NZ536661A - Non-nucleoside reverse transcriptase inhibitors for use a antiviral agents in relation to HIV and AIDS - Google Patents

Info

Publication number

NZ536661A

NZ536661A NZ536661A NZ53666103A NZ536661A NZ 536661 A NZ536661 A NZ 536661A NZ 536661 A NZ536661 A NZ 536661A NZ 53666103 A NZ53666103 A NZ 53666103A NZ 536661 A NZ536661 A NZ 536661A

Authority

NZ

New Zealand

Prior art keywords

group

alkyl

heteroaryl

compound

optionally substituted

Prior art date

2002-05-28

Links

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• Global Dossier
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• 208000030507 AIDS Diseases 0.000 title claims abstract description 83
• 239000003443 antiviral agent Substances 0.000 title claims description 10
• 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 title description 10
• 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 278
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 30
• 239000003814 drug Substances 0.000 claims abstract description 24
• 230000000840 anti-viral effect Effects 0.000 claims abstract description 21
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• -1 benzoimidazolyl Chemical group 0.000 claims description 187
• 125000001072 heteroaryl group Chemical group 0.000 claims description 183
• 238000002360 preparation method Methods 0.000 claims description 150
• 125000000217 alkyl group Chemical group 0.000 claims description 103
• 229910052736 halogen Inorganic materials 0.000 claims description 82
• 150000002367 halogens Chemical class 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
• 125000004076 pyridyl group Chemical group 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 39
• 125000002541 furyl group Chemical group 0.000 claims description 33
• 125000001544 thienyl group Chemical group 0.000 claims description 33
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 31
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 31
• 125000001425 triazolyl group Chemical group 0.000 claims description 30
• 125000002971 oxazolyl group Chemical group 0.000 claims description 28
• 125000002883 imidazolyl group Chemical group 0.000 claims description 27
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 27
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 27
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 26
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 26
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 26
• 125000000335 thiazolyl group Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 25
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000004193 piperazinyl group Chemical group 0.000 claims description 18
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 208000015181 infectious disease Diseases 0.000 claims description 11
• 125000004306 triazinyl group Chemical group 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 8
• 241000700605 Viruses Species 0.000 claims description 7
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• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 4
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 4
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000005872 benzooxazolyl group Chemical group 0.000 claims description 4
• 230000002584 immunomodulator Effects 0.000 claims description 4
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 230000002503 metabolic effect Effects 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims 5
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
• 230000037396 body weight Effects 0.000 claims 1
• 230000037213 diet Effects 0.000 claims 1
• 235000005911 diet Nutrition 0.000 claims 1
• 239000000890 drug combination Substances 0.000 claims 1
• 230000029142 excretion Effects 0.000 claims 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 229
• 229940079593 drug Drugs 0.000 abstract description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 181
• 238000006243 chemical reaction Methods 0.000 description 176
• 239000000543 intermediate Substances 0.000 description 132
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 122
• 239000000203 mixture Substances 0.000 description 118
• 239000000243 solution Substances 0.000 description 87
• 239000002904 solvent Substances 0.000 description 73
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 71
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 71
• 229910001868 water Inorganic materials 0.000 description 67
• 239000007787 solid Substances 0.000 description 65
• 238000005859 coupling reaction Methods 0.000 description 63
• 235000019439 ethyl acetate Nutrition 0.000 description 61
• 238000010168 coupling process Methods 0.000 description 58
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
• 230000008878 coupling Effects 0.000 description 57
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 55
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• 238000003786 synthesis reaction Methods 0.000 description 54
• 230000015572 biosynthetic process Effects 0.000 description 53
• 239000002253 acid Substances 0.000 description 50
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 48
• 125000000623 heterocyclic group Chemical group 0.000 description 47
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 208000031886 HIV Infections Diseases 0.000 description 44
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
• 208000037357 HIV infectious disease Diseases 0.000 description 41
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 41
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 40
• 239000003153 chemical reaction reagent Substances 0.000 description 40
• 238000007429 general method Methods 0.000 description 39
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 36
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 36
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• 101150041968 CDC13 gene Proteins 0.000 description 33
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 33
• 125000003118 aryl group Chemical group 0.000 description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 32
• 238000002953 preparative HPLC Methods 0.000 description 32
• 150000002475 indoles Chemical class 0.000 description 31
• 238000003756 stirring Methods 0.000 description 30
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 239000012044 organic layer Substances 0.000 description 29
• 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 29
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
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• 229960002555 zidovudine Drugs 0.000 description 26
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
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• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 22
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 22
• 238000000746 purification Methods 0.000 description 21
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
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• 125000003277 amino group Chemical group 0.000 description 12
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• 229910052796 boron Inorganic materials 0.000 description 9
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