PT2262505E - Sólidos de gama-carbolinas fusionadas a heterociclos substituídos - Google Patents
Sólidos de gama-carbolinas fusionadas a heterociclos substituídos Download PDFInfo
- Publication number
- PT2262505E PT2262505E PT97189518T PT09718951T PT2262505E PT 2262505 E PT2262505 E PT 2262505E PT 97189518 T PT97189518 T PT 97189518T PT 09718951 T PT09718951 T PT 09718951T PT 2262505 E PT2262505 E PT 2262505E
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- Prior art keywords
- salt
- salt crystals
- salt crystal
- disorder
- quot
- Prior art date
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- RDMFHRSPDKWERA-UHFFFAOYSA-N 5H-Pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=CC=C3NC2=C1 RDMFHRSPDKWERA-UHFFFAOYSA-N 0.000 description 2
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- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- 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
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/20—Hypnotics; Sedatives
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- 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
- A61P25/22—Anxiolytics
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- 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
- A61P25/24—Antidepressants
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
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| SI (1) | SI2262505T1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX394214B (es) | 2007-03-12 | 2025-03-24 | Intra Cellular Therapies Inc | Sintesis de gamma-carbolinas fusionadas con heterociclo substituido. |
| ES2530090T3 (es) | 2008-03-12 | 2015-02-26 | Intra-Cellular Therapies, Inc. | Sólido de gamma-carbolinas fusionadas con heterociclo sustituido |
| CA2725342C (en) | 2008-05-27 | 2024-02-20 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for sleep disorders and other disorders |
| US9107696B2 (en) * | 2008-08-06 | 2015-08-18 | Emory University | Method of embryo transfer that eliminates transferred air while hormonally inducing implantation and apparatus |
| US8993572B2 (en) | 2010-04-22 | 2015-03-31 | Intra-Cellular Therapies, Inc. | Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines derivatives and [1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole derivatives |
| US9428506B2 (en) | 2012-04-14 | 2016-08-30 | Intra-Cellular Therapies, Inc. | Substituted pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines for the treatment of nervous system disorders |
| WO2014145192A1 (en) | 2013-03-15 | 2014-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR102967223B1 (ko) | 2013-12-03 | 2026-05-19 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 신규한 방법 |
| LT3105218T (lt) | 2014-02-13 | 2019-12-10 | Incyte Corp | Ciklopropilaminai kaip lsd1 inhibitoriai |
| KR20220054908A (ko) | 2014-04-04 | 2022-05-03 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| US9745300B2 (en) | 2014-04-04 | 2017-08-29 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EA201792205A1 (ru) | 2015-04-03 | 2018-02-28 | Инсайт Корпорейшн | Гетероциклические соединения как ингибиторы lsd1 |
| DK3334709T3 (da) | 2015-08-12 | 2025-02-03 | Incyte Holdings Corp | Salte af en lsd1-hæmmer |
| RU2743513C2 (ru) | 2016-01-26 | 2021-02-19 | Интра-Селлулар Терапиз, Инк. | Органические соединения |
| IL281050B2 (en) | 2016-03-25 | 2023-04-01 | Intra Cellular Therapies Inc | A controlled or delayed release pharmaceutical preparation containing a deuterated compound |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| WO2017172811A1 (en) * | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel co-crystals |
| WO2017172784A1 (en) * | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel salts and crystals |
| HUE057055T2 (hu) | 2016-08-09 | 2022-04-28 | Teva Pharmaceuticals Int Gmbh | Lumateperon-ditozilátsó szilárd halmazállapotú formái |
| JP7013454B2 (ja) * | 2016-10-12 | 2022-02-15 | イントラ－セルラー・セラピーズ・インコーポレイテッド | アモルファス固体分散体 |
