JP2018531963A5 - - Google Patents
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- JP2018531963A5 JP2018531963A5 JP2018521548A JP2018521548A JP2018531963A5 JP 2018531963 A5 JP2018531963 A5 JP 2018531963A5 JP 2018521548 A JP2018521548 A JP 2018521548A JP 2018521548 A JP2018521548 A JP 2018521548A JP 2018531963 A5 JP2018531963 A5 JP 2018531963A5
- Authority
- JP
- Japan
- Prior art keywords
- crystalline form
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- crystalline
- 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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- 238000000034 method Methods 0.000 claims description 33
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 32
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 32
- 238000001757 thermogravimetry curve Methods 0.000 claims description 32
- 239000013078 crystal Substances 0.000 claims description 30
- 238000002411 thermogravimetry Methods 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 208000013403 hyperactivity Diseases 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- 206010008748 Chorea Diseases 0.000 claims description 4
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 4
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 4
- 208000016620 Tourette disease Diseases 0.000 claims description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 229940011051 isopropyl acetate Drugs 0.000 claims description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 150000002828 nitro derivatives Chemical class 0.000 claims description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 3
- 208000014094 Dystonic disease Diseases 0.000 claims description 2
- 108010029485 Protein Isoforms Proteins 0.000 claims description 2
- 102000001708 Protein Isoforms Human genes 0.000 claims description 2
- 102000009659 Vesicular Monoamine Transport Proteins Human genes 0.000 claims description 2
- 108010020033 Vesicular Monoamine Transport Proteins Proteins 0.000 claims description 2
- 208000012601 choreatic disease Diseases 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000010118 dystonia Diseases 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims 1
- 0 CC(C)C[C@@](CN(CCc1c2)[C@](C3)c1cc(OC)c2OC)[C@@]3OC([C@@](*)C(C)C)=O Chemical compound CC(C)C[C@@](CN(CCc1c2)[C@](C3)c1cc(OC)c2OC)[C@@]3OC([C@@](*)C(C)C)=O 0.000 description 3
- GEJDGVNQKABXKG-IRIUNPIQSA-N CC(C)CC(CN(CCc1c2)C(C3)c1cc(OC)c2OC)[C@@H]3OC([C@H](C(C)C)N)=O Chemical compound CC(C)CC(CN(CCc1c2)C(C3)c1cc(OC)c2OC)[C@@H]3OC([C@H](C(C)C)N)=O GEJDGVNQKABXKG-IRIUNPIQSA-N 0.000 description 1
- MMQDVRCFNJLGCW-UHFFFAOYSA-N Cc(cc1)ccc1N=[O]=CO Chemical compound Cc(cc1)ccc1N=[O]=CO MMQDVRCFNJLGCW-UHFFFAOYSA-N 0.000 description 1
- BXGKAGLZHGYAMW-TZYFFPFWSA-N [(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl] (2S)-2-amino-3-methylbutanoate 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.Cc1ccc(cc1)S(O)(=O)=O.COc1cc2CCN3C[C@@H](CC(C)C)[C@@H](C[C@@H]3c2cc1OC)OC(=O)[C@@H](N)C(C)C BXGKAGLZHGYAMW-TZYFFPFWSA-N 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022114755A JP2022141821A (ja) | 2015-10-30 | 2022-07-19 | バルベナジン塩およびその多形体 |
