ES2974657T3 - Derivados de n-substituido-6-oxo-1,6-dihidropirimidina-2-ilo como inhibidores de la replicación del virus de inmunodeficiencia humana - Google Patents

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Publication number

ES2974657T3

ES2974657T3 ES20789276T ES20789276T ES2974657T3 ES 2974657 T3 ES2974657 T3 ES 2974657T3 ES 20789276 T ES20789276 T ES 20789276T ES 20789276 T ES20789276 T ES 20789276T ES 2974657 T3 ES2974657 T3 ES 2974657T3

Authority

ES

Spain

Prior art keywords

chloro

ethyl

indazol

difluorophenyl

oxo

Prior art date

2019-10-01

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 241000725303 Human immunodeficiency virus Species 0.000 title abstract description 18
• 239000003112 inhibitor Substances 0.000 title description 4
• 230000029812 viral genome replication Effects 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 215
• 150000003839 salts Chemical class 0.000 claims abstract description 71
• -1 -OCHF2 Chemical group 0.000 claims description 46
• 235000019000 fluorine Nutrition 0.000 claims description 23
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 208000031886 HIV Infections Diseases 0.000 claims description 13
• 208000037357 HIV infectious disease Diseases 0.000 claims description 12
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 229950004159 bictegravir Drugs 0.000 claims description 4
• SOLUWJRYJLAZCX-LYOVBCGYSA-N bictegravir Chemical compound C([C@H]1O[C@@H]2CC[C@@H](C2)N1C(=O)C1=C(C2=O)O)N1C=C2C(=O)NCC1=C(F)C=C(F)C=C1F SOLUWJRYJLAZCX-LYOVBCGYSA-N 0.000 claims description 4
• 229950005928 cabotegravir Drugs 0.000 claims description 4
• WCWSTNLSLKSJPK-LKFCYVNXSA-N cabotegravir Chemical compound C([C@H]1OC[C@@H](N1C(=O)C1=C(O)C2=O)C)N1C=C2C(=O)NCC1=CC=C(F)C=C1F WCWSTNLSLKSJPK-LKFCYVNXSA-N 0.000 claims description 4
• 229960002542 dolutegravir Drugs 0.000 claims description 4
• RHWKPHLQXYSBKR-BMIGLBTASA-N dolutegravir Chemical compound C([C@@H]1OCC[C@H](N1C(=O)C1=C(O)C2=O)C)N1C=C2C(=O)NCC1=CC=C(F)C=C1F RHWKPHLQXYSBKR-BMIGLBTASA-N 0.000 claims description 4
• 229950010812 fostemsavir Drugs 0.000 claims description 4
• SWMDAPWAQQTBOG-UHFFFAOYSA-N fostemsavir Chemical compound C1=2N(COP(O)(O)=O)C=C(C(=O)C(=O)N3CCN(CC3)C(=O)C=3C=CC=CC=3)C=2C(OC)=CN=C1N1C=NC(C)=N1 SWMDAPWAQQTBOG-UHFFFAOYSA-N 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 229960001627 lamivudine Drugs 0.000 claims description 4
• JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 238000010255 intramuscular injection Methods 0.000 claims description 3
• 239000007927 intramuscular injection Substances 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 238000010254 subcutaneous injection Methods 0.000 claims description 2
• 239000007929 subcutaneous injection Substances 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 169
• 238000000034 method Methods 0.000 abstract description 165
• 208000015181 infectious disease Diseases 0.000 abstract description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 296
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 224
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 116
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
• 239000000243 solution Substances 0.000 description 99
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 97
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 92
• 235000019439 ethyl acetate Nutrition 0.000 description 88
• 238000005160 1H NMR spectroscopy Methods 0.000 description 85
• 238000006243 chemical reaction Methods 0.000 description 83
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
• 230000014759 maintenance of location Effects 0.000 description 78
• 150000002500 ions Chemical class 0.000 description 64
• 239000007819 coupling partner Substances 0.000 description 59
• 238000002474 experimental method Methods 0.000 description 57
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 54
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 42
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 239000012267 brine Substances 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• 239000000706 filtrate Substances 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 239000000047 product Substances 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 238000000746 purification Methods 0.000 description 28
• 239000012044 organic layer Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• 238000001914 filtration Methods 0.000 description 21
• 239000000463 material Substances 0.000 description 21
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 21
• 238000003756 stirring Methods 0.000 description 21
• 238000003828 vacuum filtration Methods 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 238000010898 silica gel chromatography Methods 0.000 description 16
• 238000004128 high performance liquid chromatography Methods 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 14
• 239000000725 suspension Substances 0.000 description 13
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 12
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
• 235000019253 formic acid Nutrition 0.000 description 11
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• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
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• 229940086542 triethylamine Drugs 0.000 description 10
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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