NO323156B1 - Benzofenoner og relaterte forbindelser, anvendelse av disse forbindelser for fremstilling av medikamenter for behandling av HIV-infeksjoner, farmasoytisk preparat inneholdende slike samt disse forbindelser for anvendelse som medikament - Google Patents
Benzofenoner og relaterte forbindelser, anvendelse av disse forbindelser for fremstilling av medikamenter for behandling av HIV-infeksjoner, farmasoytisk preparat inneholdende slike samt disse forbindelser for anvendelse som medikament Download PDFInfo
- Publication number
- NO323156B1 NO323156B1 NO20021042A NO20021042A NO323156B1 NO 323156 B1 NO323156 B1 NO 323156B1 NO 20021042 A NO20021042 A NO 20021042A NO 20021042 A NO20021042 A NO 20021042A NO 323156 B1 NO323156 B1 NO 323156B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- heterocycle
- alkyl
- halogen
- acetamide
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 288
- 238000002360 preparation method Methods 0.000 title claims description 27
- 239000003814 drug Substances 0.000 title claims description 12
- 208000031886 HIV Infections Diseases 0.000 title claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 150000008366 benzophenones Chemical class 0.000 title description 4
- 229940079593 drug Drugs 0.000 title description 3
- 239000012965 benzophenone Substances 0.000 title description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 254
- 229910052736 halogen Inorganic materials 0.000 claims description 211
- 150000002367 halogens Chemical class 0.000 claims description 211
- 125000001424 substituent group Chemical group 0.000 claims description 197
- 239000001257 hydrogen Substances 0.000 claims description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 150000002148 esters Chemical class 0.000 claims description 105
- 150000003839 salts Chemical class 0.000 claims description 104
- 150000002431 hydrogen Chemical class 0.000 claims description 102
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 99
- -1 C1alkyl Chemical group 0.000 claims description 97
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 88
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 75
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 67
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 59
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 57
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 229920006395 saturated elastomer Polymers 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 125000002950 monocyclic group Chemical group 0.000 claims description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000004043 oxo group Chemical group O=* 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 19
- 125000002619 bicyclic group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 17
- 125000005605 benzo group Chemical group 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 208000037357 HIV infectious disease Diseases 0.000 claims description 5
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- LFMFIMQKPGUOAL-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-[4-(1-hydroxyethyl)phenyl]acetamide Chemical compound C1=CC(C(O)C)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 LFMFIMQKPGUOAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- IQVFNCHDINMLAG-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-(1h-indazol-5-yl)acetamide Chemical compound C=1C(Cl)=CC=C(OCC(=O)NC=2C=C3C=NNC3=CC=2)C=1C(=O)C1=CC=CC=C1 IQVFNCHDINMLAG-UHFFFAOYSA-N 0.000 claims description 2
