JP2017502929A5 - - Google Patents
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- Publication number
- JP2017502929A5 JP2017502929A5 JP2016534904A JP2016534904A JP2017502929A5 JP 2017502929 A5 JP2017502929 A5 JP 2017502929A5 JP 2016534904 A JP2016534904 A JP 2016534904A JP 2016534904 A JP2016534904 A JP 2016534904A JP 2017502929 A5 JP2017502929 A5 JP 2017502929A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pharmaceutical composition
- pyrrole
- chloro
- dione
- 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 18
- 102100029095 Exportin-1 Human genes 0.000 claims 15
- 101100485284 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CRM1 gene Proteins 0.000 claims 15
- 101150094313 XPO1 gene Proteins 0.000 claims 15
- 108700002148 exportin 1 Proteins 0.000 claims 15
- 239000003112 inhibitor Substances 0.000 claims 12
- 238000000034 method Methods 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- -1 (E) -3- [3- (3-chloro-phenyl)-[1,2,4] -triazol-1-yl] -acrylic acid (Z) -3- [3- (3-chloro-phenyl)-[1,2,4] -triazol-1-yl] -acrylic acid tert-butyl ester Chemical compound 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 4
- 208000005980 beta thalassemia Diseases 0.000 claims 3
- 210000003743 erythrocyte Anatomy 0.000 claims 3
- 230000014509 gene expression Effects 0.000 claims 3
- 108010078791 Carrier Proteins Proteins 0.000 claims 2
- 208000002903 Thalassemia Diseases 0.000 claims 2
- LBNWRDCVNGUTBP-MDZDMXLPSA-N (e)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]-n-(4-methoxyphenyl)prop-2-enamide Chemical compound C1=CC(OC)=CC=C1NC(=O)\C=C\N1N=C(C=2C=C(Cl)C=CC=2)N=C1 LBNWRDCVNGUTBP-MDZDMXLPSA-N 0.000 claims 1
- RCDZDLFYRJZSRK-ZHACJKMWSA-N (e)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]-n-methyl-n-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1N(C)C(=O)\C=C\N(N=1)C=NC=1C1=CC=CC(Cl)=C1 RCDZDLFYRJZSRK-ZHACJKMWSA-N 0.000 claims 1
- UFBGPWSHVRYAPK-CMDGGOBGSA-N (e)-n-(4-aminophenyl)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]prop-2-enamide Chemical compound C1=CC(N)=CC=C1NC(=O)\C=C\N1N=C(C=2C=C(Cl)C=CC=2)N=C1 UFBGPWSHVRYAPK-CMDGGOBGSA-N 0.000 claims 1
- JCHAWRDHMUSLMM-UPHRSURJSA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-1-(3,3-difluoroazetidin-1-yl)prop-2-en-1-one Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)N3CC(F)(F)C3)C=N2)=C1 JCHAWRDHMUSLMM-UPHRSURJSA-N 0.000 claims 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
- DRDQGJCDVFFQMI-UHFFFAOYSA-N 1-(1-benzothiophen-3-ylmethyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CSC2=CC=CC=C12 DRDQGJCDVFFQMI-UHFFFAOYSA-N 0.000 claims 1
- MQYSATPQVZDKMW-UHFFFAOYSA-N 1-(2-thiophen-2-ylethyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCC1=CC=CS1 MQYSATPQVZDKMW-UHFFFAOYSA-N 0.000 claims 1
- KXMUNWPEHIUIET-UHFFFAOYSA-N 1-(3-benzoyl-4-methylthiophen-2-yl)pyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C(=O)C=1C(C)=CSC=1N1C(=O)C=CC1=O KXMUNWPEHIUIET-UHFFFAOYSA-N 0.000 claims 1
- VAMQLZCXRXXOSK-UHFFFAOYSA-N 1-(4-bromo-2,5-difluorophenyl)pyrrole-2,5-dione Chemical compound C1=C(Br)C(F)=CC(N2C(C=CC2=O)=O)=C1F VAMQLZCXRXXOSK-UHFFFAOYSA-N 0.000 claims 1
- FHBLPSBHNPTLLW-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(C2CCCCC2)C=C1 FHBLPSBHNPTLLW-UHFFFAOYSA-N 0.000 claims 1
- XAHCEMQKWSQGLQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)pyrrole-2,5-dione Chemical group C1=CC(OC)=CC=C1N1C(=O)C=CC1=O XAHCEMQKWSQGLQ-UHFFFAOYSA-N 0.000 claims 1
- NNBAXWAPIROUSM-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2CCOCC2)C=C1 NNBAXWAPIROUSM-UHFFFAOYSA-N 0.000 claims 1
- VTEURHGUCFTVGM-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrole-2,5-dione Chemical compound C1=C(OC)C(OC)=CC=C1CCN1C(=O)C=CC1=O VTEURHGUCFTVGM-UHFFFAOYSA-N 0.000 claims 1
- MZOKHTDHXVAGFM-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]pyrrole-2,5-dione Chemical compound C1=CC(Cl)=CC=C1CCN1C(=O)C=CC1=O MZOKHTDHXVAGFM-UHFFFAOYSA-N 0.000 claims 1
- YMGYPUVJOUFUGE-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)pyrazol-1-yl]phenyl]pyrrole-2,5-dione Chemical compound N1=C(C(F)(F)F)C=CN1C1=CC=C(N2C(C=CC2=O)=O)C=C1 YMGYPUVJOUFUGE-UHFFFAOYSA-N 0.000 claims 1
- BAWHYOHVWHQWFQ-UHFFFAOYSA-N 1-naphthalen-1-ylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC2=CC=CC=C12 BAWHYOHVWHQWFQ-UHFFFAOYSA-N 0.000 claims 1