| JP2024095055A JP2024107365A (ja) | 2015-10-30 | 2024-06-12 | バルベナジン塩およびその多形体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562249074P | 2015-10-30 | 2015-10-30 | |
| US62/249,074 | 2015-10-30 | ||
| PCT/US2016/059306 WO2017075340A1 (en) | 2015-10-30 | 2016-10-28 | Valbenazine salts and polymorphs thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022114755A Division JP2022141821A (ja) | 2015-10-30 | 2022-07-19 | バルベナジン塩およびその多形体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018531963A JP2018531963A (ja) | 2018-11-01 |
| JP2018531963A5 true JP2018531963A5 (enExample) | 2019-12-05 |
| JP7109360B2 JP7109360B2 (ja) | 2022-07-29 |
Family
ID=57281297
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018521548A Active JP7109360B2 (ja) | 2015-10-30 | 2016-10-28 | バルベナジン塩およびその多形体 |
| JP2022114755A Withdrawn JP2022141821A (ja) | 2015-10-30 | 2022-07-19 | バルベナジン塩およびその多形体 |
| JP2024095055A Pending JP2024107365A (ja) | 2015-10-30 | 2024-06-12 | バルベナジン塩およびその多形体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022114755A Withdrawn JP2022141821A (ja) | 2015-10-30 | 2022-07-19 | バルベナジン塩およびその多形体 |
| JP2024095055A Pending JP2024107365A (ja) | 2015-10-30 | 2024-06-12 | バルベナジン塩およびその多形体 |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US10065952B2 (enExample) |
| EP (3) | EP4344742A3 (enExample) |
| JP (3) | JP7109360B2 (enExample) |
| KR (2) | KR102736973B1 (enExample) |
| CN (3) | CN108473489B (enExample) |
| AU (1) | AU2016343633B2 (enExample) |
| CA (1) | CA3002074A1 (enExample) |
| CL (1) | CL2018001089A1 (enExample) |
| CO (1) | CO2018004589A2 (enExample) |
| CY (1) | CY1124002T1 (enExample) |
| DK (2) | DK3368534T3 (enExample) |
| EA (1) | EA201890852A1 (enExample) |
| ES (2) | ES2857085T3 (enExample) |
| FI (1) | FI3875459T3 (enExample) |
| HR (2) | HRP20210469T1 (enExample) |
| HU (2) | HUE065406T2 (enExample) |
| IL (2) | IL284874B2 (enExample) |
| LT (2) | LT3368534T (enExample) |
| MA (2) | MA43116B1 (enExample) |
| MX (1) | MX381258B (enExample) |
| MY (2) | MY209348A (enExample) |
| PH (1) | PH12018500900A1 (enExample) |
| PL (2) | PL3368534T3 (enExample) |
| PT (2) | PT3875459T (enExample) |
| RS (2) | RS65154B1 (enExample) |
| SA (1) | SA518391477B1 (enExample) |
| SG (1) | SG11201803408PA (enExample) |
| SI (2) | SI3875459T1 (enExample) |
| SM (1) | SMT202400177T1 (enExample) |
| TN (1) | TN2018000121A1 (enExample) |
| WO (1) | WO2017075340A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TN2018000121A1 (en) | 2015-10-30 | 2019-10-04 | Neurocrine Biosciences Inc | Valbenazine salts and polymorphs thereof |
| LT3394057T (lt) | 2015-12-23 | 2022-06-27 | Neurocrine Biosciences, Inc. | Sintezės būdas, skirtas pagaminti (s)-(2r,3r,11br)-3-izobutil-9,10-dimetoksi-2,3,4,6,7,11b-heksahidro-1h-pirido[2,1-a]izochinolin-2-ilo 2-amino-3-metilbutanoato di(4-metilbenzensulfonatą) |
| EP3523300A1 (en) | 2016-10-06 | 2019-08-14 | Assia Chemical Industries Ltd. | Solid state forms of valbenazine |
| TW202515564A (zh) * | 2016-12-02 | 2025-04-16 | 美商紐羅克里生物科學有限公司 | 戊苯那嗪（valbenazine）於治療精神分裂症或情感性精神分裂症之用途 |
| WO2018130345A1 (en) * | 2017-01-10 | 2018-07-19 | Sandoz Ag | Crystalline valbenazine free base |
| WO2018140092A1 (en) | 2017-01-27 | 2018-08-02 | Obrien Christopher F | Methods for the administration of certain vmat2 inhibitors |
