CA2816104A1 - Deuterium enriched rasagiline - Google Patents
Deuterium enriched rasagiline Download PDFInfo
- Publication number
- CA2816104A1 CA2816104A1 CA2816104A CA2816104A CA2816104A1 CA 2816104 A1 CA2816104 A1 CA 2816104A1 CA 2816104 A CA2816104 A CA 2816104A CA 2816104 A CA2816104 A CA 2816104A CA 2816104 A1 CA2816104 A1 CA 2816104A1
- Authority
- CA
- Canada
- Prior art keywords
- deuterium enriched
- pharmaceutically acceptable
- compound
- solvent
- acceptable salt
- 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
Links
- 229910052805 deuterium Inorganic materials 0.000 title claims description 104
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 title claims description 103
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 title abstract description 31
- 229960000245 rasagiline Drugs 0.000 title description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims description 131
- 238000000034 method Methods 0.000 claims description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 49
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- 239000002552 dosage form Substances 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 230000000155 isotopic effect Effects 0.000 claims description 10
- RUOKEQAAGRXIBM-UHFFFAOYSA-N n-prop-2-ynyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(NCC#C)CCC2=C1 RUOKEQAAGRXIBM-UHFFFAOYSA-N 0.000 claims description 10
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/60—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
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- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
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- 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
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
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- Ophthalmology & Optometry (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40674010P | 2010-10-26 | 2010-10-26 | |
| US61/406,740 | 2010-10-26 | ||
| PCT/US2011/057698 WO2012058219A2 (en) | 2010-10-26 | 2011-10-25 | Deuterium enriched rasagiline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2816104A1 true CA2816104A1 (en) | 2012-05-03 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2816104A Abandoned CA2816104A1 (en) | 2010-10-26 | 2011-10-25 | Deuterium enriched rasagiline |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20120101168A1 (enExample) |
| EP (1) | EP2632254A4 (enExample) |
| JP (1) | JP2014503480A (enExample) |
| KR (1) | KR20140023872A (enExample) |
| CN (1) | CN103188933A (enExample) |
| AU (1) | AU2011320611A1 (enExample) |
| BR (1) | BR112013010308A2 (enExample) |
| CA (1) | CA2816104A1 (enExample) |
| CL (1) | CL2013001101A1 (enExample) |
| EA (1) | EA201390613A1 (enExample) |
| IL (1) | IL225852A0 (enExample) |
| MX (1) | MX2013004598A (enExample) |
| NZ (1) | NZ610526A (enExample) |
| PH (1) | PH12013500821A1 (enExample) |
| SG (2) | SG10201508771TA (enExample) |
| WO (1) | WO2012058219A2 (enExample) |
| ZA (1) | ZA201303505B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1991214B1 (en) * | 2006-02-21 | 2015-08-05 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of multiple system atrophy |
| EP2007369A4 (en) | 2006-04-03 | 2009-07-01 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF LEG SYNDROME WITHOUT REST |
| EA016820B1 (ru) * | 2006-12-14 | 2012-07-30 | Тева Фармасьютикал Индастриз, Лтд. | Кристаллическое твердое основание разагилина |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| NZ586025A (en) * | 2008-01-11 | 2012-08-31 | Teva Pharma | Rasagiline mesylate tablet coated with a composisiton comprising methacrylic acid - ethyl acrylate copolymer and triethyl citrate |
| ES2389353T3 (es) * | 2008-06-10 | 2012-10-25 | Teva Pharmaceutical Industries Ltd. | Cápsulas de gelatina blanda de rasagilina |
| RS53504B1 (sr) | 2009-07-09 | 2015-02-27 | Ratiopharm Gmbh | Soli razagilina i njihovi farmaceutski preparati |
| US20110130466A1 (en) * | 2009-10-09 | 2011-06-02 | Stefan Lorenzl | Use of rasagiline for the treatment of progressive supranuclear palsy |
| EP2939669A1 (en) * | 2009-12-22 | 2015-11-04 | Teva Pharmaceutical Industries, Ltd. | 3-keto-n-propargyl-1-aminoindan |
| AU2011282716A1 (en) | 2010-07-27 | 2013-03-14 | Teva Pharmaceutical Industries Ltd. | Dispersions of rasagiline citrate |
