JP2013529602A5 - - Google Patents
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- Publication number
- JP2013529602A5 JP2013529602A5 JP2013515698A JP2013515698A JP2013529602A5 JP 2013529602 A5 JP2013529602 A5 JP 2013529602A5 JP 2013515698 A JP2013515698 A JP 2013515698A JP 2013515698 A JP2013515698 A JP 2013515698A JP 2013529602 A5 JP2013529602 A5 JP 2013529602A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- serum cmax
- mmol
- added
- metabolite
- 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 description 8
- 210000002966 serum Anatomy 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- AOYVMYGVYYGONA-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[7-(difluoromethoxy)spiro[1,3-benzodioxole-2,4'-thiane]-4-yl]ethanone Chemical compound C1=2OC3(CCSCC3)OC=2C(OC(F)F)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl AOYVMYGVYYGONA-UHFFFAOYSA-N 0.000 description 2
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 0 *c1c(CC(c(c2c3OC4(CCSCC4)O2)ccc3OC(F)F)=O)c(Cl)cnc1 Chemical compound *c1c(CC(c(c2c3OC4(CCSCC4)O2)ccc3OC(F)F)=O)c(Cl)cnc1 0.000 description 1
- -1 3,5-Dichloropyridin-4-yl Chemical group 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35820910P | 2010-06-24 | 2010-06-24 | |
| US61/358,209 | 2010-06-24 | ||
| PCT/DK2011/000069 WO2011160632A1 (en) | 2010-06-24 | 2011-06-24 | Benzodioxole or benzodioxepine heterocyclic compounds phosphodiesterase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016052707A Division JP2016164168A (ja) | 2010-06-24 | 2016-03-16 | ホスホジエステラーゼ阻害剤としてのベンゾジオキソールまたはベンゾジオキセピンヘテロ環化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013529602A JP2013529602A (ja) | 2013-07-22 |
| JP2013529602A5 true JP2013529602A5 (OSRAM) | 2014-07-03 |
| JP6174997B2 JP6174997B2 (ja) | 2017-08-02 |
Family
ID=44351701
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013515698A Active JP6174997B2 (ja) | 2010-06-24 | 2011-06-24 | ホスホジエステラーゼ阻害剤としてのベンゾジオキソールまたはベンゾジオキセピンヘテロ環化合物 |
| JP2016052707A Pending JP2016164168A (ja) | 2010-06-24 | 2016-03-16 | ホスホジエステラーゼ阻害剤としてのベンゾジオキソールまたはベンゾジオキセピンヘテロ環化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016052707A Pending JP2016164168A (ja) | 2010-06-24 | 2016-03-16 | ホスホジエステラーゼ阻害剤としてのベンゾジオキソールまたはベンゾジオキセピンヘテロ環化合物 |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US8980905B2 (OSRAM) |
| EP (2) | EP2585469B1 (OSRAM) |
| JP (2) | JP6174997B2 (OSRAM) |
| KR (1) | KR101864578B1 (OSRAM) |
| CN (1) | CN102958937B (OSRAM) |
| AU (1) | AU2011269429B2 (OSRAM) |
| BR (1) | BR112012032813B1 (OSRAM) |
| CA (1) | CA2802895C (OSRAM) |
| CY (2) | CY1117862T1 (OSRAM) |
| DK (2) | DK2585469T3 (OSRAM) |
| ES (2) | ES2584055T3 (OSRAM) |
| HR (2) | HRP20160919T1 (OSRAM) |
| HU (2) | HUE044301T2 (OSRAM) |
| IL (1) | IL223329A (OSRAM) |
| LT (2) | LT3070091T (OSRAM) |
| MX (1) | MX2012014131A (OSRAM) |
| MY (1) | MY157481A (OSRAM) |
| NZ (1) | NZ603895A (OSRAM) |
| PL (2) | PL2585469T3 (OSRAM) |
| PT (2) | PT2585469T (OSRAM) |
| RS (2) | RS58945B1 (OSRAM) |
