JP7608050B2 - デューテトラベナジンの類似体、その調製及び使用 - Google Patents
デューテトラベナジンの類似体、その調製及び使用 Download PDFInfo
- Publication number
- JP7608050B2 JP7608050B2 JP2019550774A JP2019550774A JP7608050B2 JP 7608050 B2 JP7608050 B2 JP 7608050B2 JP 2019550774 A JP2019550774 A JP 2019550774A JP 2019550774 A JP2019550774 A JP 2019550774A JP 7608050 B2 JP7608050 B2 JP 7608050B2
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- Prior art keywords
- deutetrabenazine
- compound
- pharmaceutical composition
- concentration
- area
- 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.)
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- MKJIEFSOBYUXJB-VFJJUKLQSA-N (3r,11br)-3-(2-methylpropyl)-9,10-bis(trideuteriomethoxy)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one Chemical class C1CN2C[C@@H](CC(C)C)C(=O)C[C@@H]2C2=C1C=C(OC([2H])([2H])[2H])C(OC([2H])([2H])[2H])=C2 MKJIEFSOBYUXJB-VFJJUKLQSA-N 0.000 title claims description 297
- 238000002360 preparation method Methods 0.000 title description 11
- 229950005031 deutetrabenazine Drugs 0.000 claims description 295
- 238000000034 method Methods 0.000 claims description 148
- 239000008194 pharmaceutical composition Substances 0.000 claims description 134
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 107
- 229940125782 compound 2 Drugs 0.000 claims description 99
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 80
- 229940088679 drug related substance Drugs 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 208000000269 Hyperkinesis Diseases 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 11
- 238000003860 storage Methods 0.000 claims description 8
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 206010008748 Chorea Diseases 0.000 claims description 3
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 208000012601 choreatic disease Diseases 0.000 claims description 3
- 229940125904 compound 1 Drugs 0.000 description 96
- 150000001875 compounds Chemical class 0.000 description 60
- 238000009472 formulation Methods 0.000 description 43
- 239000012535 impurity Substances 0.000 description 31
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 30
- 229910052805 deuterium Inorganic materials 0.000 description 30
- 239000000523 sample Substances 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- 208000035475 disorder Diseases 0.000 description 11
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 10
- 239000000825 pharmaceutical preparation Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
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- 238000001514 detection method Methods 0.000 description 4
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- 239000012086 standard solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229960005333 tetrabenazine Drugs 0.000 description 4
- QCTKXTXHDRLVAT-UHFFFAOYSA-M (2-acetyl-4-methylpentyl)-trimethylazanium;iodide Chemical compound [I-].CC(C)CC(C(C)=O)C[N+](C)(C)C QCTKXTXHDRLVAT-UHFFFAOYSA-M 0.000 description 3
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010067671 Disease complication Diseases 0.000 description 2
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 102000009659 Vesicular Monoamine Transport Proteins Human genes 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
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- 208000026935 allergic disease Diseases 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000005750 disease progression Effects 0.000 description 2
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- 230000006870 function Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
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- 231100000062 no-observed-adverse-effect level Toxicity 0.000 description 2
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- 238000012216 screening Methods 0.000 description 2
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- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- QCDJYGZCMGEQNF-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-5-methylhexan-2-one Chemical compound CC(C)CC(C(C)=O)CN(C)C QCDJYGZCMGEQNF-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 238000010953 Ames test Methods 0.000 description 1
- 231100000039 Ames test Toxicity 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000031404 Chromosome Aberrations Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 208000024453 abnormal involuntary movement Diseases 0.000 description 1
