JP2019508362A - 化合物 - Google Patents
化合物 Download PDFInfo
- Publication number
- JP2019508362A JP2019508362A JP2017518234A JP2017518234A JP2019508362A JP 2019508362 A JP2019508362 A JP 2019508362A JP 2017518234 A JP2017518234 A JP 2017518234A JP 2017518234 A JP2017518234 A JP 2017518234A JP 2019508362 A JP2019508362 A JP 2019508362A
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- Prior art keywords
- alkyl
- substituted
- group
- unsubstituted
- compound
- Prior art date
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- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 341
- 239000000203 mixture Substances 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- -1 Este Chemical group 0.000 claims description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 239000011521 glass Substances 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 230000000475 sunscreen effect Effects 0.000 claims description 25
- 239000000516 sunscreening agent Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 150000002081 enamines Chemical class 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 230000004224 protection Effects 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 14
- 150000003973 alkyl amines Chemical class 0.000 claims description 14
- 125000003435 aroyl group Chemical group 0.000 claims description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 239000008199 coating composition Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000004033 plastic Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 10
- 229920003023 plastic Polymers 0.000 claims description 10
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 9
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000003599 detergent Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 235000013870 dimethyl polysiloxane Nutrition 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
- 230000002633 protecting effect Effects 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 5
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 5
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 claims description 5
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 229920006254 polymer film Polymers 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical compound S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 2
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005841 biaryl group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 20
- 230000005670 electromagnetic radiation Effects 0.000 abstract description 11