- KSVBEMHNPBHJOI-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-(1h-indazol-6-yl)acetamide Chemical compound C=1C(Cl)=CC=C(OCC(=O)NC=2C=C3NN=CC3=CC=2)C=1C(=O)C1=CC=CC=C1 KSVBEMHNPBHJOI-UHFFFAOYSA-N 0.000 claims description 2
- OFHSNOJWAIZPGT-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-(4-imidazol-1-ylphenyl)acetamide Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1OCC(=O)NC(C=C1)=CC=C1N1C=CN=C1 OFHSNOJWAIZPGT-UHFFFAOYSA-N 0.000 claims description 2
- RUOIEQYQWQVPHU-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-(4-morpholin-4-ylphenyl)acetamide Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1OCC(=O)NC(C=C1)=CC=C1N1CCOCC1 RUOIEQYQWQVPHU-UHFFFAOYSA-N 0.000 claims description 2
- GGPHXQUFZNHWMY-UHFFFAOYSA-N 2-[2-(1-benzothiophene-2-carbonyl)-4-chlorophenoxy]-n-phenylacetamide Chemical compound C=1C2=CC=CC=C2SC=1C(=O)C1=CC(Cl)=CC=C1OCC(=O)NC1=CC=CC=C1 GGPHXQUFZNHWMY-UHFFFAOYSA-N 0.000 claims description 2
- NJOGYRZKARSSNF-UHFFFAOYSA-N 2-[2-(5-bromopyridine-3-carbonyl)-4-chlorophenoxy]-n-(6-methyl-1h-benzimidazol-5-yl)acetamide Chemical compound CC1=CC=2N=CNC=2C=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CN=CC(Br)=C1 NJOGYRZKARSSNF-UHFFFAOYSA-N 0.000 claims description 2
- FBYTUIKBKOZCNL-UHFFFAOYSA-N 2-[4-chloro-2-(1-methylpyrrole-2-carbonyl)phenoxy]-n-phenylacetamide Chemical compound CN1C=CC=C1C(=O)C1=CC(Cl)=CC=C1OCC(=O)NC1=CC=CC=C1 FBYTUIKBKOZCNL-UHFFFAOYSA-N 0.000 claims description 2
- FQZKJONCWUXTQN-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-dichlorobenzoyl)phenoxy]-n-(5-methyl-1h-indazol-6-yl)acetamide Chemical compound CC1=CC=2C=NNC=2C=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(Cl)=CC(Cl)=C1 FQZKJONCWUXTQN-UHFFFAOYSA-N 0.000 claims description 2
- WBDKKXLJMKGHQW-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-1-(2,3-dihydroindol-1-yl)ethanone Chemical compound FC1=CC(F)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)N2C3=CC=CC=C3CC2)=C1 WBDKKXLJMKGHQW-UHFFFAOYSA-N 0.000 claims description 2
- XKCZZEUHPXCNSG-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-n-[2-methyl-4-(3-sulfamoylpropoxy)phenyl]acetamide Chemical compound CC1=CC(OCCCS(N)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(F)=CC(F)=C1 XKCZZEUHPXCNSG-UHFFFAOYSA-N 0.000 claims description 2
- BMOJLYKWVNBRLY-UHFFFAOYSA-N 2-[4-chloro-2-(3-chloro-5-methylbenzoyl)phenoxy]-n-(2-methyl-4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(Cl)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)NC=2C(=CC(=CC=2)S(N)(=O)=O)C)=C1 BMOJLYKWVNBRLY-UHFFFAOYSA-N 0.000 claims description 2
- OQOUVXPUPLDUGS-UHFFFAOYSA-N 2-[4-chloro-2-(3-cyanobenzoyl)phenoxy]-n-(5-methyl-1h-indazol-6-yl)acetamide Chemical compound CC1=CC=2C=NNC=2C=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC(C#N)=C1 OQOUVXPUPLDUGS-UHFFFAOYSA-N 0.000 claims description 2
- GBEDTCHZQUNMSD-UHFFFAOYSA-N 2-[4-chloro-2-(5-pyridin-2-ylthiophene-2-carbonyl)phenoxy]-n-phenylacetamide Chemical compound C=1C=C(C=2N=CC=CC=2)SC=1C(=O)C1=CC(Cl)=CC=C1OCC(=O)NC1=CC=CC=C1 GBEDTCHZQUNMSD-UHFFFAOYSA-N 0.000 claims description 2
- RAZYVIZUPSVJIE-UHFFFAOYSA-N 2-[4-chloro-2-(furan-2-carbonyl)phenoxy]-n-(1h-indazol-6-yl)acetamide Chemical compound C=1C(Cl)=CC=C(OCC(=O)NC=2C=C3NN=CC3=CC=2)C=1C(=O)C1=CC=CO1 RAZYVIZUPSVJIE-UHFFFAOYSA-N 0.000 claims description 2
