JP2017524674A5 - - Google Patents
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- Publication number
- JP2017524674A5 JP2017524674A5 JP2016573765A JP2016573765A JP2017524674A5 JP 2017524674 A5 JP2017524674 A5 JP 2017524674A5 JP 2016573765 A JP2016573765 A JP 2016573765A JP 2016573765 A JP2016573765 A JP 2016573765A JP 2017524674 A5 JP2017524674 A5 JP 2017524674A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- tetramethylchroman
- carboxamide
- piperazin
- compound
- 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
- 150000001875 compounds Chemical class 0.000 claims 20
- -1 6- hydroxy-2,5,7,8-tetramethyl chroman-2-yl Chemical group 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 238000012377 drug delivery Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- NORVCWJLPOIIRS-KTQQKIMGSA-N (2s)-1-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)N1CCC[C@H]1C(O)=O NORVCWJLPOIIRS-KTQQKIMGSA-N 0.000 claims 2
- WRTIMWQNBHGKJM-FUKCDUGKSA-N 2-[[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)CN1CCC[C@H]1CO WRTIMWQNBHGKJM-FUKCDUGKSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- BADWPGYBRKNJHJ-UHFFFAOYSA-N n,6-dihydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound O1C(C)(C(=O)NO)CCC2=C1C(C)=C(C)C(O)=C2C BADWPGYBRKNJHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- GLEVLJDDWXEYCO-CQSZACIVSA-N (2r)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound O1[C@@](C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-CQSZACIVSA-N 0.000 claims 1
- GLEVLJDDWXEYCO-AWEZNQCLSA-N (2s)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound O1[C@](C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-AWEZNQCLSA-N 0.000 claims 1
- BADWPGYBRKNJHJ-AWEZNQCLSA-N (2s)-n,6-dihydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound O1[C@](C)(C(=O)NO)CCC2=C1C(C)=C(C)C(O)=C2C BADWPGYBRKNJHJ-AWEZNQCLSA-N 0.000 claims 1
- MCJPTWSIETYCSU-UHFFFAOYSA-N (6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)-morpholin-4-ylmethanone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)N1CCOCC1 MCJPTWSIETYCSU-UHFFFAOYSA-N 0.000 claims 1
- UBQNZKMELMBKHG-UHFFFAOYSA-N (6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)-piperazin-1-ylmethanone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)N1CCNCC1 UBQNZKMELMBKHG-UHFFFAOYSA-N 0.000 claims 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
- PYQVCYCHUWIDIS-UHFFFAOYSA-N 2,5,7,8-tetramethyl-3,4-dihydro-2h-chromen-6-ol Chemical compound OC1=C(C)C(C)=C2OC(C)CCC2=C1C PYQVCYCHUWIDIS-UHFFFAOYSA-N 0.000 claims 1
- GHNWQVCAHKIRIR-UHFFFAOYSA-N 2-(butylaminomethyl)-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound OC1=C(C)C(C)=C2OC(CNCCCC)(C)CCC2=C1C GHNWQVCAHKIRIR-UHFFFAOYSA-N 0.000 claims 1
- MYLUPQWCRSVVTM-UHFFFAOYSA-N 2-(hydroxymethyl)-2,8-dimethyl-5,7-di(propan-2-yl)-3,4-dihydrochromen-6-ol Chemical compound O1C(C)(CO)CCC2=C1C(C)=C(C(C)C)C(O)=C2C(C)C MYLUPQWCRSVVTM-UHFFFAOYSA-N 0.000 claims 1
- LXPYRDXEWHBDJU-HXUWFJFHSA-N 2-[4-[(2r)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbonyl]piperazin-1-yl]acetic acid Chemical compound O=C([C@]1(C)OC=2C(C)=C(C(=C(C)C=2CC1)O)C)N1CCN(CC(O)=O)CC1 LXPYRDXEWHBDJU-HXUWFJFHSA-N 0.000 claims 1
