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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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- 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
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (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)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Otolaryngology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Pest Control & Pesticides (AREA)
- Psychology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
Family
ID=45973513
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 (https=) |
| EP (1) | EP2632254A4 (https=) |
| JP (1) | JP2014503480A (https=) |
| KR (1) | KR20140023872A (https=) |
| CN (1) | CN103188933A (https=) |
| AU (1) | AU2011320611A1 (https=) |
| BR (1) | BR112013010308A2 (https=) |
| CA (1) | CA2816104A1 (https=) |
| CL (1) | CL2013001101A1 (https=) |
| EA (1) | EA201390613A1 (https=) |
| IL (1) | IL225852A0 (https=) |
| MX (1) | MX2013004598A (https=) |
| NZ (1) | NZ610526A (https=) |
| PH (1) | PH12013500821A1 (https=) |
| SG (2) | SG189454A1 (https=) |
| WO (1) | WO2012058219A2 (https=) |
| ZA (1) | ZA201303505B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2551481T3 (es) * | 2006-02-21 | 2015-11-19 | Teva Pharmaceutical Industries, Ltd. | Uso de rasagilina para el tratamiento de atrofia multisistémica |
| JP5769923B2 (ja) * | 2006-04-03 | 2015-08-26 | 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 | レストレスレッグス症候群の治療のためのラサギリンの使用 |
| CN101557706B (zh) * | 2006-12-14 | 2013-08-07 | 泰华制药工业有限公司 | 雷沙吉兰碱结晶固体 |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| EP2234478A4 (en) * | 2008-01-11 | 2013-01-23 | Teva Pharma | RASAGILINE FORMULATIONS, THEIR PREPARATION AND USE |
| WO2009151594A1 (en) * | 2008-06-10 | 2009-12-17 | Teva Pharmaceutical Industries, Ltd. | Rasagiline soft gelatin capsules |
| SI2451771T1 (sl) | 2009-07-09 | 2014-10-30 | Ratiopharm Gmbh | Soli rasagilina in njihovi farmacevtski pripravki |
| AU2010304755A1 (en) * | 2009-10-09 | 2012-05-24 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Progressive Supranuclear Palsy |
| EP2515891A4 (en) * | 2009-12-22 | 2013-06-05 | Teva Pharma | 3-keto-N-propargyl-1-aminoindan |
| AU2011282720B2 (en) | 2010-07-27 | 2016-12-22 | Teva Pharmaceutical Industries Ltd. | Use of rasagiline for the treatment of olfactory dysfunction |
| JP2013537530A (ja) | 2010-07-27 | 2013-10-03 | 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 | ラサギリンシトレートの分散物 |
| JP2014534197A (ja) | 2011-10-10 | 2014-12-18 | 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 | Ｒ（＋）−ｎ−メチル−プロパルギルアミノインダン |
| HK1200315A1 (en) | 2011-10-10 | 2015-08-07 | Teva Pharmaceutical Industries Ltd. | R(+)-n-formyl-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 |
| JP7471298B2 (ja) * | 2018-12-06 | 2024-04-19 | イントラビオ エルティーディー | アセチル－ロイシンの重水素化類似体 |
| 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 |
|---|---|---|---|---|
| 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 |
| 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 |
| WO2006014973A2 (en) * | 2004-07-26 | 2006-02-09 | Teva Pharmaceutical Industries, Ltd. | Pharmaceutical dosage forms including rasagiline |
| US20090111892A1 (en) * | 2004-11-24 | 2009-04-30 | Shulamit Patashnik | Rasagiline Orally Disintegrating Compositions |
| AU2006245349A1 (en) * | 2005-02-22 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Improved process for the synthesis of enantiomeric indanylamine derivatives |
| EP1948248A2 (en) * | 2005-11-06 | 2008-07-30 | Katz-Brull, Rachel | Magnetic resonance imaging and spectroscopy means and methods thereof |
| AU2009254929B2 (en) * | 2008-06-02 | 2014-03-13 | Generics [Uk] Limited | An improved process for the preparation of amines |
| MX2010013766A (es) * | 2008-06-13 | 2011-03-15 | Teva Pharmaceutical Ind Ltd Star | Rasagilina para modificacion de enfermedad de parkinson. |
| US20100172916A1 (en) * | 2008-11-10 | 2010-07-08 | Auspex Pharmaceuticals, Inc. | Substituted hydroxyphenylamine compounds |
| US20100189791A1 (en) * | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline malate formulation |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| US20120156139A1 (en) * | 2009-08-31 | 2012-06-21 | Rachel Katz-Brull | Isotopically labeled neurochemical agents and uses therof for diagnosing conditions and disorders |
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2011
- 2011-10-25 SG SG2013029293A patent/SG189454A1/en unknown
- 2011-10-25 EA EA201390613A patent/EA201390613A1/ru unknown
- 2011-10-25 KR KR1020137013167A patent/KR20140023872A/ko not_active Withdrawn
- 2011-10-25 MX MX2013004598A patent/MX2013004598A/es not_active Application Discontinuation
- 2011-10-25 BR BR112013010308A patent/BR112013010308A2/pt not_active IP Right Cessation
- 2011-10-25 SG SG10201508771TA patent/SG10201508771TA/en unknown
- 2011-10-25 PH PH1/2013/500821A patent/PH12013500821A1/en unknown
- 2011-10-25 US US13/281,054 patent/US20120101168A1/en not_active Abandoned
- 2011-10-25 EP EP11836950.3A patent/EP2632254A4/en not_active Withdrawn
- 2011-10-25 AU AU2011320611A patent/AU2011320611A1/en not_active Abandoned
- 2011-10-25 WO PCT/US2011/057698 patent/WO2012058219A2/en not_active Ceased
- 2011-10-25 NZ NZ610526A patent/NZ610526A/en not_active IP Right Cessation
- 2011-10-25 JP JP2013536727A patent/JP2014503480A/ja active Pending
- 2011-10-25 CA CA2816104A patent/CA2816104A1/en not_active Abandoned
- 2011-10-25 CN CN2011800519198A patent/CN103188933A/zh active Pending
-
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 |
|---|---|
| SG189454A1 (en) | 2013-05-31 |
| US20120101168A1 (en) | 2012-04-26 |
| WO2012058219A2 (en) | 2012-05-03 |
| PH12013500821A1 (en) | 2019-07-03 |
| EP2632254A2 (en) | 2013-09-04 |
| CL2013001101A1 (es) | 2013-09-06 |
| AU2011320611A1 (en) | 2013-06-13 |
| KR20140023872A (ko) | 2014-02-27 |
| JP2014503480A (ja) | 2014-02-13 |
| NZ610526A (en) | 2015-10-30 |
| SG10201508771TA (en) | 2015-11-27 |
| MX2013004598A (es) | 2013-07-17 |
| EP2632254A4 (en) | 2015-08-05 |
| ZA201303505B (en) | 2015-08-26 |
| IL225852A0 (en) | 2013-06-27 |
| US20140364506A1 (en) | 2014-12-11 |
| EA201390613A1 (ru) | 2013-11-29 |
| BR112013010308A2 (pt) | 2016-07-05 |
| CN103188933A (zh) | 2013-07-03 |
| WO2012058219A3 (en) | 2012-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20171025 |