ZA200201664B - Benzophenones as inhibitors of reverse transcriptase. - Google Patents
Benzophenones as inhibitors of reverse transcriptase. Download PDFInfo
- Publication number
- ZA200201664B ZA200201664B ZA200201664A ZA200201664A ZA200201664B ZA 200201664 B ZA200201664 B ZA 200201664B ZA 200201664 A ZA200201664 A ZA 200201664A ZA 200201664 A ZA200201664 A ZA 200201664A ZA 200201664 B ZA200201664 B ZA 200201664B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- halogen
- heterocycle
- optionally substituted
- chloro
- Prior art date
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- 102100034343 Integrase Human genes 0.000 title description 5
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 title description 4
- 150000008366 benzophenones Chemical class 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 4
- 239000012965 benzophenone Substances 0.000 title description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 191
- 150000002367 halogens Chemical group 0.000 claims description 191
- 125000001424 substituent group Chemical group 0.000 claims description 186
- 125000000623 heterocyclic group Chemical group 0.000 claims description 180
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 125
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 150000002431 hydrogen Chemical class 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- -1 Cs. scycloalkyl Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 208000031886 HIV Infections Diseases 0.000 claims description 8
- 208000037357 HIV infectious disease Diseases 0.000 claims description 7
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 48
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 42
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 22
- 239000000203 mixture Substances 0.000 claims 14
- 239000000126 substance Substances 0.000 claims 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 208000036142 Viral infection Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 101100238304 Mus musculus Morc1 gene Proteins 0.000 claims 3
- 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 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 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 1
- LYHKYHMQZWIJJZ-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-(2-methyl-4-morpholin-4-ylphenyl)acetamide Chemical compound CC1=CC(N2CCOCC2)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 LYHKYHMQZWIJJZ-UHFFFAOYSA-N 0.000 claims 1
- MDNVHOPVVRLXQE-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-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=C1 MDNVHOPVVRLXQE-UHFFFAOYSA-N 0.000 claims 1
- WSUUMRWFMIGPCA-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-[4-(4-methylpiperazin-1-yl)phenyl]acetamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WSUUMRWFMIGPCA-UHFFFAOYSA-N 0.000 claims 1
- RZMFFVBBWIDKNJ-UHFFFAOYSA-N 2-(2-benzoyl-4-chlorophenoxy)-n-[4-[3-(dimethylamino)propoxy]-2-methylphenyl]acetamide Chemical compound CC1=CC(OCCCN(C)C)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 RZMFFVBBWIDKNJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YYCFBWCSIUZKMN-UHFFFAOYSA-N 2-[2-(2-bromobenzoyl)-4-chlorophenoxy]-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=C1Br YYCFBWCSIUZKMN-UHFFFAOYSA-N 0.000 claims 1
- OKRFNLHQKXFETN-UHFFFAOYSA-N 2-[2-(3-bromobenzoyl)-4-chlorophenoxy]-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(Br)=C1 OKRFNLHQKXFETN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BDVNUIFXLBRUCK-UHFFFAOYSA-N 2-[2-[3,5-bis(trifluoromethyl)benzoyl]-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=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BDVNUIFXLBRUCK-UHFFFAOYSA-N 0.000 claims 1
- WJJYQQZCPWDZEK-UHFFFAOYSA-N 2-[4-chloro-2-(1,3-thiazole-2-carbonyl)phenoxy]-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=NC=CS1 WJJYQQZCPWDZEK-UHFFFAOYSA-N 0.000 claims 1
- XMLCGOXNAORDEL-UHFFFAOYSA-N 2-[4-chloro-2-(1,3-thiazole-2-carbonyl)phenoxy]-n-phenylacetamide Chemical compound N=1C=CSC=1C(=O)C1=CC(Cl)=CC=C1OCC(=O)NC1=CC=CC=C1 XMLCGOXNAORDEL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CPFBBSQNOVTGML-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-dicyanobenzoyl)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)=CC(C#N)=C1 CPFBBSQNOVTGML-UHFFFAOYSA-N 0.000 claims 1
- FPUWPXSISACOGT-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-1-(2,3-dihydroindol-1-yl)ethanone;2-[4-chloro-2-[3-fluoro-5-(trifluoromethyl)benzoyl]phenoxy]-n-(6-methyl-1h-benzimidazol-5-yl)acetamide Chemical compound FC1=CC(F)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)N2C3=CC=CC=C3CC2)=C1.CC1=CC=2NC=NC=2C=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(F)=CC(C(F)(F)F)=C1 FPUWPXSISACOGT-UHFFFAOYSA-N 0.000 claims 1
- WDVFJSOMJOLYNI-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)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(F)=CC(F)=C1 WDVFJSOMJOLYNI-UHFFFAOYSA-N 0.000 claims 1
- SMLSXYQFAVPGLY-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-n-[4-(1,3-oxazol-2-yl)phenyl]acetamide Chemical compound FC1=CC(F)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)NC=2C=CC(=CC=2)C=2OC=CN=2)=C1 SMLSXYQFAVPGLY-UHFFFAOYSA-N 0.000 claims 1