- LXPYRDXEWHBDJU-FQEVSTJZSA-N 2-[4-[(2s)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbonyl]piperazin-1-yl]acetic acid Chemical compound O=C([C@@]1(C)OC=2C(C)=C(C(=C(C)C=2CC1)O)C)N1CCN(CC(O)=O)CC1 LXPYRDXEWHBDJU-FQEVSTJZSA-N 0.000 claims 1
- RZEZIIXRJOPPRA-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methylamino]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)CNCC1=CC=C(F)C=C1 RZEZIIXRJOPPRA-UHFFFAOYSA-N 0.000 claims 1
- SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 claims 1
- IINWNNKUXOSZAI-UHFFFAOYSA-N 4-(2-hydroxyethyl)piperazine-1-carbaldehyde Chemical compound OCCN1CCN(C=O)CC1 IINWNNKUXOSZAI-UHFFFAOYSA-N 0.000 claims 1
- UNOFNWSNORPWDP-UHFFFAOYSA-N 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbaldehyde Chemical compound O1C(C)(C=O)CCC2=C1C(C)=C(C)C(O)=C2C UNOFNWSNORPWDP-UHFFFAOYSA-N 0.000 claims 1
- UXLOWZVVECZEMQ-UHFFFAOYSA-N 6-hydroxy-2,5,7,8-tetramethyl-n-propan-2-yl-3,4-dihydrochromene-2-carboxamide Chemical compound OC1=C(C)C(C)=C2OC(C(=O)NC(C)C)(C)CCC2=C1C UXLOWZVVECZEMQ-UHFFFAOYSA-N 0.000 claims 1
- QTKYRUJVWXFHOU-UHFFFAOYSA-N 6-hydroxy-2,8-dimethyl-5,7-di(propan-2-yl)-3,4-dihydrochromene-2-carboxylic acid Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C(C)C)C(O)=C2C(C)C QTKYRUJVWXFHOU-UHFFFAOYSA-N 0.000 claims 1
- RVGJGTWZOLYPKT-ZZWBGTBQSA-N 6-hydroxy-N-[(1S)-2-hydroxy-1-phenylethyl]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound OC=1C(=C2CCC(OC2=C(C1C)C)(C(=O)N[C@H](CO)C1=CC=CC=C1)C)C RVGJGTWZOLYPKT-ZZWBGTBQSA-N 0.000 claims 1
- AYJMGUNMVOVXSE-SUSUGVNDSA-N 6-hydroxy-N-[(2R)-1-hydroxypropan-2-yl]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound OC=1C(=C2CCC(OC2=C(C1C)C)(C(=O)N[C@@H](CO)C)C)C AYJMGUNMVOVXSE-SUSUGVNDSA-N 0.000 claims 1
- YKELKSAJFBFVOW-UHFFFAOYSA-N 6-hydroxy-N-[2-[2-hydroxyethyl(methyl)amino]ethyl]-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound OC=1C(=C2CCC(OC2=C(C1C)C)(C(=O)NCCN(C)CCO)C)C YKELKSAJFBFVOW-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- BNAHZPIZRAJVFS-FOWTUZBSSA-N N-[(2E)-3,7-dimethylocta-2,6-dienyl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound C1CC(C(=O)NC/C=C(C)/CCC=C(C)C)(C)Oc2c1c(C)c(O)c(C)c2C BNAHZPIZRAJVFS-FOWTUZBSSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical group CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical group O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- BQGMIVFITHIERB-KTQQKIMGSA-N [(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methanone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)N1CCC[C@H]1CO BQGMIVFITHIERB-KTQQKIMGSA-N 0.000 claims 1
- YJSWNTCSQVPWRJ-UHFFFAOYSA-N [4-(2-hydroxyethyl)piperazin-1-yl]-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methanone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)N1CCN(CCO)CC1 YJSWNTCSQVPWRJ-UHFFFAOYSA-N 0.000 claims 1
- MJGRHGNFMLNPKL-UHFFFAOYSA-N [4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methanone Chemical compound OC=1C(=C2CCC(OC2=C(C1C)C)(C)C(=O)N1CCN(CC1)CCOCCO)C MJGRHGNFMLNPKL-UHFFFAOYSA-N 0.000 claims 1
