CA2870303A1 - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2870303A1 CA2870303A1 CA2870303A CA2870303A CA2870303A1 CA 2870303 A1 CA2870303 A1 CA 2870303A1 CA 2870303 A CA2870303 A CA 2870303A CA 2870303 A CA2870303 A CA 2870303A CA 2870303 A1 CA2870303 A1 CA 2870303A1
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- Prior art keywords
- compound according
- disorder
- compound
- disease
- disorders
- 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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- 150000002894 organic compounds Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 155
- 150000003839 salts Chemical class 0.000 claims abstract description 77
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 47
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 230000037361 pathway Effects 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 155
- 208000035475 disorder Diseases 0.000 claims description 38
- 208000019116 sleep disease Diseases 0.000 claims description 27
- 208000028017 Psychotic disease Diseases 0.000 claims description 26
- 201000000980 schizophrenia Diseases 0.000 claims description 23
- 208000018737 Parkinson disease Diseases 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 208000012902 Nervous system disease Diseases 0.000 claims description 12
- 238000013019 agitation Methods 0.000 claims description 12
- 208000015114 central nervous system disease Diseases 0.000 claims description 12
- 206010001497 Agitation Diseases 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 8
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 claims description 8
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 8
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 7
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 7
- 208000030990 Impulse-control disease Diseases 0.000 claims description 7
- 208000015046 intermittent explosive disease Diseases 0.000 claims description 7
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 7
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 5
- 208000020706 Autistic disease Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 4
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 4
- 201000010374 Down Syndrome Diseases 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 201000002832 Lewy body dementia Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
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- 206010033799 Paralysis Diseases 0.000 claims description 4
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
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- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 206010041250 Social phobia Diseases 0.000 claims description 4
- 201000004810 Vascular dementia Diseases 0.000 claims description 4
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- 230000004064 dysfunction Effects 0.000 claims description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
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- 208000006264 Korsakoff syndrome Diseases 0.000 claims description 3
- 201000008485 Wernicke-Korsakoff syndrome Diseases 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 230000007278 cognition impairment Effects 0.000 claims description 3
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- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 2
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 9
- 239000000651 prodrug Substances 0.000 abstract description 8
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- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 5
- 102000004980 Dopamine D2 Receptors Human genes 0.000 abstract description 4
- 108090001111 Dopamine D2 Receptors Proteins 0.000 abstract description 4
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 abstract description 4
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 abstract description 4
- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 abstract description 3
- 230000011664 signaling Effects 0.000 abstract description 2
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- 239000000203 mixture Substances 0.000 description 75