- 238000009472 formulation Methods 0.000 description 24
- 238000002835 absorbance Methods 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000005540 biological transmission Effects 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 238000000411 transmission spectrum Methods 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 239000011159 matrix material Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000003973 paint Substances 0.000 description 9
- 229920000647 polyepoxide Polymers 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000006096 absorbing agent Substances 0.000 description 8
- 239000002537 cosmetic Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 239000002250 absorbent Substances 0.000 description 7
- 230000002745 absorbent Effects 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- 238000005538 encapsulation Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
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- 239000000499 gel Substances 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000008033 biological extinction Effects 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
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- 239000000975 dye Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 5
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- 230000009257 reactivity Effects 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000005347 biaryls Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000002476 indolines Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
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- 239000007787 solid Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 3
- 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 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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Abstract
Description
R2は、水素、C1〜C12アルキル、C1〜C12アルケニル、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルケニルおよび複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよく;
R3およびR4は、独立して、C1〜C20アルキル、C2〜C20アルケニル、C2〜C20アルキニル、C1〜C20アルキルアミン、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルキル、C3〜C8シクロアルケニル、C2〜C12アルカノイルオキシ、ハロアルキルおよび複素環からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR3およびR4は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造は任意に置換されている;ならびに
R5は、C1〜C20ハロアルキル、C1〜C20ハロアルケニル、フッ素含有基、C1〜C20アルキル、C2〜C20アルケニル、C1〜C20アルコキシ、エステル、アミド、C1〜C20アルカノイル、C1〜C20アルケノイル、アリール、C5〜C7シクロアルケニルおよび複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよい。