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- 239000000411 inducer Substances 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 231100000150 mutagenicity / genotoxicity testing Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Management, Administration, Business Operations System, And Electronic Commerce (AREA)
- Pens And Brushes (AREA)
- Machine Translation (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022177578A JP2023010754A (ja) | 2017-03-15 | 2022-11-04 | デューテトラベナジンの類似体、その調製及び使用 |
| JP2024011974A JP7631572B2 (ja) | 2017-03-15 | 2024-01-30 | デューテトラベナジンの類似体、その調製及び使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762471484P | 2017-03-15 | 2017-03-15 | |
| US62/471,484 | 2017-03-15 | ||
| PCT/US2018/022562 WO2018170214A1 (en) | 2017-03-15 | 2018-03-15 | Analogs of deutetrabenazine, their preparation and use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022177578A Division JP2023010754A (ja) | 2017-03-15 | 2022-11-04 | デューテトラベナジンの類似体、その調製及び使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020510073A JP2020510073A (ja) | 2020-04-02 |
| JP2020510073A5 JP2020510073A5 (cg-RX-API-DMAC10.html) | 2021-12-23 |
| JP7608050B2 true JP7608050B2 (ja) | 2025-01-06 |
Family
ID=61873991
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019550774A Active JP7608050B2 (ja) | 2017-03-15 | 2018-03-15 | デューテトラベナジンの類似体、その調製及び使用 |
| JP2022177578A Pending JP2023010754A (ja) | 2017-03-15 | 2022-11-04 | デューテトラベナジンの類似体、その調製及び使用 |
| JP2024011974A Active JP7631572B2 (ja) | 2017-03-15 | 2024-01-30 | デューテトラベナジンの類似体、その調製及び使用 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022177578A Pending JP2023010754A (ja) | 2017-03-15 | 2022-11-04 | デューテトラベナジンの類似体、その調製及び使用 |
| JP2024011974A Active JP7631572B2 (ja) | 2017-03-15 | 2024-01-30 | デューテトラベナジンの類似体、その調製及び使用 |
Country Status (20)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI772382B (zh) | 2017-03-15 | 2022-08-01 | 美商奧斯拜客斯製藥有限公司 | 氘代丁苯那嗪(deutetrabenazine)之類似物、其製備方法及用途 |
| JP2022519007A (ja) | 2018-12-13 | 2022-03-18 | オースペックス ファーマシューティカルズ インコーポレイテッド | 脳性麻痺におけるジスキネジアを処置するためのデューテトラベナジン |
| WO2020165807A1 (en) * | 2019-02-14 | 2020-08-20 | Dr. Reddy's Laboratories Limited | Solid forms of deutetrabenazine and process for the preparation thereof |
| US12599598B2 (en) | 2020-06-10 | 2026-04-14 | Auspex Pharmaceuticals Llc | Osmotic dosage forms comprising deutetrabenazine and methods of use thereof |
| CN115916154A (zh) * | 2020-06-10 | 2023-04-04 | 奥斯佩克斯医药公司 | 包括氘代丁苯那嗪的渗透剂型及其使用方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012503010A (ja) | 2008-09-18 | 2012-02-02 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | 小胞モノアミン輸送体２のベンゾキノリン阻害剤 |
| JP2013527237A (ja) | 2010-06-01 | 2013-06-27 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | ベンゾキノロン系ｖｍａｔ２阻害剤 |
| JP2015528516A (ja) | 2012-09-18 | 2015-09-28 | オースペックス・ファーマシューティカルズ・インコーポレイテッドＡｕｓｐｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | 小胞モノアミン輸送体２の重水素化ベンゾキノリン阻害剤の製剤薬物動態 |
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| DK2081929T3 (da) | 2006-11-08 | 2013-04-15 | Neurocrine Biosciences Inc | Substituerede 3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11B-hexahydro-2H-pyrido[2,1-A]isoquinolin-2-ol-forbindelser og fremgangsmåder angående disse |
| WO2012081031A1 (en) * | 2010-12-15 | 2012-06-21 | Enaltec Labs Pvt. Ltd. | Process for preparing tetrabenazine |
| US9550780B2 (en) * | 2012-09-18 | 2017-01-24 | Auspex Pharmaceuticals, Inc. | Formulations pharmacokinetics of deuterated benzoquinoline inhibitors of vesicular monoamine transporter 2 |
| PL3265085T3 (pl) | 2015-03-06 | 2022-11-07 | Auspex Pharmaceuticals, Inc. | Sposoby leczenia zaburzeń związanych z nieprawidłowymi ruchami mimowolnymi |
| TWI772382B (zh) | 2017-03-15 | 2022-08-01 | 美商奧斯拜客斯製藥有限公司 | 氘代丁苯那嗪(deutetrabenazine)之類似物、其製備方法及用途 |
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| JP2012503010A (ja) | 2008-09-18 | 2012-02-02 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | 小胞モノアミン輸送体２のベンゾキノリン阻害剤 |
| JP2013527237A (ja) | 2010-06-01 | 2013-06-27 | オースペックス・ファーマシューティカルズ・インコーポレイテッド | ベンゾキノロン系ｖｍａｔ２阻害剤 |
| JP2015528516A (ja) | 2012-09-18 | 2015-09-28 | オースペックス・ファーマシューティカルズ・インコーポレイテッドＡｕｓｐｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | 小胞モノアミン輸送体２の重水素化ベンゾキノリン阻害剤の製剤薬物動態 |
| JP2017501141A (ja) | 2013-12-03 | 2017-01-12 | オースペックス ファーマシューティカルズ インコーポレイテッド | ベンゾキノリン化合物の製造方法 |
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