PT2670764E - C-28 aminas de derivados de ácido betulínico c-3 modificado como inibidores de maturação de vih - Google Patents

Info

Publication number

PT2670764E

PT2670764E PT127029460T PT12702946T PT2670764E PT 2670764 E PT2670764 E PT 2670764E PT 127029460 T PT127029460 T PT 127029460T PT 12702946 T PT12702946 T PT 12702946T PT 2670764 E PT2670764 E PT 2670764E

Authority

PT

Portugal

Prior art keywords

alkyl

group

pentamethyl

methyl

cyclopenta

Prior art date

2011-01-31

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 34
• 150000001412 amines Chemical class 0.000 title description 216
• 230000035800 maturation Effects 0.000 title description 11
• 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 description 10
• -1 -C 1 R 2 Chemical group 0.000 claims description 555
• 238000000034 method Methods 0.000 claims description 398
• 150000001875 compounds Chemical class 0.000 claims description 280
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 238
• 208000030507 AIDS Diseases 0.000 claims description 97
• 229910052739 hydrogen Inorganic materials 0.000 claims description 64
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 55
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
• 208000031886 HIV Infections Diseases 0.000 claims description 50
• 208000037357 HIV infectious disease Diseases 0.000 claims description 49
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 33
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000001475 halogen functional group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 230000000840 anti-viral effect Effects 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 8
• 239000003443 antiviral agent Substances 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 229960005475 antiinfective agent Drugs 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 239000002955 immunomodulating agent Substances 0.000 claims description 6
• 229940121354 immunomodulator Drugs 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 239000004599 antimicrobial Substances 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 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 3
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
• 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 271
• 238000002360 preparation method Methods 0.000 description 267
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 246
• 235000010233 benzoic acid Nutrition 0.000 description 202
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
• 239000005711 Benzoic acid Substances 0.000 description 186
• 238000005481 NMR spectroscopy Methods 0.000 description 183
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 162
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 159
• 239000000203 mixture Substances 0.000 description 159
• 239000000243 solution Substances 0.000 description 152
• 239000007787 solid Substances 0.000 description 147
• 239000000047 product Substances 0.000 description 127
• 239000000376 reactant Substances 0.000 description 113
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 100
• 230000015572 biosynthetic process Effects 0.000 description 85
• 238000004949 mass spectrometry Methods 0.000 description 84
• 230000007062 hydrolysis Effects 0.000 description 82
• 238000006460 hydrolysis reaction Methods 0.000 description 82
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
• 239000002904 solvent Substances 0.000 description 69
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
• 150000001408 amides Chemical class 0.000 description 55
• 230000002829 reductive effect Effects 0.000 description 55
• 239000012043 crude product Substances 0.000 description 51
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
• 238000000746 purification Methods 0.000 description 43
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 41
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 39
• 239000012044 organic layer Substances 0.000 description 37
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• 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 34
• 238000002953 preparative HPLC Methods 0.000 description 30
• 238000005160 1H NMR spectroscopy Methods 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• 239000000706 filtrate Substances 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 28
• 230000002441 reversible effect Effects 0.000 description 25
• 238000001914 filtration Methods 0.000 description 24
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 24
• 235000011054 acetic acid Nutrition 0.000 description 23
• 150000001299 aldehydes Chemical class 0.000 description 22
• 239000000725 suspension Substances 0.000 description 22
• 229960002555 zidovudine Drugs 0.000 description 22
• 239000002274 desiccant Substances 0.000 description 21
• 238000004128 high performance liquid chromatography Methods 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 239000003153 chemical reaction reagent Substances 0.000 description 20
• 239000000463 material Substances 0.000 description 20
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 19
• 238000006243 chemical reaction Methods 0.000 description 19
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
• 229910052938 sodium sulfate Inorganic materials 0.000 description 18
• 235000011152 sodium sulphate Nutrition 0.000 description 18
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
• 150000001559 benzoic acids Chemical class 0.000 description 17
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
• 239000006260 foam Substances 0.000 description 16
• 239000003814 drug Substances 0.000 description 15
• 235000019439 ethyl acetate Nutrition 0.000 description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
• 229910052757 nitrogen Inorganic materials 0.000 description 15
• 210000004027 cell Anatomy 0.000 description 14
• 238000004811 liquid chromatography Methods 0.000 description 14
• PDLNHDSYGLTYDS-UHFFFAOYSA-N 3-aminopropanoic acid;hydrochloride Chemical compound Cl.NCCC(O)=O PDLNHDSYGLTYDS-UHFFFAOYSA-N 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 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
• 125000000753 cycloalkyl group Chemical group 0.000 description 13
• 238000003818 flash chromatography Methods 0.000 description 13
• 125000006308 propyl amino group Chemical group 0.000 description 13
• NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 238000005903 acid hydrolysis reaction Methods 0.000 description 12
• 239000012445 acidic reagent Substances 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• 238000010511 deprotection reaction Methods 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• 208000015181 infectious disease Diseases 0.000 description 12
• 229960000311 ritonavir Drugs 0.000 description 12
• NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
• 239000013058 crude material Substances 0.000 description 11
• COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 11
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
• 150000004702 methyl esters Chemical class 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 10
• 239000005695 Ammonium acetate Substances 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 10
• 241000700605 Viruses Species 0.000 description 10
• 235000019257 ammonium acetate Nutrition 0.000 description 10
• 229940043376 ammonium acetate Drugs 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• 229910004809 Na2 SO4 Inorganic materials 0.000 description 9
• XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
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• VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical class OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 9
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• FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 8
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• 102100034343 Integrase Human genes 0.000 description 7
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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• 150000004657 carbamic acid derivatives Chemical class 0.000 description 7
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
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• 238000003786 synthesis reaction Methods 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
• 239000007821 HATU Substances 0.000 description 6
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
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• 125000004104 aryloxy group Chemical group 0.000 description 6
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• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 description 6
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• 239000002777 nucleoside Substances 0.000 description 6
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• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
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• 125000005190 thiohydroxy group Chemical group 0.000 description 6
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 6
• NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 5
• FSRMWCVZAUEPEQ-UHFFFAOYSA-N 3-(1,1-dioxo-1,4-thiazinan-4-yl)propan-1-amine Chemical compound NCCCN1CCS(=O)(=O)CC1 FSRMWCVZAUEPEQ-UHFFFAOYSA-N 0.000 description 5
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