| RU (1) | RU2583787C2 (OSRAM) |
| SG (1) | SG186140A1 (OSRAM) |
| SI (2) | SI3070091T1 (OSRAM) |
| TR (1) | TR201909709T4 (OSRAM) |
| TW (1) | TWI507410B (OSRAM) |
| UA (1) | UA109140C2 (OSRAM) |
| WO (1) | WO2011160632A1 (OSRAM) |
| ZA (1) | ZA201209031B (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104822392B (zh) * | 2012-11-30 | 2017-09-08 | 利奥制药有限公司 | 抑制活化的t‑细胞中il‑22表达的方法 |
| CA2953284A1 (en) * | 2014-06-23 | 2015-12-30 | Leo Pharma A/S | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
| WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
| CA3007432A1 (en) * | 2015-12-18 | 2017-06-22 | Leo Pharma A/S | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
| IL271399B (en) * | 2017-06-20 | 2022-07-01 | Leo Pharma As | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
| US11384096B2 (en) | 2017-12-15 | 2022-07-12 | UNION therapeutics A/S | Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors |
| CA3100977A1 (en) | 2018-05-21 | 2019-11-28 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| LT3911304T (lt) * | 2019-01-15 | 2023-11-10 | UNION therapeutics A/S | Modifikuoto atpalaidavimo tablečių vaisto formos, kurių sudėtyje yra fosfodiesterazės inhibitorių |
| WO2021016409A1 (en) * | 2019-07-24 | 2021-01-28 | Constellation Pharmaceuticals, Inc. | Ezh2 inhibition in combination therapies for the treatment of cancers |
| CN112552276B (zh) * | 2019-09-25 | 2023-03-21 | 中国科学院上海药物研究所 | 苯并氧杂卓-5-酮类化合物及其制备方法和用途 |
| WO2022200339A1 (en) | 2021-03-22 | 2022-09-29 | UNION therapeutics A/S | Treatment of hidradenitis suppurativa with orismilast |
| GB202205715D0 (en) | 2022-04-19 | 2022-06-01 | Union Therapeutics As | Treatment of neutrophilic dermatoses |
| GB202306662D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Dosage regimen |
| GB202306663D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Combination therapy |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI0706513T1 (en) * | 1993-07-02 | 2002-10-31 | Altana Pharma Ag | Fluoroalkoxy-substituted benzamides and their use as cyclic nucleotide phosphodiesterase inhibitors |
| GB9507297D0 (en) | 1995-04-07 | 1995-05-31 | Rh Ne Poulenc Rorer Limited | New composition of matter |
| AU705690B2 (en) | 1995-05-19 | 1999-05-27 | Kyowa Hakko Kogyo Co. Ltd. | Oxygen-containing heterocyclic compounds |
| NZ332340A (en) * | 1996-05-20 | 2000-04-28 | Darwin Discovery Ltd | 4-(aryl or heteroaryl) substituted benzofurancarboxamide derivatives and medicaments |
| CA2272327A1 (en) * | 1996-11-19 | 1998-05-28 | Kyowa Hakko Kogyo Co., Ltd. | Oxygen-containing heterocyclic compounds |
| JP2005060375A (ja) * | 2003-07-28 | 2005-03-10 | Kyowa Hakko Kogyo Co Ltd | 含酸素複素環化合物 |
| DE10360792A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| EP1831227B1 (en) * | 2004-12-17 | 2013-06-19 | Glenmark Pharmaceuticals S.A. | Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders |
| CN101631792B (zh) * | 2007-02-28 | 2013-05-01 | 利奥制药有限公司 | 新的磷酸二酯酶抑制剂 |