またはR3およびR4は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造は以下からなる群より選択される:
式中、アスタリスクは、R3およびR4が直接結合しているエナミン窒素原子を示し;ならびに
R7およびR8は、水素、F、Br、Cl、C1〜C20アルキル、C1〜C6フルオロアルキル、ニトロ、C1〜C6アルコキシ、−C(O)O−C1〜C9アルキル、−C(O)O−C1〜C4アルキル−カルバメート、カルボキシメチル、カルボキシエチル、多価提示のさらなる式Iの化合物、−C(O)O−PEGおよび−C(O)O−PDMSからなる群より選択され、これらの各々は任意に置換されていてもよい。
式中、R12はC1〜C12アルキル、C2〜C6アルキルアルカノエート、C5またはC6アリール、C5〜C7シクロアルキルおよびアルキルアリールからなる群より選択される。
式中、R1、R3およびR4は、独立して、式Iの任意の実施形態について記載した通りであり;
Y1、Y2、Y3、Y4およびY5は、独立して、窒素または炭素原子から選択され;ならびに
R6の各出現は、独立して、水素、ヒドロキシル、ハロ、ニトロ、シアノ、C1〜C12アルキル、C1〜C12アルコール、C2〜C12アルケニル、C1〜C12アルコキシ、アルコキシシラン、C1〜C6アミド、スルホンアミド、およびC1〜C12ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい。
式中、R3、R4およびR6は、独立して、式Iおよび/または式IIの任意の実施形態について記載した通りである。
式中、R3およびR4は、独立して、式I、II、およびIIaの任意の実施形態について記載した通りであり;
R9は、アリール、C1〜C12アルキル、C1〜C12アルキルアリール、C5〜C7シクロアルキル、C5またはC6複素環およびC2〜C12アルキルアルカノエートからなる群より選択され、これらの各々は置換または非置換であってもよい。
式中、R3およびR4は、独立して、式I、II、IIaおよびIIIの任意の実施形態について記載した通りであり;ならびに
R10およびR11は、独立して、水素、C1〜C20アルキル、C2〜C20アルケニル、C2〜C20アルキニル、C1〜C20アルキルアミン、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルキル、C3〜C8シクロアルケニル、C2〜C12アルカノイルオキシ、ハロアルキル、および複素環からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR10およびR11は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造は任意に置換されている。
式中、R3およびR4は、独立して、式I、II、IIa、IIIおよびIVの任意の実施形態について記載した通りであり;ならびに
R15の各出現は、独立して、R6について記載した群から選択される。
式中、R3およびR4は、独立して、式I、II、IIa、III、IVおよびVの任意の実施形態について記載した群から選択され;
R17、R18およびR19は、独立して、メチル、エチルおよびプロピルから選択され;ならびに
R16の各出現は、独立して、R6について記載した群から選択される。
式中、R3、R4およびR5は、必要に応じて、独立して、式I、II、IIa、III、IV、VおよびVIの任意の実施形態について記載した群から選択される。
R20は、C1〜C6ハロアルキル、任意に置換されたフェニルから選択されるか、またはR20は、以下の構造を有するエステル基を含む:
式中、R12は、C1〜C12アルキル、C2〜C6アルキルアルカノエートおよびC5またはC6アリールからなる群より選択され;ならびに
R21は、水素、カルボキシメチルを含む−C(O)O−C1〜C20アルキル、および二価提示の第1の態様の化合物から選択される。
式中、R12はC1〜C6アルキルである。
ならびにその塩および/または異性体であって、式中、「Pol」は、PEG、PDMSまたはC6〜C20アルキルであってもよく、環構造内から伸びる結合は、必要に応じて、結合がその構造の環原子のいずれかに直接結合していてもよいことを示す。
(フッ素化化合物)
第1の態様の化合物は、一実施形態では、中間体エナミンの単離の必要なしに、ワンポット手順で合成され得る(以下のスキーム1中のYおよびZ)。以下のスキーム1に示す化合物142および143の合成例では、フェニルアセトアルデヒドを選択して、芳香族環との結合によるエナミン形成を容易にした。出発物質は両方とも安価であり、容易に大規模に入手可能である。一般化された手法もスキーム1に概説されており、それにより、アルキル、アリールおよび水素を含む様々なR、R’およびR’’’’基の使用を介して、多様性がどのように合成化合物に導入されるかを見ることができる。例えば、しばしば沈殿した生成物のみが回収され、液体中の残留化合物は求められないが、その目的は、単に後の試験のために十分な生成物を得ることであるため、本明細書に示された合成スキームを通して示される収率は、通常最適化されていないことに留意されたい。
スキーム2:種々のフッ素化化合物への合成経路。
特定の実施形態では、第1の態様の化合物は、ベンゾイルまたはアルカノイル部位を示してもよく、すなわち、R5は、フェニル基または短鎖アルキル基を含み得る。そのような化合物は、多くの手法により合成されてもよく、非限定的な例を以下のスキームに示す。
一連の1,2−ジカルボニル官能化化合物を、スキーム9に示す標準的な合成手順の改変を用いて一般に実施される合成で調製した。