- KVCHCVJLGDAHAJ-UHFFFAOYSA-N 2-[4-chloro-2-[3-(trifluoromethylsulfanyl)benzoyl]phenoxy]-n-(2-methyl-4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(S(N)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC(SC(F)(F)F)=C1 KVCHCVJLGDAHAJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical group FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
- OECHUGCITYQGCY-YUMQZZPRSA-N (2s)-5-amino-2-[[(2s)-2,5-diaminopentanoyl]amino]pentanoic acid Chemical compound NCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCN OECHUGCITYQGCY-YUMQZZPRSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- DSFAAAJCVJZOMX-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-n-[2-methyl-4-(3-pyrrolidin-1-ylpropoxy)phenyl]acetamide Chemical compound C=1C=C(NC(=O)COC=2C(=CC(Cl)=CC=2)C(=O)C=2C=C(F)C=C(F)C=2)C(C)=CC=1OCCCN1CCCC1 DSFAAAJCVJZOMX-UHFFFAOYSA-N 0.000 claims 1
- BTOMIMSUTLPSHA-UHFFFAOYSA-N 2-[4-chloro-2-(3-chloro-5-cyanobenzoyl)phenoxy]-n-(2-methyl-4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(S(N)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(Cl)=CC(C#N)=C1 BTOMIMSUTLPSHA-UHFFFAOYSA-N 0.000 claims 1
- JIXJHLWPWQFBOC-UHFFFAOYSA-N 2-[4-chloro-2-(3-cyanobenzoyl)phenoxy]-n-[2-methyl-4-(3-pyrrolidin-1-ylpropoxy)phenyl]acetamide Chemical compound C=1C=C(NC(=O)COC=2C(=CC(Cl)=CC=2)C(=O)C=2C=C(C=CC=2)C#N)C(C)=CC=1OCCCN1CCCC1 JIXJHLWPWQFBOC-UHFFFAOYSA-N 0.000 claims 1
- ARXFUJUBMBFEPP-UHFFFAOYSA-N 2-[4-chloro-2-(4-cyanothiophene-2-carbonyl)phenoxy]-n-(2-methyl-4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(S(N)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(C#N)=CS1 ARXFUJUBMBFEPP-UHFFFAOYSA-N 0.000 claims 1
- ADMRJVQZXOEDOB-UHFFFAOYSA-N 2-[4-chloro-2-(thiophene-2-carbonyl)phenoxy]-n-[2-methyl-4-(3-morpholin-4-ylpropoxy)phenyl]acetamide Chemical compound C=1C=C(NC(=O)COC=2C(=CC(Cl)=CC=2)C(=O)C=2SC=CC=2)C(C)=CC=1OCCCN1CCOCC1 ADMRJVQZXOEDOB-UHFFFAOYSA-N 0.000 claims 1
- WPFCQTYEMWCHTA-UHFFFAOYSA-N 2-[4-chloro-2-[3-(2-phenylethynyl)benzoyl]phenoxy]-n-(2-methyl-4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(S(N)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC(C#CC=2C=CC=CC=2)=C1 WPFCQTYEMWCHTA-UHFFFAOYSA-N 0.000 claims 1
- VMZCSGVUCCGELW-UHFFFAOYSA-N 2-[4-chloro-2-[3-fluoro-5-(trifluoromethyl)benzoyl]phenoxy]-n-[2-methyl-4-(3-sulfamoylpropoxy)phenyl]acetamide Chemical compound CC1=CC(OCCCS(N)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(F)=CC(C(F)(F)F)=C1 VMZCSGVUCCGELW-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims 1
- YIVXTPCRSIHQRZ-UHFFFAOYSA-N n-(1,3-benzothiazol-6-yl)-2-(2-benzoyl-4-chlorophenoxy)acetamide Chemical compound C=1C(Cl)=CC=C(OCC(=O)NC=2C=C3SC=NC3=CC=2)C=1C(=O)C1=CC=CC=C1 YIVXTPCRSIHQRZ-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000006000 trichloroethyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 219
- 238000000034 method Methods 0.000 description 178
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 163
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 142
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 141
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- 238000006243 chemical reaction Methods 0.000 description 132
- 239000000203 mixture Substances 0.000 description 128
- 238000005481 NMR spectroscopy Methods 0.000 description 112
- 239000007787 solid Substances 0.000 description 94
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
