JP2010524975A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- XXUSALLHYJYAGA-BUHFOSPRSA-N 3-[3-[(e)-2-(2,6-diethoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CCOC1=CC=CC(OCC)=C1\C=C\C1=CC=CC(CCCN)=C1 XXUSALLHYJYAGA-BUHFOSPRSA-N 0.000 claims 1
- CPLRGWJFPLETLO-VAWYXSNFSA-N 3-[3-[(e)-2-(2,6-dimethoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound COC1=CC=CC(OC)=C1\C=C\C1=CC=CC(CCCN)=C1 CPLRGWJFPLETLO-VAWYXSNFSA-N 0.000 claims 1
- FZHPUUJYIQGCKM-OUKQBFOZSA-N 3-[3-[(e)-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-OUKQBFOZSA-N 0.000 claims 1
- HELNQALGIJBZCO-MDZDMXLPSA-N 3-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]-4-fluorophenyl]propan-1-amine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC(CCCN)=CC=C1F HELNQALGIJBZCO-MDZDMXLPSA-N 0.000 claims 1
- ZAIOJCJMZKCELI-OUKQBFOZSA-N 3-[3-[(e)-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-OUKQBFOZSA-N 0.000 claims 1
- ACKOXNPHOJJOLZ-VAWYXSNFSA-N 3-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(CCCN)=C1 ACKOXNPHOJJOLZ-VAWYXSNFSA-N 0.000 claims 1
- YXGPTZZXMXJZIL-BUHFOSPRSA-N 3-[3-[(e)-2-(2-butoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CCCCOC1=CC=CC=C1\C=C\C1=CC=CC(CCCN)=C1 YXGPTZZXMXJZIL-BUHFOSPRSA-N 0.000 claims 1
- QQEMPACAPZMRMY-OUKQBFOZSA-N 3-[3-[(e)-2-(2-ethoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CCOC1=CC=CC=C1\C=C\C1=CC=CC(CCCN)=C1 QQEMPACAPZMRMY-OUKQBFOZSA-N 0.000 claims 1
- PSXPLPCJVGTXNT-OUKQBFOZSA-N 3-[3-[(e)-2-(2-ethyl-6-methylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CCC1=CC=CC(C)=C1\C=C\C1=CC=CC(CCCN)=C1 PSXPLPCJVGTXNT-OUKQBFOZSA-N 0.000 claims 1
- ASCQUHYFSINSDG-ACCUITESSA-N 3-[3-[(e)-2-(2-methoxynaphthalen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound COC1=CC=C2C=CC=CC2=C1\C=C\C1=CC=CC(CCCN)=C1 ASCQUHYFSINSDG-ACCUITESSA-N 0.000 claims 1
- HJUYIUKUUBCIGQ-VAWYXSNFSA-N 3-[3-[(e)-2-(2-methoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound COC1=CC=CC=C1\C=C\C1=CC=CC(CCCN)=C1 HJUYIUKUUBCIGQ-VAWYXSNFSA-N 0.000 claims 1
- LHIMPNFCTKYLTL-VAWYXSNFSA-N 3-[3-[(e)-2-(2-methylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC=CC=C1\C=C\C1=CC=CC(CCCN)=C1 LHIMPNFCTKYLTL-VAWYXSNFSA-N 0.000 claims 1
- VBOJEAGVIKVJIN-FOCLMDBBSA-N 3-[3-[(e)-2-(2-phenylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 VBOJEAGVIKVJIN-FOCLMDBBSA-N 0.000 claims 1
- ZLHZFVLOPXOLJY-CMDGGOBGSA-N 3-[3-[(e)-2-(3,5-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC(C)=CC(\C=C\C=2C=C(CCCN)C=CC=2)=C1 ZLHZFVLOPXOLJY-CMDGGOBGSA-N 0.000 claims 1
- UITGYMASHPKVQS-MDZDMXLPSA-N 3-[3-[(e)-2-(3-chlorophenyl)ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C=2C=C(Cl)C=CC=2)=C1 UITGYMASHPKVQS-MDZDMXLPSA-N 0.000 claims 1
- GGWNYPAAOSIVSI-ZHACJKMWSA-N 3-[3-[(e)-2-(3-methoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound COC1=CC=CC(\C=C\C=2C=C(CCCN)C=CC=2)=C1 GGWNYPAAOSIVSI-ZHACJKMWSA-N 0.000 claims 1
- 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
- ORCWBXAPGMTKGI-OUKQBFOZSA-N 3-[3-[(e)-2-cycloheptylethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C2CCCCCC2)=C1 ORCWBXAPGMTKGI-OUKQBFOZSA-N 0.000 claims 1
