AU2016334396B2 - (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as GABA aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma - Google Patents
(S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as GABA aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma Download PDFInfo
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- AU2016334396B2 AU2016334396B2 AU2016334396A AU2016334396A AU2016334396B2 AU 2016334396 B2 AU2016334396 B2 AU 2016334396B2 AU 2016334396 A AU2016334396 A AU 2016334396A AU 2016334396 A AU2016334396 A AU 2016334396A AU 2016334396 B2 AU2016334396 B2 AU 2016334396B2
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562239330P | 2015-10-09 | 2015-10-09 | |
| US62/239,330 | 2015-10-09 | ||
| PCT/US2016/056245 WO2017062942A2 (en) | 2015-10-09 | 2016-10-10 | (s)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as gaba aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2016334396A1 AU2016334396A1 (en) | 2018-04-19 |
| AU2016334396B2 true AU2016334396B2 (en) | 2021-04-08 |
Family
ID=58488679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016334396A Active AU2016334396B2 (en) | 2015-10-09 | 2016-10-10 | (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as GABA aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US9670141B2 (https=) |
| EP (1) | EP3341355B1 (https=) |
| JP (1) | JP6841821B2 (https=) |
| KR (1) | KR102745965B1 (https=) |
| CN (1) | CN108137484B (https=) |
| AU (1) | AU2016334396B2 (https=) |
| BR (1) | BR112018007026B1 (https=) |
| CA (1) | CA3001330A1 (https=) |
| CL (1) | CL2018000914A1 (https=) |
| CO (1) | CO2018003828A2 (https=) |
| DK (1) | DK3341355T3 (https=) |
| ES (1) | ES2825349T3 (https=) |
| HU (1) | HUE053429T2 (https=) |
| IL (1) | IL258516A (https=) |
| LT (1) | LT3341355T (https=) |
| MX (1) | MX380592B (https=) |
| PE (1) | PE20190349A1 (https=) |
| PL (1) | PL3341355T3 (https=) |
| PT (1) | PT3341355T (https=) |
| WO (1) | WO2017062942A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS59111B1 (sr) | 2014-08-21 | 2019-09-30 | Boehringer Ingelheim Int | Nova jedinjenja spiro[3h-indol-3,2´-pirolidin]-2(1h)-ona i derivati kao mdm2-p53 inhibitori |
| JP6841821B2 (ja) * | 2015-10-09 | 2021-03-10 | ノースウェスタン ユニバーシティ | てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物 |
| KR20240158360A (ko) | 2015-10-09 | 2024-11-04 | 베링거 인겔하임 인터내셔날 게엠베하 | Mdm2-p53 억제제로서의 스피로[3h-인돌-3,2'-피롤리딘]-2(1h)-온 화합물 및 유도체 |
| EP4692048A3 (en) * | 2017-02-08 | 2026-04-01 | Ovid Therapeutics Inc. | Methods of treating cdkl5 disorders with the compound ov329 |
| US11771671B2 (en) | 2018-02-08 | 2023-10-03 | Ovid Therapeutics Inc. | Use of (1S,3S)-3-amino-4-(difluoromethylidene) cyclopentane-1-carboxylic acid and (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid in the treatment of tinnitus, acute sensorineural hearing loss, Meniere's disease, Tourette's syndrome, attention deficit hyperactivity disorder and addiction |
| KR20250167147A (ko) | 2018-02-08 | 2025-11-28 | 오비드 테라퓨틱스 인크. | 이명, 급성 감각신경성 난청, 메니에르병, 투렛 증후군, 주의력 결핍 과잉행동 장애 및 중독의 치료에 있어서 (1s,3s)-3-아미노-4-(디플루오로메틸리덴) 시클로펜탄-1-카르복시산 및 (s)-3-아미노-4-(디플루오로메틸리덴)시클로펜트-1-엔-1-카르복시산의 용도 |
