FR3049603A1 - - Google Patents

Info

Publication number

FR3049603A1

FR3049603A1 FR1752607A FR1752607A FR3049603A1 FR 3049603 A1 FR3049603 A1 FR 3049603A1 FR 1752607 A FR1752607 A FR 1752607A FR 1752607 A FR1752607 A FR 1752607A FR 3049603 A1 FR3049603 A1 FR 3049603A1

Authority

FR

France

Prior art keywords

amino

diamine

imidazole

group

methyl

Prior art date

2016-04-05

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.)

Pending

Links

• Espacenet
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• 239000003795 chemical substances by application Substances 0.000 claims abstract description 105
• 150000001875 compounds Chemical class 0.000 claims abstract description 83
• 230000003647 oxidation Effects 0.000 claims abstract description 71
• 238000007254 oxidation reaction Methods 0.000 claims abstract description 71
• 239000002243 precursor Substances 0.000 claims abstract description 44
• 210000004209 hair Anatomy 0.000 claims abstract description 35
• 239000000835 fiber Substances 0.000 claims abstract description 24
• 239000002537 cosmetic Substances 0.000 claims abstract description 10
• 230000004048 modification Effects 0.000 claims abstract description 7
• 238000012986 modification Methods 0.000 claims abstract description 7
• -1 4-N-methyl-1H-imidazole-4,5-diamine 1,4-N-dimethyl-1H-imidazole-4,5-diamine Chemical compound 0.000 claims description 78
• 239000001257 hydrogen Substances 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• WCPGNFONICRLCL-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C(N)=C1 WCPGNFONICRLCL-UHFFFAOYSA-N 0.000 claims description 13
• BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 claims description 13
• ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• SYRZWFBWUASJJI-UHFFFAOYSA-N 3-amino-2,4-dichlorophenol Chemical compound NC1=C(Cl)C=CC(O)=C1Cl SYRZWFBWUASJJI-UHFFFAOYSA-N 0.000 claims description 12
• XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 claims description 12
• FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 11
• BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 11
• DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 11
• ATCBPVDYYNJHSG-UHFFFAOYSA-N 6-methoxy-2-n-methylpyridine-2,3-diamine Chemical compound CNC1=NC(OC)=CC=C1N ATCBPVDYYNJHSG-UHFFFAOYSA-N 0.000 claims description 11
• MWKPYVXITDAZLL-UHFFFAOYSA-N 4-[3-(2,4-diaminophenoxy)propoxy]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OCCCOC1=CC=C(N)C=C1N MWKPYVXITDAZLL-UHFFFAOYSA-N 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 claims description 10
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 6
• 229940018563 3-aminophenol Drugs 0.000 claims description 6
• GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
• WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 4
• SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 claims description 4
• KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 claims description 4
• CUICFFAIFHJGBA-UHFFFAOYSA-N 1-ethyl-5-N-methylimidazole-4,5-diamine Chemical compound C(C)N1C=NC(=C1NC)N CUICFFAIFHJGBA-UHFFFAOYSA-N 0.000 claims description 3
• XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 claims description 3
• ORVPXPKEZLTMNW-UHFFFAOYSA-N 1h-indol-7-ol Chemical compound OC1=CC=CC2=C1NC=C2 ORVPXPKEZLTMNW-UHFFFAOYSA-N 0.000 claims description 3
• OWWAUBQOFLVUMS-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-ol Chemical compound OC1=CC=CC2=C1CCN2 OWWAUBQOFLVUMS-UHFFFAOYSA-N 0.000 claims description 3
• BXBOXUNPNIJELB-UHFFFAOYSA-N 2,6-dimethoxypyridine-3,5-diamine Chemical compound COC1=NC(OC)=C(N)C=C1N BXBOXUNPNIJELB-UHFFFAOYSA-N 0.000 claims description 3
• ILDXSRFKXABMHH-UHFFFAOYSA-N 2-(2-aminophenyl)ethanol Chemical compound NC1=CC=CC=C1CCO ILDXSRFKXABMHH-UHFFFAOYSA-N 0.000 claims description 3
• FZQCIWKUHYZRGY-UHFFFAOYSA-N 4-(2-methoxyethoxy)-5-methylbenzene-1,3-diamine Chemical compound COCCOC1=C(C)C=C(N)C=C1N FZQCIWKUHYZRGY-UHFFFAOYSA-N 0.000 claims description 3
• JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 claims description 3
• NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 3
• YGRFRBUGAPOJDU-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-2-methylphenol Chemical compound CC1=CC=C(NCCO)C=C1O YGRFRBUGAPOJDU-UHFFFAOYSA-N 0.000 claims description 3
• WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 claims description 3
• KIEGFAYDOKCBOK-UHFFFAOYSA-N 6-hydroxy-4,5-dimethyl-1h-pyridin-2-one Chemical compound CC1=CC(=O)NC(O)=C1C KIEGFAYDOKCBOK-UHFFFAOYSA-N 0.000 claims description 3
• SUQYMOUHKJQBFC-UHFFFAOYSA-N N-acetyl-N-(5-amino-1H-imidazol-4-yl)acetamide Chemical compound C(C)(=O)N(C(C)=O)C=1N=CNC=1N SUQYMOUHKJQBFC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
• SARALLORMJLZBH-UHFFFAOYSA-N 2-[3-(2-hydroxyethylamino)-4-methoxy-5-methylanilino]ethanol Chemical compound COC1=C(C)C=C(NCCO)C=C1NCCO SARALLORMJLZBH-UHFFFAOYSA-N 0.000 claims description 2
• MBEMOPZODLTRQR-UHFFFAOYSA-N 4-N-ethyl-5-N,1-dimethylimidazole-4,5-diamine Chemical compound C(C)NC=1N=CN(C=1NC)C MBEMOPZODLTRQR-UHFFFAOYSA-N 0.000 claims description 2
• IDMNXIMPWQGMDO-UHFFFAOYSA-N 4-[3-(2,4-diaminophenyl)propyl]benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1CCCC1=CC=C(N)C=C1N IDMNXIMPWQGMDO-UHFFFAOYSA-N 0.000 claims description 2
• SPNBXQUPIHKTMI-UHFFFAOYSA-N 5-amino-2-(1-hydroxyethoxy)phenol Chemical compound CC(O)OC1=CC=C(N)C=C1O SPNBXQUPIHKTMI-UHFFFAOYSA-N 0.000 claims description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• 125000000217 alkyl group Chemical group 0.000 claims 1
• 239000000975 dye Substances 0.000 description 49
• 239000002253 acid Substances 0.000 description 30
• 239000007800 oxidant agent Substances 0.000 description 24
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 21
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 20
• 238000004040 coloring Methods 0.000 description 18
• 238000002360 preparation method Methods 0.000 description 16
• 239000003607 modifier Substances 0.000 description 14
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 13
• 239000000203 mixture Substances 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• 239000003086 colorant Substances 0.000 description 12
• 239000000982 direct dye Substances 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 11
• 239000003581 cosmetic carrier Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 9
• NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 8
• OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 7
• 229960001484 edetic acid Drugs 0.000 description 7
• RBUQOUQQUQCSAU-UHFFFAOYSA-N 2-(4-aminoanilino)ethanol Chemical compound NC1=CC=C(NCCO)C=C1 RBUQOUQQUQCSAU-UHFFFAOYSA-N 0.000 description 6
• AVKBLCWBDLLVRL-UHFFFAOYSA-N 2-(methoxymethyl)benzene-1,4-diamine Chemical compound COCC1=CC(N)=CC=C1N AVKBLCWBDLLVRL-UHFFFAOYSA-N 0.000 description 6
• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
• OBKIYHLUVHZNHW-UHFFFAOYSA-N N-(5-amino-1H-imidazol-4-yl)acetamide Chemical compound NC1=C(N=CN1)NC(C)=O OBKIYHLUVHZNHW-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 229920001577 copolymer Polymers 0.000 description 6
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 6
• IGBSXRIJNMDLFB-UHFFFAOYSA-N ethane-1,2-diamine;pentanedioic acid Chemical compound NCCN.OC(=O)CCCC(O)=O.OC(=O)CCCC(O)=O IGBSXRIJNMDLFB-UHFFFAOYSA-N 0.000 description 6
• 239000002453 shampoo Substances 0.000 description 6
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 5
• SNICMBLBGTVRFJ-UHFFFAOYSA-N 1h-imidazole-4,5-diamine Chemical compound NC=1N=CNC=1N SNICMBLBGTVRFJ-UHFFFAOYSA-N 0.000 description 5
• KDBUTNSQYYLYOY-UHFFFAOYSA-N 2-(4,5-diaminopyrazol-1-yl)ethanol Chemical compound NC=1C=NN(CCO)C=1N KDBUTNSQYYLYOY-UHFFFAOYSA-N 0.000 description 5
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