- FTTGXOXGHQOGFL-VAWYXSNFSA-N 3-[3-[(e)-2-cyclohexylethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C2CCCCC2)=C1 FTTGXOXGHQOGFL-VAWYXSNFSA-N 0.000 claims 1
- USEKNVKYSIYZOO-ZHACJKMWSA-N 3-[3-[(e)-2-cyclopentylethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C\C2CCCC2)=C1 USEKNVKYSIYZOO-ZHACJKMWSA-N 0.000 claims 1
- 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
- YVZJGLCOOBNTSC-RMKNXTFCSA-N 3-[3-[(e)-hept-1-enyl]phenyl]propan-1-amine Chemical compound CCCCC\C=C\C1=CC=CC(CCCN)=C1 YVZJGLCOOBNTSC-RMKNXTFCSA-N 0.000 claims 1
- 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
- HAQXUGGJYHMFOB-QPJJXVBHSA-N 3-[3-[(e)-pent-1-enyl]phenyl]propan-1-amine Chemical compound CCC\C=C\C1=CC=CC(CCCN)=C1 HAQXUGGJYHMFOB-QPJJXVBHSA-N 0.000 claims 1
- 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
- PSLCOWYOXIZZBN-SEYXRHQNSA-N 3-[3-[(z)-2-(2-ethynylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C/C=2C(=CC=CC=2)C#C)=C1 PSLCOWYOXIZZBN-SEYXRHQNSA-N 0.000 claims 1
- LHIMPNFCTKYLTL-QXMHVHEDSA-N 3-[3-[(z)-2-(2-methylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC1=CC=CC=C1\C=C/C1=CC=CC(CCCN)=C1 LHIMPNFCTKYLTL-QXMHVHEDSA-N 0.000 claims 1
- VJSVUJKPWBEQKS-SEYXRHQNSA-N 3-[3-[(z)-2-(2-propan-2-yloxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC(C)OC1=CC=CC=C1\C=C/C1=CC=CC(CCCN)=C1 VJSVUJKPWBEQKS-SEYXRHQNSA-N 0.000 claims 1
- OUORLZBLDICSNK-SEYXRHQNSA-N 3-[3-[(z)-2-(2-propan-2-ylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CC(C)C1=CC=CC=C1\C=C/C1=CC=CC(CCCN)=C1 OUORLZBLDICSNK-SEYXRHQNSA-N 0.000 claims 1
- ZDQHOHLUNXUQHK-SEYXRHQNSA-N 3-[3-[(z)-2-(2-propoxyphenyl)ethenyl]phenyl]propan-1-amine Chemical compound CCCOC1=CC=CC=C1\C=C/C1=CC=CC(CCCN)=C1 ZDQHOHLUNXUQHK-SEYXRHQNSA-N 0.000 claims 1
- JUUQPSIAQIZOGP-KHPPLWFESA-N 3-[3-[(z)-2-(3,4-dimethylphenyl)ethenyl]phenyl]propan-1-amine Chemical compound C1=C(C)C(C)=CC=C1\C=C/C1=CC=CC(CCCN)=C1 JUUQPSIAQIZOGP-KHPPLWFESA-N 0.000 claims 1
- LGLOMWKWZRFVPM-QXMHVHEDSA-N 3-[3-[(z)-2-(3-methoxynaphthalen-2-yl)ethenyl]phenyl]propan-1-amine Chemical compound COC1=CC2=CC=CC=C2C=C1\C=C/C1=CC=CC(CCCN)=C1 LGLOMWKWZRFVPM-QXMHVHEDSA-N 0.000 claims 1
- 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
- ZEVVCNAXJAQWFP-QXMHVHEDSA-N 3-[3-[(z)-2-[2-(2-methoxyethoxy)phenyl]ethenyl]phenyl]propan-1-amine Chemical compound COCCOC1=CC=CC=C1\C=C/C1=CC=CC(CCCN)=C1 ZEVVCNAXJAQWFP-QXMHVHEDSA-N 0.000 claims 1
- NXDBEZGJSOCPAL-YPKPFQOOSA-N 3-[3-[(z)-2-naphthalen-1-ylethenyl]phenyl]propan-1-amine Chemical compound NCCCC1=CC=CC(\C=C/C=2C3=CC=CC=C3C=CC=2)=C1 NXDBEZGJSOCPAL-YPKPFQOOSA-N 0.000 claims 1
- RXVRCNUGGRIQOS-UHFFFAOYSA-N 3-[3-[2-(2,6-dimethylphenyl)ethenyl]phenyl]-3-hydroxypropanimidamide Chemical compound CC1=CC=CC(C)=C1C=CC1=CC=CC(C(O)CC(N)=N)=C1 RXVRCNUGGRIQOS-UHFFFAOYSA-N 0.000 claims 1
- AILVLYLDTGIMED-VQHVLOKHSA-N 3-[5-[(e)-2-(2,6-dichlorophenyl)ethenyl]-2-methoxyphenyl]propan-1-amine Chemical compound C1=C(CCCN)C(OC)=CC=C1\C=C\C1=C(Cl)C=CC=C1Cl AILVLYLDTGIMED-VQHVLOKHSA-N 0.000 claims 1
- QCFDVSIWQVALQQ-CSKARUKUSA-N 3-[5-[(e)-2-(2-chloro-6-methylsulfanylphenyl)ethenyl]-2-methoxyphenyl]propan-1-amine Chemical compound C1=C(CCCN)C(OC)=CC=C1\C=C\C1=C(Cl)C=CC=C1SC QCFDVSIWQVALQQ-CSKARUKUSA-N 0.000 claims 1