| JP2021519753A (ja) * | 2018-03-29 | 2021-08-12 | オービッド・セラピューティクス・インコーポレイテッドＯｖｉｄ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 眼障害の治療における（１ｓ，３ｓ）−３−アミノ−４−（ジフルオロメチリデン）シクロペンタン−１−カルボン酸および（ｓ）−３−アミノ−４−（ジフルオロメチルエニル）シクロペンタ−１−エン−１−カルボン酸の使用 |
| US10822301B2 (en) | 2018-04-12 | 2020-11-03 | Northwestern University | 3-carbon substituted 4-aminocyclopent-1-ene-1-carboxylic acid compounds as inhibitors of gamma-aminobutyric acid (GABA) aminotransferase |
| MX2020012691A (es) * | 2018-05-25 | 2021-02-15 | Univ Northwestern | Proceso para la sintesis del acido (s)-3-amino-4-(difluorometileni l)ciclopent-1-eno-1-carboxilico. |
| CA3102786A1 (en) * | 2018-06-07 | 2019-12-12 | Ovid Therapeutics Inc. | Use of (s)-3-amino-4-(difluoromethylenyl) cyclopent-1-ene-1-carboxylic acid and related compounds, (1s,3s)-3-amino-4-(difluoromethylidene) cyclopentane-1-carboxylic acid and vigab atrin in the treatment of developmental disorders |
| US11203596B2 (en) | 2019-02-25 | 2021-12-21 | Northwestern University | Analogs of 3-amino-4-(propan-2-ylidene)cyclopentane-1-carboxylic acid and uses thereof for treating diseases and disorders associated with ornithine aminotransferase activity |
| US11078153B2 (en) | 2019-04-03 | 2021-08-03 | Northwestern University | 2-difluoro substituted 4-aminocyclopentanecarboxylic acids as inhibitors of gamma-aminobutyric acid aminotransferase and human ornithine aminotransferase |
| CN110935495B (zh) * | 2019-11-29 | 2021-02-23 | 中国科学院电子学研究所 | Gaba和电生理微纳同步传感检测芯片及其制备方法 |
| US11993569B2 (en) | 2020-01-23 | 2024-05-28 | Northwestern University | 3-amino-4-halocyclopentene carboxylic acids as inactivators of aminotransferases |
| WO2022187523A1 (en) * | 2021-03-03 | 2022-09-09 | Northwestern University | (s)-3-amino-4,4-dihalocyclopent-1-enecarboxylic acid as selective inactivators of human ornithine aminotransferase |
| EP4482478A4 (en) * | 2022-02-27 | 2026-03-04 | Univ Northwestern | (3S,4R)-3-AMINO-4-(DIFLUOROMETHYL)CYCLOPENT-1-ENE-1-CARBOXYLIC ACID AND RELATED COMPOUNDS USED AS SELECTIVE ORNITHIN AMINOTRANSFERASE ACTIVATORS |
| KR20250034134A (ko) * | 2022-07-06 | 2025-03-10 | 오비드 테라퓨틱스 인크. | 암 치료에 있어서 (s)-3-아미노-4-(디플루오로메틸렌일)사이클로펜트-1-엔-1-카르복실산의 사용 |
| US20240285563A1 (en) * | 2023-02-17 | 2024-08-29 | Ovid Therapeutics Inc. | Use of (s)-3-amino-4-(difluoromethylenyl) cyclopent-1-ene-1-carboxylic acid in the treatment of rheumatoid arthritis |
| EP4648757A4 (en) * | 2023-02-17 | 2026-01-07 | Ovid Therapeutics Inc | USE OF (S)-3-AMINO-4-(DIFLUOROMETHYLENYL)CYCLOPENT-1-ENE-1-CARBOXYLIC ACID FOR THE TREATMENT OF GASTROINTESTINAL TRACT DISORDERS AND AS AN IMMUNOMODULATING AGENT |
| JP2026506097A (ja) * | 2023-02-17 | 2026-02-20 | オービッド・セラピューティクス・インコーポレイテッド | 多発性硬化症の処置における（ｓ）－３－アミノ－４－（ジフルオロメチレニル）シクロペント－１－エン－１－カルボン酸の使用 |
| US20240285565A1 (en) * | 2023-02-17 | 2024-08-29 | Ovid Therapeutics Inc. | Use of (s)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid in the treatment of diabetes and pre-diabetes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6794413B1 (en) * | 2002-07-19 | 2004-09-21 | Northwestern University | Compounds and related methods for inhibition of γ-aminobutyric acid aminotransferase |
