JP2010524975A5 - - Google Patents
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- Publication number
- JP2010524975A5 JP2010524975A5 JP2010504313A JP2010504313A JP2010524975A5 JP 2010524975 A5 JP2010524975 A5 JP 2010524975A5 JP 2010504313 A JP2010504313 A JP 2010504313A JP 2010504313 A JP2010504313 A JP 2010504313A JP 2010524975 A5 JP2010524975 A5 JP 2010524975A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- propan
- amine
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 131
- 229910052739 hydrogen Inorganic materials 0.000 claims 131
- 239000001257 hydrogen Substances 0.000 claims 129
- 150000002431 hydrogen Chemical class 0.000 claims 67
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 62
- 125000004452 carbocyclyl group Chemical group 0.000 claims 48
- 229910052736 halogen Inorganic materials 0.000 claims 43
- 150000002367 halogens Chemical class 0.000 claims 43
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 38
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 35
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 17
- 208000017442 Retinal disease Diseases 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 210000001525 retina Anatomy 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- -1 3-hydroxy-5-[(1E) -2- (4-hydroxyphenyl) ethenyl] phenyl ester Chemical class 0.000 claims 6
- 206010057430 Retinal injury Diseases 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 208000030533 eye disease Diseases 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 150000001204 N-oxides Chemical class 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 230000002207 retinal effect Effects 0.000 claims 5
- WPWFMRDPTDEJJA-FAXVYDRBSA-N N-retinylidene-N-retinylethanolamine Chemical group C=1C(\C=C\C=C(/C)\C=C\C=2C(CCCC=2C)(C)C)=CC=[N+](CCO)C=1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C WPWFMRDPTDEJJA-FAXVYDRBSA-N 0.000 claims 4
- 206010038923 Retinopathy Diseases 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 210000004027 cell Anatomy 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 4
- 208000002780 macular degeneration Diseases 0.000 claims 4
- 239000000049 pigment Substances 0.000 claims 4
- 210000000880 retinal rod photoreceptor cell Anatomy 0.000 claims 4
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- 208000022758 Sorsby fundus dystrophy Diseases 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 3
- 125000005504 styryl group Chemical group 0.000 claims 3
- NCYCYZXNIZJOKI-IOUUIBBYSA-N 11-cis-retinal Chemical compound O=C/C=C(\C)/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-IOUUIBBYSA-N 0.000 claims 2
- OQKSTWHBLYTRLR-MDZDMXLPSA-N 2-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]ethanamine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(CCN)=C1 OQKSTWHBLYTRLR-MDZDMXLPSA-N 0.000 claims 2
- GDKGYVQAUIRZBX-VAWYXSNFSA-N 3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]prop-2-yn-1-amine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C#CCN)=C1 GDKGYVQAUIRZBX-VAWYXSNFSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 208000032578 Inherited retinal disease Diseases 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- 208000035719 Maculopathy Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 206010061876 Obstruction Diseases 0.000 claims 2