- MVNYXEAZKVOLLN-MDZDMXLPSA-N 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(O)CCN)=C1 MVNYXEAZKVOLLN-MDZDMXLPSA-N 0.000 claims 1
- BUUMFQMGBUREOX-MDZDMXLPSA-N 3-amino-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-one Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(=O)CCN)=C1 BUUMFQMGBUREOX-MDZDMXLPSA-N 0.000 claims 1
- JNCYMQSTWYVZCF-BQYQJAHWSA-N 3-amino-1-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]propan-1-ol Chemical compound NCCC(O)C1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 JNCYMQSTWYVZCF-BQYQJAHWSA-N 0.000 claims 1
- IXEDDGWFONXBHR-BQYQJAHWSA-N 3-amino-1-[3-[(e)-2-(2,6-dichlorophenyl)ethenyl]phenyl]propan-1-one Chemical compound NCCC(=O)C1=CC=CC(\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 IXEDDGWFONXBHR-BQYQJAHWSA-N 0.000 claims 1
- SCVHVGHEAYRPBI-CMDGGOBGSA-N 3-amino-1-[3-[(e)-2-(2-chloro-6-methylphenyl)ethenyl]phenyl]propan-1-ol Chemical compound CC1=CC=CC(Cl)=C1\C=C\C1=CC=CC(C(O)CCN)=C1 SCVHVGHEAYRPBI-CMDGGOBGSA-N 0.000 claims 1
- FALVZABGRYNOON-VAWYXSNFSA-N 3-amino-2,2-dimethyl-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(O)C(C)(C)CN)=C1 FALVZABGRYNOON-VAWYXSNFSA-N 0.000 claims 1
- RBRQNNZLCPSMMQ-VAWYXSNFSA-N 3-amino-2,2-dimethyl-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-one Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(=O)C(C)(C)CN)=C1 RBRQNNZLCPSMMQ-VAWYXSNFSA-N 0.000 claims 1
- MPBBVYAEAAQSRC-MDZDMXLPSA-N 3-amino-2-fluoro-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-one Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(=O)C(F)CN)=C1 MPBBVYAEAAQSRC-MDZDMXLPSA-N 0.000 claims 1
- FXKCGXJBFRUOSM-ZHACJKMWSA-N 3-amino-2-methyl-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-ol Chemical compound NCC(C)C(O)C1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 FXKCGXJBFRUOSM-ZHACJKMWSA-N 0.000 claims 1
- OGYCIYIBRQOPIT-ZHACJKMWSA-N 3-amino-2-methyl-1-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-one Chemical compound NCC(C)C(=O)C1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 OGYCIYIBRQOPIT-ZHACJKMWSA-N 0.000 claims 1
- FBSOLVONTKXSJE-MDZDMXLPSA-N 3-fluoro-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(F)CCN)=C1 FBSOLVONTKXSJE-MDZDMXLPSA-N 0.000 claims 1
- SWELBYUDHIFUBI-ZHACJKMWSA-N 3-methoxy-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound NCCC(OC)C1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 SWELBYUDHIFUBI-ZHACJKMWSA-N 0.000 claims 1
- FEYOSYWCENBTJX-VAWYXSNFSA-N 3-methoxy-n-methyl-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]propan-1-amine Chemical compound CNCCC(OC)C1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 FEYOSYWCENBTJX-VAWYXSNFSA-N 0.000 claims 1
- UHFQKWZTHVORII-MDZDMXLPSA-N 4,4,4-trifluoro-3-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]butan-1-amine Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(CCN)C(F)(F)F)=C1 UHFQKWZTHVORII-MDZDMXLPSA-N 0.000 claims 1
- HGAFCTJJXJRDBW-DHZHZOJOSA-N 4-[(e)-2-[3-(2-aminoethoxy)phenyl]ethenyl]heptan-4-ol Chemical compound CCCC(O)(CCC)\C=C\C1=CC=CC(OCCN)=C1 HGAFCTJJXJRDBW-DHZHZOJOSA-N 0.000 claims 1