- -1 glutamic Chemical group 0.000 description 66
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- 239000000556 agonist Substances 0.000 description 22
- 239000011159 matrix material Substances 0.000 description 21
- 239000000544 cholinesterase inhibitor Substances 0.000 description 18
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- 239000011859 microparticle Substances 0.000 description 17
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000013270 controlled release Methods 0.000 description 14
- 239000007903 gelatin capsule Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 13
- GIYXAJPCNFJEHY-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine hydrochloride (1:1) Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 GIYXAJPCNFJEHY-UHFFFAOYSA-N 0.000 description 12
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
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- 239000005557 antagonist Substances 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- 230000003204 osmotic effect Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 9
- 229940122041 Cholinesterase inhibitor Drugs 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 9
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 9
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 229960005426 doxepin Drugs 0.000 description 9
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 8
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 229960004502 levodopa Drugs 0.000 description 8
- 229920000747 poly(lactic acid) Polymers 0.000 description 8
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 8
- 229960001534 risperidone Drugs 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 208000019022 Mood disease Diseases 0.000 description 7
- 230000001430 anti-depressive effect Effects 0.000 description 7
- 239000000935 antidepressant agent Substances 0.000 description 7
- 239000000164 antipsychotic agent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 229960002296 paroxetine Drugs 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WIHMBLDNRMIGDW-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydron;bromide Chemical compound [Br-].O1CC2=CC(C#N)=CC=C2C1(CCC[NH+](C)C)C1=CC=C(F)C=C1 WIHMBLDNRMIGDW-UHFFFAOYSA-N 0.000 description 6
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LFMYNZPAVPMEGP-PIDGMYBPSA-N Fluvoxamine maleate Chemical compound OC(=O)\C=C/C(O)=O.COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 LFMYNZPAVPMEGP-PIDGMYBPSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 6
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 6
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- 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
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Landscapes
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| US201261671723P | 2012-07-14 | 2012-07-14 | |
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| PCT/US2013/036514 WO2013155505A1 (en) | 2012-04-14 | 2013-04-14 | Organic compounds |
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| PL2262505T3 (pl) | 2008-03-12 | 2015-04-30 | Intra Cellular Therapies Inc | Podstawione heterocykliczne skondensowane gamma-karboliny w postaci stałej |
| JP6106361B2 (ja) | 2008-05-27 | 2017-03-29 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 睡眠障害および他の障害のための方法および組成物 |
| 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 |
| WO2013119800A1 (en) | 2012-02-07 | 2013-08-15 | Massachusetts Institute Of Technology | Use of antagonists of ghrelin or ghrelin receptor to prevent or treat stress-sensitive psychiatric illness |
| ES2727815T3 (es) | 2012-04-14 | 2019-10-18 | Intra Cellular Therapies Inc | Tratamiento del TEPT y de trastornos del control de impulsos |
| WO2014144231A1 (en) | 2013-03-15 | 2014-09-18 | Massachusetts Institute Of Technology | Use of antagonists of growth hormone or growth hormone receptor to prevent or treat stress-sensitive psychiatric illness |
| PL2968320T3 (pl) | 2013-03-15 | 2021-05-17 | Intra-Cellular Therapies, Inc. | Związki organiczne |
