IL176740A - Non-nucleotide reverse transcriptase inhibitors - Google Patents

Info

Publication number

IL176740A

IL176740A IL176740A IL17674006A IL176740A IL 176740 A IL176740 A IL 176740A IL 176740 A IL176740 A IL 176740A IL 17674006 A IL17674006 A IL 17674006A IL 176740 A IL176740 A IL 176740A

Authority

IL

Israel

Prior art keywords

mmol

alkyl

difluoro

tetrahydro

cyclopropa

Prior art date

2004-01-08

Links

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• 239000003814 drug Substances 0.000 title claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
• 238000011282 treatment Methods 0.000 title claims description 7
• 208000031886 HIV Infections Diseases 0.000 title claims description 4
• 238000011321 prophylaxis Methods 0.000 title claims description 3
• 238000002360 preparation method Methods 0.000 title description 10
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title description 5
• 239000002773 nucleotide Substances 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 138
• 125000001424 substituent group Chemical group 0.000 claims abstract description 17
• 150000003839 salts Chemical class 0.000 claims abstract description 12
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
• 239000003443 antiviral agent Substances 0.000 claims abstract description 4
• 229940121357 antivirals Drugs 0.000 claims abstract description 4
• 125000003118 aryl group Chemical group 0.000 claims abstract description 4
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
• 239000000203 mixture Substances 0.000 claims description 97
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 95
• -1 amino, carboxy, carbamoyl Chemical group 0.000 claims description 58
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 36
• 239000004202 carbamide Substances 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 229940079593 drug Drugs 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 230000035772 mutation Effects 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001589 carboacyl group Chemical group 0.000 claims description 4
• 125000000468 ketone group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 3
• 229930194542 Keto Natural products 0.000 claims description 3
• NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 3
• 125000002720 diazolyl group Chemical group 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 230000003287 optical effect Effects 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 229960000311 ritonavir Drugs 0.000 claims description 3
• NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims description 2
• 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 claims description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
• 150000002148 esters Chemical class 0.000 abstract description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 7
• 239000000651 prodrug Substances 0.000 abstract description 5
• 229940002612 prodrug Drugs 0.000 abstract description 5
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 177
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 106
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
• 229910001868 water Inorganic materials 0.000 description 96
• 239000011541 reaction mixture Substances 0.000 description 93
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 89
• 238000005160 1H NMR spectroscopy Methods 0.000 description 81
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
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• 239000000243 solution Substances 0.000 description 65
• 239000000047 product Substances 0.000 description 52
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• 238000004440 column chromatography Methods 0.000 description 43
• 238000006243 chemical reaction Methods 0.000 description 42
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
• 235000019439 ethyl acetate Nutrition 0.000 description 41
• 239000000741 silica gel Substances 0.000 description 39
• 229910002027 silica gel Inorganic materials 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• 239000012267 brine Substances 0.000 description 33
• 239000012043 crude product Substances 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• 239000002253 acid Substances 0.000 description 32
• 229940093499 ethyl acetate Drugs 0.000 description 31
• 239000012074 organic phase Substances 0.000 description 30
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 28
• 235000011121 sodium hydroxide Nutrition 0.000 description 27
• XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 26
• 239000003921 oil Substances 0.000 description 26
• 239000002904 solvent Substances 0.000 description 26
• 239000000377 silicon dioxide Substances 0.000 description 22
• 238000000034 method Methods 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• 238000010898 silica gel chromatography Methods 0.000 description 19
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 18
• 239000007787 solid Substances 0.000 description 17
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
• 235000019441 ethanol Nutrition 0.000 description 16
• 238000000746 purification Methods 0.000 description 16
• 230000002829 reductive effect Effects 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• 239000012071 phase Substances 0.000 description 15
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 15
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 238000002390 rotary evaporation Methods 0.000 description 14
• ZCQSJUGIZGMDDA-UHFFFAOYSA-N 4-(methylsulfinyl)phenol Chemical compound CS(=O)C1=CC=C(O)C=C1 ZCQSJUGIZGMDDA-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• 238000005481 NMR spectroscopy Methods 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• 238000004587 chromatography analysis Methods 0.000 description 12
• 238000001704 evaporation Methods 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
• 239000013543 active substance Substances 0.000 description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
• YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000000284 extract Substances 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 125000006239 protecting group Chemical group 0.000 description 10
• 235000002639 sodium chloride Nutrition 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 238000000605 extraction Methods 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
• KECCFSZFXLAGJS-UHFFFAOYSA-N 4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C=C1 KECCFSZFXLAGJS-UHFFFAOYSA-N 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 239000006227 byproduct Substances 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• LNETULKMXZVUST-UHFFFAOYSA-M 1-naphthoate Chemical compound C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-M 0.000 description 7
• ATXXLNCPVSUCNK-UHFFFAOYSA-N 5-bromo-2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Br)C=N1 ATXXLNCPVSUCNK-UHFFFAOYSA-N 0.000 description 7
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• 229910052786 argon Inorganic materials 0.000 description 7
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
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• 229940083608 sodium hydroxide Drugs 0.000 description 7
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• LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 6
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• 230000000840 anti-viral effect Effects 0.000 description 6
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• 210000004027 cell Anatomy 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000004494 ethyl ester group Chemical group 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 6
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• 238000003556 assay Methods 0.000 description 5
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• UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
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• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
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• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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• 125000005907 alkyl ester group Chemical group 0.000 description 4
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 239000003638 chemical reducing agent Substances 0.000 description 4
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
• XCTLDQQOHIEUCJ-UHFFFAOYSA-N ethyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC=CC2=C1 XCTLDQQOHIEUCJ-UHFFFAOYSA-N 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
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