| WO2018126140A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP3562484B1 (en) | 2016-12-29 | 2021-08-25 | Intra-Cellular Therapies, Inc. | Pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline derivatives useful in the treatment of cns disorders |
| EP3600325A4 (en) | 2017-03-24 | 2021-01-06 | Intra-Cellular Therapies, Inc. | UNIQUE COMPOSITIONS AND PROCESSES |
| WO2018189646A1 (en) * | 2017-04-10 | 2018-10-18 | Dr. Reddy's Laboratories Limited | AMORPHOUS FORM AND SOLID DISPERSIONS OF LUMATEPERONE p-TOSYLATE |
| WO2019023062A1 (en) | 2017-07-26 | 2019-01-31 | Intra-Cellular Therapies, Inc. | ORGANIC COMPOUNDS |
| JP7224333B2 (ja) | 2017-07-26 | 2023-02-17 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| WO2019067591A1 (en) | 2017-09-26 | 2019-04-04 | Intra-Cellular Therapies, Inc. | NEW SALTS AND CRYSTALS |
| WO2019102240A1 (en) | 2017-11-27 | 2019-05-31 | Egis Gyógyszergyár Zrt. | Method for the manufacture of lumateperone and its salts |
| CN109867674A (zh) * | 2017-12-05 | 2019-06-11 | 上海度德医药科技有限公司 | 一种取代的杂环稠合γ-咔啉的新盐及其制备方法和晶型 |
| WO2019178484A1 (en) | 2018-03-16 | 2019-09-19 | Intra-Cellular Therapies, Inc. | Novel methods |
| SMT202600133T1 (it) | 2018-03-23 | 2026-05-12 | Intra Cellular Therapies Inc | Composti organici |
| AU2019240226B2 (en) | 2018-03-23 | 2024-11-28 | Intra-Cellular Therapies, Inc. | Organic compounds |
| BR112020024885A2 (pt) | 2018-06-06 | 2021-03-09 | Intra-Cellular Therapies, Inc. | Novos sais e cristais |
| EP3801527B1 (en) | 2018-06-08 | 2025-02-19 | Intra-Cellular Therapies, Inc. | Fused gamma-carbolines for acute treatment of anxiety or depression |
| RS67906B1 (sr) | 2018-06-11 | 2026-04-30 | Intra Cellular Therapies Inc | Sinteza supstituisanih heterociklično fuzionisanih gama-karbolina |
| EP3811371A1 (en) | 2018-06-21 | 2021-04-28 | Aquestive Therapeutics, Inc. | System and method for making personalized individual unit doses containing pharmaceutical actives |
| US12144808B2 (en) | 2018-08-29 | 2024-11-19 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| AU2019328528B2 (en) * | 2018-08-31 | 2025-01-23 | Intra-Cellular Therapies, Inc. | Novel methods |
| WO2020047408A1 (en) * | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| WO2020051317A1 (en) | 2018-09-07 | 2020-03-12 | Aquestive Therapeutics, Inc. | Oral film compositions and dosage forms having precise active dissolution profiles |
| WO2020112941A2 (en) | 2018-11-27 | 2020-06-04 | Teva Czech Industries S.R.O | Solid state forms of lumateperone salts and processes for preparation of lumateperone and salts thereof |
| KR20210104785A (ko) | 2018-12-17 | 2021-08-25 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| IL315005B2 (en) | 2018-12-17 | 2026-04-01 | Intra Cellular Therapies Inc | Substituted heterocycle fused gamma-carbolines synthesis |
| ES3047409T3 (en) | 2018-12-17 | 2025-12-03 | Intra Cellular Therapies Inc | Substituted heterocycle fused gamma-carbolines synthesis |
| US12331052B2 (en) | 2018-12-21 | 2025-06-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP7377871B2 (ja) | 2018-12-21 | 2023-11-10 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| WO2020182978A1 (en) | 2019-03-13 | 2020-09-17 | Sandoz Ag | Crystalline salt of a 5-ht2a receptor antagonist |
| EP4134101A1 (en) | 2019-07-07 | 2023-02-15 | Intra-Cellular Therapies, Inc. | Deuterated lumateperone for the treatment of the bipolar ii disorder |
| JP2022549335A (ja) | 2019-09-25 | 2022-11-24 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
| MX2022004983A (es) | 2019-11-01 | 2022-09-23 | Aquestive Therapeutics Inc | Composiciones de profarmaco y metodos de tratamiento. |
| CA3159389A1 (en) | 2019-11-14 | 2021-05-20 | Aquestive Therapeutics, Inc. | Multimodal compositions comprising diazepam and methods of treatment |
| WO2021119334A1 (en) | 2019-12-11 | 2021-06-17 | Intra-Cellular Therapies, Inc. | Organic compound |