- 206010061323 Optic neuropathy Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010038848 Retinal detachment Diseases 0.000 claims 2
- 208000032430 Retinal dystrophy Diseases 0.000 claims 2
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 102000004330 Rhodopsin Human genes 0.000 claims 2
- 108090000820 Rhodopsin Proteins 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000004300 dark adaptation Effects 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 230000004907 flux Effects 0.000 claims 2
- 201000006321 fundus dystrophy Diseases 0.000 claims 2
- 230000002008 hemorrhagic effect Effects 0.000 claims 2
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 2
- 210000004276 hyalin Anatomy 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000017532 inherited retinal dystrophy Diseases 0.000 claims 2
- 208000038015 macular disease Diseases 0.000 claims 2
- 208000001491 myopia Diseases 0.000 claims 2
- 230000004379 myopia Effects 0.000 claims 2
- 208000020911 optic nerve disease Diseases 0.000 claims 2
- 210000000608 photoreceptor cell Anatomy 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 230000008929 regeneration Effects 0.000 claims 2
- 238000011069 regeneration method Methods 0.000 claims 2
- 230000004264 retinal detachment Effects 0.000 claims 2
- 210000001210 retinal vessel Anatomy 0.000 claims 2
- 150000004492 retinoid derivatives Chemical class 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- MVNYXEAZKVOLLN-JBVUFVISSA-N (1r)-3-amino-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-ol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC([C@H](O)CCN)=C1 MVNYXEAZKVOLLN-JBVUFVISSA-N 0.000 claims 1
- MVNYXEAZKVOLLN-YXBWYFRISA-N (1s)-3-amino-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-ol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC([C@@H](O)CCN)=C1 MVNYXEAZKVOLLN-YXBWYFRISA-N 0.000 claims 1
- JNCYMQSTWYVZCF-OZSKJFCKSA-N (1s)-3-amino-1-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]propan-1-ol Chemical compound NCC[C@H](O)C1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 JNCYMQSTWYVZCF-OZSKJFCKSA-N 0.000 claims 1
- IJQYSIVMJQRXLY-ALIVOICLSA-N (2S,3R)-2-amino-3-hydroxy-N-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]butanamide Chemical compound N[C@H](C(=O)NC1=C(C=CC(=C1)\C=C/C1=CC(=C(C(=C1)OC)OC)OC)OC)[C@@H](C)O IJQYSIVMJQRXLY-ALIVOICLSA-N 0.000 claims 1
- GFQWMSQANCSPPQ-HSBSLETESA-N (2r)-1-amino-3-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]propan-2-ol Chemical compound NC[C@H](O)CC1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 GFQWMSQANCSPPQ-HSBSLETESA-N 0.000 claims 1
- GFQWMSQANCSPPQ-NPQIQWPPSA-N (2s)-1-amino-3-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]propan-2-ol Chemical compound NC[C@@H](O)CC1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 GFQWMSQANCSPPQ-NPQIQWPPSA-N 0.000 claims 1