- WLWUDXUFJYCNRD-UHFFFAOYSA-N [6-hydroxy-2,8-dimethyl-5,7-di(propan-2-yl)-3,4-dihydrochromen-2-yl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound C1CC=2C(C(C)C)=C(O)C(C(C)C)=C(C)C=2OC1(C)C(=O)N1CCN(CCO)CC1 WLWUDXUFJYCNRD-UHFFFAOYSA-N 0.000 claims 1
- JBBRRAJZYGAEQN-UHFFFAOYSA-N [6-hydroxy-2,8-dimethyl-5,7-di(propan-2-yl)-3,4-dihydrochromen-2-yl]-piperazin-1-ylmethanone Chemical compound C1CC=2C(C(C)C)=C(O)C(C(C)C)=C(C)C=2OC1(C)C(=O)N1CCNCC1 JBBRRAJZYGAEQN-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000002648 combination therapy Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical group CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002466 imines Chemical group 0.000 claims 1
- YXXFTTZFYNUVND-UHFFFAOYSA-N n'-(2-cyanoethyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbohydrazide Chemical compound O1C(C)(C(=O)NNCCC#N)CCC2=C1C(C)=C(C)C(O)=C2C YXXFTTZFYNUVND-UHFFFAOYSA-N 0.000 claims 1
- ZSQGXBMCMLZYOY-UHFFFAOYSA-N n-(2-bromoethyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound O1C(C)(C(=O)NCCBr)CCC2=C1C(C)=C(C)C(O)=C2C ZSQGXBMCMLZYOY-UHFFFAOYSA-N 0.000 claims 1
- GWSCFSULJBQQAF-UHFFFAOYSA-N n-(2-cyanoethyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound O1C(C)(C(=O)NCCC#N)CCC2=C1C(C)=C(C)C(O)=C2C GWSCFSULJBQQAF-UHFFFAOYSA-N 0.000 claims 1
- IXEOWYNUAYRQIK-UHFFFAOYSA-N n-(4-fluorophenyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)NC1=CC=C(F)C=C1 IXEOWYNUAYRQIK-UHFFFAOYSA-N 0.000 claims 1
- IKQNSCUNASIWRL-PLEWWHCXSA-N n-[(1r)-2-amino-2-oxo-1-phenylethyl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound C1([C@H](C(N)=O)NC(=O)C2(C)OC=3C(C)=C(C(=C(C)C=3CC2)O)C)=CC=CC=C1 IKQNSCUNASIWRL-PLEWWHCXSA-N 0.000 claims 1
- SPMIORDLEGBRNU-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)C(=O)NCC1=CC=C(F)C=C1 SPMIORDLEGBRNU-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2013012 | 2014-06-17 | ||
| NL2013012A NL2013012B1 (en) | 2014-06-17 | 2014-06-17 | Compounds for the treatment of chronic obstructive airway diseases. |
| PCT/EP2015/063579 WO2015193365A1 (en) | 2014-06-17 | 2015-06-17 | 6-hydroxy-2,5,7,8-tetramethylchroman-compounds for the treatment of chronic obstructive airway diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524674A JP2017524674A (ja) | 2017-08-31 |
| JP2017524674A5 true JP2017524674A5 (enExample) | 2018-07-26 |
| JP6711488B2 JP6711488B2 (ja) | 2020-06-17 |
Family
ID=51358046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016573765A Active JP6711488B2 (ja) | 2014-06-17 | 2015-06-17 | 慢性閉塞性気道疾患の治療のための６−ヒドロキシ−２，５，７，８−テトラメチルクロマン−化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US9913841B2 (enExample) |
| EP (1) | EP3157518B1 (enExample) |
| JP (1) | JP6711488B2 (enExample) |
| AU (1) | AU2015276186B2 (enExample) |
| CA (1) | CA2952288C (enExample) |
| ES (1) | ES2784475T3 (enExample) |
| NL (1) | NL2013012B1 (enExample) |
| WO (1) | WO2015193365A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL2010010C2 (en) * | 2012-12-19 | 2014-06-23 | Sulfateq B V | Compounds for protection of cells. |
| US11730741B2 (en) * | 2017-08-25 | 2023-08-22 | Sulfateq B.V. | 6-chromanol derivatives for use as a medicament |
