EA027861B1 - C-3 алкил- и алкенилмодифицированные производные бетулиновой кислоты или их фармацевтические соли, противовирусная фармацевтическая композиция и фармацевтическая композиция для лечения вич на их основе - Google Patents

Info

Publication number

EA027861B1

EA027861B1 EA201591545A EA201591545A EA027861B1 EA 027861 B1 EA027861 B1 EA 027861B1 EA 201591545 A EA201591545 A EA 201591545A EA 201591545 A EA201591545 A EA 201591545A EA 027861 B1 EA027861 B1 EA 027861B1

Authority

EA

Eurasian Patent Office

Prior art keywords

mmol

prop

pentamethyl

mixture

cyclopenta

Prior art date

2013-02-25

Links

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• 238000011282 treatment Methods 0.000 title claims abstract description 24
• 230000000840 anti-viral effect Effects 0.000 title claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
• 150000003839 salts Chemical class 0.000 title claims description 14
• -1 alkenyl modified betulinic acid derivatives Chemical class 0.000 title abstract description 306
• 125000000217 alkyl group Chemical group 0.000 title abstract description 29
• 208000030507 AIDS Diseases 0.000 claims abstract description 98
• 150000001875 compounds Chemical class 0.000 claims abstract description 96
• 239000003112 inhibitor Substances 0.000 claims abstract description 41
• 239000000203 mixture Substances 0.000 claims description 170
• 208000031886 HIV Infections Diseases 0.000 claims description 66
• 208000037357 HIV infectious disease Diseases 0.000 claims description 65
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 65
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 230000035515 penetration Effects 0.000 claims description 10
• 239000003443 antiviral agent Substances 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 239000002955 immunomodulating agent Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 229940121354 immunomodulator Drugs 0.000 claims description 7
• 229960005475 antiinfective agent Drugs 0.000 claims description 6
• 239000004599 antimicrobial Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 230000002584 immunomodulator Effects 0.000 claims description 4
• 238000000034 method Methods 0.000 abstract description 128
• 229940079593 drug Drugs 0.000 abstract description 17
• 239000003814 drug Substances 0.000 abstract description 17
• 230000035800 maturation Effects 0.000 abstract description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 191
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 166
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 126
• 239000000243 solution Substances 0.000 description 116
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 111
• 239000002904 solvent Substances 0.000 description 98
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
• 230000002829 reductive effect Effects 0.000 description 68
• 238000002360 preparation method Methods 0.000 description 66
• 238000005481 NMR spectroscopy Methods 0.000 description 64
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 51
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
• 239000000741 silica gel Substances 0.000 description 48
• 229910002027 silica gel Inorganic materials 0.000 description 48
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 47
• 241000725303 Human immunodeficiency virus Species 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 43
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 42
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
• 239000011541 reaction mixture Substances 0.000 description 39
• 239000007787 solid Substances 0.000 description 39
• 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 31
• 238000003818 flash chromatography Methods 0.000 description 30
• 229910052739 hydrogen Inorganic materials 0.000 description 30
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 30
• 238000002953 preparative HPLC Methods 0.000 description 28
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• 239000012267 brine Substances 0.000 description 25
• 239000000047 product Substances 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
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• 235000019341 magnesium sulphate Nutrition 0.000 description 24
• 229910052757 nitrogen Inorganic materials 0.000 description 22
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• 125000001072 heteroaryl group Chemical group 0.000 description 20
• 239000000706 filtrate Substances 0.000 description 19
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• 235000011054 acetic acid Nutrition 0.000 description 18
• 239000012043 crude product Substances 0.000 description 18
• 239000006260 foam Substances 0.000 description 18
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• 229910052938 sodium sulfate Inorganic materials 0.000 description 17
• 235000011152 sodium sulphate Nutrition 0.000 description 17
• NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 16
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 16
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
• 210000004027 cell Anatomy 0.000 description 15
• 238000010438 heat treatment Methods 0.000 description 15
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 14
• 239000005695 Ammonium acetate Substances 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 235000019257 ammonium acetate Nutrition 0.000 description 14
• 229940043376 ammonium acetate Drugs 0.000 description 14
• 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 14
• 230000015572 biosynthetic process Effects 0.000 description 14
• 125000003373 pyrazinyl group Chemical group 0.000 description 14
• 230000000694 effects Effects 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
• 125000003118 aryl group Chemical group 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 230000014759 maintenance of location Effects 0.000 description 12
• 241000700605 Viruses Species 0.000 description 11
• 125000000753 cycloalkyl group Chemical group 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 11
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• 239000000126 substance Substances 0.000 description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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• 238000003786 synthesis reaction Methods 0.000 description 9
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• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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