TW200407125A - Indolinones substituted by heterocycles, the preparation thereof and their use as medicaments - Google Patents

Info

Publication number

TW200407125A

TW200407125A TW092125060A TW92125060A TW200407125A TW 200407125 A TW200407125 A TW 200407125A TW 092125060 A TW092125060 A TW 092125060A TW 92125060 A TW92125060 A TW 92125060A TW 200407125 A TW200407125 A TW 200407125A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

amino

methylene

phenylamino

Prior art date

2002-09-12

Links

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• Global Dossier
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• 238000002360 preparation method Methods 0.000 title claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 title claims description 7
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical group C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title abstract description 13
• 239000003814 drug Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 136
• 239000000203 mixture Substances 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 239000000651 prodrug Substances 0.000 claims abstract description 14
• 229940002612 prodrug Drugs 0.000 claims abstract description 14
• 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 claims abstract description 11
• 238000000034 method Methods 0.000 claims abstract description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
• -1 phenyl Chemical group 0.000 claims description 767
• 125000000217 alkyl group Chemical group 0.000 claims description 270
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 159
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 147
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 125
• QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 123
• 125000003277 amino group Chemical group 0.000 claims description 107
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
• 239000000460 chlorine Substances 0.000 claims description 97
• 150000002576 ketones Chemical class 0.000 claims description 97
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 79
• FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 claims description 76
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 72
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 71
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
• 229910052757 nitrogen Inorganic materials 0.000 claims description 65
• 150000001412 amines Chemical class 0.000 claims description 59
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 57
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 54
• 125000003282 alkyl amino group Chemical group 0.000 claims description 51
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 48
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 43
• 229910052717 sulfur Inorganic materials 0.000 claims description 43
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 42
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 41
• 125000004434 sulfur atom Chemical group 0.000 claims description 40
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 36
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 35
• 229910052760 oxygen Inorganic materials 0.000 claims description 35
• 239000001301 oxygen Substances 0.000 claims description 35
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 31
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
• 229910052731 fluorine Inorganic materials 0.000 claims description 29
• 125000004076 pyridyl group Chemical group 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 27
• 229910052801 chlorine Inorganic materials 0.000 claims description 27
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 26
• 239000011737 fluorine Chemical group 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 26
• 150000003254 radicals Chemical class 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 23
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
• 239000007789 gas Chemical group 0.000 claims description 22
• 150000001721 carbon Chemical group 0.000 claims description 21
• 238000006243 chemical reaction Methods 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 238000006467 substitution reaction Methods 0.000 claims description 21
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 16
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
• 239000005977 Ethylene Substances 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000000879 imine group Chemical group 0.000 claims description 15
• 125000006239 protecting group Chemical group 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
• 241000790917 Dioxys <bee> Species 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 235000019256 formaldehyde Nutrition 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
• 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 239000007790 solid phase Substances 0.000 claims description 9
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 8
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 150000007857 hydrazones Chemical class 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 150000003973 alkyl amines Chemical class 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 238000003776 cleavage reaction Methods 0.000 claims description 5
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 150000003951 lactams Chemical group 0.000 claims description 5
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 5
• 230000003647 oxidation Effects 0.000 claims description 5
• 238000007254 oxidation reaction Methods 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 230000007017 scission Effects 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000000732 arylene group Chemical group 0.000 claims description 4
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
• 238000001727 in vivo Methods 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000006850 spacer group Chemical group 0.000 claims description 4
• 239000004575 stone Substances 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
• 230000007062 hydrolysis Effects 0.000 claims description 3
• 238000006460 hydrolysis reaction Methods 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• 235000013336 milk Nutrition 0.000 claims description 3
• 239000008267 milk Substances 0.000 claims description 3
• 210000004080 milk Anatomy 0.000 claims description 3
• 150000007522 mineralic acids Chemical class 0.000 claims description 3
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 150000007524 organic acids Chemical class 0.000 claims description 3
• 229910052700 potassium Inorganic materials 0.000 claims description 3
• 125000006308 propyl amino group Chemical group 0.000 claims description 3
• 229910052701 rubidium Inorganic materials 0.000 claims description 3
• 239000007787 solid Substances 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
• 239000011593 sulfur Chemical group 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 2
• FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 claims description 2
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical group NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
• YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
• 150000001298 alcohols Chemical group 0.000 claims description 2
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 150000004808 allyl alcohols Chemical group 0.000 claims description 2
• JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
• 230000009435 amidation Effects 0.000 claims description 2
• 238000007112 amidation reaction Methods 0.000 claims description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 230000000747 cardiac effect Effects 0.000 claims description 2
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
• 150000001924 cycloalkanes Chemical class 0.000 claims description 2
• 125000005597 hydrazone group Chemical group 0.000 claims description 2
• 150000002825 nitriles Chemical class 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 2
• UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims 2
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical group NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims 2
• VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical group CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 claims 2
• 125000002947 alkylene group Chemical group 0.000 claims 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
• 125000001725 pyrenyl group Chemical group 0.000 claims 2
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
• NPEJFBUPPBOECB-UHFFFAOYSA-N C(Cl)Cl.ClC1=CC=C2CC(NC2=C1)=O Chemical compound C(Cl)Cl.ClC1=CC=C2CC(NC2=C1)=O NPEJFBUPPBOECB-UHFFFAOYSA-N 0.000 claims 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
• 241000272165 Charadriidae Species 0.000 claims 1
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
• 241000282376 Panthera tigris Species 0.000 claims 1
• 230000002159 abnormal effect Effects 0.000 claims 1
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
• 125000006319 alkynyl amino group Chemical group 0.000 claims 1
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
• 239000003963 antioxidant agent Substances 0.000 claims 1
• CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 1
• 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
• 210000000988 bone and bone Anatomy 0.000 claims 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
• 239000003575 carbonaceous material Substances 0.000 claims 1
• 239000013256 coordination polymer Substances 0.000 claims 1
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical group N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• 230000000694 effects Effects 0.000 claims 1
• 230000007613 environmental effect Effects 0.000 claims 1
• 230000000762 glandular Effects 0.000 claims 1
• 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• 150000003949 imides Chemical class 0.000 claims 1
• 239000011630 iodine Substances 0.000 claims 1
• 239000011733 molybdenum Substances 0.000 claims 1
• 229910052750 molybdenum Inorganic materials 0.000 claims 1
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims 1
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims 1
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• 230000020477 pH reduction Effects 0.000 claims 1
• 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 claims 1
• 125000001151 peptidyl group Chemical group 0.000 claims 1
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