- RATBBFVZXHSDRR-NJRZHNRPSA-N (2s)-2-amino-n-[2-methoxy-5-[(z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-3-methylbutanamide Chemical compound C1=C(NC(=O)[C@@H](N)C(C)C)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 RATBBFVZXHSDRR-NJRZHNRPSA-N 0.000 claims 1
- KNFOKBZURYUWOW-ZEVQVBBLSA-N (2s)-2-amino-n-[2-methoxy-5-[(z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-4-methylpentanamide Chemical compound C1=C(NC(=O)[C@@H](N)CC(C)C)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 KNFOKBZURYUWOW-ZEVQVBBLSA-N 0.000 claims 1
- MYUPODARKKQONN-NPQIQWPPSA-N (2s)-3-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]-2-fluoropropan-1-amine Chemical compound NC[C@@H](F)CC1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 MYUPODARKKQONN-NPQIQWPPSA-N 0.000 claims 1
- ADNOXSJYZLHHRZ-KIRNREEKSA-N (3Z)-3-[3-[2-(2,6-dimethylphenyl)ethenyl]phenyl]-3-hydrazinylidenepropan-1-amine Chemical compound Cc1cccc(C)c1C=Cc1cccc(C(\CCN)=N/N)c1 ADNOXSJYZLHHRZ-KIRNREEKSA-N 0.000 claims 1
- ZAPIUEIQSYXBEM-UOBXZYDMSA-N (3z)-3-hydrazinylidene-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(\CCN)=N/N)=C1 ZAPIUEIQSYXBEM-UOBXZYDMSA-N 0.000 claims 1
- AFAKLPFUAPIXGQ-MBDWYYTESA-N (E)-3-[3-[2-(2,6-dimethylphenyl)ethenyl]phenyl]prop-2-en-1-amine Chemical compound Cc1cccc(C)c1C=Cc1cccc(\C=C\CN)c1 AFAKLPFUAPIXGQ-MBDWYYTESA-N 0.000 claims 1
- CMIVHTLFBIUJTH-MGAHFUHESA-N (NZ)-N-[3-amino-1-[3-[2-(2,6-dimethylphenyl)ethenyl]phenyl]propylidene]hydroxylamine Chemical compound NCC/C(=N/O)/C1=CC(=CC=C1)C=CC1=C(C=CC=C1C)C CMIVHTLFBIUJTH-MGAHFUHESA-N 0.000 claims 1
- WZAMHIIJKHBBSF-ZHACJKMWSA-N (e)-1-[3-(3-aminopropyl)phenyl]-3-ethylpent-1-en-3-ol Chemical compound CCC(O)(CC)\C=C\C1=CC=CC(CCCN)=C1 WZAMHIIJKHBBSF-ZHACJKMWSA-N 0.000 claims 1
- VLSXCDGACFQSQF-PKNBQFBNSA-N (e)-1-[3-(3-aminopropyl)phenyl]-3-methylhex-1-en-3-ol Chemical compound CCCC(C)(O)\C=C\C1=CC=CC(CCCN)=C1 VLSXCDGACFQSQF-PKNBQFBNSA-N 0.000 claims 1
- HEHHAZWIYHQNJM-MDZDMXLPSA-N (e)-1-[3-(3-aminopropyl)phenyl]hex-1-en-3-ol Chemical compound CCCC(O)\C=C\C1=CC=CC(CCCN)=C1 HEHHAZWIYHQNJM-MDZDMXLPSA-N 0.000 claims 1
- JMZLSKWRWCNXSD-BXCLKCLZSA-N (e)-2-fluoro-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]prop-2-en-1-amine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(\C=C(\F)CN)=C1 JMZLSKWRWCNXSD-BXCLKCLZSA-N 0.000 claims 1
- XQNSRHAJJXWIKR-XVNBXDOJSA-N (e)-3-[3-(3-aminopropyl)phenyl]prop-2-en-1-ol Chemical compound NCCCC1=CC=CC(\C=C\CO)=C1 XQNSRHAJJXWIKR-XVNBXDOJSA-N 0.000 claims 1
- QQKHNSWZQLKIDO-CMDGGOBGSA-N (e)-4-[3-(3-aminopropyl)phenyl]-2-methylbut-3-en-2-ol Chemical compound CC(C)(O)\C=C\C1=CC=CC(CCCN)=C1 QQKHNSWZQLKIDO-CMDGGOBGSA-N 0.000 claims 1
- CUVAQHRQKYFPLN-KSAPZYQLSA-N (nz)-n-[3-amino-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propylidene]hydroxylamine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(\CCN)=N/O)=C1 CUVAQHRQKYFPLN-KSAPZYQLSA-N 0.000 claims 1
- GZUHDMIETMZNIN-MDZDMXLPSA-N 1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propane-1,3-diamine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(N)CCN)=C1 GZUHDMIETMZNIN-MDZDMXLPSA-N 0.000 claims 1