- GAJKHSVAJBMBMM-UHFFFAOYSA-N 2-[4-chloro-2-(3,5-difluorobenzoyl)phenoxy]-n-[4-(1,3-thiazol-2-yl)phenyl]acetamide Chemical compound FC1=CC(F)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)NC=2C=CC(=CC=2)C=2SC=CN=2)=C1 GAJKHSVAJBMBMM-UHFFFAOYSA-N 0.000 claims 1
- RXQSMZOUOHXYOX-UHFFFAOYSA-N 2-[4-chloro-2-(3-cyano-5-methylbenzoyl)phenoxy]-n-(2-methyl-4-sulfamoylphenyl)acetamide Chemical compound CC1=CC(C#N)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)NC=2C(=CC(=CC=2)S(N)(=O)=O)C)=C1 RXQSMZOUOHXYOX-UHFFFAOYSA-N 0.000 claims 1
- KLMNQDGJZUNXGC-UHFFFAOYSA-N 2-[4-chloro-2-(3-cyano-5-methylbenzoyl)phenoxy]-n-(2-methyl-6-sulfamoylpyridin-3-yl)acetamide Chemical compound CC1=CC(C#N)=CC(C(=O)C=2C(=CC=C(Cl)C=2)OCC(=O)NC=2C(=NC(=CC=2)S(N)(=O)=O)C)=C1 KLMNQDGJZUNXGC-UHFFFAOYSA-N 0.000 claims 1
- NISMLHBLUCFLGW-UHFFFAOYSA-N 2-[4-chloro-2-(3-cyanobenzoyl)phenoxy]-n-(2-methyl-1,3-benzothiazol-5-yl)acetamide Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC(C#N)=C1 NISMLHBLUCFLGW-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- NKXNTQKSZINDNY-UHFFFAOYSA-N 2-[4-chloro-2-(3-ethynylbenzoyl)phenoxy]-n-(2-methyl-4-methylsulfonylphenyl)acetamide Chemical compound CC1=CC(S(C)(=O)=O)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC=CC(C#C)=C1 NKXNTQKSZINDNY-UHFFFAOYSA-N 0.000 claims 1
- WXKIVDYVYSICPA-UHFFFAOYSA-N 2-[4-chloro-2-(3-ethynylbenzoyl)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#C)=C1 WXKIVDYVYSICPA-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
- 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 1
- CNIQLQPZLOWPEN-UHFFFAOYSA-N 2-[4-chloro-2-(furan-2-carbonyl)phenoxy]-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=CO1 CNIQLQPZLOWPEN-UHFFFAOYSA-N 0.000 claims 1
- GZSOQJPKIGDUCR-UHFFFAOYSA-N 2-[4-chloro-2-[3-fluoro-5-(trifluoromethyl)benzoyl]phenoxy]-n-(6-methyl-1,3-benzothiazol-5-yl)acetamide Chemical compound CC1=CC=2SC=NC=2C=C1NC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CC(F)=CC(C(F)(F)F)=C1 GZSOQJPKIGDUCR-UHFFFAOYSA-N 0.000 claims 1
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical group FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000006333 difluoro benzoyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 9
- 208000030507 AIDS Diseases 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 5
- 229940124821 NNRTIs Drugs 0.000 description 4
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 3
- 101900297506 Human immunodeficiency virus type 1 group M subtype B Reverse transcriptase/ribonuclease H Proteins 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 206010049025 Persistent generalised lymphadenopathy Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 229940042443 other antivirals in atc Drugs 0.000 description 1
- 201000003450 persistent generalized lymphadenopathy Diseases 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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Classifications
-
- 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
-
- 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
- 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
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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 |
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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 (en) | 2003-04-25 | 2004-11-11 | Gilead Sciences, Inc. | Anti-infective phosphonate conjugates |
WO2005002626A2 (en) | 2003-04-25 | 2005-01-13 | Gilead Sciences, Inc. | Therapeutic phosphonate compounds |
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 (en) | 2003-10-24 | 2006-07-12 | Gilead Sciences, Inc. | Methods and compositions for identifying therapeutic compounds |
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 (en) | 2003-12-22 | 2010-09-21 | Basilea Pharmaceutica Ag | Aroylfuranes and aroylthiophenes |
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 (en) * | 2004-06-09 | 2005-12-22 | Pfizer Limited | Piperazine and piperidine derivatives as anti-hiv-agents |
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 (en) * | 2004-09-30 | 2011-06-21 | Boehringer Ingelheim International Gmbh | Alkynyl compounds as non-nucleoside reverse transcriptase inhibitors |
EP1819348A1 (en) * | 2004-12-01 | 2007-08-22 | Boehringer Ingelheim International Gmbh | Method for treating hiv infection through co-administration of tipranavir and 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 (en) * | 2009-11-16 | 2011-05-19 | Schering Corporation | Compounds useful as chemokine receptor antagonists |
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 |
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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 |
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FR1552793A (zh) | 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 (zh) | 1987-07-21 | 1990-10-20 | Hoffmann La Roche | |
WO1993015043A1 (en) | 1992-01-24 | 1993-08-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Arylalkananilide compound and pharmaceutical use thereof |
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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