BR112021002089A2 - benzimidazóis substituídos como inibidores de pad4 - Google Patents

Info

Publication number

BR112021002089A2

BR112021002089A2 BR112021002089-6A BR112021002089A BR112021002089A2 BR 112021002089 A2 BR112021002089 A2 BR 112021002089A2 BR 112021002089 A BR112021002089 A BR 112021002089A BR 112021002089 A2 BR112021002089 A2 BR 112021002089A2

Authority

BR

Brazil

Prior art keywords

substituted

occurrence

independently selected

alkyl

4alkyl

Prior art date

2018-08-08

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• 239000003112 inhibitor Substances 0.000 title abstract description 21
• 150000001556 benzimidazoles Chemical class 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 237
• 239000000203 mixture Substances 0.000 claims abstract description 179
• 238000000034 method Methods 0.000 claims abstract description 139
• 101100406797 Arabidopsis thaliana PAD4 gene Proteins 0.000 claims abstract description 62
• 101150094373 Padi4 gene Proteins 0.000 claims abstract description 62
• 102100035731 Protein-arginine deiminase type-4 Human genes 0.000 claims abstract description 62
• -1 -ORb Chemical group 0.000 claims description 202
• 229910052731 fluorine Inorganic materials 0.000 claims description 152
• 229910052801 chlorine Inorganic materials 0.000 claims description 137
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 133
• 125000000623 heterocyclic group Chemical group 0.000 claims description 119
• 229910052794 bromium Inorganic materials 0.000 claims description 111
• 229910052739 hydrogen Inorganic materials 0.000 claims description 105
• 150000003839 salts Chemical class 0.000 claims description 105
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 103
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 102
• 229910052705 radium Inorganic materials 0.000 claims description 102
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 72
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 68
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 57
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 54
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 229910052702 rhenium Inorganic materials 0.000 claims description 46
• 229910021481 rutherfordium Inorganic materials 0.000 claims description 45
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 35
• 239000003814 drug Substances 0.000 claims description 32
• 229910052701 rubidium Inorganic materials 0.000 claims description 31
• 201000010099 disease Diseases 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 26
• 208000035475 disorder Diseases 0.000 claims description 24
• 101150105130 RORB gene Proteins 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 20
• 230000001404 mediated effect Effects 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229940124597 therapeutic agent Drugs 0.000 claims description 14
• 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 12
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 12
• 201000011510 cancer Diseases 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 9
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 9
• 239000003981 vehicle Substances 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 206010025135 lupus erythematosus Diseases 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
• 206010009887 colitis Diseases 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 3
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 3
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 3
• 101150063022 CHRD gene Proteins 0.000 claims description 3
• 101100274355 Danio rerio chd gene Proteins 0.000 claims description 3
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 3
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 3
• 239000012472 biological sample Substances 0.000 claims description 3
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 3
• 230000005764 inhibitory process Effects 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 190
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 189
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 146
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 133
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 105
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
• 238000006243 chemical reaction Methods 0.000 description 98
• 235000002639 sodium chloride Nutrition 0.000 description 96
• 239000000460 chlorine Substances 0.000 description 95
• 229910052796 boron Inorganic materials 0.000 description 94
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 73
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 71
• 239000012071 phase Substances 0.000 description 71
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 70
• 239000000047 product Substances 0.000 description 61
• 239000000243 solution Substances 0.000 description 61
• 230000014759 maintenance of location Effects 0.000 description 54
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 52
• 238000001023 centrifugal evaporation Methods 0.000 description 52
• 238000005160 1H NMR spectroscopy Methods 0.000 description 51
• 238000004128 high performance liquid chromatography Methods 0.000 description 50
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 50
• 239000005695 Ammonium acetate Substances 0.000 description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
• 235000019257 ammonium acetate Nutrition 0.000 description 48
• 229940043376 ammonium acetate Drugs 0.000 description 48
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
• 235000019439 ethyl acetate Nutrition 0.000 description 36
• 239000007787 solid Substances 0.000 description 36
• 239000002245 particle Substances 0.000 description 33
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 32
• 239000000543 intermediate Substances 0.000 description 32
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
• IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 30
• 235000011152 sodium sulphate Nutrition 0.000 description 26
• 239000002253 acid Substances 0.000 description 25
• 239000013058 crude material Substances 0.000 description 25
• 229910052938 sodium sulfate Inorganic materials 0.000 description 25
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
• 239000013014 purified material Substances 0.000 description 24
• 230000001960 triggered effect Effects 0.000 description 23
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 17
• 239000002552 dosage form Substances 0.000 description 17
• 239000012267 brine Substances 0.000 description 16
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 15
• 230000000694 effects Effects 0.000 description 15
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 13
• 201000004681 Psoriasis Diseases 0.000 description 13
• 206010047115 Vasculitis Diseases 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 150000002500 ions Chemical class 0.000 description 13
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• 239000007858 starting material Substances 0.000 description 13
• 239000012258 stirred mixture Substances 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
• 239000000463 material Substances 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• 238000001914 filtration Methods 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• 208000006673 asthma Diseases 0.000 description 10
• 230000005587 bubbling Effects 0.000 description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• OCZTYXQNTCGWTC-ZJSFPPFMSA-N tert-butyl N-[(1R,4R,7R)-2-[2-[7-bromo-1-(cyclopropylmethyl)indol-2-yl]-7-methoxy-1-methylbenzimidazole-5-carbonyl]-2-azabicyclo[2.2.1]heptan-7-yl]carbamate Chemical compound BrC=1C=CC=C2C=C(N(C=12)CC1CC1)C1=NC2=C(N1C)C(=CC(=C2)C(=O)N1[C@@H]2CC[C@H](C1)[C@H]2NC(OC(C)(C)C)=O)OC OCZTYXQNTCGWTC-ZJSFPPFMSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
• TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical compound CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 206010061218 Inflammation Diseases 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
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• 238000010828 elution Methods 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 125000000524 functional group Chemical group 0.000 description 8
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• 239000012453 solvate Substances 0.000 description 8
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
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• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 231100000252 nontoxic Toxicity 0.000 description 7
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• 235000017550 sodium carbonate Nutrition 0.000 description 7
• 230000001629 suppression Effects 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
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• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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• 125000001072 heteroaryl group Chemical group 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
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