- UPWIXROBQHXMSV-UHFFFAOYSA-N 3-methyl-1-(1-methylpyrazol-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C1=NN(C)C=C1 UPWIXROBQHXMSV-UHFFFAOYSA-N 0.000 claims 1
- 108090000994 Catalytic RNA Proteins 0.000 claims 1
- 102000053642 Catalytic RNA Human genes 0.000 claims 1
- WDIIIHNJKLSKNH-XIBRBONQSA-N ClC1=C(C=CC=C1)NC(\C=C\N1N=C(N=C1)C1=CC(=CC=C1)Cl)=O.ClC=1C=C(C=CC1)C1=NN(C=N1)/C=C/C(=O)NC1=CC=CC=C1 Chemical compound ClC1=C(C=CC=C1)NC(\C=C\N1N=C(N=C1)C1=CC(=CC=C1)Cl)=O.ClC=1C=C(C=CC1)C1=NN(C=N1)/C=C/C(=O)NC1=CC=CC=C1 WDIIIHNJKLSKNH-XIBRBONQSA-N 0.000 claims 1
- 102100031690 Erythroid transcription factor Human genes 0.000 claims 1
- 101710100588 Erythroid transcription factor Proteins 0.000 claims 1
- 229940122498 Gene expression inhibitor Drugs 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- 108020004459 Small interfering RNA Proteins 0.000 claims 1
- 239000000074 antisense oligonucleotide Substances 0.000 claims 1
- 238000012230 antisense oligonucleotides Methods 0.000 claims 1
- 230000011748 cell maturation Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- ZIDYPKUSLUFJCE-VOTSOKGWSA-N ethyl (e)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]prop-2-enoate Chemical compound CCOC(=O)\C=C\N1C=NC(C=2C=C(Cl)C=CC=2)=N1 ZIDYPKUSLUFJCE-VOTSOKGWSA-N 0.000 claims 1
- ZIDYPKUSLUFJCE-SREVYHEPSA-N ethyl (z)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]prop-2-enoate Chemical group CCOC(=O)\C=C/N1C=NC(C=2C=C(Cl)C=CC=2)=N1 ZIDYPKUSLUFJCE-SREVYHEPSA-N 0.000 claims 1
- 230000002779 inactivation Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000035800 maturation Effects 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- KLXKTTGROYBSDM-SREVYHEPSA-N propan-2-yl (z)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]prop-2-enoate Chemical compound CC(C)OC(=O)\C=C/N1C=NC(C=2C=C(Cl)C=CC=2)=N1 KLXKTTGROYBSDM-SREVYHEPSA-N 0.000 claims 1
- 230000002797 proteolythic effect Effects 0.000 claims 1
- 108091092562 ribozyme Proteins 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- VYXKJDGAVZVZAA-FPLPWBNLSA-N tert-butyl (z)-3-[3-(3-chlorophenyl)-1,2,4-triazol-1-yl]prop-2-enoate Chemical compound CC(C)(C)OC(=O)\C=C/N1C=NC(C=2C=C(Cl)C=CC=2)=N1 VYXKJDGAVZVZAA-FPLPWBNLSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13306628.2 | 2013-11-28 | ||
| EP13306628 | 2013-11-28 | ||
| PCT/EP2014/075980 WO2015079031A1 (en) | 2013-11-28 | 2014-11-28 | Methods and pharmaceutical compositions for the treatment of beta-thalassemias |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017502929A JP2017502929A (ja) | 2017-01-26 |
| JP2017502929A5 true JP2017502929A5 (enExample) | 2017-12-28 |
| JP6527149B2 JP6527149B2 (ja) | 2019-06-05 |
Family
ID=49713040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016534904A Expired - Fee Related JP6527149B2 (ja) | 2013-11-28 | 2014-11-28 | ベータ−サラセミアの処置のための方法及び医薬組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9861615B2 (enExample) |
| EP (1) | EP3074007B1 (enExample) |
| JP (1) | JP6527149B2 (enExample) |
| ES (1) | ES2739637T3 (enExample) |
| WO (1) | WO2015079031A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020247654A1 (en) * | 2019-06-06 | 2020-12-10 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine, Inc. | Setbp1 and xpo1 inhibitors for the treatment of sickle cell disease and beta-thalassemia |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8513230B2 (en) * | 2010-03-05 | 2013-08-20 | Karyopharm Therapeutics, Inc. | Nuclear transport modulators and uses thereof |
| CN103402359B (zh) * | 2011-01-17 | 2016-08-24 | 卡尔约药物治疗公司 | 含烯烃核运输调节剂及其用途 |
| EP2736883B1 (en) * | 2011-07-29 | 2019-09-04 | Karyopharm Therapeutics, Inc. | Nuclear transport modulators and uses thereof |
| EP2736887B1 (en) * | 2011-07-29 | 2017-10-18 | Karyopharm Therapeutics, Inc. | Hydrazide containing nuclear transport modulators and uses thereof |
| WO2013020024A2 (en) * | 2011-08-03 | 2013-02-07 | Karyopharm Therapeutics, Inc. | Maleimide compounds and methods of treatment |
-
2014
- 2014-11-28 WO PCT/EP2014/075980 patent/WO2015079031A1/en not_active Ceased
- 2014-11-28 ES ES14808905T patent/ES2739637T3/es active Active
- 2014-11-28 JP JP2016534904A patent/JP6527149B2/ja not_active Expired - Fee Related
- 2014-11-28 EP EP14808905.5A patent/EP3074007B1/en not_active Not-in-force
- 2014-11-28 US US15/039,230 patent/US9861615B2/en not_active Expired - Fee Related
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