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 (enExample) | 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 (enExample) |
| EP (2) | EP3070091B1 (enExample) |
| JP (2) | JP6174997B2 (enExample) |
| KR (1) | KR101864578B1 (enExample) |
| CN (1) | CN102958937B (enExample) |
| AU (1) | AU2011269429B2 (enExample) |
| BR (1) | BR112012032813B1 (enExample) |
| CA (1) | CA2802895C (enExample) |
| CY (2) | CY1117862T1 (enExample) |
| DK (2) | DK3070091T3 (enExample) |
| ES (2) | ES2733092T3 (enExample) |
| HR (2) | HRP20160919T1 (enExample) |
| HU (2) | HUE030081T2 (enExample) |
| IL (1) | IL223329A (enExample) |
| LT (2) | LT3070091T (enExample) |
| MX (1) | MX2012014131A (enExample) |
| MY (1) | MY157481A (enExample) |
| NZ (1) | NZ603895A (enExample) |
| PL (2) | PL2585469T3 (enExample) |
| PT (2) | PT3070091T (enExample) |
| RS (2) | RS58945B1 (enExample) |
| RU (1) | RU2583787C2 (enExample) |
| SG (1) | SG186140A1 (enExample) |
| SI (2) | SI3070091T1 (enExample) |
| TR (1) | TR201909709T4 (enExample) |
| TW (1) | TWI507410B (enExample) |
| UA (1) | UA109140C2 (enExample) |
| WO (1) | WO2011160632A1 (enExample) |
| ZA (1) | ZA201209031B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9855285B2 (en) * | 2012-11-30 | 2018-01-02 | Leo Pharma A/S | Method of inhibiting the expression of IL-22 in activated T-cells |
| 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 |
| WO2018234299A1 (en) * | 2017-06-20 | 2018-12-27 | Leo Pharma A/S | Methods for the preparation of 1,3-benzodioxole heterocyclic compounds |
| CN111727191B (zh) | 2017-12-15 | 2024-01-05 | 联合疗法公司 | 取代的氮杂环丁烷二氢噻吩并吡啶类化合物及其作为磷酸二酯酶抑制剂的用途 |
| US11919912B2 (en) | 2018-05-21 | 2024-03-05 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| IL284815B2 (en) * | 2019-01-15 | 2025-10-01 | Union Therapeutics As | Modified-release tablet formulations containing phosphodiesterase inhibitors |
| EP4003343A1 (en) * | 2019-07-24 | 2022-06-01 | 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 |
| AU2022245186A1 (en) | 2021-03-22 | 2023-10-05 | 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 |
|---|---|---|---|---|
| KR100331255B1 (ko) | 1993-07-02 | 2002-10-25 | 빅굴덴 롬베르그 케미쉐 화부리크 게엠베하 | 플루오로알콕시-치환된벤즈아미드및시클릭뉴클레오티드포스포디에스테라아제억제제로서의그의용도 |
| 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 |
| CA2252537A1 (en) * | 1996-05-20 | 1997-11-27 | Darwin Discovery Limited | Benzofuran carboxamides and their therapeutic use |
| WO1998022455A1 (en) | 1996-11-19 | 1998-05-28 | Kyowa Hakko Kogyo Co., Ltd. | Oxygenic 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 |
| EA014956B1 (ru) * | 2004-12-17 | 2011-04-29 | ГЛЕНМАРК ФАРМАСЬЮТИКАЛС Эс.Эй. | Гетероциклические соединения, применяемые для лечения воспалительных и аллергических нарушений |
| UA98639C2 (en) * | 2007-02-28 | 2012-06-11 | Лео Фарма А/С | Phosphodiesterase inhibitors |
| JP5501770B2 (ja) * | 2007-02-28 | 2014-05-28 | レオ ファーマ アクティーゼルスカブ | 新規ホスホジエステラーゼ阻害剤 |
| PT2794603T (pt) * | 2011-12-21 | 2016-07-26 | Leo Pharma As | [1,2,4] triazolopiridinas e seu uso como inibidores de fosfodiesterase |
-
2011
- 2011-06-24 UA UAA201300812A patent/UA109140C2/uk unknown
- 2011-06-24 SI SI201131743T patent/SI3070091T1/sl unknown
- 2011-06-24 RS RS20190851A patent/RS58945B1/sr unknown
- 2011-06-24 MY MYPI2012005553A patent/MY157481A/en unknown
- 2011-06-24 HR HRP20160919TT patent/HRP20160919T1/hr unknown
- 2011-06-24 ES ES16020112T patent/ES2733092T3/es active Active
- 2011-06-24 JP JP2013515698A patent/JP6174997B2/ja active Active
- 2011-06-24 EP EP16020112.5A patent/EP3070091B1/en active Active
- 2011-06-24 DK DK16020112.5T patent/DK3070091T3/da active
- 2011-06-24 HU HUE11729889A patent/HUE030081T2/en unknown
- 2011-06-24 RS RS20160581A patent/RS55104B1/sr unknown
- 2011-06-24 PT PT16020112T patent/PT3070091T/pt unknown
- 2011-06-24 PL PL11729889T patent/PL2585469T3/pl unknown
- 2011-06-24 NZ NZ603895A patent/NZ603895A/en unknown
- 2011-06-24 PT PT117298893T patent/PT2585469T/pt unknown
- 2011-06-24 SG SG2012088761A patent/SG186140A1/en unknown
- 2011-06-24 TR TR2019/09709T patent/TR201909709T4/tr unknown
- 2011-06-24 AU AU2011269429A patent/AU2011269429B2/en active Active
- 2011-06-24 LT LTEP16020112.5T patent/LT3070091T/lt unknown
- 2011-06-24 WO PCT/DK2011/000069 patent/WO2011160632A1/en not_active Ceased
- 2011-06-24 SI SI201130896A patent/SI2585469T1/sl unknown
- 2011-06-24 KR KR1020137001855A patent/KR101864578B1/ko active Active
- 2011-06-24 DK DK11729889.3T patent/DK2585469T3/en active
- 2011-06-24 CN CN201180031069.5A patent/CN102958937B/zh active Active
- 2011-06-24 MX MX2012014131A patent/MX2012014131A/es active IP Right Grant
- 2011-06-24 CA CA2802895A patent/CA2802895C/en active Active
- 2011-06-24 TW TW100122303A patent/TWI507410B/zh active
- 2011-06-24 PL PL16020112T patent/PL3070091T3/pl unknown
- 2011-06-24 BR BR112012032813-1A patent/BR112012032813B1/pt active IP Right Grant
- 2011-06-24 RU RU2013103079/04A patent/RU2583787C2/ru active
- 2011-06-24 ES ES11729889.3T patent/ES2584055T3/es active Active
- 2011-06-24 LT LTEP11729889.3T patent/LT2585469T/lt 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 HU HUE16020112 patent/HUE044301T2/hu unknown
-
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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