| WO2008023364A1 (en) * | 2006-08-21 | 2008-02-28 | Hadasit Medical Research Services & Development Ltd. | Inhibition of ornithine aminotransferase for the treatment of proliferative disorders |
| US9670141B2 (en) * | 2015-10-09 | 2017-06-06 | Northwestern University | (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as GABA aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2790820A1 (en) * | 2010-02-25 | 2011-09-01 | Northwestern University | Use (1s,3s)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid as a gaba aminotransferse inhibitor |
| TWI468403B (zh) * | 2011-08-30 | 2015-01-11 | Gilead Sciences Inc | 用於治療成癮之ａｌｄｈ－２抑制劑 |
-
2016
- 2016-10-10 JP JP2018517734A patent/JP6841821B2/ja active Active
- 2016-10-10 ES ES16854531T patent/ES2825349T3/es active Active
- 2016-10-10 PL PL16854531T patent/PL3341355T3/pl unknown
- 2016-10-10 HU HUE16854531A patent/HUE053429T2/hu unknown
- 2016-10-10 US US15/289,480 patent/US9670141B2/en active Active
- 2016-10-10 PT PT168545317T patent/PT3341355T/pt unknown
- 2016-10-10 WO PCT/US2016/056245 patent/WO2017062942A2/en not_active Ceased
- 2016-10-10 AU AU2016334396A patent/AU2016334396B2/en active Active
- 2016-10-10 DK DK16854531.7T patent/DK3341355T3/da active
- 2016-10-10 CN CN201680059069.9A patent/CN108137484B/zh active Active
- 2016-10-10 CA CA3001330A patent/CA3001330A1/en active Pending
- 2016-10-10 LT LTEP16854531.7T patent/LT3341355T/lt unknown
- 2016-10-10 KR KR1020187013228A patent/KR102745965B1/ko active Active
- 2016-10-10 BR BR112018007026-2A patent/BR112018007026B1/pt active IP Right Grant
- 2016-10-10 EP EP16854531.7A patent/EP3341355B1/en active Active
- 2016-10-10 PE PE2018000517A patent/PE20190349A1/es unknown
- 2016-10-10 MX MX2018004302A patent/MX380592B/es unknown
-
2017
- 2017-05-04 US US15/586,730 patent/US9993449B2/en active Active
-
2018
- 2018-04-05 IL IL258516A patent/IL258516A/en active IP Right Grant
- 2018-04-09 CL CL2018000914A patent/CL2018000914A1/es unknown
- 2018-04-10 CO CONC2018/0003828A patent/CO2018003828A2/es unknown
- 2018-05-29 US US15/991,323 patent/US20180271816A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6794413B1 (en) * | 2002-07-19 | 2004-09-21 | Northwestern University | Compounds and related methods for inhibition of γ-aminobutyric acid aminotransferase |
| WO2008023364A1 (en) * | 2006-08-21 | 2008-02-28 | Hadasit Medical Research Services & Development Ltd. | Inhibition of ornithine aminotransferase for the treatment of proliferative disorders |
| US9670141B2 (en) * | 2015-10-09 | 2017-06-06 | Northwestern University | (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as GABA aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma |
Non-Patent Citations (3)
| Title |
|---|
| European Journal of Pharmacology, 2001, 430(2-3), 185-192 * |
| Indian Journal of Chemistry, 2005, 44, 595-599 * |
| Journal of Medicinal Chemistry, 2006, 49(25), 7404-7412 * |
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