| KR101571654B1 (ko) * | 2007-02-28 | 2015-11-25 | 레오 파마 에이/에스 | 신규한 포스포디에스테라제 억제제 |
| ES2583478T3 (es) * | 2011-12-21 | 2016-09-21 | Leo Pharma A/S | [1,2,4] triazolopiridinas y su uso como inhibidores de fosfodiesterasa |
-
2011
- 2011-06-24 NZ NZ603895A patent/NZ603895A/en unknown
- 2011-06-24 SI SI201131743T patent/SI3070091T1/sl unknown
- 2011-06-24 HU HUE16020112 patent/HUE044301T2/hu unknown
- 2011-06-24 WO PCT/DK2011/000069 patent/WO2011160632A1/en not_active Ceased
- 2011-06-24 AU AU2011269429A patent/AU2011269429B2/en active Active
- 2011-06-24 LT LTEP16020112.5T patent/LT3070091T/lt unknown
- 2011-06-24 MY MYPI2012005553A patent/MY157481A/en unknown
- 2011-06-24 KR KR1020137001855A patent/KR101864578B1/ko active Active
- 2011-06-24 RU RU2013103079/04A patent/RU2583787C2/ru active
- 2011-06-24 PT PT117298893T patent/PT2585469T/pt unknown
- 2011-06-24 DK DK11729889.3T patent/DK2585469T3/en active
- 2011-06-24 CA CA2802895A patent/CA2802895C/en active Active
- 2011-06-24 RS RS20190851A patent/RS58945B1/sr unknown
- 2011-06-24 LT LTEP11729889.3T patent/LT2585469T/lt unknown
- 2011-06-24 PT PT16020112T patent/PT3070091T/pt unknown
- 2011-06-24 RS RS20160581A patent/RS55104B1/sr unknown
- 2011-06-24 TR TR2019/09709T patent/TR201909709T4/tr unknown
- 2011-06-24 UA UAA201300812A patent/UA109140C2/uk unknown
- 2011-06-24 MX MX2012014131A patent/MX2012014131A/es active IP Right Grant
- 2011-06-24 PL PL11729889T patent/PL2585469T3/pl unknown
- 2011-06-24 CN CN201180031069.5A patent/CN102958937B/zh active Active
- 2011-06-24 ES ES11729889.3T patent/ES2584055T3/es active Active
- 2011-06-24 HU HUE11729889A patent/HUE030081T2/en unknown
- 2011-06-24 US US13/806,659 patent/US8980905B2/en active Active
- 2011-06-24 EP EP11729889.3A patent/EP2585469B1/en active Active
- 2011-06-24 ES ES16020112T patent/ES2733092T3/es active Active
- 2011-06-24 PL PL16020112T patent/PL3070091T3/pl unknown
- 2011-06-24 SG SG2012088761A patent/SG186140A1/en unknown
- 2011-06-24 BR BR112012032813-1A patent/BR112012032813B1/pt active IP Right Grant
- 2011-06-24 SI SI201130896A patent/SI2585469T1/sl unknown
- 2011-06-24 DK DK16020112.5T patent/DK3070091T3/da active
- 2011-06-24 EP EP16020112.5A patent/EP3070091B1/en active Active
- 2011-06-24 HR HRP20160919TT patent/HRP20160919T1/hr unknown
- 2011-06-24 JP JP2013515698A patent/JP6174997B2/ja active Active
- 2011-06-24 TW TW100122303A patent/TWI507410B/zh active
-
2012
- 2012-11-28 IL IL223329A patent/IL223329A/en active IP Right Grant
- 2012-11-29 ZA ZA2012/09031A patent/ZA201209031B/en unknown
-
2014
- 2014-12-30 US US14/586,681 patent/US9273064B2/en active Active
-
2015
- 2015-10-01 US US14/872,487 patent/US9637499B2/en active Active
-
2016
- 2016-03-16 JP JP2016052707A patent/JP2016164168A/ja active Pending
- 2016-07-28 CY CY20161100745T patent/CY1117862T1/el unknown
-
2019
- 2019-06-21 HR HRP20191136TT patent/HRP20191136T1/hr unknown
- 2019-06-28 CY CY20191100679T patent/CY1122201T1/el unknown
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