CA2802895C - Benzodioxole or benzodioxepine heterocyclic compounds as phosphodiesterase inhibitors - Google Patents
Benzodioxole or benzodioxepine heterocyclic compounds as phosphodiesterase inhibitors Download PDFInfo
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- CA2802895C CA2802895C CA2802895A CA2802895A CA2802895C CA 2802895 C CA2802895 C CA 2802895C CA 2802895 A CA2802895 A CA 2802895A CA 2802895 A CA2802895 A CA 2802895A CA 2802895 C CA2802895 C CA 2802895C
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- Prior art keywords
- compound
- spiro
- difluoromethoxy
- dichloro
- pharmaceutically acceptable
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- -1 benzodioxepine heterocyclic compounds Chemical class 0.000 title abstract description 24
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 title description 3
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title description 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
- 239000012453 solvate Substances 0.000 claims abstract description 29
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 68
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- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims description 4
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- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims description 4
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 claims description 4
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 3
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- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
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- 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 abstract description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract description 4
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Classifications
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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| PCT/DK2011/000069 WO2011160632A1 (en) | 2010-06-24 | 2011-06-24 | Benzodioxole or benzodioxepine heterocyclic compounds phosphodiesterase inhibitors |
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| PL3157930T3 (pl) * | 2014-06-23 | 2019-04-30 | Leo Pharma As | Sposoby wytwarzania związków heterocyklicznych 1,3-benzodioksolu |
| 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 |
| PT3390407T (pt) * | 2015-12-18 | 2023-11-03 | Union Therapeutics As | Métodos para a preparação de compostos heterocíclicos de 1,3-benzodioxole |
| MX394835B (es) | 2017-06-20 | 2025-03-24 | Union Therapeutics As | Metodos para la preparacion de compuestos heterociclicos de 1,3-benzodioxol. |
| PT3724196T (pt) | 2017-12-15 | 2023-01-13 | Union Therapeutics As | Azetidina di-hidrotienopiridinas substituídas e a sua utilização como inibidores de fosfodiesterase |
| CN120097995A (zh) | 2018-05-21 | 2025-06-06 | 星座制药公司 | 甲基修饰酶的调节剂、其组合物和用途 |
| EA202191955A1 (ru) * | 2019-01-15 | 2021-10-07 | Юнион Терапьютикс А/С | Таблетированные составы с модифицированным высвобождением, содержащие ингибиторы фосфодиэстеразы |
| JP7530420B2 (ja) * | 2019-07-24 | 2024-08-07 | コンステレーション・ファーマシューティカルズ・インコーポレイテッド | がんの治療のためのｅｚｈ２阻害併用療法 |
| 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 |
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| DK0771794T3 (da) | 1995-05-19 | 2006-09-11 | Kyowa Hakko Kogyo Kk | Oxygenholdige heterocykliske forbindelser |
| 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 |
| AU2005315319B2 (en) * | 2004-12-17 | 2011-07-07 | Glenmark Pharmaceuticals S.A. | Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders |
| UA98639C2 (en) * | 2007-02-28 | 2012-06-11 | Лео Фарма А/С | Phosphodiesterase inhibitors |
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| EP2794603B1 (en) * | 2011-12-21 | 2016-06-15 | Leo Pharma A/S | [1,2,4]triazolopyridines and their use as phospodiesterase inhibitors |
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| CA2802895C (en) | Benzodioxole or benzodioxepine heterocyclic compounds as phosphodiesterase inhibitors | |
| CA2676933C (en) | Novel phosphodiesterase inhibitors | |
| HK1182699B (en) | Benzodioxole or benzodioxepine heterocyclic compounds phosphodiesterase inhibitors |
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