| AU2011282720B2 (en) | 2010-07-27 | 2016-12-22 | Teva Pharmaceutical Industries Ltd. | Use of rasagiline for the treatment of olfactory dysfunction |
| KR20140090996A (ko) | 2011-10-10 | 2014-07-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | R(+)-n-폼일-프로파길-아미노인단 |
| AU2012323351A1 (en) | 2011-10-10 | 2014-05-22 | Teva Pharmaceutical Industries Ltd. | R(+)-N-methyl-propargyl-aminoindan |
| JP2015529196A (ja) | 2012-08-17 | 2015-10-05 | テバ ファーマシューティカル インダストリーズ リミティド | ラサギリンの非経口製剤 |
| CN113348018B (zh) * | 2018-12-06 | 2025-04-01 | 内在生物技术有限公司 | 乙酰基-亮氨酸的氘代类似物 |
| CN111323524B (zh) * | 2020-04-08 | 2022-04-15 | 重庆华森制药股份有限公司 | 一种炔丙胺及其杂质的检测方法 |
| CN115947675B (zh) * | 2022-12-21 | 2024-05-31 | 博济医药科技股份有限公司 | 一种雷沙吉兰中间体及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744500A (en) | 1990-01-03 | 1998-04-28 | Teva Pharmaceutical Industries, Ltd. | Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof |
| IL92952A (en) | 1990-01-03 | 1994-06-24 | Teva Pharma | R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them |
| EP1778196A4 (en) * | 2004-07-26 | 2008-12-17 | Teva Pharma | PHARMACEUTICAL DOSAGES CONTAINING RASAGILINE |
| CN101098685A (zh) * | 2004-11-24 | 2008-01-02 | 特瓦制药工业有限公司 | 雷沙吉兰经口崩解组合物 |
| CA2600008A1 (en) * | 2005-02-22 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Improved process for the synthesis of enantiomeric indanylamine derivatives |
| AU2006310100B2 (en) * | 2005-11-06 | 2012-12-06 | Brain Watch Ltd. | Magnetic resonance imaging and spectroscopy means and methods thereof |
| CN102203053B (zh) * | 2008-06-02 | 2015-11-25 | 基因里克斯(英国)有限公司 | 用于制备胺的改进方法 |
| JP2011522892A (ja) * | 2008-06-13 | 2011-08-04 | テバ ファーマシューティカル インダストリーズ リミティド | パーキンソン病緩和のためのラサギリン |
| US20100172916A1 (en) * | 2008-11-10 | 2010-07-08 | Auspex Pharmaceuticals, Inc. | Substituted hydroxyphenylamine compounds |
| US8080584B2 (en) * | 2009-01-23 | 2011-12-20 | Teva Pharmaceuticals Industries, Ltd. | Delayed release rasagiline citrate formulation |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| EP2473199A1 (en) * | 2009-08-31 | 2012-07-11 | Brain Watch Ltd. | Isotopically labeled neurochemical agents and uses thereof for diagnosing conditions and disorders |
-
2011
- 2011-10-25 EA EA201390613A patent/EA201390613A1/ru unknown
- 2011-10-25 JP JP2013536727A patent/JP2014503480A/ja active Pending
- 2011-10-25 CA CA2816104A patent/CA2816104A1/en not_active Abandoned
- 2011-10-25 AU AU2011320611A patent/AU2011320611A1/en not_active Abandoned
- 2011-10-25 SG SG10201508771TA patent/SG10201508771TA/en unknown
- 2011-10-25 CN CN2011800519198A patent/CN103188933A/zh active Pending
- 2011-10-25 EP EP11836950.3A patent/EP2632254A4/en not_active Withdrawn
- 2011-10-25 MX MX2013004598A patent/MX2013004598A/es not_active Application Discontinuation
- 2011-10-25 KR KR1020137013167A patent/KR20140023872A/ko not_active Withdrawn
- 2011-10-25 PH PH1/2013/500821A patent/PH12013500821A1/en unknown
- 2011-10-25 BR BR112013010308A patent/BR112013010308A2/pt not_active IP Right Cessation
- 2011-10-25 SG SG2013029293A patent/SG189454A1/en unknown
- 2011-10-25 NZ NZ610526A patent/NZ610526A/en not_active IP Right Cessation
- 2011-10-25 WO PCT/US2011/057698 patent/WO2012058219A2/en not_active Ceased
- 2011-10-25 US US13/281,054 patent/US20120101168A1/en not_active Abandoned
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2013
- 2013-04-21 IL IL225852A patent/IL225852A0/en unknown
- 2013-04-22 CL CL2013001101A patent/CL2013001101A1/es unknown
- 2013-05-14 ZA ZA2013/03505A patent/ZA201303505B/en unknown
-
2014
- 2014-06-20 US US14/310,321 patent/US20140364506A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20140364506A1 (en) | 2014-12-11 |
| PH12013500821A1 (en) | 2019-07-03 |
| WO2012058219A3 (en) | 2012-07-26 |
| SG10201508771TA (en) | 2015-11-27 |
| CL2013001101A1 (es) | 2013-09-06 |
| EP2632254A2 (en) | 2013-09-04 |
| AU2011320611A1 (en) | 2013-06-13 |
| NZ610526A (en) | 2015-10-30 |
| MX2013004598A (es) | 2013-07-17 |
| SG189454A1 (en) | 2013-05-31 |
| EA201390613A1 (ru) | 2013-11-29 |
| CN103188933A (zh) | 2013-07-03 |
| EP2632254A4 (en) | 2015-08-05 |
| WO2012058219A2 (en) | 2012-05-03 |
| ZA201303505B (en) | 2015-08-26 |
| KR20140023872A (ko) | 2014-02-27 |
| BR112013010308A2 (pt) | 2016-07-05 |
| JP2014503480A (ja) | 2014-02-13 |
| US20120101168A1 (en) | 2012-04-26 |
| IL225852A0 (en) | 2013-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20171025 |