以下のスキーム13は、様々なクラスの第1の態様の化合物をもたらす多数の合成経路を示す。このスキームは、本明細書に記載された手法および当該分野で知られている手法を使用して、非常に多様なエナミン化合物が入手可能であることを示す。スキーム13は単なる指標であり、決して合成され得る化合物のクラスを限定するものではない。
第1の態様の多数の他の化合物を、非ベンゾイルまたはジカルボニル官能基を用いて合成した。電子求引性シアノアセチル基を有する化合物249の合成を、スキーム14に示す。化合物238を同様の方法で調製した。
R1がフェニルまたはクロロフェニルであり、R2が水素であり、R5がCF3である場合、R3およびR4は、(i)エチルまたはイソプロピルの両方ではなく;および(ii)R3またはR4の一方がベンジルである場合、他方はエステル基ではない;
R1およびR2は環構造を形成しない;
R3またはR4は、R1および/もしくはR2と共に環構造または縮合環構造を形成しない;
R3またはR4は、それらが結合している式I〜VIII中の窒素原子と共にアジリジン環を形成しない;
エナミンのアルケン炭素原子はエナミンの窒素原子と共に環状構造を形成しない;
R1、R5およびR3またはR4の一方が非置換フェニルであり、R2が水素である場合、R3またはR4の他方はメチル、非置換フェニルもしくはCH2CH2NH−Phではない;
R1、R2、R5およびR3またはR4の一方が非置換フェニルである場合、R3またはR4の他方はベンゾイルではない;
R3またはR4の一方がアルキルである場合、他方は水素またはメチルであることはできない;
R1が水素である場合、R5はC1〜C6より大きなアルキルではない;
R1がピリジンである場合、R3またはR4はメチルではない;
R5がフェニルである場合、それはニトロ基でパラ置換されていない;
R5がメチルであり、R1が非置換フェニルであり、R3またはR4の一方が非置換フェニルである場合、R3またはR4の他方はメチルもしくは非置換フェニルではない;
R5が
であり、R’が水素またはカルボキシルである場合、R3およびR4は同時に非置換フェニルおよびメチルではなく、同時にフェノールおよびアセチル基ではなく、両方とも非置換フェニルではなく、同時に非置換フェニルおよび非置換ベンジルではなく、一緒にメチル置換インドールまたはベンズイミダゾールを形成しない; ならびに
R3およびR4は、
を含まない。
多数の合成経路を、先に議論したスキームにおいて示している。したがって、化合物142および143についての詳細な手順のみを提供する。特性データが全ての化合物について得られたが、同様に、簡潔さのために含めない。
CHCl3(体積:10ml)中の2−フェニルアセトアルデヒド(0.643ml、5.78mmol)の溶液を、4Åシーブス(0.5g、4.13mmol)、次いでN−エチルアニリン(0.505ml、4.13mmol)(フェニルアセトアルデヒドの純度の欠如を考慮して調整された量)で処理した。室温(RT)で2時間撹拌した後、アリコートの分析は、ほとんどが生成物であることを示し、出発アニリンおよびアルデヒドは少量であった。20%のN−エチルアニリンおよび10%の2−フェニルアセトアルデヒド(0.45g、2.015mmol)を含む、このN−エチル−N−スチリルアニリンのCHCl3中の混合物の一部を、トリエチルアミン(0.562ml、4.03mmol)で処理し、次いでTFAA (0.313ml、2.217mmol)を滴加し、室温で一晩撹拌した。アリコートのNMRは、微量のエナミンしか残っていないことを示唆している。混合物を水/DCMで希釈し、振盪し、有機相を分離し、NaHCO3で洗浄し、乾燥(MgSO4)後、蒸発させてオレンジ色の甘い香油(710mg)を得た。粗物質を0−5%EtOAc/石油エーテルで溶離するカラムクロマトグラフィーにより精製し、142を淡黄色油状物として得て、これを放置して固化させてオフホワイト固体(362mg、56%)として得た。
4−(エチル(フェニル)アミノ)−1,1,1−トリフルオロ−3−フェニルブタ−3−エン−2−オンの調製に関する上記の手順に従って、142を淡黄色固体として、収率43%で調製した。
2つのレンズ配合物を使用した。第1(CR−39)は、開始剤として3重量%の過酸化ベンゾイルを含むジ(エチレングリコール)ビス(アリルカーボネート)で構成されていた。第2のレンズ配合物(NK)は、開始剤として0.4重量%のAIBNを含む4部のNKエステルBPE100N(エトキシル化ビスフェノールAジメタクリレート)対1部のNKエステル9G(PEG400ジメタクリレート)で構成されていた。
典型的なエポキシ樹脂硬化系に対する多数の化合物の安定性を試験するために、エポキシ接着剤パックを得た(Parfix 5分毎日エポキシ接着剤、24ml)。これは標準的な2部エポキシ樹脂であり、第1部は粘性ビスフェノールA/エピクロルヒドリンポリマー反応生成物からなる。第2部は、アミノフェノール硬化剤T(以下に示す)の粘性30%溶液である。1級および2級アミンにより硬化されたエポキシ樹脂も利用可能である。
塗料における第1の態様の化合物の使用のモデルとして、ブリティッシュペイント油系ポリウレタンワニス中の化合物の1質量%溶液(1g中10mg)を顕微鏡スライドの表面に適用し、暗所で一晩乾燥させた。次いで、スライドの透過率を測定し、試料をキセノンアークランプ(溶液相薄膜試料の場合)で2時間照射し、透過率を再測定した。得られたフィルムの厚さのわずかな変化は、透過率の変化をもたらすのに十分であるので、ここでの変更はおそらく分解の指標であったため、放射線の前後の試料の勾配を観察することが重要であると判断された。ワニス自体は、約350〜370nmの光の透過を阻止する。
