JP2016534134A5 - - Google Patents
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- JP2016534134A5 JP2016534134A5 JP2016540436A JP2016540436A JP2016534134A5 JP 2016534134 A5 JP2016534134 A5 JP 2016534134A5 JP 2016540436 A JP2016540436 A JP 2016540436A JP 2016540436 A JP2016540436 A JP 2016540436A JP 2016534134 A5 JP2016534134 A5 JP 2016534134A5
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- JP
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- Prior art keywords
- hydroxy
- alkyl
- cyano
- compound
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- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- -1 sulfonamido, sulfonyl Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- MXUSGDMIHGLCNC-HNNXBMFYSA-N 3-[[(1s)-7-(difluoromethylsulfonyl)-2,2-difluoro-1-hydroxy-1,3-dihydroinden-4-yl]oxy]-5-fluorobenzonitrile Chemical compound C=1C=C(S(=O)(=O)C(F)F)C([C@@H](C(C2)(F)F)O)=C2C=1OC1=CC(F)=CC(C#N)=C1 MXUSGDMIHGLCNC-HNNXBMFYSA-N 0.000 claims description 2
- GTHLUQQEKIJSME-CXAGYDPISA-N FC=1C=C(C#N)C=C(C=1)OC1=C2C[C@H]([C@H](C2=C(C=C1)S(=O)(=O)C)O)F Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=C2C[C@H]([C@H](C2=C(C=C1)S(=O)(=O)C)O)F GTHLUQQEKIJSME-CXAGYDPISA-N 0.000 claims description 2
- VHWGCWVDVWACAH-CVEARBPZSA-N FC=1C=C(C#N)C=C(C=1)OC1=C2[C@H](C([C@H](C2=C(C=C1)S(=O)(=O)C)O)(F)F)F Chemical compound FC=1C=C(C#N)C=C(C=1)OC1=C2[C@H](C([C@H](C2=C(C=C1)S(=O)(=O)C)O)(F)F)F VHWGCWVDVWACAH-CVEARBPZSA-N 0.000 claims description 2
- LOMMPXLFBTZENJ-ZACQAIPSSA-N F[C@H]1[C@H](C2=C(C=CC(=C2[C@H]1F)OC=1C=C(C#N)C=C(C=1)F)S(=O)(=O)C)O Chemical compound F[C@H]1[C@H](C2=C(C=CC(=C2[C@H]1F)OC=1C=C(C#N)C=C(C=1)F)S(=O)(=O)C)O LOMMPXLFBTZENJ-ZACQAIPSSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 0 *#Cc(c([C@]1N=O)c2CC1(F)F)ccc2Oc1cc(F)cc(F)c1 Chemical compound *#Cc(c([C@]1N=O)c2CC1(F)F)ccc2Oc1cc(F)cc(F)c1 0.000 description 6
- 229940124530 sulfonamide Drugs 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- 208000030808 Clear cell renal carcinoma Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 206010073251 clear cell renal cell carcinoma Diseases 0.000 description 2
- 201000011330 nonpapillary renal cell carcinoma Diseases 0.000 description 2
- ZGVWZAJMWJIHNT-HNNXBMFYSA-N CS(c(c([C@@H]1O)c2CC1(F)F)ccc2Oc1cc(F)cc(F)c1)(=O)=O Chemical compound CS(c(c([C@@H]1O)c2CC1(F)F)ccc2Oc1cc(F)cc(F)c1)(=O)=O ZGVWZAJMWJIHNT-HNNXBMFYSA-N 0.000 description 1
- YSQBDUMLHQLQBH-HPGBDJQBSA-N C[S@](c(cc1)c([C@@H](C(C2)(F)F)O)c2c1Oc1cc(C#N)cc(F)c1)(=NC#N)=O Chemical compound C[S@](c(cc1)c([C@@H](C(C2)(F)F)O)c2c1Oc1cc(C#N)cc(F)c1)(=NC#N)=O YSQBDUMLHQLQBH-HPGBDJQBSA-N 0.000 description 1
- KXKBSLFAMIIKMT-UHFFFAOYSA-N OC(C(Cc1c(cc2)Oc(cc3)c(cn[nH]4)c4c3F)(F)F)c1c2S(C(F)(F)F)(=O)=O Chemical compound OC(C(Cc1c(cc2)Oc(cc3)c(cn[nH]4)c4c3F)(F)F)c1c2S(C(F)(F)F)(=O)=O KXKBSLFAMIIKMT-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N cyanamide group Chemical group C(#N)[NH-] ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361875674P | 2013-09-09 | 2013-09-09 | |
| US61/875,674 | 2013-09-09 | ||
| US201461978421P | 2014-04-11 | 2014-04-11 | |
| US61/978,421 | 2014-04-11 | ||
| PCT/US2014/054375 WO2015035223A1 (en) | 2013-09-09 | 2014-09-05 | Aryl ethers and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019018100A Division JP6746733B2 (ja) | 2013-09-09 | 2019-02-04 | アリールエーテルおよびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016534134A JP2016534134A (ja) | 2016-11-04 |
| JP2016534134A5 true JP2016534134A5 (enExample) | 2017-10-12 |
| JP6486940B2 JP6486940B2 (ja) | 2019-03-20 |
Family
ID=52628976
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016540436A Active JP6486940B2 (ja) | 2013-09-09 | 2014-09-05 | アリールエーテルおよびその使用 |
| JP2019018100A Active JP6746733B2 (ja) | 2013-09-09 | 2019-02-04 | アリールエーテルおよびその使用 |
| JP2019052947A Active JP6918039B2 (ja) | 2013-09-09 | 2019-03-20 | アリールエーテルおよびその使用 |
| JP2019052946A Pending JP2019089855A (ja) | 2013-09-09 | 2019-03-20 | アリールエーテルおよびその使用 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019018100A Active JP6746733B2 (ja) | 2013-09-09 | 2019-02-04 | アリールエーテルおよびその使用 |
| JP2019052947A Active JP6918039B2 (ja) | 2013-09-09 | 2019-03-20 | アリールエーテルおよびその使用 |
| JP2019052946A Pending JP2019089855A (ja) | 2013-09-09 | 2019-03-20 | アリールエーテルおよびその使用 |
Country Status (33)
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