- LWJFQTAZQWZGON-CCEZHUSRSA-N 1-[3-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propyl]piperidine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(CCCN2CCCCC2)=C1 LWJFQTAZQWZGON-CCEZHUSRSA-N 0.000 claims 1
- ZHRBINGNIDPHQF-BUHFOSPRSA-N 1-[3-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propyl]pyrrolidine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(CCCN2CCCC2)=C1 ZHRBINGNIDPHQF-BUHFOSPRSA-N 0.000 claims 1
- LWJFQTAZQWZGON-PFONDFGASA-N 1-[3-[3-[(z)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propyl]piperidine Chemical compound CC1=CC=CC(C)=C1\C=C/C1=CC=CC(CCCN2CCCCC2)=C1 LWJFQTAZQWZGON-PFONDFGASA-N 0.000 claims 1
- ZHRBINGNIDPHQF-YPKPFQOOSA-N 1-[3-[3-[(z)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propyl]pyrrolidine Chemical compound CC1=CC=CC(C)=C1\C=C/C1=CC=CC(CCCN2CCCC2)=C1 ZHRBINGNIDPHQF-YPKPFQOOSA-N 0.000 claims 1
- PQALEEGHDDHZMT-MDZDMXLPSA-N 1-amino-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-2-ol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(CC(O)CN)=C1 PQALEEGHDDHZMT-MDZDMXLPSA-N 0.000 claims 1
- KSDLTQDAZDWFKK-ZHACJKMWSA-N 2-[(e)-2-[3-(3-aminopropyl)phenyl]ethenyl]phenol Chemical compound NCCCC1=CC=CC(\C=C\C=2C(=CC=CC=2)O)=C1 KSDLTQDAZDWFKK-ZHACJKMWSA-N 0.000 claims 1
- DRHCFRQFKCNMCN-MDZDMXLPSA-N 2-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenoxy]ethanamine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(OCCN)=C1 DRHCFRQFKCNMCN-MDZDMXLPSA-N 0.000 claims 1
- GOBTZDDLKTZYBH-MDZDMXLPSA-N 2-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]ethanamine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(CCN)=C1 GOBTZDDLKTZYBH-MDZDMXLPSA-N 0.000 claims 1
- JXMWFGDSUMHILQ-MDZDMXLPSA-N 2-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]sulfanylethanamine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(SCCN)=C1 JXMWFGDSUMHILQ-MDZDMXLPSA-N 0.000 claims 1
- CDVGWPIVOINQCB-MDZDMXLPSA-N 2-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]sulfinylethanamine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(S(=O)CCN)=C1 CDVGWPIVOINQCB-MDZDMXLPSA-N 0.000 claims 1
- ONRQGKXNZHJUFA-MDZDMXLPSA-N 2-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]sulfonylethanamine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(S(=O)(=O)CCN)=C1 ONRQGKXNZHJUFA-MDZDMXLPSA-N 0.000 claims 1
- AETORJPTIHURGC-VAWYXSNFSA-N 2-[3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propylamino]ethanol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(CCCNCCO)=C1 AETORJPTIHURGC-VAWYXSNFSA-N 0.000 claims 1
- QSYKFFVERNGYGE-MDZDMXLPSA-N 2-[[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]methylamino]ethanol Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(CNCCO)=C1 QSYKFFVERNGYGE-MDZDMXLPSA-N 0.000 claims 1
- RBXQXOPQBYVQIS-MDZDMXLPSA-N 2-amino-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]ethanol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(O)CN)=C1 RBXQXOPQBYVQIS-MDZDMXLPSA-N 0.000 claims 1