| AU2014360452C1 (en) | 2013-12-03 | 2019-05-16 | Intra-Cellular Therapies, Inc. | Novel methods |
| KR20170012210A (ko) * | 2014-04-04 | 2017-02-02 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
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| CN104003987B (zh) * | 2014-06-03 | 2016-03-23 | 中国药科大学 | 他克林-β-咔啉异二连体类多功能胆碱酯酶抑制剂 |
| WO2015191554A1 (en) | 2014-06-09 | 2015-12-17 | Intra-Cellular Therapies, Inc. | Compounds and methods of use to treat schizophrenia |
| WO2016138099A1 (en) | 2015-02-24 | 2016-09-01 | Massachusetts Institute Of Technology | Use of ghrelin or functional ghrelin receptor agonists to prevent and treat stress-sensitive psychiatric illness |
| US20170007618A1 (en) * | 2015-06-17 | 2017-01-12 | Massachusetts Institute Of Technology | Serotonin 2c receptor antagonists to prevent and treat stress-related trauma disorders |
| IL309536B2 (en) | 2016-01-26 | 2025-07-01 | Intra Cellular Therapies Inc | Pharmaceutical preparation for injection containing (Sa10, Rb6)-3-)8-(4-fluorophenoxy)propyl)-b6, 7, 8, 9, 10, 10a- hexahydro-H1- pyrido[3',4' :4,5]pyrrolo[1,2,3 -de]quinoxalin-2(H3)-one |
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| EP3436083A4 (en) | 2016-03-28 | 2019-11-27 | Intra-Cellular Therapies, Inc. | NOVEL COMPOSITIONS AND METHOD |
| JP2019513143A (ja) | 2016-03-28 | 2019-05-23 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規塩類および結晶 |
| US11014925B2 (en) | 2016-03-28 | 2021-05-25 | Intra-Cellular Therapies, Inc. | Co-crystals of 1-(4-fluoro-phenyl)-4-((6bR,1OaS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,51_pyrrolo [1,2,3-delqcuinoxalin-8-yl)-butan-1-one with nicotinamide or isonicotinamide |
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| US10961245B2 (en) | 2016-12-29 | 2021-03-30 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for treatment of central nervous system disorders |
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| US11433253B2 (en) | 2017-02-15 | 2022-09-06 | The Regents Of The University Of California | Light therapy system and methods of use |
| JP7458786B2 (ja) * | 2017-02-15 | 2024-04-01 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 改善された光療法システムおよび使用方法 |
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| US11427587B2 (en) | 2017-07-26 | 2022-08-30 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP3658145A4 (en) | 2017-07-26 | 2021-04-21 | Intra-Cellular Therapies, Inc. | ORGANIC COMPOUNDS |
| WO2019067591A1 (en) * | 2017-09-26 | 2019-04-04 | Intra-Cellular Therapies, Inc. | NEW SALTS AND CRYSTALS |
| EP3765021A4 (en) | 2018-03-16 | 2022-03-09 | Intra-Cellular Therapies, Inc. | NOVEL PROCESSES |
| BR112020019119A2 (pt) | 2018-03-23 | 2021-01-12 | Intra-Cellular Therapies, Inc. | Compostos orgânicos |
| WO2019183546A1 (en) | 2018-03-23 | 2019-09-26 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP3788046B1 (en) | 2018-05-04 | 2025-12-10 | Incyte Corporation | Salts of an fgfr inhibitor |
| IL279195B1 (en) | 2018-06-06 | 2025-08-01 | Intra Cellular Therapies Inc | A method of making bis-tosylate salt of lumateparone |
| CA3102948A1 (en) | 2018-06-08 | 2019-12-12 | Intra-Cellular Therapies, Inc. | Novel methods |
| KR102778034B1 (ko) * | 2018-06-11 | 2025-03-12 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| CN112585690B (zh) | 2018-06-21 | 2025-04-15 | 阿奎斯蒂弗医疗股份有限公司 | 用于制作含有药物活性物质的个性化个体单位剂量的系统和方法 |
| JP2022500362A (ja) | 2018-08-29 | 2022-01-04 | イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. | 新規組成物および方法 |
| WO2020047408A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| CN112584837A (zh) * | 2018-08-31 | 2021-03-30 | 细胞内治疗公司 | 新方法 |
| WO2020051317A1 (en) | 2018-09-07 | 2020-03-12 | Aquestive Therapeutics, Inc. | Oral film compositions and dosage forms having precise active dissolution profiles |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| US12297200B2 (en) | 2018-12-17 | 2025-05-13 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
| CN113423568A (zh) | 2018-12-17 | 2021-09-21 | 细胞内治疗公司 | 有机化合物 |
| US12358916B2 (en) | 2018-12-17 | 2025-07-15 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
