JP5465667B2 - 抗ウイルス化合物 - Google Patents

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Publication number

JP5465667B2

JP5465667B2 JP2010514802A JP2010514802A JP5465667B2 JP 5465667 B2 JP5465667 B2 JP 5465667B2 JP 2010514802 A JP2010514802 A JP 2010514802A JP 2010514802 A JP2010514802 A JP 2010514802A JP 5465667 B2 JP5465667 B2 JP 5465667B2

Authority

JP

Japan

Prior art keywords

alkyl

optionally substituted

alkoxy

compound

alkenyl

Prior art date

2007-06-29

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 328
• 230000000840 anti-viral effect Effects 0.000 title description 5
• -1 pyrrol-1-ylcarbonyl Chemical group 0.000 claims description 362
• 125000000217 alkyl group Chemical group 0.000 claims description 233
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 211
• 125000003342 alkenyl group Chemical group 0.000 claims description 201
• 125000000304 alkynyl group Chemical group 0.000 claims description 201
• 125000003118 aryl group Chemical group 0.000 claims description 145
• 125000005843 halogen group Chemical group 0.000 claims description 145
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 143
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 135
• 239000000203 mixture Substances 0.000 claims description 113
• 229910052717 sulfur Inorganic materials 0.000 claims description 112
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 111
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 110
• 125000001072 heteroaryl group Chemical group 0.000 claims description 103
• 125000000623 heterocyclic group Chemical group 0.000 claims description 103
• 229910052760 oxygen Inorganic materials 0.000 claims description 94
• 125000004423 acyloxy group Chemical group 0.000 claims description 92
• 150000003839 salts Chemical class 0.000 claims description 88
• 125000003545 alkoxy group Chemical group 0.000 claims description 77
• 125000004432 carbon atom Chemical group C* 0.000 claims description 71
• 125000001188 haloalkyl group Chemical group 0.000 claims description 58
• 229910052801 chlorine Inorganic materials 0.000 claims description 56
• 229910052731 fluorine Inorganic materials 0.000 claims description 56
• 239000003112 inhibitor Substances 0.000 claims description 56
• 229910052794 bromium Inorganic materials 0.000 claims description 53
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 49
• 229910052736 halogen Inorganic materials 0.000 claims description 45
• 150000002367 halogens Chemical class 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 125000004429 atom Chemical group 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 229910052740 iodine Inorganic materials 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims description 32
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 29
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 27
• 125000003386 piperidinyl group Chemical group 0.000 claims description 25
• 125000005110 aryl thio group Chemical group 0.000 claims description 22
• 239000002777 nucleoside Substances 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 21
• 108010050904 Interferons Proteins 0.000 claims description 19
• 102000014150 Interferons Human genes 0.000 claims description 19
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 19
• 229940124597 therapeutic agent Drugs 0.000 claims description 19
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 208000005176 Hepatitis C Diseases 0.000 claims description 14
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
• 229940079322 interferon Drugs 0.000 claims description 13
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 12
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical class N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 10
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 10
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 230000001225 therapeutic effect Effects 0.000 claims description 9
• 229920002554 vinyl polymer Polymers 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 7
• 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 7
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• 229910052727 yttrium Inorganic materials 0.000 claims description 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
• IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 229940047124 interferons Drugs 0.000 claims description 6
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 6
• 229950006081 taribavirin Drugs 0.000 claims description 6
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 229950003954 isatoribine Drugs 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• CRCTZWNJRMZUIO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)[CH]C(F)(F)F CRCTZWNJRMZUIO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 3
• 238000013160 medical therapy Methods 0.000 claims description 3
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
• 229960000329 ribavirin Drugs 0.000 claims description 3
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 3
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
• 230000000069 prophylactic effect Effects 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
• 239000005969 1-Methyl-cyclopropene Substances 0.000 claims 1
• SHDPRTQPPWIEJG-UHFFFAOYSA-N 1-methylcyclopropene Chemical compound CC1=CC1 SHDPRTQPPWIEJG-UHFFFAOYSA-N 0.000 claims 1
• TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical group C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 112
• 125000002252 acyl group Chemical group 0.000 description 102
• 238000006243 chemical reaction Methods 0.000 description 99
• 238000000034 method Methods 0.000 description 90
• 125000004122 cyclic group Chemical group 0.000 description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 62
• 239000000651 prodrug Substances 0.000 description 57
• 229940002612 prodrug Drugs 0.000 description 57