- FXWOEVCVWRWPQP-MDZDMXLPSA-N 2-amino-1-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]ethanol Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(C(O)CN)=C1 FXWOEVCVWRWPQP-MDZDMXLPSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- FPTVZUBIWQGPBX-MDZDMXLPSA-N 2-amino-n-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]acetamide Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(NC(=O)CN)=C1 FPTVZUBIWQGPBX-MDZDMXLPSA-N 0.000 claims 1
- LCADTYPEALEUAO-ZHACJKMWSA-N 2-methyl-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound NCC(C)CC1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 LCADTYPEALEUAO-ZHACJKMWSA-N 0.000 claims 1
- UNFGQCCHVMMMRF-UHFFFAOYSA-N 2-phenylbutanamide Chemical compound CCC(C(N)=O)C1=CC=CC=C1 UNFGQCCHVMMMRF-UHFFFAOYSA-N 0.000 claims 1
- RDQLTOZPSLWFBC-VAWYXSNFSA-N 3-[2-methyl-5-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=C(C)C(CCCN)=C1 RDQLTOZPSLWFBC-VAWYXSNFSA-N 0.000 claims 1
- SMMRJLXBUXPNJB-VAWYXSNFSA-N 3-[3-[(e)-2-(1-methoxynaphthalen-2-yl)ethenyl]phenyl]propan-1-amine Chemical compound C1=CC2=CC=CC=C2C(OC)=C1\C=C\C1=CC=CC(CCCN)=C1 SMMRJLXBUXPNJB-VAWYXSNFSA-N 0.000 claims 1
- QLLVSACPOAJGDL-MDZDMXLPSA-N 3-[3-[(e)-2-(2,4,6-trimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC(C)=CC(C)=C1\C=C\C1=CC=CC(CCCN)=C1 QLLVSACPOAJGDL-MDZDMXLPSA-N 0.000 claims 1
- HNPWYERMGSZQFN-ZHACJKMWSA-N 3-[3-[(e)-2-(2,5-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC=C(C)C(\C=C\C=2C=C(CCCN)C=CC=2)=C1 HNPWYERMGSZQFN-ZHACJKMWSA-N 0.000 claims 1
- COHVBBAMZSZFSV-ZHACJKMWSA-N 3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]butan-1-amine Chemical compound NCCC(C)C1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 COHVBBAMZSZFSV-ZHACJKMWSA-N 0.000 claims 1
- SQPRVQOLIZOHKE-VAWYXSNFSA-N 3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(CCCN)=C1 SQPRVQOLIZOHKE-VAWYXSNFSA-N 0.000 claims 1
- CICOWLFEHIFHJR-BQYQJAHWSA-N 3-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]-2,2-difluoropropan-1-amine Chemical compound NCC(F)(F)CC1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 CICOWLFEHIFHJR-BQYQJAHWSA-N 0.000 claims 1
- OFLQNOFHNYJMRM-MDZDMXLPSA-N 3-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 OFLQNOFHNYJMRM-MDZDMXLPSA-N 0.000 claims 1
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- CYHDTIBJYIKSQN-BQYQJAHWSA-N 3-[3-[(e)-2-(4-methoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=CC(CCCN)=C1 CYHDTIBJYIKSQN-BQYQJAHWSA-N 0.000 claims 1
- NGNAJYMEOALPDA-MDZDMXLPSA-N 3-[3-[(e)-2-[2,6-bis(trifluoromethyl)phenyl]ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C=2C(=CC=CC=2C(F)(F)F)C(F)(F)F)=C1 NGNAJYMEOALPDA-MDZDMXLPSA-N 0.000 claims 1
- PJUJZHNFELIJSY-ZHACJKMWSA-N 3-[3-[(e)-2-[2-(trifluoromethyl)phenyl]ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C=2C(=CC=CC=2)C(F)(F)F)=C1 PJUJZHNFELIJSY-ZHACJKMWSA-N 0.000 claims 1
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- AZSQWTFLGQISGL-XBXARRHUSA-N 3-[3-[(e)-3-methoxyprop-1-enyl]phenyl]propan-1-amine Chemical compound COC\C=C\C1=CC=CC(CCCN)=C1 AZSQWTFLGQISGL-XBXARRHUSA-N 0.000 claims 1
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- WZLGJPFVKKGSPB-GZTJUZNOSA-N 3-[3-[(e)-non-4-en-5-yl]phenyl]propan-1-amine Chemical compound CCCC\C(=C/CCC)C1=CC=CC(CCCN)=C1 WZLGJPFVKKGSPB-GZTJUZNOSA-N 0.000 claims 1
