CA3039045A1 - Carbamoyl phenylalaninol compounds and uses thereof - Google Patents
Carbamoyl phenylalaninol compounds and uses thereof Download PDFInfo
- Publication number
- CA3039045A1 CA3039045A1 CA3039045A CA3039045A CA3039045A1 CA 3039045 A1 CA3039045 A1 CA 3039045A1 CA 3039045 A CA3039045 A CA 3039045A CA 3039045 A CA3039045 A CA 3039045A CA 3039045 A1 CA3039045 A1 CA 3039045A1
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- CA
- Canada
- Prior art keywords
- optionally substituted
- compound
- carbon atoms
- pharmaceutically acceptable
- composition
- 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.)
- Abandoned
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- NJVZDURTFWBXAM-VIFPVBQESA-N [(2S)-1-hydroxy-3-phenylpropan-2-yl]urea Chemical class C(N)(=O)N[C@@H](CC1=CC=CC=C1)CO NJVZDURTFWBXAM-VIFPVBQESA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 114
- 239000000203 mixture Substances 0.000 claims description 39
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000002552 dosage form Substances 0.000 claims description 19
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 19
- -1 nitro, hydroxy Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
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- 125000005309 thioalkoxy group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
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- 239000002775 capsule Substances 0.000 claims description 7
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/66—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/58—Y being a hetero atom
- C07C275/60—Y being an oxygen atom, e.g. allophanic acids
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- 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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
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| PCT/US2017/055598 WO2018067971A1 (en) | 2016-10-06 | 2017-10-06 | Carbamoyl phenylalaninol compounds and uses therof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11400065B2 (en) | 2019-03-01 | 2022-08-02 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11839597B2 (en) | 2016-07-22 | 2023-12-12 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| MX2020001146A (es) | 2017-07-31 | 2020-08-20 | Jazz Pharmaceuticals Ireland Ltd | Analogos de carbamoil fenilalaninol y usos de los mismos. |
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| KR100197892B1 (ko) | 1994-09-09 | 1999-06-15 | 남창우 | 신규한 페닐알킬아미노 카바메이트 화합물과 그의 제조방법 |
| KR0173862B1 (ko) | 1995-02-11 | 1999-04-01 | 조규향 | O-카바모일-(d)-페닐알라닌올 화합물과 그의 약제학적으로 유용한 염 및 이들의 제조방법 |
| US5756817C1 (en) | 1995-02-11 | 2001-04-17 | Sk Corp | O-carbamoyl-phenylananinol compounds their pharmaceutically useful salts and process for preparing the same |
| KR0173863B1 (ko) | 1995-04-10 | 1999-04-01 | 조규향 | 페닐에 치환체가 있는 o-카바모일-페닐알라닌올 화합물과 그의 약제학적으로 유용한 염 및 이들의 제조방법 |
| CA2355293C (en) | 1998-12-23 | 2005-08-16 | Orphan Medical, Inc. | Microbiologically sound and stable solutions of gamma-hydroxybutyrate salt for the treatment of narcolepsy |
| US6680322B2 (en) | 1999-12-02 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US6680324B2 (en) | 2000-12-01 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US6680299B2 (en) | 2001-07-27 | 2004-01-20 | Enanta Pharmaceuticals, Inc. | 4'-substituted leucomycins |
| WO2006050037A1 (en) | 2004-10-28 | 2006-05-11 | Sk Corporation | Adjunctive therapy for depression |
| DK1890684T3 (da) | 2005-06-08 | 2013-10-14 | Sk Biopharmaceuticals Co Ltd | Behandling af søvn/vågenhedsforstyrrelser |
| WO2007001841A1 (en) | 2005-06-22 | 2007-01-04 | Sk Holdings Co., Ltd. | Treatment of sexual dysfunction |