ポリマーマトリックス中の化合物の安定性を測定するために、薄膜をポリ(メチルメタクリレート)(PMMA)中に投入した。これは、当該化合物をDCM中のPMMA(Mw240,000)の溶液に添加し、得られた溶液をガラススライド上に広げることにより達成され、一晩蒸発させて所望のフィルムを得た。次いで、膜を2枚のスライドガラスの間に挟んで変形を防止し、照射した。ブランクの膜は約250nmまでの光を遮断し、ガラス顕微鏡スライドは約295nmまでの光を遮断した(照射に使用されたキセノンランプはPyrex膜であり、いずれの場合もこれらの波長を遮断するであろう)。このようにして、化合物164の膜を調製した。膜を1時間、2時間照射し、さらに外に放置して直射日光および大気条件に3週間ばく露させた(メルボルンの夏時間)。
第1の態様の化合物は、提示された光安定性データに示されるように、電磁放射線へのばく露時に向上した安定性を示し得る。これを試験するために、以下の手法を使用した。
Claims (40)
- 式Iの化合物、またはその塩もしくは異性体:
式中、R1は、C1〜C20アルキル、C2〜C20アルケニル、C2〜C20アルキニル、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルケニルおよび複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよく;
R2は、水素、C1〜C12アルキル、C2〜C12アルケニル、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルケニルおよび複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよく;
R3およびR4は、独立して、C1〜C20アルキル、C2〜C20アルケニル、C2〜C20アルキニル、C1〜C20アルキルアミン、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルキル、C3〜C8シクロアルケニル、C2〜C12アルカノイルオキシ、ハロアルキルおよび複素環からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR3およびR4は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造は任意に置換されている;ならびに
R5は、C1〜C20ハロアルキル、C1〜C20ハロアルケニル、フッ素含有基、C1〜C20アルキル、C2〜C20アルケニル、C1〜C20アルコキシ、エステル、アミド、C1〜C20アルカノイル、C1〜C20アルケノイル、アリール、C5〜C7シクロアルケニルおよび複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよい。 - R1が、C2〜C12アルケニル、C2〜C12アルキニル、C5またはC6アリール、C5またはC6ヘテロアリール、C5またはC6アロイル、C5またはC6シクロアルケニル、縮合アリール−複素環およびC5またはC6複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよい、請求項1に記載の化合物。
- R1が、フェニル、ピリジル、ピラン、チオピラン、ジアジン、オキサジン、チアジン、ジオキシン、ジチイン、ピロール、フラン、チオフェン、イミダゾール、ピラゾール、オキサゾール、イソオキサゾール、チアゾール、イソチアゾール、インドールおよびイソインドールからなる群より選択され、これらの基の各々は置換または非置換であってもよい、請求項1または2に記載の化合物。
- R2が、水素、C1〜C6アルキル、C2〜C6アルケニル、C5またはC6アリール、C5またはC6ヘテロアリール、C5またはC6アロイル、C5またはC6シクロアルケニルおよびC5またはC6複素環からなる群より選択され、これらの基の各々は置換または非置換であってもよい、請求項1〜3のいずれか一項に記載の化合物。
- R3およびR4が、独立して、C1〜C12アルキル、C2〜C12アルケニル、C2〜C12アルキニル、C1〜C12アルキルアミン、C5〜C7アリール、ビアリール、二環式、C5〜C7ヘテロアリール、C5〜C7アロイル、C4〜C7シクロアルケニルおよびC5〜C7複素環からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR3およびR4は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造はC5〜C7飽和窒素複素環およびC5〜C7不飽和窒素複素環から選択され、これらの各々は任意に置換されていてもよい、請求項1〜4のいずれか一項に記載の化合物。
- R3およびR4が、独立して、C1〜C9アルキル、C2〜C9アルケニル、C1〜C9アルキルアミン、フェニル、ナフチル、トリアジン、C5、C6またはC7窒素複素環および二価提示のさらなる式Iの化合物からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR3およびR4は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造はピロリジン、ピペリジン、アゼパン、ホモピペラジン、ピペラジンから選択され、これらの各々は置換もしくは非置換であってもよく、または1つ以上のC5もしくはC6アリール、C5もしくはC6シクロアルキル、C5もしくはC6ヘテロアリールまたはC5もしくはC6複素環と縮合していてもよく、これらの各々はそれ自体が置換または非置換であってもよい、請求項1〜5のいずれか一項に記載の化合物。