- YKDDVFPUWDDOOM-JLHYYAGUSA-N 4-[(e)-2-[3-(3-aminopropyl)phenyl]ethenyl]heptan-4-ol Chemical compound CCCC(O)(CCC)\C=C\C1=CC=CC(CCCN)=C1 YKDDVFPUWDDOOM-JLHYYAGUSA-N 0.000 claims 1
- OIOADURUGJUHOS-OUKQBFOZSA-N 4-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]butan-2-amine Chemical compound CC(N)CCC1=CC=CC(\C=C\C=2C(CCCC=2C)(C)C)=C1 OIOADURUGJUHOS-OUKQBFOZSA-N 0.000 claims 1
- IWPIWJMSAYHJPN-VAWYXSNFSA-N 4-[3-[3-[(e)-2-(2,6-dimethylphenyl)ethenyl]phenyl]propyl]morpholine Chemical compound CC1=CC=CC(C)=C1\C=C\C1=CC=CC(CCCN2CCOCC2)=C1 IWPIWJMSAYHJPN-VAWYXSNFSA-N 0.000 claims 1
- UOKDLUNJHPODHZ-MDZDMXLPSA-N 4-amino-1,1,1-trifluoro-2-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]butan-2-ol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(O)(CCN)C(F)(F)F)=C1 UOKDLUNJHPODHZ-MDZDMXLPSA-N 0.000 claims 1
- KHMHQHSWFSLHTL-ZHACJKMWSA-N 4-amino-2-[3-[(e)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl]phenyl]butan-2-ol Chemical compound CC1(C)CCCC(C)=C1\C=C\C1=CC=CC(C(C)(O)CCN)=C1 KHMHQHSWFSLHTL-ZHACJKMWSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229960002989 glutamic acid Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000001116 retinal neuron Anatomy 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91324107P | 2007-04-20 | 2007-04-20 | |
| US60/913,241 | 2007-04-20 | ||
| US93700207P | 2007-06-22 | 2007-06-22 | |
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010524975A JP2010524975A (ja) | 2010-07-22 |
| JP2010524975A5 true JP2010524975A5 (https=) | 2012-04-05 |
| JP5371953B2 JP5371953B2 (ja) | 2013-12-18 |
Family
ID=39876187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010504313A Expired - Fee Related JP5371953B2 (ja) | 2007-04-20 | 2008-04-21 | 眼の疾患及び障害を治療するスチレニル誘導体化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (7) | US20090170841A1 (https=) |
| EP (1) | EP2076124A4 (https=) |
| JP (1) | JP5371953B2 (https=) |
| KR (2) | KR101368248B1 (https=) |
| CN (1) | CN101686665B (https=) |
| AU (1) | AU2008242626B2 (https=) |
| BR (1) | BRPI0810063A2 (https=) |
| CA (1) | CA2681850C (https=) |
| CO (1) | CO6251201A2 (https=) |
| EC (1) | ECSP099695A (https=) |
| IL (1) | IL201285A (https=) |
| MX (1) | MX2009011360A (https=) |
| MY (1) | MY161818A (https=) |
| RU (1) | RU2494089C2 (https=) |
| WO (1) | WO2008131368A2 (https=) |
| ZA (1) | ZA200907313B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0810063A2 (pt) | 2007-04-20 | 2014-10-14 | Acucela Inc | Composto, composição farmacêutica, e, métodos para modular fluxo de cromóforo em um ciclo retinóide, para tratar uma doença ou distúrbio oftálmico em um indivíduo, para inibir adaptação ao escuro em uma célula fotorreceptora de bastão da retina, para inibir regeneração de rodopsina em uma célula fotoreceptora de bastão da retina, para reduzir isquemia em um olho de um indivíduo, para inibir neovascularização na retina de um olho de um indivíduo, e para inibir degeneração de uma célula da retina em uma retina |
| KR101270122B1 (ko) | 2007-11-01 | 2013-05-31 | 어큐셀라 인코포레이티드 | 안과 질환 및 장애를 치료하기 위한 아민 유도체 화합물 |