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- XPVSROPKQGCQNT-QXMHVHEDSA-N 3-[3-[(z)-2-(2,3-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC=CC(\C=C/C=2C=C(CCCN)C=CC=2)=C1C XPVSROPKQGCQNT-QXMHVHEDSA-N 0.000 claims 1
- HAZWTJPUNVFXKC-LUAWRHEFSA-N 3-[3-[(z)-2-(2,4-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC(C)=CC=C1\C=C/C1=CC=CC(CCCN)=C1 HAZWTJPUNVFXKC-LUAWRHEFSA-N 0.000 claims 1
- FZHPUUJYIQGCKM-SEYXRHQNSA-N 3-[3-[(z)-2-(2,6-dimethylphenyl)ethenyl]-2-methylphenyl]propan-1-amine Chemical compound CC1=CC=CC(C)=C1\C=C/C1=CC=CC(CCCN)=C1C FZHPUUJYIQGCKM-SEYXRHQNSA-N 0.000 claims 1
- ZAIOJCJMZKCELI-SEYXRHQNSA-N 3-[3-[(z)-2-(2,6-dimethylphenyl)ethenyl]phenyl]-n-methylpropan-1-amine Chemical compound CNCCCC1=CC=CC(\C=C/C=2C(=CC=CC=2C)C)=C1 ZAIOJCJMZKCELI-SEYXRHQNSA-N 0.000 claims 1
- ACKOXNPHOJJOLZ-QXMHVHEDSA-N 3-[3-[(z)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC=CC(C)=C1\C=C/C1=CC=CC(CCCN)=C1 ACKOXNPHOJJOLZ-QXMHVHEDSA-N 0.000 claims 1
- FCPKJVMGYPHQLU-SEYXRHQNSA-N 3-[3-[(z)-2-(2-ethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CCC1=CC=CC=C1\C=C/C1=CC=CC(CCCN)=C1 FCPKJVMGYPHQLU-SEYXRHQNSA-N 0.000 claims 1
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- JCRJEGIYIWJLQS-SREVYHEPSA-N 3-[3-[(z)-2-(4-chlorophenyl)ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C/C=2C=CC(Cl)=CC=2)=C1 JCRJEGIYIWJLQS-SREVYHEPSA-N 0.000 claims 1
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| US60/937,002 | 2007-06-22 | ||
| PCT/US2008/061073 WO2008131368A2 (en) | 2007-04-20 | 2008-04-21 | Styrenyl derivative compounds for treating ophthalmic diseases and disorders |
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| US (7) | US20090170841A1 (OSRAM) |
| EP (1) | EP2076124A4 (OSRAM) |
| JP (1) | JP5371953B2 (OSRAM) |
| KR (2) | KR101368248B1 (OSRAM) |
| CN (1) | CN101686665B (OSRAM) |
| AU (1) | AU2008242626B2 (OSRAM) |
| BR (1) | BRPI0810063A2 (OSRAM) |
| CA (1) | CA2681850C (OSRAM) |
| CO (1) | CO6251201A2 (OSRAM) |
| EC (1) | ECSP099695A (OSRAM) |
| IL (1) | IL201285A (OSRAM) |
| MX (1) | MX2009011360A (OSRAM) |
| MY (1) | MY161818A (OSRAM) |
| RU (1) | RU2494089C2 (OSRAM) |
| WO (1) | WO2008131368A2 (OSRAM) |
| ZA (1) | ZA200907313B (OSRAM) |
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| JP5592265B2 (ja) | 2007-11-01 | 2014-09-17 | アキュセラ インコーポレイテッド | 眼の疾患及び障害治療用のアミン誘導体化合物 |
| NZ592993A (en) | 2008-10-22 | 2013-02-22 | Acucela Inc | Compounds for treating ophthalmic diseases and disorders |
| WO2012150208A1 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Verwendung von substituierten benzylalkoholestern der cyclopropancarbonsäure zur bekämpfung von insektizid-resistenten insekten |
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| JP6155332B2 (ja) * | 2012-06-28 | 2017-06-28 | ノバルティス アーゲー | ピロリジン誘導体、および補体経路調節因子としてのその使用 |
| WO2014002052A1 (en) * | 2012-06-28 | 2014-01-03 | Novartis Ag | Pyrrolidine derivatives and their use as complement pathway modulators |
