DK2576586T3 - C-28 AMINES OF MODIFIED C-3-BETULIN ACID DERIVATIVES AS ANTI-HUMIDITY INHIBITORS - Google Patents

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Publication number

DK2576586T3

DK2576586T3 DK11726564.5T DK11726564T DK2576586T3 DK 2576586 T3 DK2576586 T3 DK 2576586T3 DK 11726564 T DK11726564 T DK 11726564T DK 2576586 T3 DK2576586 T3 DK 2576586T3

Authority

DK

Denmark

Prior art keywords

group

cyclopenta

pentamethyl

octadecahydro

prop

Prior art date

2010-06-04

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 30
• 239000002253 acid Substances 0.000 title claims description 11
• 150000001412 amines Chemical class 0.000 title description 121
• 150000001875 compounds Chemical class 0.000 claims description 263
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 65
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• -1 substituted Chemical class 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 208000030507 AIDS Diseases 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 230000000840 anti-viral effect Effects 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000001475 halogen functional group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 208000031886 HIV Infections Diseases 0.000 claims description 7
• 208000037357 HIV infectious disease Diseases 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 229910006069 SO3H Inorganic materials 0.000 claims description 5
• 239000002955 immunomodulating agent Substances 0.000 claims description 5
• 229940121354 immunomodulator Drugs 0.000 claims description 5
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 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 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 230000002924 anti-infective effect Effects 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 3
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 241000209094 Oryza Species 0.000 claims 2
• 235000007164 Oryza sativa Nutrition 0.000 claims 2
• 235000009566 rice Nutrition 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 230000000903 blocking effect Effects 0.000 claims 1
• 239000012678 infectious agent Substances 0.000 claims 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 description 333
• 238000002360 preparation method Methods 0.000 description 224
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 189
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
• 239000000047 product Substances 0.000 description 171
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• 239000007787 solid Substances 0.000 description 164
• 239000000376 reactant Substances 0.000 description 107
• 230000007062 hydrolysis Effects 0.000 description 103
• 238000006460 hydrolysis reaction Methods 0.000 description 103
• 238000010640 amide synthesis reaction Methods 0.000 description 102
• 239000000543 intermediate Substances 0.000 description 102
• 239000000203 mixture Substances 0.000 description 81
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 77
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
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• 239000011541 reaction mixture Substances 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 230000002829 reductive effect Effects 0.000 description 54
• QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 53
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 239000000243 solution Substances 0.000 description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000005711 Benzoic acid Substances 0.000 description 32
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
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• 229960004365 benzoic acid Drugs 0.000 description 32
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 31
• 229940050390 benzoate Drugs 0.000 description 29
• 230000015572 biosynthetic process Effects 0.000 description 29
• 239000007858 starting material Substances 0.000 description 29
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 27
• 235000019439 ethyl acetate Nutrition 0.000 description 25
• 239000002904 solvent Substances 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 239000000284 extract Substances 0.000 description 19