| US8741950B2 (en) * | 2009-06-22 | 2014-06-03 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating or preventing fatigue |
| US8232315B2 (en) | 2009-06-26 | 2012-07-31 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating drug addiction and improving addiction-related behavior |
| JP5901528B2 (ja) | 2009-11-06 | 2016-04-13 | エスケー バイオファーマスティカルズ カンパニー リミテッド | 線維筋痛症候群の治療方法 |
| JP5836280B2 (ja) | 2009-11-06 | 2015-12-24 | エスケー バイオファーマスティカルズ カンパニー リミテッド | 注意欠陥／多動性障害（ａｄｈｄ）の治療方法 |
| US9610274B2 (en) | 2010-06-30 | 2017-04-04 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating bipolar disorder |
| US8623913B2 (en) | 2010-06-30 | 2014-01-07 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating restless legs syndrome |
| US9050302B2 (en) | 2013-03-01 | 2015-06-09 | Jazz Pharmaceuticals Ireland Limited | Method of administration of gamma hydroxybutyrate with monocarboxylate transporters |
| AU2014248849B2 (en) | 2013-03-13 | 2018-08-30 | Jazz Pharmaceuticals Ireland Limited | Treatment of cataplexy |
| CN105848650A (zh) | 2013-07-12 | 2016-08-10 | 爵士制药国际Iii有限公司 | 促进吸烟停止 |
| CN105873576B (zh) * | 2013-07-18 | 2019-07-19 | 爵士制药国际Iii有限公司 | 治疗肥胖 |
| US10888542B2 (en) | 2014-02-28 | 2021-01-12 | Sk Biopharmaceuticals Co., Ltd. | Aminocarbonylcarbamate compounds |
| TWI655179B (zh) | 2014-02-28 | 2019-04-01 | 南韓商愛思開生物製藥股份有限公司 | 胺基羰基胺基甲酸酯化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US12115145B2 (en) | 2016-07-22 | 2024-10-15 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12115143B2 (en) | 2016-07-22 | 2024-10-15 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11766418B2 (en) | 2016-07-22 | 2023-09-26 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12097175B2 (en) | 2016-07-22 | 2024-09-24 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| US12263150B2 (en) | 2016-07-22 | 2025-04-01 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| US12144793B2 (en) | 2016-07-22 | 2024-11-19 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| US12239625B2 (en) | 2016-07-22 | 2025-03-04 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| US12226388B2 (en) | 2016-07-22 | 2025-02-18 | Flamel Ireland Limited | Modified release gamma- hydroxybutyrate formulations having improved pharmacokinetics |
| US12226377B2 (en) | 2019-03-01 | 2025-02-18 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US12167992B2 (en) | 2019-03-01 | 2024-12-17 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US12167991B2 (en) | 2019-03-01 | 2024-12-17 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11400065B2 (en) | 2019-03-01 | 2022-08-02 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US12303478B2 (en) | 2019-03-01 | 2025-05-20 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12295926B1 (en) | 2022-02-07 | 2025-05-13 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
Also Published As
| Publication number | Publication date |
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| MY202185A (en) | 2024-04-15 |
| US11780805B2 (en) | 2023-10-10 |
| SG11201903076QA (en) | 2019-05-30 |
| KR20190072561A (ko) | 2019-06-25 |
| US11149000B2 (en) | 2021-10-19 |
| US20190218175A1 (en) | 2019-07-18 |
| US20200290955A1 (en) | 2020-09-17 |
| EP4316592A3 (en) | 2024-05-01 |
| KR102616545B1 (ko) | 2023-12-26 |
| WO2018067971A1 (en) | 2018-04-12 |
| EP4316592A2 (en) | 2024-02-07 |
| ES2964943T3 (es) | 2024-04-10 |
| US20240018098A1 (en) | 2024-01-18 |
| US20250059136A1 (en) | 2025-02-20 |
| US10710958B2 (en) | 2020-07-14 |
| JP2020503246A (ja) | 2020-01-30 |
| CN110049966A (zh) | 2019-07-23 |
| PH12019500751A1 (en) | 2019-08-05 |
| US20220098145A1 (en) | 2022-03-31 |
| JP7074750B2 (ja) | 2022-05-24 |
| EP3523275B1 (en) | 2023-09-27 |
| EP3523275A1 (en) | 2019-08-14 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20240117 |