 reservoirs of the brain | |
Fraternale et al. | Macrophage protection by addition of glutathione (GSH)-loaded erythrocytes to AZT and DDI in a murine AIDS model | |
Lim et al. | Synergistic reactivation of latent HIV-1 provirus by PKA activator dibutyryl-cAMP in combination with an HDAC inhibitor | |
US20150031739A1 (en) | Panobinostat for use in the treatment of hiv-1 | |
WO2022053993A2 (en) | Treatments for sars-cov-2 infection (covid-19) | |
US6649644B1 (en) | Method of treating HIV infection by combined use of a cytotoxic agent and a non-nucleoside reverse transcriptase inhibitor | |
US10688152B2 (en) | Compositions and methods for treating a viral infection | |
EP1257261B1 (en) | Antiviral pharmaceutical compositions containing iron chelators | |
WO2021209740A1 (en) | Methods involving neutrophil elastase inhibitor alvelestat for treating coronavirus infection | |
JP2023540466A (ja) | 抗ウイルス組成物及びその使用法 | |
CZ269699A3 (cs) | Chinoxaliny v trojité kombinaci s inhibitory proteas a inhibitory reversní transkriptasy jako léčiva pro ošetření AIDS | |
CN116600797A (zh) | 用于治疗急性呼吸衰竭和/或急性呼吸窘迫综合征的包含四氢大麻酚的组合物 | |
MXPA99007077A (en) | Quinoxaline in triple combination with protease inhibitors and reverse transcriptase inhibitors as medicines for treating aids | |
EA030197B1 (ru) | Таблетированная форма противовирусного лекарственного средства | |
KR20180081598A (ko) | Hiv 성숙 억제제 제형 | |
Davids et al. | Integrated safety analysis of umbralisib, a dual PI3Kd/CK1 «inhibitor, in relapsed/refractory lymphoid malignancies |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
OBST | Application withdrawn |