• 235000019439 ethyl acetate Nutrition 0.000 description 50
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 50
• 239000004480 active ingredient Substances 0.000 description 45
• 239000002904 solvent Substances 0.000 description 41
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• 239000000243 solution Substances 0.000 description 37
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
• 238000009472 formulation Methods 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
• 229910052938 sodium sulfate Inorganic materials 0.000 description 35
• 235000011152 sodium sulphate Nutrition 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• 239000000047 product Substances 0.000 description 34
• 238000003786 synthesis reaction Methods 0.000 description 33
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 239000002253 acid Chemical group 0.000 description 29
• 230000015572 biosynthetic process Effects 0.000 description 29
• 238000003756 stirring Methods 0.000 description 29
• 238000005481 NMR spectroscopy Methods 0.000 description 28
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
• 239000012043 crude product Substances 0.000 description 27
• 125000004421 aryl sulphonamide group Chemical group 0.000 description 26
• 125000004193 piperazinyl group Chemical group 0.000 description 25
• 229920006395 saturated elastomer Polymers 0.000 description 25
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
• 239000007787 solid Substances 0.000 description 23
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 22
• 125000006239 protecting group Chemical group 0.000 description 22
• 239000000126 substance Substances 0.000 description 22
• 125000004422 alkyl sulphonamide group Chemical group 0.000 description 21
• 125000003710 aryl alkyl group Chemical group 0.000 description 20
• XXKQACFOJGQZTB-UHFFFAOYSA-N cyclopropyl sulfamate Chemical compound NS(=O)(=O)OC1CC1 XXKQACFOJGQZTB-UHFFFAOYSA-N 0.000 description 20
• 239000007821 HATU Substances 0.000 description 19
• 101710144111 Non-structural protein 3 Proteins 0.000 description 19
• 238000004440 column chromatography Methods 0.000 description 18
• 230000000694 effects Effects 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 16
• 108010022999 Serine Proteases Proteins 0.000 description 15
• 102000012479 Serine Proteases Human genes 0.000 description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
• 230000003993 interaction Effects 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• 125000001424 substituent group Chemical group 0.000 description 15
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 14
• 125000004104 aryloxy group Chemical group 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 239000000377 silicon dioxide Substances 0.000 description 14
• 125000002619 bicyclic group Chemical group 0.000 description 13
• 230000002401 inhibitory effect Effects 0.000 description 13
• 239000000546 pharmaceutical excipient Substances 0.000 description 13
• 239000011780 sodium chloride Substances 0.000 description 13
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 229940024606 amino acid Drugs 0.000 description 12
• 235000001014 amino acid Nutrition 0.000 description 12
• 238000000926 separation method Methods 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 238000004007 reversed phase HPLC Methods 0.000 description 11
• IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 11
• 239000003826 tablet Substances 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 10
• 150000001721 carbon Chemical group 0.000 description 10
• 125000000524 functional group Chemical group 0.000 description 10
• 238000001727 in vivo Methods 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 239000000523 sample Substances 0.000 description 10
• 229940124530 sulfonamide Drugs 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 229940090438 infergen Drugs 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
• 235000019198 oils Nutrition 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 230000008569 process Effects 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• 108010010648 interferon alfacon-1 Proteins 0.000 description 8
• 102000004190 Enzymes Human genes 0.000 description 7
• 108090000790 Enzymes Proteins 0.000 description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
• 125000005213 alkyl heteroaryl group Chemical group 0.000 description 7
• 125000005037 alkyl phenyl group Chemical group 0.000 description 7
• 125000002393 azetidinyl group Chemical group 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
• 239000012620 biological material Substances 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 229940125904 compound 1 Drugs 0.000 description 7
• 229940088598 enzyme Drugs 0.000 description 7
• 150000003949 imides Chemical class 0.000 description 7
• 125000001841 imino group Chemical group [H]N=* 0.000 description 7
• 239000004615 ingredient Substances 0.000 description 7
• 239000002207 metabolite Substances 0.000 description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 description 7
• 230000003287 optical effect Effects 0.000 description 7
• 125000000962 organic group Chemical group 0.000 description 7
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 7
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
• XOIYZMDJFLKIEI-UHFFFAOYSA-N (hydroxysulfonimidoyl)oxybenzene Chemical compound NS(=O)(=O)OC1=CC=CC=C1 XOIYZMDJFLKIEI-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
• MAQDQJWCSSCURR-UHFFFAOYSA-N 4-[5-(cyclopropanecarbonylamino)-2-(trifluoromethoxy)phenyl]-n-[4-[(4-propylsulfonylpiperazin-1-yl)methyl]phenyl]benzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=2C(=CC=C(NC(=O)C3CC3)C=2)OC(F)(F)F)C=C1 MAQDQJWCSSCURR-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 239000004215 Carbon black (E152) Substances 0.000 description 6
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