JP6285917B2 - 反応性代謝物質のスクリーニングのための捕獲剤 - Google Patents
反応性代謝物質のスクリーニングのための捕獲剤Info
- Publication number
- JP6285917B2 JP6285917B2 JP2015514156A JP2015514156A JP6285917B2 JP 6285917 B2 JP6285917 B2 JP 6285917B2 JP 2015514156 A JP2015514156 A JP 2015514156A JP 2015514156 A JP2015514156 A JP 2015514156A JP 6285917 B2 JP6285917 B2 JP 6285917B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- group
- alkyl
- certain embodiments
- Prior art date
- 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
Links
- 239000002207 metabolite Substances 0.000 title claims description 61
- 239000003795 chemical substances by application Substances 0.000 title description 19
- 238000012216 screening Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 134
- 125000000623 heterocyclic group Chemical group 0.000 claims description 116
- -1 fluoro compound Chemical class 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 75
- 125000000304 alkynyl group Chemical group 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 72
- 125000003342 alkenyl group Chemical group 0.000 claims description 70
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 61
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000006239 protecting group Chemical group 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 108090000790 Enzymes Proteins 0.000 claims description 27
- 102000004190 Enzymes Human genes 0.000 claims description 27
- 238000012360 testing method Methods 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 150000001450 anions Chemical class 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 238000001514 detection method Methods 0.000 claims description 16
- 238000004811 liquid chromatography Methods 0.000 claims description 14
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 101150053185 P450 gene Proteins 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 230000003228 microsomal effect Effects 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 210000001589 microsome Anatomy 0.000 claims description 5
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims description 3
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 claims description 3
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 10
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 claims 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 description 50
- 125000004432 carbon atom Chemical group C* 0.000 description 46
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 35
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- 229960003180 glutathione Drugs 0.000 description 17
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- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 13
- 150000001412 amines Chemical group 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 11
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 10
- 235000018417 cysteine Nutrition 0.000 description 10
- 238000002372 labelling Methods 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 229940000406 drug candidate Drugs 0.000 description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000011534 incubation Methods 0.000 description 7
- 210000001853 liver microsome Anatomy 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000000132 electrospray ionisation Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000002757 morpholinyl group Chemical group 0.000 description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 description 4
- 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 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 229960004170 clozapine Drugs 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000011533 pre-incubation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 3
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001944 cysteine derivatives Chemical class 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
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- 150000003573 thiols Chemical class 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
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- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
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- BDEZGPKAMAVGBE-UHFFFAOYSA-N s-(3-nitropyridin-2-yl)thiohydroxylamine Chemical compound NSC1=NC=CC=C1[N+]([O-])=O BDEZGPKAMAVGBE-UHFFFAOYSA-N 0.000 description 1
- LOFZYSZWOLKUGE-UHFFFAOYSA-N s-benzyl carbamothioate Chemical compound NC(=O)SCC1=CC=CC=C1 LOFZYSZWOLKUGE-UHFFFAOYSA-N 0.000 description 1
- MAGSSGQAJNNDLU-UHFFFAOYSA-N s-phenylthiohydroxylamine Chemical compound NSC1=CC=CC=C1 MAGSSGQAJNNDLU-UHFFFAOYSA-N 0.000 description 1
- PIDYQAYNSQSDQY-UHFFFAOYSA-N s-tritylthiohydroxylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SN)C1=CC=CC=C1 PIDYQAYNSQSDQY-UHFFFAOYSA-N 0.000 description 1
- BPELEZSCHIEMAE-UHFFFAOYSA-N salicylaldehyde imine Chemical compound OC1=CC=CC=C1C=N BPELEZSCHIEMAE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000003774 sulfhydryl reagent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
- 125000005886 tetrahydrobenzothienyl group Chemical group 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005305 thiadiazolinyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005458 thianyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