- 239000002904 solvent Substances 0.000 description 91
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 71
- 239000000047 product Substances 0.000 description 71
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 70
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 230000002829 reductive effect Effects 0.000 description 61
- 239000000460 chlorine Substances 0.000 description 58
- 238000003818 flash chromatography Methods 0.000 description 58
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 55
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 52
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 52
- 238000000746 purification Methods 0.000 description 50
- 235000019439 ethyl acetate Nutrition 0.000 description 47
- 239000003921 oil Substances 0.000 description 43
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 42
- 235000019198 oils Nutrition 0.000 description 42
- 239000012267 brine Substances 0.000 description 41
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 40
- 239000012044 organic layer Substances 0.000 description 40
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- 239000003153 chemical reaction reagent Substances 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
- 239000002253 acid Substances 0.000 description 34
- 150000001412 amines Chemical class 0.000 description 34
- 235000019441 ethanol Nutrition 0.000 description 33
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 29
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 27
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
- 235000019341 magnesium sulphate Nutrition 0.000 description 27
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 26
- 239000000010 aprotic solvent Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
- 229910052794 bromium Inorganic materials 0.000 description 23
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000003480 eluent Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
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- JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
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- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=O)N[C@H](CO)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](CO)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(O)=O)C(O)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 description 1
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- 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
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/44—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms at least one of the singly-bound nitrogen atoms being acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/40—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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- C07D307/80—Radicals substituted by oxygen atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/56—Radicals substituted by oxygen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Organic Chemistry (AREA)
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- Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB9920872.0A GB9920872D0 (en) | 1999-09-04 | 1999-09-04 | Benzophenones as inhibitors of reverse transcriptase |
PCT/EP2000/008487 WO2001017982A1 (fr) | 1999-09-04 | 2000-08-31 | Benzophenones agissant comme inhibiteurs de la transcriptase inverse |