- R3およびR4が、一緒になって、ベンゼン環と縮合したC5窒素複素環を形成する、請求項1〜6のいずれか一項に記載の化合物。
- 請求項1〜7のいずれか一項に記載の化合物であって、R3およびR4が、独立して、以下からなる群より選択される:
またはR3およびR4が、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造は以下からなる群より選択される:
式中、アスタリスクは、R3およびR4が直接結合しているエナミン窒素原子を示し;ならびに
R7およびR8は、水素、F、Br、Cl、C1〜C20アルキル、C1〜C6フルオロアルキル、ニトロ、C1〜C6アルコキシ、−C(O)O−C1〜C9アルキル、−C(O)O−C1〜C4アルキル−カルバメート、カルボキシメチル、カルボキシエチル、多価提示のさらなる式Iの化合物、−C(O)O−PEGおよび−C(O)O−PDMSからなる群より選択され、これらの各々は任意に置換されていてもよい、化合物。 - R5が、C1〜C12ハロアルキル、C2〜C12ハロアルケニル、C5またはC6アリール、C1〜C12ペルハロアルキル、C1〜C12アルキル、C1〜C12アルケニル、C1〜C12アルコキシ、C1〜C12アルカノイル、フェニル、エステル、アミド、C5〜C7複素環および二価提示のさらなる式Iの化合物としてのエナミンからなる群より選択され、これらの基の全ては置換または非置換であってもよい、請求項1〜8のいずれか一項に記載の化合物。
- R5が、C1〜C6フルオロアルキル、C2〜C6フルオロアルケニル、C5またはC6フルオロアリール、C1〜C6ペルフルオロアルキル、C1〜C6アルキル、C1〜C9アルケニル、C1〜C6アルコキシ、C1〜C9アルカノイル、C1〜C6シアノアルキル、フェニル、C1〜C9エステル、C1〜C9アミド、C5〜C7複素環および二価提示のさらなる式Iの化合物としてのエナミンからなる群より選択され、これらの基の全ては置換または非置換であってもよい、請求項1〜9のいずれか一項に記載の化合物。
- R5がアミドである場合、該アミドの窒素が、置換されていてもよいもしくはアリール環と縮合していてもよい5または6員窒素複素環の一部を形成してもよい、請求項8または9に記載の化合物。
- R5が、以下からなる群より選択される、請求項1〜11のいずれか一項に記載の化合物:
- 式IIの化合物、またはその塩もしくは異性体:
式中、R1、R3およびR4は、独立して、請求項1〜12のいずれか一項において定義された通りであり;
Y1、Y2、Y3、Y4およびY5は、独立して、窒素または炭素原子から選択され;ならびに
R6の各出現は、独立して、水素、ヒドロキシル、ハロ、ニトロ、シアノ、C1〜C12アルキル、C1〜C12アルコール、C2〜C12アルケニル、C1〜C12アルコキシ、アルコキシシラン、C1〜C6アミド、スルホンアミド、およびC1〜C12ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい。 - R6の各出現が、独立して、水素、ヒドロキシル、Br、F、Cl、ニトロ、シアノ、C1〜C9アルキル、C1〜C9アルコール、C2〜C9アルケニル、C1〜C9アルコキシ、スルホンアミド、およびC1〜C9ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい、請求項13に記載の化合物。
- 該化合物が、式IIaの化合物、またはその塩もしくは異性体である、請求項13または14に記載の化合物:
式中、R3およびR4は、独立して、請求項1〜14のいずれか一項において定義された通りであり、R6は、請求項13または14において定義された通りである。 - R6の各出現が、独立して、水素、ヒドロキシル、Br、F、C1〜C4アルキル、C1〜C4アルコール、C1〜C4アルコキシ、およびC1〜C4ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい、請求項15に記載の化合物。
- 式IIIの化合物、またはその塩もしくは異性体:
式中、R3およびR4は、独立して、請求項1〜16のいずれか一項において定義された通りであり;
R9は、アリール、C1〜C12アルキル、C1〜C12アルキルアリール、C5〜C7シクロアルキル、C5またはC6複素環およびC2〜C12アルキルアルカノエートからなる群より選択され、これらの各々は置換または非置換であってもよい。 - R9が、C5またはC6アリール、C1〜C9アルキル、C1〜C6アルキルアリール、C5またはC6シクロアルキル、C5またはC6窒素複素環およびC2〜C9アルキルアルカノエートから選択され、これらの各々は置換または非置換であってもよい、請求項17に記載の化合物。
- 式IVの化合物、またはその塩もしくは異性体:
式中、R3およびR4は、独立して、請求項1〜18のいずれか一項において定義された通りであり;
R10およびR11は、独立して、水素、C1〜C20アルキル、C2〜C20アルケニル、C2〜C20アルキニル、C1〜C20アルキルアミン、アリール、ヘテロアリール、アロイル、C5〜C7シクロアルキル、C3〜C8シクロアルケニル、C2〜C12アルカノイルオキシ、ハロアルキル、および複素環からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR10およびR11は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造は任意に置換されている。 - R10およびR11が、独立して、水素、C1〜C12アルキル、C2〜C12アルケニル、C2〜C12アルキニル、C1〜C12アルキルアミン、C5〜C7アリール、ビアリール、二環式、C5〜C7ヘテロアリール、C5〜C7アロイル、C4〜C7シクロアルケニル、およびC5〜C7複素環からなる群より選択され、これらの基の全ては置換もしくは非置換であってもよく、またはR10およびR11は、一緒になって、それらが結合している窒素原子を含む環構造を形成してもよく、前記環構造はC5〜C7飽和窒素複素環およびC5〜C7不飽和窒素複素環から選択され、これらの各々は任意に置換されていてもよい、請求項19に記載の化合物。
