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 (cg-RX-API-DMAC7.html) | 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)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007217349B9 (en) * | 2006-02-21 | 2013-06-27 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Multiple System Atrophy |
| CA2646250A1 (en) | 2006-04-03 | 2007-10-18 | Teva Pharmaceutical Industries Ltd. | Use of rasagiline for the treatment of restless legs syndrome |
| PT2101569E (pt) * | 2006-12-14 | 2012-01-13 | Teva Pharma | Base de rasagilina sólida cristalina |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| KR20100107028A (ko) * | 2008-01-11 | 2010-10-04 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라사길린 제형, 그들의 제법 및 용도 |
| EP2285214B1 (en) * | 2008-06-10 | 2012-05-16 | Teva Pharmaceutical Industries Ltd. | Rasagiline soft gelatin capsules |
| PL2451771T3 (pl) | 2009-07-09 | 2014-12-31 | Ratiopharm Gmbh | Sole rasagiliny i ich preparaty farmaceutyczne |
| WO2011042812A1 (en) * | 2009-10-09 | 2011-04-14 | Stefan Lorenzl | Use of rasagiline for the treatment of progressive supranuclear palsy |
| MX2012007375A (es) * | 2009-12-22 | 2012-07-30 | Teva Pharma | 3-ceto-n-propargil 1-aminoindano. |
| 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 |
| EP2603212A4 (en) | 2010-07-27 | 2014-01-08 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF SMOKING DISORDER |
| BR112014008555A2 (pt) | 2011-10-10 | 2017-04-18 | Teva Pharma | r(+)-n-formil-propargil-aminoindano |
| AU2012323351A1 (en) | 2011-10-10 | 2014-05-22 | Teva Pharmaceutical Industries Ltd. | R(+)-N-methyl-propargyl-aminoindan |
| WO2014028868A1 (en) | 2012-08-17 | 2014-02-20 | Teva Pharmaceutical Industries Ltd. | Parenteral formulation of rasagiline |
| IL319687A (en) * | 2018-12-06 | 2025-05-01 | Intrabio Ltd | Deuterated acetyl-leucine analogs |
| 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 |
| US20090111892A1 (en) * | 2004-11-24 | 2009-04-30 | Shulamit Patashnik | 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 |
| EP1948248A2 (en) * | 2005-11-06 | 2008-07-30 | Katz-Brull, Rachel | Magnetic resonance imaging and spectroscopy means and methods thereof |
| CA2723870C (en) * | 2008-06-02 | 2015-04-21 | Generics [Uk] Limited | An improved process for the preparation of amines |
| BRPI0909894A2 (pt) * | 2008-06-13 | 2015-07-28 | Teva Pharma | "método de redução da velocidade de progressão de mal de parkinson em um paciente com mal de parkinson em estágio inicial, método de redução da velocidade de progressão de mal de parkinson, método de atraso da necessidade de terapia antiparkinsoniana sintomática em um paciente de mal de parkinson em estágio inicial, método de redução do risco de um paciente com mal de parkinson que necessita de terapia antiparkinsoniana, método de redução do declínio funcional de um paciente com mal de parkinson em estágio inicial, método de redução do declínio funcional em um paciente com mal de parkinson, método de tratamento de um paciente que exibe sinais iniciais de mal de parkinson, método de redução da fadiga em um paciente com mal de parkinson em estágio inicial, método de redução da velocidade de progressão clínica e tratamento de sintomas de mal de parkinson em um paciente com mal de parkinson, rasagilina ou um sal farmaceuticamente aceitável de rasagilina, composição farmacêutica. |
| WO2010054286A2 (en) * | 2008-11-10 | 2010-05-14 | 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 |
| CA2772489A1 (en) * | 2009-08-31 | 2011-03-03 | Brain Watch Ltd. | Isotopically labeled neurochemical agents and uses thereof for diagnosing conditions and disorders |
-
2011
- 2011-10-25 BR BR112013010308A patent/BR112013010308A2/pt not_active IP Right Cessation
- 2011-10-25 CN CN2011800519198A patent/CN103188933A/zh active Pending
- 2011-10-25 PH PH1/2013/500821A patent/PH12013500821A1/en unknown
- 2011-10-25 SG SG10201508771TA patent/SG10201508771TA/en unknown
- 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 AU AU2011320611A patent/AU2011320611A1/en not_active Abandoned
- 2011-10-25 EA EA201390613A patent/EA201390613A1/ru unknown
- 2011-10-25 SG SG2013029293A patent/SG189454A1/en unknown
- 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 WO PCT/US2011/057698 patent/WO2012058219A2/en not_active Ceased
- 2011-10-25 CA CA2816104A patent/CA2816104A1/en not_active Abandoned
- 2011-10-25 US US13/281,054 patent/US20120101168A1/en not_active Abandoned
- 2011-10-25 KR KR1020137013167A patent/KR20140023872A/ko not_active Withdrawn
-
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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