JP2014503480A5 - - Google Patents
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- Publication number
- JP2014503480A5 JP2014503480A5 JP2013536727A JP2013536727A JP2014503480A5 JP 2014503480 A5 JP2014503480 A5 JP 2014503480A5 JP 2013536727 A JP2013536727 A JP 2013536727A JP 2013536727 A JP2013536727 A JP 2013536727A JP 2014503480 A5 JP2014503480 A5 JP 2014503480A5
- Authority
- JP
- Japan
- Prior art keywords
- deuterium
- rich
- pharmaceutical composition
- compound
- pharmaceutically acceptable
- 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.)
- Pending
Links
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 58
- 229910052805 deuterium Inorganic materials 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 11
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 230000000155 isotopic effect Effects 0.000 claims description 7
- 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 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- XJEVHMGJSYVQBQ-SECBINFHSA-N (1r)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2[C@H](N)CCC2=C1 XJEVHMGJSYVQBQ-SECBINFHSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 206010011878 Deafness Diseases 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 2
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims description 2
- 229920002253 Tannate Polymers 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 230000010370 hearing loss Effects 0.000 claims description 2
- 231100000888 hearing loss Toxicity 0.000 claims description 2
- 208000016354 hearing loss disease Diseases 0.000 claims description 2
- 208000002780 macular degeneration Diseases 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- NIOPZPCMRQGZCE-WEVVVXLNSA-N 2,4-dinitro-6-(octan-2-yl)phenyl (E)-but-2-enoate Chemical compound CCCCCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)\C=C\C NIOPZPCMRQGZCE-WEVVVXLNSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical group [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 2
- 229960000245 rasagiline Drugs 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 1
- PIXDGZHWRVYNAU-UHFFFAOYSA-N C=NC(C#C)(C#C)N=O Chemical compound C=NC(C#C)(C#C)N=O PIXDGZHWRVYNAU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QUUSLJRWTDZCBF-UHFFFAOYSA-N OC1(c2ccccc2CC1)O Chemical compound OC1(c2ccccc2CC1)O QUUSLJRWTDZCBF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2014503480A JP2014503480A (ja) | 2014-02-13 |
| JP2014503480A5 true JP2014503480A5 (enExample) | 2014-12-11 |
Family
ID=45973513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013536727A Pending JP2014503480A (ja) | 2010-10-26 | 2011-10-25 | ジュウテリウムリッチなラサギリン |
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) | SG189454A1 (enExample) |
| WO (1) | WO2012058219A2 (enExample) |
| ZA (1) | ZA201303505B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8809310B2 (en) * | 2006-02-21 | 2014-08-19 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of multiple system atrophy |
| WO2007117431A2 (en) | 2006-04-03 | 2007-10-18 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of restless legs syndrome |
| 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 |
| CA2711817A1 (en) * | 2008-01-11 | 2009-07-16 | Teva Pharmaceutical Industries Ltd. | Rasagiline formulations, their preparation and use |
| WO2009151594A1 (en) * | 2008-06-10 | 2009-12-17 | Teva Pharmaceutical Industries, Ltd. | Rasagiline soft gelatin capsules |
| PT2451771E (pt) | 2009-07-09 | 2014-09-19 | Ratiopharm Gmbh | Sais de rasagilina e suas preparações farmacêuticas |
| AU2010304755A1 (en) * | 2009-10-09 | 2012-05-24 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Progressive Supranuclear Palsy |
| CA2785501A1 (en) * | 2009-12-22 | 2011-07-21 | Teva Pharmaceutical Industries Ltd. | 3-keto-n-propargyl-1-aminoindan |
| RU2587330C2 (ru) | 2010-07-27 | 2016-06-20 | Тева Фармасьютикал Индастриз Лтд. | Применение разагилина для лечения обонятельной дисфункции |
| EP2598136A4 (en) | 2010-07-27 | 2015-03-25 | Teva Pharma | DISPERSIONS OF RASAGILINE CITRATE |
| EA201490760A1 (ru) | 2011-10-10 | 2014-09-30 | Тева Фармасьютикал Индастриз Лтд. | R(+)-n-метилпропаргиламиноиндан |
| EA201490761A1 (ru) | 2011-10-10 | 2014-11-28 | Тева Фармасьютикал Индастриз Лтд. | R(+)-n-формилпропаргиламиноиндан |
| AR092168A1 (es) | 2012-08-17 | 2015-03-25 | Teva Pharma | Formulaciones parenterales de rasagilina |
| WO2020115715A1 (en) * | 2018-12-06 | 2020-06-11 | Intrabio Ltd. | Deuterated analogs of acetyl-leucine |
| 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 |
| AU2005269416B2 (en) * | 2004-07-26 | 2011-07-28 | Teva Pharmaceutical Industries, Ltd. | Pharmaceutical dosage forms including rasagiline |
| ZA200704917B (en) * | 2004-11-24 | 2008-11-26 | Teva Pharma | Rasagiline orally disintegrating compositions |
| EP1851188A1 (en) * | 2005-02-22 | 2007-11-07 | Teva Pharmaceutical Industries Limited | Improved process for the synthesis of enantiomeric indanylamine derivatives |
| WO2007052274A2 (en) * | 2005-11-06 | 2007-05-10 | 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 |
| US20090312436A1 (en) * | 2008-06-13 | 2009-12-17 | Ruth Levy | Rasagiline for parkinson's disease modification |
| 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 WO PCT/US2011/057698 patent/WO2012058219A2/en not_active Ceased
- 2011-10-25 SG SG2013029293A patent/SG189454A1/en unknown
- 2011-10-25 US US13/281,054 patent/US20120101168A1/en not_active Abandoned
- 2011-10-25 MX MX2013004598A patent/MX2013004598A/es not_active Application Discontinuation
- 2011-10-25 SG SG10201508771TA patent/SG10201508771TA/en unknown
- 2011-10-25 CA CA2816104A patent/CA2816104A1/en not_active Abandoned
- 2011-10-25 NZ NZ610526A patent/NZ610526A/en not_active IP Right Cessation
- 2011-10-25 KR KR1020137013167A patent/KR20140023872A/ko not_active Withdrawn
- 2011-10-25 EA EA201390613A patent/EA201390613A1/ru unknown
- 2011-10-25 CN CN2011800519198A patent/CN103188933A/zh active Pending
- 2011-10-25 AU AU2011320611A patent/AU2011320611A1/en not_active Abandoned
- 2011-10-25 JP JP2013536727A patent/JP2014503480A/ja active Pending
- 2011-10-25 BR BR112013010308A patent/BR112013010308A2/pt not_active IP Right Cessation
- 2011-10-25 EP EP11836950.3A patent/EP2632254A4/en not_active Withdrawn
- 2011-10-25 PH PH1/2013/500821A patent/PH12013500821A1/en unknown
-
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
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