EA022470B1 - C-17 и c-3 модифицированные тритерпеноиды с ингибиторной активностью созревания вич - Google Patents

Info

Publication number

EA022470B1

EA022470B1 EA201391127A EA201391127A EA022470B1 EA 022470 B1 EA022470 B1 EA 022470B1 EA 201391127 A EA201391127 A EA 201391127A EA 201391127 A EA201391127 A EA 201391127A EA 022470 B1 EA022470 B1 EA 022470B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pentamethyl

prop

group

cyclopenta

chrysen

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 4
• 230000002401 inhibitory effect Effects 0.000 title description 3
• 238000000034 method Methods 0.000 claims abstract description 389
• 150000001875 compounds Chemical class 0.000 claims abstract description 245
• 208000030507 AIDS Diseases 0.000 claims abstract description 94
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 230000000840 anti-viral effect Effects 0.000 claims abstract description 10
• -1 dimethylamino, thiazol-2-ylamino, cyclohexylamino Chemical group 0.000 claims description 785
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 341
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 166
• 208000031886 HIV Infections Diseases 0.000 claims description 68
• 208000037357 HIV infectious disease Diseases 0.000 claims description 63
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 63
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 229910052700 potassium Inorganic materials 0.000 claims description 14
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 239000003443 antiviral agent Substances 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 239000002835 hiv fusion inhibitor Substances 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
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• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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• 241000124008 Mammalia Species 0.000 claims description 4
• 239000004599 antimicrobial Substances 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 3
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
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• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
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• 210000002445 nipple Anatomy 0.000 claims description 2
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 229940126154 HIV entry inhibitor Drugs 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 27
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• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 425
• 239000005711 Benzoic acid Substances 0.000 description 247
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• 238000002360 preparation method Methods 0.000 description 233
• 239000000203 mixture Substances 0.000 description 196
• 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 149
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 130
• 239000007787 solid Substances 0.000 description 130
• 239000002904 solvent Substances 0.000 description 129
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• 238000002953 preparative HPLC Methods 0.000 description 110
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• 230000015572 biosynthetic process Effects 0.000 description 91
• 239000000047 product Substances 0.000 description 86
• 230000002441 reversible effect Effects 0.000 description 85
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• 239000012071 phase Substances 0.000 description 83
• 238000000746 purification Methods 0.000 description 81
• 230000014759 maintenance of location Effects 0.000 description 79
• 230000007062 hydrolysis Effects 0.000 description 76
• 238000006460 hydrolysis reaction Methods 0.000 description 76
• 239000000243 solution Substances 0.000 description 72
• 150000001412 amines Chemical class 0.000 description 71
• 235000013877 carbamide Nutrition 0.000 description 66
• 150000002148 esters Chemical class 0.000 description 66
• 239000004202 carbamide Substances 0.000 description 65
• 239000011541 reaction mixture Substances 0.000 description 61
• 239000000376 reactant Substances 0.000 description 56
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 52
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
• DWPVVZZGGGCRRM-UHFFFAOYSA-N (4-methoxyphenyl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCN(C)CC1 DWPVVZZGGGCRRM-UHFFFAOYSA-N 0.000 description 41
• 238000003786 synthesis reaction Methods 0.000 description 29
• JTNKXYWGZCNBCH-UHFFFAOYSA-N 3-(dimethylamino)propanoic acid;hydron;chloride Chemical compound Cl.CN(C)CCC(O)=O JTNKXYWGZCNBCH-UHFFFAOYSA-N 0.000 description 28
• 101150072179 ATP1 gene Proteins 0.000 description 28
• 101100003366 Arabidopsis thaliana ATPA gene Proteins 0.000 description 28
• 102100021649 Elongator complex protein 6 Human genes 0.000 description 28
• 101100065219 Homo sapiens ELP6 gene Proteins 0.000 description 28
• 101150105046 atpI gene Proteins 0.000 description 28
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• 229960000583 acetic acid Drugs 0.000 description 27
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 26
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• 235000011054 acetic acid Nutrition 0.000 description 26
• 239000002253 acid Substances 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 239000000741 silica gel Substances 0.000 description 23
• 229910002027 silica gel Inorganic materials 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
• 235000019257 ammonium acetate Nutrition 0.000 description 20
• 229940043376 ammonium acetate Drugs 0.000 description 20
• 239000003921 oil Substances 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
• 239000000706 filtrate Substances 0.000 description 17
• 238000004128 high performance liquid chromatography Methods 0.000 description 16
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 15
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 15
• 150000001408 amides Chemical class 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
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• 101000587820 Homo sapiens Selenide, water dikinase 1 Proteins 0.000 description 12
• 101000701815 Homo sapiens Spermidine synthase Proteins 0.000 description 12
• 102100031163 Selenide, water dikinase 1 Human genes 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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• 125000000753 cycloalkyl group Chemical group 0.000 description 11
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