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
• 238000006069 Suzuki reaction reaction Methods 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 229910052938 sodium sulfate Inorganic materials 0.000 description 18
• 235000011152 sodium sulphate Nutrition 0.000 description 18
• 238000002953 preparative HPLC Methods 0.000 description 17
• 150000001408 amides Chemical class 0.000 description 16
• 229910052796 boron Inorganic materials 0.000 description 16
• 239000012153 distilled water Substances 0.000 description 16
• 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 15
• 239000000706 filtrate Substances 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• 239000000741 silica gel Substances 0.000 description 13
• 229910002027 silica gel Inorganic materials 0.000 description 13
• 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 13
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 238000010511 deprotection reaction Methods 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
• 241000700605 Viruses Species 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• 238000004809 thin layer chromatography Methods 0.000 description 10
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
• 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 9
• KAALSBMCRVYZDM-JENLPSNGSA-N 4-[(1r,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[2-[bis(carboxymethyl)amino]ethylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid Chemical compound C([C@]1(C)[C@H]2CC[C@H]3[C@@]([C@@]2(CC[C@H]1C1(C)C)C)(C)CC[C@]2(CC[C@H]([C@H]32)C(=C)C)C(=O)NCCN(CC(O)=O)CC(O)=O)C=C1C1=CC=C(C(O)=O)C=C1 KAALSBMCRVYZDM-JENLPSNGSA-N 0.000 description 9
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• BHFLUDRTVIDDOR-QMMMGPOBSA-N methyl (2s)-2-amino-2-phenylacetate Chemical compound COC(=O)[C@@H](N)C1=CC=CC=C1 BHFLUDRTVIDDOR-QMMMGPOBSA-N 0.000 description 1
• CEMZBWPSKYISTN-YFKPBYRVSA-N methyl (2s)-2-amino-3-methylbutanoate Chemical compound COC(=O)[C@@H](N)C(C)C CEMZBWPSKYISTN-YFKPBYRVSA-N 0.000 description 1
• UIHPNZDZCOEZEN-YFKPBYRVSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate Chemical compound COC(=O)[C@@H](N)CCSC UIHPNZDZCOEZEN-YFKPBYRVSA-N 0.000 description 1
• UJNNCGWBDJHCEM-UHFFFAOYSA-N methyl 2-amino-1,3-thiazole-5-carboxylate Chemical compound COC(=O)C1=CN=C(N)S1 UJNNCGWBDJHCEM-UHFFFAOYSA-N 0.000 description 1
• LFVPHXOOLUCFFB-UHFFFAOYSA-N methyl 3-amino-2-hydroxypropanoate Chemical compound COC(=O)C(O)CN LFVPHXOOLUCFFB-UHFFFAOYSA-N 0.000 description 1
• CHDVFHGMKRKZJV-MSEMWXCYSA-N methyl 4-[(1r,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[2-[(2-methoxy-2-oxoethyl)-propylamino]ethylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoate Chemical compound C([C@]1(C)[C@H]2CC[C@@H]3[C@H]4[C@@H](CC[C@@]4(CC[C@@]3(C)[C@]2(C)CC[C@H]1C1(C)C)C(=O)NCCN(CCC)CC(=O)OC)C(C)=C)C=C1C1=CC=C(C(=O)OC)C=C1 CHDVFHGMKRKZJV-MSEMWXCYSA-N 0.000 description 1
• SUHHOKAEBHSLPA-MSEMWXCYSA-N methyl 4-[(1r,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[3-[(4-methoxy-4-oxobutyl)amino]propylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoate Chemical compound C([C@]1(C)[C@H]2CC[C@@H]3[C@H]4[C@@H](CC[C@@]4(CC[C@@]3(C)[C@]2(C)CC[C@H]1C1(C)C)C(=O)NCCCNCCCC(=O)OC)C(C)=C)C=C1C1=CC=C(C(=O)OC)C=C1 SUHHOKAEBHSLPA-MSEMWXCYSA-N 0.000 description 1
• LXZJMIMQHBMKIP-MGKHDQODSA-N methyl 4-[(1r,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[3-[ethyl-(4-methoxy-4-oxobutyl)amino]propylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoate Chemical compound C([C@]1(C)[C@H]2CC[C@@H]3[C@H]4[C@@H](CC[C@@]4(CC[C@@]3(C)[C@]2(C)CC[C@H]1C1(C)C)C(=O)NCCCN(CC)CCCC(=O)OC)C(C)=C)C=C1C1=CC=C(C(=O)OC)C=C1 LXZJMIMQHBMKIP-MGKHDQODSA-N 0.000 description 1
• ADBVTNHLSCIOBK-WECSNRJHSA-N methyl 4-[(1s,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[2-(dimethylamino)ethylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC[C@]2(C)[C@@H](CC[C@H]3[C@]4(CC[C@]5(CC[C@H]([C@@H]53)C(C)C)C(=O)NCCN(C)C)C)[C@@]4(C)CC[C@H]2C1(C)C ADBVTNHLSCIOBK-WECSNRJHSA-N 0.000 description 1
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