ES2886964T3 - Compuestos de indol sustituidos con [1,2,4]triazolo[1,5-a]piridinilo - Google Patents

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Publication number

ES2886964T3

ES2886964T3 ES17737442T ES17737442T ES2886964T3 ES 2886964 T3 ES2886964 T3 ES 2886964T3 ES 17737442 T ES17737442 T ES 17737442T ES 17737442 T ES17737442 T ES 17737442T ES 2886964 T3 ES2886964 T3 ES 2886964T3

Authority

ES

Spain

Prior art keywords

crxrx

triazolo

isopropyl

indol

piperidin

Prior art date

2016-06-29

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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• -1 [1,2,4]triazolo[1,5-a]pyridinyl-substituted indole compounds Chemical class 0.000 title claims abstract description 336
• 150000001875 compounds Chemical class 0.000 claims abstract description 317
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 168
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 146
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 125
• 150000003839 salts Chemical class 0.000 claims abstract description 86
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 60
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 57
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 56
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 52
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 49
• 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 48
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 45
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 41
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 40
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 39
• 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 37
• 125000001425 triazolyl group Chemical group 0.000 claims abstract description 37
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 34
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 32
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 31
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 31
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 29
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 29
• 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 27
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 27
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 26
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
• 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 24
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 22
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 22
• 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 20
• 125000001424 substituent group Chemical group 0.000 claims abstract description 19
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 18
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 15
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
• 125000002541 furyl group Chemical group 0.000 claims abstract description 13
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 11
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 9
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000004799 bromophenyl group Chemical group 0.000 claims abstract description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
• 235000019256 formaldehyde Nutrition 0.000 claims abstract description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 8
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 7
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 7
• 125000005843 halogen group Chemical group 0.000 claims abstract description 6
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims abstract description 4
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims abstract description 4
• 239000000203 mixture Substances 0.000 claims description 74
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 69
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 46
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 34
• 201000006417 multiple sclerosis Diseases 0.000 claims description 28
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 25
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 24
• 238000011282 treatment Methods 0.000 claims description 24
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 23
• DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 17
• VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 12
• 208000023275 Autoimmune disease Diseases 0.000 claims description 11
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 6
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
• 208000037976 chronic inflammation Diseases 0.000 claims description 3
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004428 fluoroalkoxy group Chemical group 0.000 abstract description 8
• 125000000532 dioxanyl group Chemical group 0.000 abstract description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 187
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 129
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
• 239000011541 reaction mixture Substances 0.000 description 108
• 239000000243 solution Substances 0.000 description 95
• 239000000543 intermediate Substances 0.000 description 81
• 235000002639 sodium chloride Nutrition 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 71
• 235000019439 ethyl acetate Nutrition 0.000 description 68
• 239000012071 phase Substances 0.000 description 59
• 238000000034 method Methods 0.000 description 58
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• 238000006243 chemical reaction Methods 0.000 description 55
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
• 239000007787 solid Substances 0.000 description 48
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
• 229910052938 sodium sulfate Inorganic materials 0.000 description 40
• 235000011152 sodium sulphate Nutrition 0.000 description 40
• 125000004093 cyano group Chemical group *C#N 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 32
• 229910052796 boron Inorganic materials 0.000 description 31
• 239000012267 brine Substances 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• 239000012044 organic layer Substances 0.000 description 29
• 239000000725 suspension Substances 0.000 description 29
• 239000010410 layer Substances 0.000 description 28
• 102100039390 Toll-like receptor 7 Human genes 0.000 description 27
• 239000000460 chlorine Substances 0.000 description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 26
• 239000000047 product Substances 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 239000000463 material Substances 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 20
• 238000010898 silica gel chromatography Methods 0.000 description 20
• 201000010099 disease Diseases 0.000 description 19
• 239000002904 solvent Substances 0.000 description 19
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 19
• 102100033110 Toll-like receptor 8 Human genes 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 238000005160 1H NMR spectroscopy Methods 0.000 description 17
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 17
• 239000007832 Na2SO4 Substances 0.000 description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 239000012453 solvate Substances 0.000 description 16
• 239000003039 volatile agent Substances 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• 239000003814 drug Substances 0.000 description 15
• 238000004519 manufacturing process Methods 0.000 description 15
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 14
• 238000007792 addition Methods 0.000 description 14
• 230000014759 maintenance of location Effects 0.000 description 14
• 230000007170 pathology Effects 0.000 description 14
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 13
• 239000013058 crude material Substances 0.000 description 13
• 102000002689 Toll-like receptor Human genes 0.000 description 12
• 108020000411 Toll-like receptor Proteins 0.000 description 12
• 239000003643 water by type Substances 0.000 description 12
• 239000005695 Ammonium acetate Substances 0.000 description 11
• 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 description 11
• 241000124008 Mammalia Species 0.000 description 11
• 235000019257 ammonium acetate Nutrition 0.000 description 11
• 229940043376 ammonium acetate Drugs 0.000 description 11
• 238000001514 detection method Methods 0.000 description 11
• 239000003208 petroleum Substances 0.000 description 11
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
• WUCKVOFPRDTZDL-UHFFFAOYSA-N 6-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC=2N(C=1)N=CN=2 WUCKVOFPRDTZDL-UHFFFAOYSA-N 0.000 description 10
• 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Substances BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
• 238000004128 high performance liquid chromatography Methods 0.000 description 10
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 10
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• 239000002671 adjuvant Substances 0.000 description 9
• 239000012043 crude product Substances 0.000 description 9
• 239000003995 emulsifying agent Substances 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• 239000002245 particle Substances 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 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
• NZMVKBPHIXDNBP-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C)C NZMVKBPHIXDNBP-UHFFFAOYSA-N 0.000 description 8
• OYGHORQLTGXZKY-UHFFFAOYSA-N 6-bromo-8-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC(Br)=CN2N=CN=C12 OYGHORQLTGXZKY-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 8
• 150000001721 carbon Chemical group 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 239000003755 preservative agent Substances 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• YRHLNCNBWPTVPJ-UHFFFAOYSA-N tert-butyl 4-(2-bromo-3-propan-2-yl-1H-indol-5-yl)piperidine-1-carboxylate Chemical compound BrC=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(=O)OC(C)(C)C YRHLNCNBWPTVPJ-UHFFFAOYSA-N 0.000 description 8
• DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 7
• LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 7
• 108010060825 Toll-Like Receptor 7 Proteins 0.000 description 7
• 108010060752 Toll-Like Receptor 8 Proteins 0.000 description 7
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 239000000872 buffer Substances 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 235000014113 dietary fatty acids Nutrition 0.000 description 7
• 229910001873 dinitrogen Inorganic materials 0.000 description 7
• 208000035475 disorder Diseases 0.000 description 7
• 239000000194 fatty acid Substances 0.000 description 7
• 229930195729 fatty acid Natural products 0.000 description 7
• 150000004665 fatty acids Chemical class 0.000 description 7
• 239000000796 flavoring agent Substances 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000000546 pharmaceutical excipient Substances 0.000 description 7
• 229940124597 therapeutic agent Drugs 0.000 description 7
• BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 6
• SNFVHLQYHFQOEP-UHFFFAOYSA-N 2-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]acetamide Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CCN(CC1)CC(=O)N)N=CN=2)C SNFVHLQYHFQOEP-UHFFFAOYSA-N 0.000 description 6
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