NZ554232A - Phosphoindoles as HIV inhibitors - Google Patents

Info

Publication number

NZ554232A

NZ554232A NZ554232A NZ55423205A NZ554232A NZ 554232 A NZ554232 A NZ 554232A NZ 554232 A NZ554232 A NZ 554232A NZ 55423205 A NZ55423205 A NZ 55423205A NZ 554232 A NZ554232 A NZ 554232A

Authority

NZ

New Zealand

Prior art keywords

alkyl

aryl

pharmaceutically acceptable

compound

hiv

Prior art date

2004-09-17

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title description 9
• 150000003006 phosphoindoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 258
• 150000003839 salts Chemical class 0.000 claims abstract description 77
• 238000011282 treatment Methods 0.000 claims abstract description 75
• 239000003814 drug Substances 0.000 claims abstract description 64
• 208000031886 HIV Infections Diseases 0.000 claims abstract description 43
• 208000037357 HIV infectious disease Diseases 0.000 claims abstract description 42
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 42
• 150000001412 amines Chemical group 0.000 claims abstract description 36
• 238000011321 prophylaxis Methods 0.000 claims abstract description 31
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
• 238000004519 manufacturing process Methods 0.000 claims abstract description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 243
• 229910052739 hydrogen Inorganic materials 0.000 claims description 131
• 125000005843 halogen group Chemical group 0.000 claims description 113
• 125000000623 heterocyclic group Chemical group 0.000 claims description 110
• 125000003118 aryl group Chemical group 0.000 claims description 98
• 229910052736 halogen Inorganic materials 0.000 claims description 88
• 239000001257 hydrogen Substances 0.000 claims description 84
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 74
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
• 239000000203 mixture Substances 0.000 claims description 59
• 125000002947 alkylene group Chemical group 0.000 claims description 52
• 125000003342 alkenyl group Chemical group 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 41
• 150000002367 halogens Chemical class 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
• 125000004450 alkenylene group Chemical group 0.000 claims description 32
• 125000004419 alkynylene group Chemical group 0.000 claims description 31
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 239000003085 diluting agent Substances 0.000 claims description 26
• 239000003937 drug carrier Substances 0.000 claims description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• 125000006850 spacer group Chemical group 0.000 claims description 24
• 125000002252 acyl group Chemical group 0.000 claims description 22
• 229940024606 amino acid Drugs 0.000 claims description 22
• 230000006870 function Effects 0.000 claims description 22
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
• 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims description 19
• 229940124411 anti-hiv antiviral agent Drugs 0.000 claims description 17
• 125000000732 arylene group Chemical group 0.000 claims description 17
• 230000035772 mutation Effects 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000003107 substituted aryl group Chemical group 0.000 claims description 17
• 150000003568 thioethers Chemical class 0.000 claims description 17
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 238000006467 substitution reaction Methods 0.000 claims description 13
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 10
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 10
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 10
• 125000005518 carboxamido group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 9
• 239000004472 Lysine Substances 0.000 claims description 9
• 229960001230 asparagine Drugs 0.000 claims description 9
• 235000009582 asparagine Nutrition 0.000 claims description 9
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 9
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 8
• 235000018417 cysteine Nutrition 0.000 claims description 8
• 239000002552 dosage form Substances 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 150000002923 oximes Chemical class 0.000 claims description 8
• 125000000539 amino acid group Chemical group 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 238000009118 salvage therapy Methods 0.000 claims description 7
• 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 6
• 230000037396 body weight Effects 0.000 claims description 5
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 5
• 229910014033 C-OH Inorganic materials 0.000 claims description 4
• 229910014570 C—OH Inorganic materials 0.000 claims description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
• 150000003857 carboxamides Chemical class 0.000 claims 2
• 150000001733 carboxylic acid esters Chemical class 0.000 claims 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
• JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 abstract description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 366
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 293
• 101150041968 CDC13 gene Proteins 0.000 description 262
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 262
• 238000004679 31P NMR spectroscopy Methods 0.000 description 250
• ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 114
• 239000003921 oil Substances 0.000 description 106
• 235000019198 oils Nutrition 0.000 description 106
• 239000007787 solid Substances 0.000 description 96
• 238000000034 method Methods 0.000 description 92
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 91
• 239000000843 powder Substances 0.000 description 86
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
• 229910052727 yttrium Inorganic materials 0.000 description 77
• 241000725303 Human immunodeficiency virus Species 0.000 description 60
• 239000012230 colorless oil Substances 0.000 description 59
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
• -1 2-hydroxyethoxy Chemical group 0.000 description 58
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 55
• 238000004293 19F NMR spectroscopy Methods 0.000 description 54
• 150000002431 hydrogen Chemical class 0.000 description 52
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 48
• 229940002612 prodrug Drugs 0.000 description 43
• 239000000651 prodrug Substances 0.000 description 43
• 229940079593 drug Drugs 0.000 description 40
• 229910052760 oxygen Inorganic materials 0.000 description 40
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 39
• 239000000243 solution Substances 0.000 description 39
• 229910052717 sulfur Inorganic materials 0.000 description 37
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 125000000547 substituted alkyl group Chemical group 0.000 description 36
• 235000019439 ethyl acetate Nutrition 0.000 description 35
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 125000001072 heteroaryl group Chemical group 0.000 description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
• KJDLQEJTNPEOLU-UHFFFAOYSA-N C1=CC=C2C(P(=O)=O)=CNC2=C1 Chemical class C1=CC=C2C(P(=O)=O)=CNC2=C1 KJDLQEJTNPEOLU-UHFFFAOYSA-N 0.000 description 30
• 238000004587 chromatography analysis Methods 0.000 description 30
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 230000000694 effects Effects 0.000 description 26
• 229910001868 water Inorganic materials 0.000 description 26
• 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 26
• WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 25
• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 23
• 230000036436 anti-hiv Effects 0.000 description 22
• 230000000840 anti-viral effect Effects 0.000 description 21
• 238000006243 chemical reaction Methods 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 20
• 229960002555 zidovudine Drugs 0.000 description 20
• 208000030507 AIDS Diseases 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 19
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• QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 19
• 238000003786 synthesis reaction Methods 0.000 description 19
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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• 150000002475 indoles Chemical class 0.000 description 18
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 18
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 17
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