| LT4076461T (lt) | 2019-12-19 | 2026-06-25 | Intra-Cellular Therapies, Inc. | Lumateperonas, skirtas panaudoti šizofrenijos gydymui |
| JP2024505429A (ja) | 2021-01-15 | 2024-02-06 | アクエスティブ セラピューティクス インコーポレイテッド | プロドラッグ組成物及び治療の方法 |
| US20220347117A1 (en) | 2021-03-09 | 2022-11-03 | Aquestive Therapeutics, Inc. | Dosage forms having equivalent biocomparable profiles |
| IL308750A (en) * | 2021-06-07 | 2024-01-01 | Intra Cellular Therapies Inc | Novel salts and crystals |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
| US20250195510A1 (en) | 2022-05-18 | 2025-06-19 | Intra-Cellular Therapies, Inc. | Novel methods |
| TWI902035B (zh) * | 2022-10-26 | 2025-10-21 | 大陸商上海樞境生物科技有限公司 | 一種雜環取代的稠合γ-咔啉類衍生物的甲磺酸鹽、晶型及其製備方法和應用 |
| CN117924288A (zh) * | 2022-10-26 | 2024-04-26 | 上海枢境生物科技有限公司 | 一种杂环取代的稠合γ-咔啉类衍生物的盐酸盐、晶型及其制备方法和应用 |
| KR20250123225A (ko) | 2022-12-30 | 2025-08-14 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| CN121152625A (zh) | 2023-02-17 | 2025-12-16 | 细胞内治疗公司 | 用于调节神经系统的卢美哌隆和其衍生物 |
| WO2025111568A1 (en) | 2023-11-22 | 2025-05-30 | Intra-Cellular Therapies, Inc. | Lumateperone and analogues, as 5-ht2a or 5-ht2a/d2 receptor modulators, for use in the treatment of psychiatric disorders caused by viral, bacterial, or autoimmune encephalitis, and of psychiatric symptoms thereof |
| US20250352469A1 (en) | 2024-05-16 | 2025-11-20 | Intra-Cellular Therapies, Inc. | Novel compositions, devices, and methods |
| WO2026011136A1 (en) | 2024-07-03 | 2026-01-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2026011166A1 (en) | 2024-07-03 | 2026-01-08 | Intra-Cellular Therapies, Inc. | Substituted heterocycles for use in the treatment of diseases involving the 5-ht2a receptor |
Family Cites Families (11)
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| US7071186B2 (en) * | 1999-06-15 | 2006-07-04 | Bristol-Myers Squibb Pharma Co. | Substituted heterocycle fused gamma-carbolines |
| WO2000077001A1 (en) * | 1999-06-15 | 2000-12-21 | Du Pont Pharmaceuticals Company | Substituted heterocycle fused gamma-carbolines |
| US6713471B1 (en) * | 1999-06-15 | 2004-03-30 | Bristol-Myers Squibb Pharma Company | Substituted heterocycle fused gamma-carbolines |
| FR2796644B1 (fr) * | 1999-07-23 | 2001-09-07 | Adir | Nouveaux derives de beta-carboline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU2004259741A1 (en) * | 2003-07-21 | 2005-02-03 | Smithkline Beecham Corporation | (2S,4S)-4-fluoro-1-[4-fluoro-beta-(4-fluorophenyl)-L-phenylalanyl]-2-pyrrolidinecarbonitrile p-toluenesulfonic acid salt and anhydrous crystalline forms thereof |
| MX394214B (es) * | 2007-03-12 | 2025-03-24 | Intra Cellular Therapies Inc | Sintesis de gamma-carbolinas fusionadas con heterociclo substituido. |
| ES2530090T3 (es) | 2008-03-12 | 2015-02-26 | Intra-Cellular Therapies, Inc. | Sólido de gamma-carbolinas fusionadas con heterociclo sustituido |
| CA2725342C (en) | 2008-05-27 | 2024-02-20 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for sleep disorders and other disorders |
| US8993572B2 (en) | 2010-04-22 | 2015-03-31 | Intra-Cellular Therapies, Inc. | Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines derivatives and [1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole derivatives |
| US9428506B2 (en) | 2012-04-14 | 2016-08-30 | Intra-Cellular Therapies, Inc. | Substituted pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines for the treatment of nervous system disorders |
| WO2014145192A1 (en) | 2013-03-15 | 2014-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
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2009
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- 2009-03-12 DK DK09718951.8T patent/DK2262505T3/en active
- 2009-03-12 PT PT97189518T patent/PT2262505E/pt unknown
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- 2009-03-12 KR KR1020107022312A patent/KR101610977B1/ko active Active
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