SG192144A1 - C-17 and c-3 modified triterpenoids with hiv maturation inhibitory activity - Google Patents

Info

Publication number

SG192144A1

SG192144A1 SG2013056858A SG2013056858A SG192144A1 SG 192144 A1 SG192144 A1 SG 192144A1 SG 2013056858 A SG2013056858 A SG 2013056858A SG 2013056858 A SG2013056858 A SG 2013056858A SG 192144 A1 SG192144 A1 SG 192144A1

Authority

SG

Singapore

Prior art keywords

alkyl

group

pentamethyl

cyclopenta

octadecahydro

Prior art date

2011-01-31

Links

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• Global Dossier
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• 230000035800 maturation Effects 0.000 title abstract description 13
• 150000003648 triterpenes Chemical class 0.000 title abstract description 5
• 230000002401 inhibitory effect Effects 0.000 title description 4
• 238000000034 method Methods 0.000 claims abstract description 401
• 150000001875 compounds Chemical class 0.000 claims abstract description 289
• 208000030507 AIDS Diseases 0.000 claims abstract description 83
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 230000000840 anti-viral effect Effects 0.000 claims abstract description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 153
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• -1 -COOR3 Chemical group 0.000 claims description 93
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 31
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 239000003443 antiviral agent Substances 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
• 208000015181 infectious disease Diseases 0.000 claims description 7
• 229960005475 antiinfective agent Drugs 0.000 claims description 6
• 125000001475 halogen functional group Chemical group 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
• 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
• 239000004927 clay Substances 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 32
• 239000003814 drug Substances 0.000 abstract description 15
• 229940079593 drug Drugs 0.000 abstract description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 400
• 238000002360 preparation method Methods 0.000 description 304
• 239000005711 Benzoic acid Substances 0.000 description 233
• 235000010233 benzoic acid Nutrition 0.000 description 233
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 207
• 239000000203 mixture Substances 0.000 description 206
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 190
• 238000005481 NMR spectroscopy Methods 0.000 description 170
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 150
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 132
• 239000007787 solid Substances 0.000 description 130
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 127
• 238000002953 preparative HPLC Methods 0.000 description 108
• 239000000047 product Substances 0.000 description 98
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 97
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
• 230000015572 biosynthetic process Effects 0.000 description 93
• 239000012071 phase Substances 0.000 description 87
• 230000002441 reversible effect Effects 0.000 description 82
• 238000000746 purification Methods 0.000 description 81
• 239000000243 solution Substances 0.000 description 78
• 150000001412 amines Chemical class 0.000 description 77
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 73
• 230000014759 maintenance of location Effects 0.000 description 73
• 239000002904 solvent Substances 0.000 description 69
• 235000013877 carbamide Nutrition 0.000 description 67
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
• 238000010931 ester hydrolysis Methods 0.000 description 66
• 239000004202 carbamide Substances 0.000 description 64
• 208000031886 HIV Infections Diseases 0.000 description 61
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• 239000000376 reactant Substances 0.000 description 56
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 56
• 239000011541 reaction mixture Substances 0.000 description 49
• 229910052739 hydrogen Inorganic materials 0.000 description 47
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 39
• JTNKXYWGZCNBCH-UHFFFAOYSA-N 3-(dimethylamino)propanoic acid;hydron;chloride Chemical compound Cl.CN(C)CCC(O)=O JTNKXYWGZCNBCH-UHFFFAOYSA-N 0.000 description 38
• 235000019439 ethyl acetate Nutrition 0.000 description 38
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 32
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
• JAOINXWEFKZYIL-UHFFFAOYSA-N 4-(1-methyl-2-oxoquinolin-4-yl)oxy-n-(4-methylpyridin-2-yl)butanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=NC(NC(=O)CCCOC=2C3=CC=CC=C3N(C)C(=O)C=2)=C1 JAOINXWEFKZYIL-UHFFFAOYSA-N 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 230000002829 reductive effect Effects 0.000 description 30
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 30
• 238000003786 synthesis reaction Methods 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 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 238000004128 high performance liquid chromatography Methods 0.000 description 24
• 239000000463 material Substances 0.000 description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
• 229960002555 zidovudine Drugs 0.000 description 23
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• 229960001866 silicon dioxide Drugs 0.000 description 22
• QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound 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 description 21
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 20
• 239000005695 Ammonium acetate Substances 0.000 description 20
• 235000019257 ammonium acetate Nutrition 0.000 description 20
• 229940043376 ammonium acetate Drugs 0.000 description 20
• QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 18
• 239000000706 filtrate Substances 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
• 150000001408 amides Chemical class 0.000 description 15
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 15
• 230000007062 hydrolysis Effects 0.000 description 15
• 238000006460 hydrolysis reaction Methods 0.000 description 15
• 239000012044 organic layer Substances 0.000 description 15
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 13
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 13
• XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 12
• 101100108562 Escherichia coli (strain K12) aldA gene Proteins 0.000 description 12
• 101100054327 Mus musculus Abcd1 gene Proteins 0.000 description 12
• WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 12
• 101150049512 ald gene Proteins 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• 239000003643 water by type Substances 0.000 description 12
• 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 description 11
• 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 description 11
• 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 description 11
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 11
• 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 description 11
• 238000001914 filtration Methods 0.000 description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
• 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 description 11
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• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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