Publications (3)
Publication Number | Publication Date |
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NO20021042D0 NO20021042D0 (no) | 2002-03-01 |
NO20021042L NO20021042L (no) | 2002-04-30 |
NO323156B1 true NO323156B1 (no) | 2007-01-08 |
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NO20021042A NO323156B1 (no) | 1999-09-04 | 2002-03-01 | Benzofenoner og relaterte forbindelser, anvendelse av disse forbindelser for fremstilling av medikamenter for behandling av HIV-infeksjoner, farmasoytisk preparat inneholdende slike samt disse forbindelser for anvendelse som medikament |
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US (1) | US7273863B1 (fr) |
EP (2) | EP1208091B1 (fr) |
JP (2) | JP3739704B2 (fr) |
KR (2) | KR20070093152A (fr) |
CN (4) | CN1636984A (fr) |
AR (1) | AR033344A1 (fr) |
AT (1) | ATE325106T1 (fr) |
AU (1) | AU770302C (fr) |
BR (1) | BR0013771A (fr) |
CA (1) | CA2383782A1 (fr) |
CZ (1) | CZ2002807A3 (fr) |
DE (1) | DE60027729T2 (fr) |
ES (1) | ES2261242T3 (fr) |
GB (1) | GB9920872D0 (fr) |
HU (1) | HUP0202593A3 (fr) |
IL (1) | IL148322A0 (fr) |
MX (1) | MXPA02002347A (fr) |
MY (1) | MY142948A (fr) |
NO (1) | NO323156B1 (fr) |
NZ (1) | NZ517451A (fr) |
PE (1) | PE20010539A1 (fr) |
PL (1) | PL354760A1 (fr) |
TR (1) | TR200201187T2 (fr) |
TW (1) | TWI286550B (fr) |
WO (1) | WO2001017982A1 (fr) |
ZA (1) | ZA200201664B (fr) |
Families Citing this family (43)
Publication number | Priority date | Publication date | Assignee | Title |
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JP3942897B2 (ja) | 2000-04-28 | 2007-07-11 | エフ.ホフマン−ラ ロシュ アーゲー | p−(スルホニル)アリール及びヘテロアリール |
BR0309557A (pt) | 2002-04-26 | 2005-03-01 | Gilead Sciences Inc | Inibidores da transcriptase reversa não nucleosìdeos |
JP2006521402A (ja) * | 2003-03-27 | 2006-09-21 | スミスクライン ビーチャム コーポレーション | 逆転写酵素阻害剤を調製するための方法 |
US7470724B2 (en) | 2003-04-25 | 2008-12-30 | Gilead Sciences, Inc. | Phosphonate compounds having immuno-modulatory activity |
US7432261B2 (en) | 2003-04-25 | 2008-10-07 | Gilead Sciences, Inc. | Anti-inflammatory phosphonate compounds |
US7407965B2 (en) | 2003-04-25 | 2008-08-05 | Gilead Sciences, Inc. | Phosphonate analogs for treating metabolic diseases |
AU2004233897A1 (en) | 2003-04-25 | 2004-11-11 | Gilead Sciences, Inc. | Kinase inhibitor phosphonate conjugates |
WO2004096285A2 (fr) | 2003-04-25 | 2004-11-11 | Gilead Sciences, Inc. | Analogues anti-infectieux du phosphonate |
WO2005002626A2 (fr) | 2003-04-25 | 2005-01-13 | Gilead Sciences, Inc. | Composes de phosphonate therapeutiques |
US7452901B2 (en) | 2003-04-25 | 2008-11-18 | Gilead Sciences, Inc. | Anti-cancer phosphonate analogs |
US7427636B2 (en) | 2003-04-25 | 2008-09-23 | Gilead Sciences, Inc. | Inosine monophosphate dehydrogenase inhibitory phosphonate compounds |
EA014685B1 (ru) | 2003-04-25 | 2010-12-30 | Джилид Сайэнс, Инк. | Фосфонатсодержащие антивирусные соединения (варианты) и фармацевтическая композиция на их основе |
US7427624B2 (en) | 2003-10-24 | 2008-09-23 | Gilead Sciences, Inc. | Purine nucleoside phosphorylase inhibitory phosphonate compounds |
US7432273B2 (en) | 2003-10-24 | 2008-10-07 | Gilead Sciences, Inc. | Phosphonate analogs of antimetabolites |
EP1678321A1 (fr) | 2003-10-24 | 2006-07-12 | Gilead Sciences, Inc. | Procedes et compositions permettant d'identifier des composes therapeutiques |