| JP5773877B2 (ja) | 2008-10-22 | 2015-09-02 | アキュセラ インコーポレイテッド | 眼の疾患及び障害を治療する化合物 |
| WO2012150208A1 (de) | 2011-05-04 | 2012-11-08 | Bayer Cropscience Ag | Verwendung von substituierten benzylalkoholestern der cyclopropancarbonsäure zur bekämpfung von insektizid-resistenten insekten |
| AU2012346214B2 (en) * | 2011-11-30 | 2017-09-14 | Bikam Pharmaceuticals, Inc. | Opsin-binding ligands, compositions and methods of use |
| HK1210969A1 (en) | 2012-01-20 | 2016-05-13 | 奥克塞拉有限公司 | Substituted heterocyclic compounds for disease treatment |
| TW201406707A (zh) * | 2012-05-04 | 2014-02-16 | Acucela Inc | 用以治療糖尿病性視網膜病變及其他眼部疾病之方法 |
| CN104379579B (zh) * | 2012-06-28 | 2017-03-08 | 诺华股份有限公司 | 吡咯烷衍生物及其作为补体途径调节剂的用途 |
| EP2867222A1 (en) * | 2012-06-28 | 2015-05-06 | Novartis AG | Pyrrolidine derivatives and their use as complement pathway modulators |
| ES2644700T3 (es) * | 2012-06-28 | 2017-11-30 | Novartis Ag | Derivados de pirrolidina y su uso como moduladores de la ruta del complemento |
| WO2014002054A1 (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) |
| WO2018208709A1 (en) * | 2017-05-09 | 2018-11-15 | Warner Babcock Institute For Green Chemistry, Llc | Stilbene derivatives for the treatment of cns and other disorders |
| US11325883B2 (en) | 2017-11-22 | 2022-05-10 | Temple University—Of the Commonwealth System of Higher Education | 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 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB815211A (en) | 1957-08-13 | 1959-06-17 | Bayer Ag | Basic ethers |
| US2566360A (en) * | 1948-08-30 | 1951-09-04 | Schering Corp | Aminoalkyl ethers of pyridyl alkylene aryl compounds |
| CH368181A (de) * | 1956-11-13 | 1963-03-31 | Geigy Ag J R | Verfahren zur Herstellung von N-Aminoalkylderivaten von Azepinen |
| US3095449A (en) * | 1957-08-06 | 1963-06-25 | Bayer Ag | 1-(gamma-dimethylaminopropoxy)-2-alkoxy alkenylbenzenes |
| NL255316A (https=) | 1959-08-28 | |||
| US3746768A (en) * | 1970-10-02 | 1973-07-17 | Scm Corp | Substituted phenyl ethers and thioethers as insect repellents |
| GB1433595A (en) * | 1972-07-06 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
| DE2547524A1 (de) * | 1975-10-23 | 1977-04-28 | Bayer Ag | Disubstituierte phenolaether des 3-amino-2-hydroxypropans, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4569354A (en) | 1982-03-22 | 1986-02-11 | Boston University | Method and apparatus for measuring natural retinal fluorescence |
| FR2558158B1 (fr) * | 1984-01-13 | 1986-05-16 | Roussel Uclaf | Derives de l'indole ethenyl phenol, leurs sels, procede de preparation, application a titre de medicaments, compositions les renfermant et intermediaires |
| US4861897A (en) * | 1987-06-22 | 1989-08-29 | Ortho Pharmaceutical Corporation | 2-Aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles |
| US5217999A (en) * | 1987-12-24 | 1993-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Styryl compounds which inhibit EGF receptor protein tyrosine kinase |
| US5141959A (en) * | 1990-09-21 | 1992-08-25 | Bristol-Myers Squibb Company | Isoprenoid phospholipase a2 inhibitors and preparations comprising same |
