CA2971252C - POLYMORPHIC AND AMORPHIC FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE - Google Patents
POLYMORPHIC AND AMORPHIC FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDEInfo
- Publication number
- CA2971252C CA2971252C CA2971252A CA2971252A CA2971252C CA 2971252 C CA2971252 C CA 2971252C CA 2971252 A CA2971252 A CA 2971252A CA 2971252 A CA2971252 A CA 2971252A CA 2971252 C CA2971252 C CA 2971252C
- Authority
- CA
- Canada
- Prior art keywords
- polymorph
- composition
- angular positions
- hydroxy
- butanamide
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
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- Biomedical Technology (AREA)
- Diabetes (AREA)
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- Toxicology (AREA)
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- Vascular Medicine (AREA)
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- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462092743P | 2014-12-16 | 2014-12-16 | |
| US62/092,743 | 2014-12-16 | ||
| US201562133276P | 2015-03-13 | 2015-03-13 | |
| US62/133,276 | 2015-03-13 | ||
| PCT/US2015/066211 WO2016100579A1 (en) | 2014-12-16 | 2015-12-16 | Polymorphic and amorphous forms of (r)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2971252A1 CA2971252A1 (en) | 2016-06-23 |
| CA2971252C true CA2971252C (en) | 2025-05-27 |
Family
ID=55071223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2971252A Active CA2971252C (en) | 2014-12-16 | 2015-12-16 | POLYMORPHIC AND AMORPHIC FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE |
Country Status (21)
| Country | Link |
|---|---|
| US (5) | US10251847B2 (https=) |
| EP (2) | EP3233786B1 (https=) |
| JP (4) | JP6810692B2 (https=) |
| KR (1) | KR102626895B1 (https=) |
| CN (2) | CN107531616B (https=) |
| AU (3) | AU2015364640B2 (https=) |
| BR (1) | BR112017012988B1 (https=) |
| CA (1) | CA2971252C (https=) |
| DK (1) | DK3233786T3 (https=) |
| ES (1) | ES2912585T3 (https=) |
| HU (1) | HUE058877T2 (https=) |
| IL (1) | IL252953A0 (https=) |
| MX (2) | MX385049B (https=) |
| NZ (1) | NZ733528A (https=) |
| PL (1) | PL3233786T3 (https=) |
| PT (1) | PT3233786T (https=) |
| RU (1) | RU2770091C2 (https=) |
| SG (2) | SG11201704968XA (https=) |
| SI (1) | SI3233786T1 (https=) |
| WO (1) | WO2016100579A1 (https=) |
| ZA (1) | ZA201704639B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2471530B1 (en) | 2005-06-01 | 2017-01-11 | Edison Pharmaceuticals, Inc. | Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| WO2009061744A2 (en) | 2007-11-06 | 2009-05-14 | Edison Pharmaceuticals, Inc. | 4- (p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases |
| CA2741767C (en) | 2008-10-28 | 2017-09-12 | Ptc Therapeutics, Inc. | Process for the production of alpha-tocotrienol and derivatives |
| JP2014520894A (ja) | 2011-07-19 | 2014-08-25 | エジソン ファーマシューティカルズ, インコーポレイテッド | 非アルファトコトリエノールの存在下でのアルファトコトリエノールの選択的酸化のための方法 |
| AU2015364640B2 (en) | 2014-12-16 | 2020-08-13 | Ptc Therapeutics, Inc. | Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide |
| EP3390377B1 (en) | 2015-12-16 | 2026-03-25 | PTC Therapeutics, Inc. | Improved methods for enriching alpha-tocotrienol from mixed tocol compositions |
| WO2017106803A1 (en) | 2015-12-17 | 2017-06-22 | Bioelectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
| JP2018083799A (ja) | 2016-11-15 | 2018-05-31 | バイオエレクトロン テクノロジー コーポレイション | 2−置換アミノ−ナフト[1,2−d]イミダゾール−5−オン化合物またはその製薬学上許容される塩 |
| KR20210076956A (ko) | 2018-10-17 | 2021-06-24 | 피티씨 테라퓨틱스, 인크. | α-시누클레인병증, 타우병증 및 기타 장애를 억제 및 치료하기 위한 2,3,5-트리메틸-6-노닐사이클로헥사-2,5-디엔-1,4-디온 |
| TWI886158B (zh) | 2019-10-10 | 2025-06-11 | 加拿大商再諾製藥公司 | 選擇性鉀通道調節劑之固態晶型 |
| KR20220143897A (ko) * | 2020-02-21 | 2022-10-25 | 스미토모 파마 가부시키가이샤 | 광학 분할된 트롤록스 중간체 및 그 제조 방법 |
| PE20240893A1 (es) | 2021-07-08 | 2024-04-24 | Ptc Therapeutics Inc | Composiciones farmaceuticas que comprenden 2,3,5-trimetil-6-nonilciclohexa-2,5-dien-1,4-diona |
| EP4588473A1 (en) * | 2022-09-12 | 2025-07-23 | PTC Therapeutics, Inc. | Granules for suspension |
| EP4596530A1 (en) * | 2022-09-30 | 2025-08-06 | PTC Therapeutics, Inc. | Oxidative cleavage method of trolox amide |
| WO2025193975A1 (en) | 2024-03-13 | 2025-09-18 | Ptc Therapeutics, Inc. | Formulations for stabilizing dissolution of medicaments |
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| US4018799A (en) | 1973-11-19 | 1977-04-19 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| US4026907A (en) | 1973-11-19 | 1977-05-31 | Hoffmann-La Roche Inc. | Antioxidant chroman compounds |
| JPS5640651A (en) | 1979-09-12 | 1981-04-16 | Takeda Chem Ind Ltd | Quinone compound and its preparation |
| US5272180A (en) | 1987-07-29 | 1993-12-21 | Takeda Chemical Industries, Ltd. | Cell proliferation inhibitor |
| US5348973A (en) | 1990-10-09 | 1994-09-20 | Rhone-Poulenc Chimie | Resolution of hydroxychroman-2-carboxylic acid esters by enantiomeric hydrolysis |
| US6150402A (en) | 1994-08-15 | 2000-11-21 | Loma Linda University Medical Center | Natriuretic compounds |
| SK282144B6 (sk) | 1994-12-28 | 2001-11-06 | Janssen Pharmaceutica N. V. | Liečivo na terapeutické a profylaktické ošetrenie degeneratívnych chorôb vaskulárneho systému a nervovej sústavy, ktoré súvisia s oxidačným stresom |
| AU6709896A (en) | 1995-08-21 | 1997-03-12 | Takeda Chemical Industries Ltd. | Quinone compound, its production and use |
| US6232060B1 (en) | 1996-01-19 | 2001-05-15 | Galileo Laboratories, Inc. | Assay system for anti-stress agents |
| US5801159A (en) | 1996-02-23 | 1998-09-01 | Galileo Laboratories, Inc. | Method and composition for inhibiting cellular irreversible changes due to stress |
| DE69712888D1 (de) | 1996-07-11 | 2002-07-04 | Takeda Chemical Industries Ltd | ZUSAMMENSTELLUNGEN DIE beta-AMYLOID PROTEIN BEDINGTE ZYTOTOXIZITÄT VERHINDERN |
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