NZ547907A (en) | 2003-12-22 | 2010-07-30 | Gilead Sciences Inc | 4'-Substituted carbovir-and abacavir-derivatives as well as related compounds with HIV and HCV antiviral activity |
CA2545821C (fr) | 2003-12-22 | 2010-09-21 | Basilea Pharmaceutica Ag | Furanes d'aryle et thiophenes d'aryle |
FR2866880A1 (fr) * | 2004-02-27 | 2005-09-02 | Oreal | Para-phenylenediamine secondaire n-alkylaminee ortho-et/ou meta-substituee, composition de teinture des fibres keratiniques contenant une telle para-phenylenediamine, procedes mettant en oeuvre cette composition et utilisations |
US7166738B2 (en) | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
PL1742908T3 (pl) * | 2004-04-23 | 2010-04-30 | Hoffmann La Roche | Nienukleozydowe inhibitory odwrotnej transkryptazy |
US7625949B2 (en) | 2004-04-23 | 2009-12-01 | Roche Palo Alto Llc | Methods for treating retroviral infections |
WO2005121094A1 (fr) * | 2004-06-09 | 2005-12-22 | Pfizer Limited | Derives de piperazine et de piperidine utilises comme agents anti-vih |
UA88313C2 (ru) | 2004-07-27 | 2009-10-12 | Гилиад Сайенсиз, Инк. | Фосфонатные аналоги соединений ингибиторов вич |
US20060025480A1 (en) | 2004-08-02 | 2006-02-02 | Boehringer Ingelheim International Gmbh | Benzoic acid derivatives as non nucleoside reverse transcriptase inhibitors |
CA2577144C (fr) * | 2004-09-30 | 2011-06-21 | Boehringer Ingelheim International Gmbh | Derives de benzophenone a base d'alkynyle utilises comme inhibiteurs de transcriptase inverse de non nucleoside |
EP1819348A1 (fr) * | 2004-12-01 | 2007-08-22 | Boehringer Ingelheim International Gmbh | Procede de traitement des infections a vih par administration conjointe de tipranavir et de gw695634 |
AR057455A1 (es) | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
CN101291905A (zh) | 2005-10-19 | 2008-10-22 | 弗·哈夫曼-拉罗切有限公司 | 苯乙酰胺nnrt抑制剂 |
CN101108178B (zh) * | 2006-07-20 | 2010-09-15 | 复旦大学 | 一种亲环素a抑制剂在制备抗艾滋病药物中的应用 |
US20100311965A1 (en) | 2007-12-28 | 2010-12-09 | Carna Biosciences Inc. | 2-aminoquinazoline derivative |
EA018308B1 (ru) | 2008-07-08 | 2013-07-30 | Джилид Сайэнс, Инк. | Соли соединений ингибиторов вич |
WO2011060394A1 (fr) * | 2009-11-16 | 2011-05-19 | Schering Corporation | Composes utilises comme antagonistes des recepteurs de la chemokine |
CN102212022A (zh) * | 2011-04-20 | 2011-10-12 | 复旦大学 | 二苯甲醇衍生物及其制备方法和用途 |
CN102229547A (zh) * | 2011-04-20 | 2011-11-02 | 复旦大学 | 一种萘苯醚类苯磺酰胺衍生物及其制备方法和用途 |
CN102219717A (zh) * | 2011-04-20 | 2011-10-19 | 复旦大学 | N-苯基芳基甲酰胺衍生物及其制备方法和用途 |
CN102206177A (zh) * | 2011-04-20 | 2011-10-05 | 复旦大学 | 1-萘基苯甲酮衍生物及其制备方法和用途 |
US10138255B2 (en) | 2014-03-10 | 2018-11-27 | Merck Sharp & Dohme Corp. | Piperazine derivatives as HIV protease inhibitors |
PL3661937T3 (pl) | 2017-08-01 | 2021-12-20 | Gilead Sciences, Inc. | Formy krystaliczne ((s)-((((2r,5r)-5-(6-amino-9h-puryn-9-ylo)-4-fluoro-2,5-dihydrofuran-2-ylo)oksy)metylo)(fenoksy)fosforylo)-l-alaninianu etylu (gs-9131) do leczenia zakażeń wirusowych |
RU2729792C1 (ru) * | 2019-07-29 | 2020-08-12 | Акционерное общество "Научно-производственное объединение "ДОМ ФАРМАЦИИ" | Способы повышения растворимости лекарственного средства на основе пиримидинового производного бензофенона |
CN113444010B (zh) * | 2020-03-28 | 2023-09-05 | 南京正大天晴制药有限公司 | 一种沙芬酰胺有关物质的制备方法 |
CN113461502B (zh) * | 2021-07-15 | 2023-07-28 | 台州臻挚生物科技有限公司 | 2-羟基二苯甲酮类化合物及其卤化衍生物的制备方法 |
CN114163361B (zh) * | 2021-12-14 | 2023-08-01 | 无锡捷化医药科技有限公司 | 一种3-溴-5-羟基苯磺酰胺的制备方法 |
