TW201201792A - C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors - Google Patents

Info

Publication number

TW201201792A

TW201201792A TW100119710A TW100119710A TW201201792A TW 201201792 A TW201201792 A TW 201201792A TW 100119710 A TW100119710 A TW 100119710A TW 100119710 A TW100119710 A TW 100119710A TW 201201792 A TW201201792 A TW 201201792A

Authority

TW

Taiwan

Prior art keywords

doc

group

lla

compound

cyclopenta

Prior art date

2010-06-04

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• 239000003112 inhibitor Substances 0.000 title abstract description 25
• QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title abstract description 11
• 230000035800 maturation Effects 0.000 title abstract description 7
• 150000001408 amides Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 302
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• -1 substituted Chemical class 0.000 claims description 91
• 208000030507 AIDS Diseases 0.000 claims description 84
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• 208000015181 infectious disease Diseases 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 230000000840 anti-viral effect Effects 0.000 claims description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
• 239000003443 antiviral agent Substances 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000001475 halogen functional group Chemical group 0.000 claims description 5
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
• 229960005475 antiinfective agent Drugs 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 4
• 239000002955 immunomodulating agent Substances 0.000 claims description 4
• 229940121354 immunomodulator Drugs 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 229910052707 ruthenium Inorganic materials 0.000 claims description 3
• 229940124597 therapeutic agent Drugs 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• 229940126154 HIV entry inhibitor Drugs 0.000 claims description 2
• ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 2
• 230000002584 immunomodulator Effects 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 229910052720 vanadium Inorganic materials 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
• 239000012895 dilution Substances 0.000 claims 1
• 238000010790 dilution Methods 0.000 claims 1
• 229910052747 lanthanoid Inorganic materials 0.000 claims 1
• 150000002602 lanthanoids Chemical class 0.000 claims 1
• 150000003536 tetrazoles Chemical class 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 327
• 238000002360 preparation method Methods 0.000 abstract description 214
• QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 abstract description 7
• CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 abstract description 7
• DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 abstract description 7
• PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 abstract description 7
• MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 abstract description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 206
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 169
• 239000000047 product Substances 0.000 description 156
• 238000005481 NMR spectroscopy Methods 0.000 description 155
• 239000007787 solid Substances 0.000 description 128
• 150000001412 amines Chemical class 0.000 description 118
• 235000019439 ethyl acetate Nutrition 0.000 description 101
• 239000000543 intermediate Substances 0.000 description 94
• 230000015572 biosynthetic process Effects 0.000 description 93
• 230000007062 hydrolysis Effects 0.000 description 91
• 238000006460 hydrolysis reaction Methods 0.000 description 91
• 239000000203 mixture Substances 0.000 description 90
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
• 239000002253 acid Substances 0.000 description 56
• 239000011541 reaction mixture Substances 0.000 description 56
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 55
• 208000031886 HIV Infections Diseases 0.000 description 53
• 208000037357 HIV infectious disease Diseases 0.000 description 52
• 239000003153 chemical reaction reagent Substances 0.000 description 52
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 52
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 239000002585 base Substances 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
• 239000000376 reactant Substances 0.000 description 41
• 239000000243 solution Substances 0.000 description 33
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
• 241000725303 Human immunodeficiency virus Species 0.000 description 32
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 31
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 30
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 29
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
• 239000005711 Benzoic acid Substances 0.000 description 28
• 201000010099 disease Diseases 0.000 description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
• 230000002829 reductive effect Effects 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 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 27
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 26
• 238000010640 amide synthesis reaction Methods 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 239000007858 starting material Substances 0.000 description 24
• 229960002555 zidovudine Drugs 0.000 description 22
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 20
• 239000002904 solvent Substances 0.000 description 20
• 235000010233 benzoic acid Nutrition 0.000 description 19
• 238000006243 chemical reaction Methods 0.000 description 19
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 18
• 239000000052 vinegar Substances 0.000 description 18
• 235000021419 vinegar Nutrition 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000007789 gas Substances 0.000 description 15
• DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 14
• 229940095102 methyl benzoate Drugs 0.000 description 14
• 125000003396 thiol group Chemical group [H]S* 0.000 description 14
• 238000006069 Suzuki reaction reaction Methods 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 241000700605 Viruses Species 0.000 description 12
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• 238000001914 filtration Methods 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
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