• OZCJSIBGTRKJGX-UHFFFAOYSA-N 4-methylcyclohexa-1,5-diene-1,4-diamine Chemical compound CC1(N)CC=C(N)C=C1 OZCJSIBGTRKJGX-UHFFFAOYSA-N 0.000 description 5
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
• QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 5
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
• DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 5
• 238000000034 method Methods 0.000 description 5
• 230000021962 pH elevation Effects 0.000 description 5
• 229960003330 pentetic acid Drugs 0.000 description 5
• 229920001296 polysiloxane Polymers 0.000 description 5
• 150000003254 radicals Chemical class 0.000 description 5
• DIQACTBUSSPHPP-UHFFFAOYSA-N 1-methylimidazole-4,5-diamine Chemical compound CN1C=NC(N)=C1N DIQACTBUSSPHPP-UHFFFAOYSA-N 0.000 description 4
• AEIPQBDABDYFRX-UHFFFAOYSA-N 4-N-ethyl-1H-imidazole-4,5-diamine Chemical compound C(C)NC=1N=CNC=1N AEIPQBDABDYFRX-UHFFFAOYSA-N 0.000 description 4
• FXJVOMGEEWGLDV-UHFFFAOYSA-N 4-N-methyl-1H-imidazole-4,5-diamine Chemical compound CNC=1N=CNC=1N FXJVOMGEEWGLDV-UHFFFAOYSA-N 0.000 description 4
• RJSKHKSQNARRMQ-UHFFFAOYSA-N 5-N-ethyl-4-N-methyl-1H-imidazole-4,5-diamine Chemical compound C(C)NC=1N=CNC=1NC RJSKHKSQNARRMQ-UHFFFAOYSA-N 0.000 description 4
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
• 239000005977 Ethylene Substances 0.000 description 4
• BOYRWCXPJFESEB-UHFFFAOYSA-N N-(5-amino-1-ethylimidazol-4-yl)acetamide Chemical compound NC1=C(N=CN1CC)NC(C)=O BOYRWCXPJFESEB-UHFFFAOYSA-N 0.000 description 4
• 229930182559 Natural dye Natural products 0.000 description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 230000003113 alkalizing effect Effects 0.000 description 4
• 239000008139 complexing agent Substances 0.000 description 4
• 239000006071 cream Substances 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 150000002191 fatty alcohols Chemical class 0.000 description 4
• 230000037308 hair color Effects 0.000 description 4
• 239000000978 natural dye Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 3
• VKZRWSNIWNFCIQ-WDSKDSINSA-N (2s)-2-[2-[[(1s)-1,2-dicarboxyethyl]amino]ethylamino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NCCN[C@H](C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-WDSKDSINSA-N 0.000 description 3
• MHANKXPPKNGTID-UHFFFAOYSA-N 1,3-bis(2,5-diaminophenoxy)propan-2-ol Chemical compound NC1=CC=C(N)C(OCC(O)COC=2C(=CC=C(N)C=2)N)=C1 MHANKXPPKNGTID-UHFFFAOYSA-N 0.000 description 3
• JDTDIZGWSVNMDX-UHFFFAOYSA-N 1-(5-amino-2-hydroxyphenyl)ethane-1,2-diol Chemical compound NC1=CC=C(O)C(C(O)CO)=C1 JDTDIZGWSVNMDX-UHFFFAOYSA-N 0.000 description 3
• ZTDGTZYKYHLCEP-UHFFFAOYSA-N 1-ethylimidazole-4,5-diamine Chemical compound CCN1C=NC(N)=C1N ZTDGTZYKYHLCEP-UHFFFAOYSA-N 0.000 description 3
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 description 3
• DMUXRIHPNREBPF-UHFFFAOYSA-N 2-[2-[2-[2-(2,5-diaminophenoxy)ethoxy]ethoxy]ethoxy]benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(OCCOCCOCCOC=2C(=CC=C(N)C=2)N)=C1 DMUXRIHPNREBPF-UHFFFAOYSA-N 0.000 description 3
• ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 description 3
• UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 3
• GJVMTMXQJDQJSS-UHFFFAOYSA-N 3-methyl-5-nitroimidazol-4-amine Chemical compound CN1C=NC([N+]([O-])=O)=C1N GJVMTMXQJDQJSS-UHFFFAOYSA-N 0.000 description 3
• YVHADNHJPSBNRQ-UHFFFAOYSA-N 4-[4-(4-aminophenyl)-1,4-diazepan-1-yl]aniline Chemical compound C1=CC(N)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CCC1 YVHADNHJPSBNRQ-UHFFFAOYSA-N 0.000 description 3
• PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 description 3
• KRQUHMFZMVSALZ-UHFFFAOYSA-N 4-amino-2-(diethylaminomethyl)phenol Chemical compound CCN(CC)CC1=CC(N)=CC=C1O KRQUHMFZMVSALZ-UHFFFAOYSA-N 0.000 description 3
• HLIGKHFHQXRAOX-UHFFFAOYSA-N 4-amino-2-[(5-amino-2-hydroxyphenyl)methyl]phenol Chemical compound NC1=CC=C(O)C(CC=2C(=CC=C(N)C=2)O)=C1 HLIGKHFHQXRAOX-UHFFFAOYSA-N 0.000 description 3
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