CN114292248A (zh) * | 2022-01-18 | 2022-04-08 | 广东莱佛士制药技术有限公司 | 一种合成莱特莫韦中间体的方法 |
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FR1552793A (fr) | 1966-12-07 | 1969-01-10 | ||
US4207234A (en) * | 1975-07-07 | 1980-06-10 | Fujisawa Pharmaceutical Co., Ltd. | 4-Unsubstituted azetidinone derivatives and process for preparation thereof |
JPS5973579A (ja) * | 1982-10-19 | 1984-04-25 | Kotobuki Seiyaku Kk | ベンゾフラン又はベンゾチオフェン誘導体,この化合物を有効成分とする尿酸排泄剤及びその製造方法 |
JPS59181246A (ja) | 1983-03-31 | 1984-10-15 | Chugai Pharmaceut Co Ltd | ベンゾフエノン誘導体 |
IN167395B (fr) | 1987-07-21 | 1990-10-20 | Hoffmann La Roche | |
WO1993015043A1 (fr) | 1992-01-24 | 1993-08-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose arylalkananilide et utilisation pharmaceutique |
FR2716195B1 (fr) | 1994-02-14 | 1996-06-21 | Sanofi Sa | Dérivés de 3-acylamino-5-phényl-1,4-benzodiazépin-2-one polysubstitués, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
CN1048239C (zh) | 1994-05-31 | 2000-01-12 | 帝人株式会社 | 萘衍生物 |
JP2002513008A (ja) | 1998-04-29 | 2002-05-08 | ジョージタウン ユニヴァーシティー | Hla−作動薬及び拮抗薬としてのhla結合性化合物の同定及び使用方法 |
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- 2000-08-31 CN CNA2004100956223A patent/CN1636985A/zh active Pending
- 2000-08-31 IL IL14832200A patent/IL148322A0/xx unknown
- 2000-08-31 NZ NZ517451A patent/NZ517451A/en unknown
- 2000-08-31 ES ES00967637T patent/ES2261242T3/es not_active Expired - Lifetime
- 2000-08-31 KR KR1020077019984A patent/KR20070093152A/ko not_active Application Discontinuation
- 2000-08-31 KR KR1020027002871A patent/KR20020086850A/ko active IP Right Grant
- 2000-08-31 CZ CZ2002807A patent/CZ2002807A3/cs unknown
- 2000-08-31 JP JP2001521729A patent/JP3739704B2/ja not_active Expired - Fee Related
- 2000-08-31 MX MXPA02002347A patent/MXPA02002347A/es active IP Right Grant
- 2000-08-31 AT AT00967637T patent/ATE325106T1/de not_active IP Right Cessation
- 2000-08-31 CA CA002383782A patent/CA2383782A1/fr not_active Abandoned
- 2000-08-31 AU AU77743/00A patent/AU770302C/en not_active Ceased
- 2000-08-31 WO PCT/EP2000/008487 patent/WO2001017982A1/fr not_active Application Discontinuation
- 2000-08-31 HU HU0202593A patent/HUP0202593A3/hu unknown
- 2000-08-31 EP EP00967637A patent/EP1208091B1/fr not_active Expired - Lifetime
- 2000-08-31 BR BR0013771-5A patent/BR0013771A/pt not_active Application Discontinuation
- 2000-08-31 US US10/070,084 patent/US7273863B1/en not_active Expired - Fee Related
- 2000-08-31 CN CNB008152497A patent/CN1213038C/zh not_active Expired - Fee Related
- 2000-08-31 EP EP06075956A patent/EP1710238A1/fr not_active Withdrawn
- 2000-08-31 DE DE60027729T patent/DE60027729T2/de not_active Expired - Fee Related
- 2000-08-31 TR TR2002/01187T patent/TR200201187T2/xx unknown
- 2000-09-01 TW TW089117846A patent/TWI286550B/zh not_active IP Right Cessation
- 2000-09-01 PE PE2000000897A patent/PE20010539A1/es not_active Application Discontinuation
- 2000-09-01 AR ARP000104592A patent/AR033344A1/es not_active Application Discontinuation
- 2000-09-01 MY MYPI20004058A patent/MY142948A/en unknown
-
2002
- 2002-02-27 ZA ZA200201664A patent/ZA200201664B/en unknown
- 2002-03-01 NO NO20021042A patent/NO323156B1/no unknown
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2005
- 2005-09-20 JP JP2005272533A patent/JP2006077019A/ja not_active Withdrawn
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