| WO2001009327A2 (en) | 1999-07-28 | 2001-02-08 | Genentech, Inc. | Method of preventing the injury or death of retinal cells and treating ocular diseases |
| JP3163391B2 (ja) * | 1995-03-07 | 2001-05-08 | 味の素株式会社 | スチルベン誘導体及びそれを含有する制癌剤 |
| TW334418B (en) * | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
| US5641750A (en) | 1995-11-29 | 1997-06-24 | Amgen Inc. | Methods for treating photoreceptors using glial cell line-derived neurotrophic factor (GDNF) protein product |
| US6878544B2 (en) | 1996-04-19 | 2005-04-12 | Neurotech Sa | Retinal cell lines with extended life-span and their applications |
| FR2747690B1 (fr) | 1996-04-19 | 1998-06-12 | Neurotech Sa | Lignees immortalisees de cellules retiniennes et leurs applications au traitement de differents troubles primaires ou secondaires ophtalmologiques ou neurologiques |
| US6090624A (en) * | 1996-04-19 | 2000-07-18 | Brown University Research Foundation | Immortalized retinal cell lines and their applications |
| RU2188819C2 (ru) * | 1996-08-12 | 2002-09-10 | Селджин Корпорейшн | НОВЫЕ ИММУНОТЕРАПЕВТИЧЕСКИЕ СОЕДИНЕНИЯ, СОДЕРЖАЩАЯ ИХ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ СНИЖЕНИЯ УРОВНЕЙ ФДЭ, TNFα И NFκB |
| AUPO235996A0 (en) | 1996-09-16 | 1996-10-10 | Garvan Institute Of Medical Research | Method of cell culture |
| CA2216439A1 (en) | 1996-09-25 | 1998-03-25 | Derek Van Der Kooy | Pharmaceuticals containing retinal stem cells |
| US6713300B1 (en) | 1997-02-27 | 2004-03-30 | University Of Utah Research Foundation | Nucleic acid and amino acid sequences for ATP-binding cassette transporter and methods of screening for agents that modify ATP-binding cassette transporter |
| AU1996599A (en) | 1997-12-05 | 1999-06-28 | Board Of Trustees Of The Leland Stanford Junior University | Long-term survival and regeneration of central nervous system neurons |
| IL143382A0 (en) | 1999-01-05 | 2002-04-21 | Aventis Pharma Sa | Human adult astrocytes, their preparation and uses thereof |
| EP1107003A1 (en) | 1999-12-09 | 2001-06-13 | Trophos | Methods for screening compounds active on neurons |
| US6406840B1 (en) * | 1999-12-17 | 2002-06-18 | Biomosaic Systems, Inc. | Cell arrays and the uses thereof |
| WO2001074810A2 (en) * | 2000-03-31 | 2001-10-11 | Ortho Mcneil Pharmaceutical, Inc. | Method for using 2-aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles as h3 antagonists |
| DE10021246A1 (de) | 2000-04-25 | 2001-10-31 | Schering Ag | Substituierte Benzoesäureamide und deren Verwendung als Arzneimittel |
| WO2001083714A2 (en) | 2000-05-02 | 2001-11-08 | Central Institute For The Deaf | Composition and methods for treating photoreceptor degeneration |
| US20020009713A1 (en) * | 2000-05-11 | 2002-01-24 | Miller Freda D. | Methods for identifying modulators of neuronal growth |
| AU2002216228A1 (en) * | 2000-12-21 | 2002-07-01 | Cancer Research Ventures Limited | Substituted stilbenes, their reactions and anticancer activity |
| US20030032078A1 (en) * | 2001-01-23 | 2003-02-13 | Board Of Regents, The University Of Texas System | Methods and compositions for the treatment of macular and retinal degenerations |
