Carbamoyl pyridone HIV-1 integrase inhibitors. 2. Bi- and tricyclic derivatives result in superior antiviral and pharmacokinetic profiles

Journal of Medicinal Chemistry

Volumn 56, Issue 3, 2013, Pages 1124-1135

  Kawasuji, Takashi ^a   Johns, Brian A ^b   Yoshida, Hiroshi ^a   Weatherhead, Jason G ^b   Akiyama, Toshiyuki ^a   Taishi, Teruhiko ^a   Taoda, Yoshiyuki ^a   Mikamiyama Iwata, Minako ^a   Murai, Hitoshi ^a   Kiyama, Ryuichi ^a   Fuji, Masahiro ^a   Tanimoto, Norihiko ^a   Yoshinaga, Tomokazu ^a   Seki, Takahiro ^a   Kobayashi, Masanori ^a   Sato, Akihiko ^a   Garvey, Edward P ^b   Fujiwara, Tamio ^a  

^a SHIONOGI AND CO LTD   (Japan)

^b GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ACETYL 5 BENZYLOXY 6,10 DIOXO 1,2,3,4,6,9,9A,10 OCTAHYDRO 1,4A,8A TRIAZAANTHRACENE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 1 BENZYLOXY 2,11 DIOXO 2,5,5A,7,8,9,10,11 OCTAHYDRO 6 OXA 4A,10A DIAZACYCLOHEPTA[B]NAPHTHALENE 3 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 1 BENZYLOXY 6 ISOBUTYL 2,11 DIOXO 2,5A,6,7,8,9,10,11 OCTAHYDRO 5H 4A,6,10A TRIAZACYCLOHEPTA[B]NAPHTHALENE 3 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 1 BENZYLOXY 6 METHYL 2,11 DIOXO 2,5A,6,7,8,9,10,11 OCTAHYDRO 5H 4A,6,10A TRIAZACYCLOHEPTA[B]NAPHTHALENE 3 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 3 BENZYLOXY 2 METHYL 1H PYRIDINE 4 ONE; 3 BENZYLOXY 2 METHYLPYRAN 4 ONE; 3 BENZYLOXY 5 (4 FLUOROBENZYLCARBAMOYL) 4 OXO 1,4 DIHYDROPYRIDINE 2 CARBOXYLIC ACID; 3 BENZYLOXY 5 BROMO 2 METHYL 1H PYRIDINE 4 ONE; 3,9 DIHYDROXY 2 (2 METHOXYETHYL) 1,8 DIOXO 1,3,4,8 TETRAHYDRO 2H PYRID[1, 2 A]PYRAZINE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 5 BENZYLOXY 1 ISOPROPYL 6,10 DIOXO 1,2,3,4,6,9,9A,10 OCTAHYDRO 1,4A,8A TRIAZAANTHRACENE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 5 BENZYLOXY 1 METHANESULFONYL 6,10 DIOXO 1,2,3,4,6,9,9A,10 OCTAHYDRO 1,4A,8A TRIAZAANTHRACENE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 5 BENZYLOXY 1 METHYL 6,10 DIOXO 1,2,3,4,6,9,9A,10 OCTAHYDRO 1,4A,8A TRIAZAANTHRACENE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 5 BENZYLOXY 6,10 DIOXO 1,2,3,4,6,9,9A,10 OCTAHYDRO 1,4A,8A TRIAZAANTHRACENE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; 5 BENZYLOXY N (4 FLUOROBENZYL) 6 FORMYL 4 OXO 1,4 DIHYDROPYRIDINE 3 CARBOXAMIDE; 5 BENZYLOXY N (4 FLUOROBENZYL) 6 HYDROXYMETHYL 4 OXO 1,4 DIHYDROPYRIDINE 3 CARBOXAMIDE; 6 BENZYLOXY N (4 FLUOROBENZYL) 1 ISOPROPYL 5,7 DIOXO 2,3,5,7,11,11A HEXAHYDRO 1H IMIDAZO[1,2 D]PYRIDO[1,2 A] PYRAZINE 8 CARBOXAMIDE; 7 BENZYLOXY N (4 FLUOROBENZYL) 6,8 DIOXO 3,4,6,8,12,12A HEXAHYDRO 2H [1,3]OXAZINO[3,2 D]PYRIDO[1,2 A]PYRAZINE 9 CARBOXAMIDE; 9 BENZYLOXY 2 CYCLOHEXYL 1,8 DIOXO 1,8 DIHYDRO 2H PYRIDO [1,2 A]PYRAZINE 7 CARBOXYLIC ACID 4 FLUOROBENZYLAMIDE; ANTIVIRUS AGENT; CARBAMOYL PYRIDONE; DOLUTEGRAVIR; INTEGRASE INHIBITOR; METHYL 1 ALLYL 3 BENZYLOXY 5 (4 FLUOROBENZYLCARBAMOYL) 4 OXO 1,4 DIHYDROPYRIDINE 2 CARBOXYLATE; METHYL 3 BENZYLOXY 5 (4 FLUOROBENZYLCARBAMOYL) 4 OXO 1 (2 OXOETHYL) 1,4 DIHYDROPYRIDINE 2 CARBOXYLATE; METHYL 4 ACETOXY 5 BENZYLOXY 6 METHYL 1 OXYNICOTINATE; METHYL 4 ACETOXY 5 BENZYLOXY 6 METHYLNICOTINATE; METHYL 4 ACETOXY 6 ACETOXYMETHYL 5 BENZYLOXYNICOTINATE; METHYL 5 BENZYLOXY 6 HYDROXYMETHYL 4 OXO 1,4 DIHYDROPYRIDINE 3 CARBOXYLATE; METHYL 5 BENZYLOXY 6 METHYL 4 OXO 1,4 DIHYDROPYRIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG STRUCTURE; IC 50; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PHARMACOKINETICS; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHROMATOGRAPHY, LIQUID; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PYRIDONES; RATS;

EID: 84873906217     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301550c     Document Type: Article

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