| JP2020508337A (ja) * | 2017-02-27 | 2020-03-19 | サンド・アクチエンゲゼルシヤフト | バルベナジン塩の結晶形態 |
| WO2018200605A1 (en) * | 2017-04-26 | 2018-11-01 | Neurocrine Biosciences, Inc. | Use of valbenazine for treating levodopa-induced dyskinesia |
| US20200276184A1 (en) | 2017-09-21 | 2020-09-03 | Neurocrine Biosciences, Inc. | High Dosage Valbenazine Formulation and Compositions, Methods, and Kits Related Thereto |
| KR20250070134A (ko) | 2017-10-10 | 2025-05-20 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 특정 vmat2 억제제의 투여 방법 |
| EA202090932A1 (ru) | 2017-10-10 | 2021-05-20 | Нейрокрин Байосайенсиз, Инк | Способы введения некоторых vmat2-ингибиторов |
| US11384077B2 (en) | 2017-11-22 | 2022-07-12 | Assia Chemical Industries Ltd. | Solid state form of Valbenazine |
| CN110621674B (zh) * | 2017-12-26 | 2022-03-29 | 苏州科睿思制药有限公司 | 一种Valbenazine二对甲苯磺酸盐的晶型及其制备方法和用途 |
| CN110818705A (zh) * | 2018-08-14 | 2020-02-21 | 苏州鹏旭医药科技有限公司 | 缬苯那嗪的盐型和相应晶型与其制备方法 |
| JP2021528481A (ja) * | 2018-08-15 | 2021-10-21 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | 特定のｖｍａｔ２阻害剤を投与するための方法 |
| CA3065236A1 (en) * | 2018-12-27 | 2020-06-27 | Apotex Inc. | Novel crystalline form of valbenazine dibesylate |
| WO2020213014A1 (en) | 2019-04-19 | 2020-10-22 | Mylan Laboratories Limited | An improved process for the preparation of valbenazine and its salts |
| US10689380B1 (en) * | 2019-07-30 | 2020-06-23 | Farmhispania S.A. | Crystalline forms of valbenazine ditosylate |
| US10940141B1 (en) | 2019-08-23 | 2021-03-09 | Neurocrine Biosciences, Inc. | Methods for the administration of certain VMAT2 inhibitors |
| EP4028397A1 (en) * | 2019-09-13 | 2022-07-20 | Neurocrine Biosciences, Inc. | Processes for the synthesis of valbenazine |
| MD4210700T2 (ro) * | 2020-09-09 | 2025-11-30 | Crinetics Pharmaceuticals Inc | Preparate ale unui modulator al somatostatinei |
| CN112569465B (zh) * | 2020-12-29 | 2022-07-19 | 华东理工大学 | 一种微针贴片的制备方法 |
| CN117062815A (zh) * | 2021-03-22 | 2023-11-14 | 纽罗克里生物科学有限公司 | Vmat2抑制剂及使用方法 |
| US20240239791A1 (en) | 2021-04-26 | 2024-07-18 | Neurocrine Biosciences, Inc. | Processes for the synthesis of valbenazine |
| MX2023014977A (es) * | 2021-06-30 | 2024-02-09 | Neurocrine Biosciences Inc | Valbenazina para usarse en el tratamiento de discinesia debido a paralisis cerebral. |
| US20240342159A1 (en) | 2021-06-30 | 2024-10-17 | Neurocrine Biosciences, Inc. | Valbenazine for use in the add-on treatment of schizophrenia |
| US20250064990A1 (en) | 2021-08-20 | 2025-02-27 | Neurocrine Biosciences, Inc. | Methods of screening for vmat2 inhibitors |
| CN118284409A (zh) * | 2021-10-29 | 2024-07-02 | 纽罗克里生物科学有限公司 | 缬苯那嗪组合物 |
| TW202521119A (zh) | 2023-08-17 | 2025-06-01 | 美商紐羅克里生物科學有限公司 | 用於投與特定vmat2抑制劑之方法 |
| WO2025038959A1 (en) | 2023-08-17 | 2025-02-20 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
| WO2025096823A1 (en) | 2023-11-01 | 2025-05-08 | Neurocrine Biosciences, Inc. | Improvement, maintenance or reduction of decline of motor function associated with huntington disease using valbenazine |
| WO2025188830A1 (en) * | 2024-03-06 | 2025-09-12 | Neurocrine Biosciences, Inc. | Methods for the administration of certain vmat2 inhibitors |
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