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- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005881 triazolinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/94—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving narcotics or drugs or pharmaceuticals, neurotransmitters or associated receptors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
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- Microbiology (AREA)
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- Pathology (AREA)
- Cell Biology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Pharmacology & Pharmacy (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Plural Heterocyclic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201261650448P | 2012-05-22 | 2012-05-22 | |
| US61/650,448 | 2012-05-22 | ||
| PCT/US2013/042246 WO2013177293A1 (en) | 2012-05-22 | 2013-05-22 | Trapping reagents for reactive metabolites screening |
Publications (3)
| Publication Number | Publication Date |
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| JP2015524058A JP2015524058A (ja) | 2015-08-20 |
| JP2015524058A5 JP2015524058A5 (enExample) | 2016-07-14 |
| JP6285917B2 true JP6285917B2 (ja) | 2018-02-28 |
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| EP (1) | EP2852678B1 (enExample) |
| JP (1) | JP6285917B2 (enExample) |
| WO (1) | WO2013177293A1 (enExample) |
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| WO2013177293A1 (en) | 2012-05-22 | 2013-11-28 | Biogen Idec Ma Inc. | Trapping reagents for reactive metabolites screening |
| EP3468563B1 (en) * | 2016-06-09 | 2023-09-13 | Oregon State University | Compounds for delivering glutathione to a target and methods of making and using the same |
| US11084897B2 (en) * | 2017-12-12 | 2021-08-10 | International Business Machines Corporation | Chemical compounds with perfluoroaryl groups that can facilitate post-synthesis functionalization |
| US11118008B2 (en) | 2018-07-06 | 2021-09-14 | International Business Machines Corporation | Ring-opening polymerizations using a flow reactor |
| JP2023525915A (ja) * | 2020-05-20 | 2023-06-19 | エフ． ホフマン－ラ ロシュ アーゲー | 質量分析のための試薬 |
| JP2023091200A (ja) * | 2021-12-20 | 2023-06-30 | 花王株式会社 | 有機化合物、試薬、及び分析方法 |
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| US5478723A (en) | 1993-09-27 | 1995-12-26 | Parkinson; Andrew | Method and apparatus for determining the role of cytochrome P450 and related enzymes in the metabolism of drugs and other chemicals |
| US5891696A (en) | 1996-08-02 | 1999-04-06 | Panvera Corporation | Compositions for cytochrome P450 biotransformation reactions |
| US6830897B2 (en) * | 2000-04-26 | 2004-12-14 | Pfizer Inc. | High throughput screen for reducing drug candidate attrition |
| DK1425586T3 (da) * | 2001-09-14 | 2008-02-11 | Electrophoretics Ltd | Massemarkörer |
| AU2002952747A0 (en) | 2002-11-18 | 2002-12-05 | Ludwig Institute For Cancer Research | Method for analysing peptides |
| WO2004109279A2 (en) | 2003-06-09 | 2004-12-16 | Pfizer Products Inc. | Sensitive and selective in vitro assay for the detection of reactive drug intermediates |
| US7169576B2 (en) | 2004-01-08 | 2007-01-30 | Bristol-Myers Squibb Company | Method for identifying drug metabolites with dansylated glutathione |
| JP4566604B2 (ja) * | 2004-03-31 | 2010-10-20 | 塩野義製薬株式会社 | 糖鎖標識試薬 |
| US7445909B2 (en) * | 2004-06-28 | 2008-11-04 | Janssen Phamaceutica N.V. | Method for detecting reactive metabolites using a combination of glutathione and a stable isotopic derivative of glutathione and mass spectroscopy-based pattern recognition |
| JPWO2006080210A1 (ja) * | 2005-01-27 | 2008-06-19 | 国立大学法人 北海道大学 | イオン化効率を向上させるための試薬、方法およびキット、並びにその利用 |
| WO2008042634A2 (en) * | 2006-09-29 | 2008-04-10 | Janssen Pharmaceutica, N.V. | Isotopically labeled trapping agent and method for identifying reactive metabolites |
| CA2686997A1 (en) | 2007-05-11 | 2008-11-20 | Mpex Pharmaceuticals, Inc. | Quaternary alkyl ammonium bacterial efflux pump inhibitors and therapeutic uses thereof |
| PL2225261T3 (pl) | 2007-12-03 | 2016-09-30 | Inhibitory boropeptydowe enteropeptydaz i ich zastosowania w leczeniu otyłości, nadwagi i/lub chorób związanych z nieprawidłowym metabolizmem tłuszczów | |
| WO2010122673A1 (en) * | 2009-04-23 | 2010-10-28 | Eisai R&D Management Co., Ltd. | Trapping compounds and method for identifying reactive metabolites |
| WO2011025366A1 (en) * | 2009-08-25 | 2011-03-03 | Antec Leyden B.V. | A method of screening agents for their impact on nucleic acid oxidation reactions |
| WO2011159685A2 (en) | 2010-06-16 | 2011-12-22 | The Regents Of The University Of Michigan | Inhibition of wdr5 interaction with its binding partners and therapeutic methods |
| WO2013177293A1 (en) | 2012-05-22 | 2013-11-28 | Biogen Idec Ma Inc. | Trapping reagents for reactive metabolites screening |
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| US10100081B2 (en) | 2018-10-16 |
| JP2015524058A (ja) | 2015-08-20 |
| US9581605B2 (en) | 2017-02-28 |
| US20150168430A1 (en) | 2015-06-18 |
| WO2013177293A1 (en) | 2013-11-28 |
| EP2852678B1 (en) | 2017-08-23 |
| US20170183378A1 (en) | 2017-06-29 |
| EP2852678A1 (en) | 2015-04-01 |
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