| RU2515502C1 (ru) * | 2012-12-21 | 2014-05-10 | федеральное государственное автономное образовательное учреждение высшего профессионального образования "Московский физико-технический институт (государственный университет) | Поверхностно-активный фотосенсибилизатор, представляющий собой бромид 2-{ 4-[(е)-2-(4-этоксифенил)винил]фенокси} -n, n, n-триметилэтаманамина (с-таб) |
| US11286233B2 (en) | 2017-05-09 | 2022-03-29 | Ambient Photonics, Inc. | Stilbene derivatives for the treatment of CNS and other disorders |
| WO2019103989A1 (en) * | 2017-11-22 | 2019-05-31 | Temple University-Of The Commonwealth System Of Higher Education | Novel functionalized n,n-dialkylamino phenyl ethers and their method of use |
| CN110938003B (zh) * | 2018-09-25 | 2022-11-22 | 新发药业有限公司 | 一种芬戈莫德盐酸盐的制备方法 |
| CN112920081B (zh) * | 2021-02-06 | 2023-01-31 | 许昌学院 | 一种选择性识别次氯酸的荧光探针及其制备方法和应用 |
| WO2024196850A1 (en) * | 2023-03-17 | 2024-09-26 | University Of Southern California | Development of highly fluorogenic styrene probes for visualizing rna in live cells |
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-
2008
- 2008-04-21 MX MX2009011360A patent/MX2009011360A/es active IP Right Grant
- 2008-04-21 RU RU2009136911/04A patent/RU2494089C2/ru not_active IP Right Cessation
- 2008-04-21 BR BRPI0810063-2A2A patent/BRPI0810063A2/pt not_active IP Right Cessation
- 2008-04-21 CA CA2681850A patent/CA2681850C/en not_active Expired - Fee Related
- 2008-04-21 KR KR1020097024142A patent/KR101368248B1/ko not_active Expired - Fee Related
- 2008-04-21 WO PCT/US2008/061073 patent/WO2008131368A2/en not_active Ceased
- 2008-04-21 KR KR1020127030994A patent/KR20120137513A/ko not_active Withdrawn
- 2008-04-21 JP JP2010504313A patent/JP5371953B2/ja not_active Expired - Fee Related
- 2008-04-21 MY MYPI20094213A patent/MY161818A/en unknown
- 2008-04-21 CN CN200880021041.1A patent/CN101686665B/zh not_active Expired - Fee Related
- 2008-04-21 AU AU2008242626A patent/AU2008242626B2/en not_active Ceased
- 2008-04-21 US US12/107,040 patent/US20090170841A1/en not_active Abandoned
- 2008-04-21 EP EP08746483A patent/EP2076124A4/en not_active Withdrawn
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2009
- 2009-10-01 IL IL201285A patent/IL201285A/en not_active IP Right Cessation
- 2009-10-16 EC EC2009009695A patent/ECSP099695A/es unknown
- 2009-10-19 ZA ZA2009/07313A patent/ZA200907313B/en unknown
- 2009-10-20 CO CO09117150A patent/CO6251201A2/es not_active Application Discontinuation
-
2012
- 2012-01-27 US US13/360,285 patent/US8420863B2/en not_active Expired - Fee Related
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2013
- 2013-03-07 US US13/789,259 patent/US8653142B2/en not_active Expired - Fee Related
-
2015
- 2015-02-25 US US14/630,897 patent/US9421210B2/en not_active Expired - Fee Related
- 2015-02-25 US US14/631,711 patent/US10201545B2/en active Active
- 2015-02-25 US US14/630,889 patent/US9314467B2/en not_active Expired - Fee Related
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2016
- 2016-03-16 US US15/072,250 patent/US20160193160A1/en not_active Abandoned
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