- R10およびR11が、独立して、水素、C6アリールまたはビアリール、C1〜C6アルキル、C1〜C12アルキルアミンから選択されてもよく、これらの基の各々は置換もしくは非置換であってもよく、およびC5、C6またはC7窒素複素環から選択されてもよく、これらの複素環の各々は、置換もしくは非置換ベンゼン環と任意に縮合していてもよい、請求項19または請求項20に記載の化合物。
- R10およびR11が、一緒になって、ベンゼン環と縮合したC5窒素複素環を形成する場合、形成される構造が任意に置換されているインドリンである、請求項19〜21のいずれか一項に記載の化合物。
- 式Vの化合物、またはその塩もしくは異性体:
式中、R3およびR4は、独立して、請求項1〜22のいずれか一項において定義された通りであり;
R15の各出現は、独立して、水素、ヒドロキシル、ハロ、ニトロ、シアノ、C1〜C12アルキル、C1〜C12アルコール、C2〜C12アルケニル、C1〜C12アルコキシ、スルホンアミド、およびC1〜C12ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい。 - R15の各出現が、独立して、水素、ヒドロキシル、Br、F、Cl、ニトロ、シアノ、C1〜C9アルキル、C1〜C9アルコール、C2〜C9アルケニル、C1〜C9アルコキシ、スルホンアミド、およびC1〜C9ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい、請求項23に記載の化合物。
- 式VIの化合物、またはその塩もしくは異性体:
式中、R3およびR4は、独立して、請求項1〜24のいずれか一項において定義された通りであり;
R17、R18およびR19は、独立して、メチル、エチルおよびプロピルから選択され;ならびに
R16の各出現は、独立して、水素、ヒドロキシル、ハロ、ニトロ、シアノ、C1〜C12アルキル、C1〜C12アルコール、C2〜C12アルケニル、C1〜C12アルコキシ、スルホンアミド、およびC1〜C12ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい。 - R16の各出現が、独立して、水素、ヒドロキシル、Br、F、Cl、ニトロ、シアノ、C1〜C9アルキル、C1〜C9アルコール、C2〜C9アルケニル、C1〜C9アルコキシ、スルホンアミド、およびC1〜C9ハロアルキルからなる群より選択され、これらの各々は置換または非置換であってもよい、請求項25に記載の化合物。
- R16が水素であり、R3およびR4が、一緒になって、任意に置換されたインドリン環系を形成する、請求項25または26に記載の化合物。
- 式VIIの化合物、またはその塩もしくは異性体:
式中、R3、R4およびR5は、必要に応じて、独立して、請求項1〜27のいずれか一項において定義された通りである。 - R5が、C1〜C6アルキルおよび任意に置換されたフェニルから選択される、請求項28に記載の化合物。
- R3およびR4が、独立して、C1〜C6アルキルおよびC5もしくはC6アリールからなる群より選択されるか、または一緒になってインドリン基を形成してもよく、これらの基の各々は置換または非置換であってもよい、請求項1〜29のいずれか一項に記載の化合物。
- 該化合物が、以下からなる群より選択される、請求項1〜30のいずれか一項に記載の化合物:
ならびにその塩および/または異性体であって、式中、「Pol」は、PEG、PDMSまたはC6〜C20アルキルであってもよく、環構造内から伸びる結合は、必要に応じて、結合がその構造の環原子のいずれかに直接結合していてもよいことを示す。 - 請求項1〜31のいずれか一項に記載の化合物、またはその塩もしくは異性体、および適切な担体を含む組成物。
- 該組成物が、日焼け止め組成物、塗装組成物、洗剤組成物、毛髪ケア組成物、包装組成物、レンズ形成用組成物、およびガラスまたはポリマー膜形成組成物からなる群より選択される、請求項32に記載の組成物。
- 請求項1〜31のいずれか一項に記載の化合物、またはその塩もしくは異性体の、電磁エネルギー吸収化合物としての使用。
- 該電磁エネルギーが、UV−A、UV−B、可視光またはそれらの任意の組み合わせである、請求項34に記載の使用。
- 該使用が、日焼け止め組成物、塗装組成物、洗剤組成物、毛髪ケア組成物、包装組成物、レンズ形成組成物、およびガラスまたはポリマー膜形成組成物の1つ以上の成分としてのものである、請求項34または35に記載の使用。
- UVもしくは可視光保護眼用レンズ、またはガラスもしくはプラスチック用のUVもしくは可視光線保護塗装の形成における、請求項36の使用。
- UV線から表面または組織を保護する方法であって、請求項1〜31のいずれか一項に記載の化合物、またはその塩もしくは異性体を、該表面または組織に適用する工程を含む方法。
- 該表面が、布地、衣料品、レンズ、プラスチック、木材、石材およびガラスの表面から選択される、請求項38に記載の方法。
- 該組織が哺乳動物の皮膚である、請求項38に記載の方法。
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