| WO2019038361A1 (en) | 2017-08-25 | 2019-02-28 | Sulfateq B.V. | MEDICAMENTS FOR THE TREATMENT OF DISEASES OR DISORDERS RELATED TO VASOCONSTRICTION |
| CA3079483A1 (en) * | 2017-11-22 | 2019-05-31 | Khondrion Ip B.V. | Compounds as mpges-1 inhibitors |
| AU2020370210A1 (en) * | 2019-10-23 | 2022-04-21 | Chong Kun Dang Pharmaceutical Corp. | Compositions for preventing or treating chronic obstructive pulmonary diseases (COPD) |
| NL2031091B1 (en) * | 2022-02-28 | 2023-09-07 | Sulfateq Bv | Chromanol compounds for treatment or prophylaxis of ageing and ageing-associated disorders |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59222415A (ja) * | 1983-05-31 | 1984-12-14 | Kuraray Co Ltd | 免疫調節剤 |
| US4728650A (en) * | 1985-05-13 | 1988-03-01 | Kuraray Co., Ltd. | 3,4-dihydrobenzopyran derivatives and medicinal uses thereof |
| CA1338012C (en) * | 1987-04-27 | 1996-01-30 | John Michael Mccall | Pharmaceutically active amines |
| FR2673629B1 (fr) * | 1991-03-08 | 1993-05-07 | Adir | Nouveaux derives du benzopyrane leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2676056B1 (fr) * | 1991-05-03 | 1993-07-16 | Adir | Nouveaux derives du benzopyranne leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US20040122059A1 (en) * | 2002-10-01 | 2004-06-24 | The Penn State Research Foundation | PPAR-gamma ligands in the treatment of asthma and allergies |
| DE60325633D1 (de) | 2002-11-05 | 2009-02-12 | Ranpak Corp | Polsterumwandlungsmaschine mit aufwickelhaspel und befestigungsvorrichtung |
| AU2003297294A1 (en) * | 2002-11-20 | 2004-06-15 | Board Of Regents, The University Of Texas System | Methods for inhibiting allergic inflammation and other responses initiated by pollens, molds, and other non-animal derived allergens |
| CA2580584C (en) * | 2003-09-19 | 2015-07-28 | Galileo Pharmaceuticals, Inc. | Use of alpha-tocotrienol for treatment of mitochondrial diseases |
| WO2005079300A2 (en) * | 2004-02-13 | 2005-09-01 | Albert Einstein College Of Medicine Of Yeshiva University | Protein kinase inhibitors and methods for identifying same |
| NL2010010C2 (en) * | 2012-12-19 | 2014-06-23 | Sulfateq B V | Compounds for protection of cells. |
| MX2016014738A (es) * | 2014-05-12 | 2017-03-06 | Gruenenthal Gmbh | Formulacion en capsula de liberacion inmediata resistente a alteraciones que comprende tapentadol. |
-
2014
- 2014-06-17 NL NL2013012A patent/NL2013012B1/en active
-
2015
- 2015-06-17 AU AU2015276186A patent/AU2015276186B2/en active Active
- 2015-06-17 JP JP2016573765A patent/JP6711488B2/ja active Active
- 2015-06-17 WO PCT/EP2015/063579 patent/WO2015193365A1/en not_active Ceased
- 2015-06-17 US US15/318,635 patent/US9913841B2/en active Active
- 2015-06-17 EP EP15730478.3A patent/EP3157518B1/en active Active
- 2015-06-17 CA CA2952288A patent/CA2952288C/en active Active
- 2015-06-17 ES ES15730478T patent/ES2784475T3/es active Active
-
2018
- 2018-01-26 US US15/880,634 patent/US10426771B2/en active Active
- 2018-01-26 US US15/880,628 patent/US10322124B2/en active Active
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