| DE10141018A1 (de) | 2001-08-22 | 2003-03-13 | Eth Zuerich Eidgenoessische Te | Verwendung von negativ geladenen Phospholipiden, sowie Zusammensetzungen umfassend Phospholipide zur Behandlung des Auges |
| CA2463902A1 (en) * | 2001-10-26 | 2003-05-01 | Oxigene, Inc. | Functionalized stilbene derivatives as improved vascular targeting agents |
| AU2002319899A1 (en) * | 2002-06-25 | 2004-01-06 | Raju Gokaraju Ganga | Novel resveratrol analogs |
| JP2006506970A (ja) | 2002-07-12 | 2006-03-02 | ユニバーシティ オブ ワシントン | 神経細胞の延長されたインビトロ培養のための方法および系 |
| US20060089343A1 (en) | 2002-12-06 | 2006-04-27 | Alcon, Inc. | Superoxide dismutase mimics for the treatment of ocular disorders and diseases |
| WO2004056806A1 (en) * | 2002-12-19 | 2004-07-08 | Pfizer Inc. | 2-(1h-indazol-6-ylamino)-benzamide compounds as protein kinases inhibitors useful for the treatment of ophtalmic diseases |
| JP3793759B2 (ja) | 2003-03-07 | 2006-07-05 | 憲敬 谷水 | 有孔パネル構体及びその製造方法 |
| EP1608352B1 (en) * | 2003-04-02 | 2009-12-30 | Taigen Biotechnology | Polyamine compounds for treating chemokine receptor mediated diseases |
| US20050074497A1 (en) * | 2003-04-09 | 2005-04-07 | Schultz Clyde L. | Hydrogels used to deliver medicaments to the eye for the treatment of posterior segment diseases |
| WO2004101505A1 (en) * | 2003-05-14 | 2004-11-25 | Novo Nordisk A/S | Novel compounds for treatment of obesity |
| EP1649009A2 (en) | 2003-07-30 | 2006-04-26 | Acucela, Inc. | Extended primary retinal cell culture and stress models, and methods of use |
| WO2005025498A2 (en) * | 2003-09-08 | 2005-03-24 | Corus Pharma | Substituted acetanilides and benzamides for the treatment of asthma and pulmonary inflammation |
| TW200529812A (en) | 2003-12-26 | 2005-09-16 | Chugai Pharmaceutical Co Ltd | Benzamide derivatives |
| US7706863B2 (en) | 2004-01-21 | 2010-04-27 | University Of Washington | Methods for assessing a physiological state of a mammalian retina |
| US7566808B2 (en) * | 2004-02-17 | 2009-07-28 | President And Fellows Of Harvard College | Management of ophthalmologic disorders, including macular degeneration |
| JP2007525496A (ja) * | 2004-02-17 | 2007-09-06 | プレジデント・アンド・フェロウズ・オブ・ハーバード・カレッジ | 黄班変性症を含む眼科疾患の管理 |
| EP1722766A2 (en) * | 2004-02-17 | 2006-11-22 | President And Fellows Of Harvard College | Management of ophthalmologic disorders, including macular degeneration |
| BRPI0511396B1 (pt) * | 2004-06-18 | 2021-07-27 | University Of Washington | Uso de 9-cis-retinil éster e uso de um derivado de retinal sintético |
| DE102004034957A1 (de) * | 2004-07-16 | 2006-02-02 | Carl Zeiss Jena Gmbh | Anordnung zur mikroskopischen Beobachtung und/oder Detektion und Verwendung |
| CA2638753A1 (en) * | 2004-12-08 | 2006-06-15 | Sirion Therapeutics, Inc. | Methods, assays and compositions for treating retinol-related diseases |
| US20080275134A1 (en) * | 2005-02-24 | 2008-11-06 | University Of Washington | Methods for Treatment of Retinal Degenerative Disease |
| US8098907B2 (en) * | 2005-07-01 | 2012-01-17 | Siemens Corporation | Method and system for local adaptive detection of microaneurysms in digital fundus images |
| JP2009524684A (ja) | 2006-01-26 | 2009-07-02 | アキュセラ， インコーポレイテッド | 眼疾患および障害の治療のための組成物および方法 |
| CN100398624C (zh) | 2006-03-24 | 2008-07-02 | 大连理工大学 | 高分子配位接枝的碱土铝酸盐长余辉发光材料及制备方法 |
| BRPI0810063A2 (pt) * | 2007-04-20 | 2014-10-14 | Acucela Inc | Composto, composição farmacêutica, e, métodos para modular fluxo de cromóforo em um ciclo retinóide, para tratar uma doença ou distúrbio oftálmico em um indivíduo, para inibir adaptação ao escuro em uma célula fotorreceptora de bastão da retina, para inibir regeneração de rodopsina em uma célula fotoreceptora de bastão da retina, para reduzir isquemia em um olho de um indivíduo, para inibir neovascularização na retina de um olho de um indivíduo, e para inibir degeneração de uma célula da retina em uma retina |
-
2008
- 2008-04-21 BR BRPI0810063-2A2A patent/BRPI0810063A2/pt not_active IP Right Cessation
- 2008-04-21 WO PCT/US2008/061073 patent/WO2008131368A2/en not_active Ceased
- 2008-04-21 AU AU2008242626A patent/AU2008242626B2/en not_active Ceased
- 2008-04-21 MX MX2009011360A patent/MX2009011360A/es active IP Right Grant
- 2008-04-21 CN CN200880021041.1A patent/CN101686665B/zh not_active Expired - Fee Related
- 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 US US12/107,040 patent/US20090170841A1/en not_active Abandoned
- 2008-04-21 RU RU2009136911/04A patent/RU2494089C2/ru not_active IP Right Cessation
- 2008-04-21 KR KR1020097024142A patent/KR101368248B1/ko not_active Expired - Fee Related
- 2008-04-21 KR KR1020127030994A patent/KR20120137513A/ko not_active Withdrawn
- 2008-04-21 CA CA2681850A patent/CA2681850C/en not_active Expired - Fee Related
- 2008-04-21 EP EP08746483A patent/EP2076124A4/en not_active Withdrawn
-
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
-
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
-
2016
- 2016-03-16 US US15/072,250 patent/US20160193160A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010524975A5 (https=) | ||
| RU2009136911A (ru) | Соединения, представляющие собой стиролильные производные, для лечения офтальмических заболеваний и расстройств | |
| JP2012515166A5 (https=) | ||
| JP2021502323A5 (https=) | ||
| JP2013542929A5 (https=) | ||
| JP2010526145A5 (https=) | ||
| JP2021529812A5 (https=) | ||
| RU2006107653A (ru) | Связующее вспомогательное вещество и приготовленная на его основе таблетка в форме капли | |
| RU2009148137A (ru) | Соединения, представляющие собой алкинилфенильные производные, для лечения офтальмических заболеваний и расстройств | |
| JP2018518537A5 (https=) | ||
| TW555735B (en) | Diarylpropylamines, methods for their preparation and pharmaceutical compositions containing them | |
| JP2020502047A5 (https=) | ||
| RU2010122261A (ru) | Производные амина и их применение для лечения офтальмологических заболеваний и расстройств | |
| JP2014051526A5 (https=) | ||
| JP2011509916A5 (https=) | ||
| JP2005505506A5 (https=) | ||
| JP2009541270A5 (https=) | ||
| JP2020506171A5 (https=) | ||
| JPH10279578A5 (https=) | ||
| JP2009527462A5 (https=) | ||
| JP2019501130A5 (https=) | ||
| JP2008510691A5 (https=) | ||
| JP2022141835A5 (https=) | ||
| JP2010530847A5 (https=) | ||
| JP2013526494A5 (https=) |