| US12331052B2 (en) | 2018-12-21 | 2025-06-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP3897643B1 (en) | 2018-12-21 | 2023-11-15 | Intra-Cellular Therapies, Inc. | A pyridopyrroloquinoxaline compound and its medical use |
| MX2022000143A (es) | 2019-07-07 | 2022-02-17 | Intra Cellular Therapies Inc | Metodos novedosos. |
| EP4034119A4 (en) | 2019-09-25 | 2023-10-18 | Intra-Cellular Therapies, Inc. | NOVEL METHODS |
| AU2020373100A1 (en) | 2019-11-01 | 2022-05-19 | Aquestive Therapeutics, Inc. | Prodrug compositions and methods of treatment |
| BR112022008784A2 (pt) | 2019-11-14 | 2022-07-26 | Aquestive Therapeutics Inc | Composições multimodais e métodos de tratamento |
| JP7261942B2 (ja) | 2019-12-11 | 2023-04-20 | 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 |
| WO2022155544A1 (en) | 2021-01-15 | 2022-07-21 | Aquestive Therapeutics, Inc. | Prodrug compositions and methods of treatment |
| WO2022192476A1 (en) | 2021-03-09 | 2022-09-15 | Aquestive Therapeutics, Inc. | Dosage forms having equivalent biocomparable profiles |
| EP4525874A1 (en) | 2022-05-18 | 2025-03-26 | Intra-Cellular Therapies, Inc. | Novel methods |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
| WO2024173901A1 (en) | 2023-02-17 | 2024-08-22 | Intra-Cellular Therapies, Inc. | Lumateperone and derivatives thereof for modulating the nervous system |
| 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 |
Family Cites Families (95)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2490813A (en) | 1944-11-29 | 1949-12-13 | Standard Oil Co | Continuous process for making aryl amines |
| US3299078A (en) | 1962-10-01 | 1967-01-17 | Smith Kline French Lab | Pyrido [3', 4': 4, 5] pyrrolo [3, 2, 1-hi] indoles and-[3, 2, 1-ij] quinolines |
| US3813392A (en) | 1969-06-09 | 1974-05-28 | J Sellstedt | Pyrrolo(1,2,3-alpha epsilon)quinoxalin-2(3h)-ones and related compounds |
| US3606908A (en) | 1969-11-26 | 1971-09-21 | Trico Products Corp | Ventilation system for volatile fluid |
| US4183936A (en) | 1972-06-19 | 1980-01-15 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| US3914421A (en) | 1972-06-19 | 1975-10-21 | Endo Lab | Pyridopyrrolobenzheterocycles for combatting depression |
| US4238607A (en) | 1972-06-19 | 1980-12-09 | Endo Laboratories Inc. | Pyridopyrrolo benzheterocycles |
| US4115577A (en) | 1972-06-19 | 1978-09-19 | Endo Laboratories, Inc. | Pyridopyrrolobenzheterocycles |
| JPS5014494A (enExample) * | 1973-06-11 | 1975-02-15 | ||
| US4001263A (en) | 1974-04-01 | 1977-01-04 | Pfizer Inc. | 5-Aryl-1,2,3,4-tetrahydro-γ-carbolines |
| IE41352B1 (en) | 1974-04-01 | 1979-12-19 | Pfizer | 5-aryl-1,2,3,4-tetrahydro- -carbolines |
| US4219550A (en) | 1978-11-09 | 1980-08-26 | E. I. Du Pont De Nemours And Company | Cis- and trans- octahydropyridopyrrolobenzheterocycles |
| US4389330A (en) | 1980-10-06 | 1983-06-21 | Stolle Research And Development Corporation | Microencapsulation process |
| IE52535B1 (en) | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| US4530840A (en) | 1982-07-29 | 1985-07-23 | The Stolle Research And Development Corporation | Injectable, long-acting microparticle formulation for the delivery of anti-inflammatory agents |
| US4522944A (en) | 1982-12-23 | 1985-06-11 | Erba Farmitalia | Carboxamido-derivatives of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidines, compositions and use |
| SE8304361D0 (sv) * | 1983-08-10 | 1983-08-10 | Ferrosan Ab | Novel 1-acylpiperazine derivatives novel 1-acylpiperazine derivatives |
| CH656884A5 (de) | 1983-08-26 | 1986-07-31 | Sandoz Ag | Polyolester, deren herstellung und verwendung. |
| JPS6175A (ja) * | 1984-03-06 | 1986-01-06 | ブリストル−マイア−ズ コムパニ− | 神経弛緩剤、１‐フルオロフェニルブチル‐４‐（５‐ハロ‐２‐ピリミジニル）ピペラジン誘導体 |
| IL74497A (en) | 1985-03-05 | 1990-02-09 | Proterra Ag | Pharmaceutical compositions containing phenyl carbamate derivatives and certain phenyl carbamate derivatives |
| EP0238059B1 (en) | 1986-03-19 | 1993-06-16 | Kumiai Chemical Industry Co., Ltd. | 5H-1,3,4-Thiazole[3,2-a]pyrimidin-5-one derivatives and fungicidal compositions containing the same |
| ES2058069T3 (es) | 1986-04-07 | 1994-11-01 | Kumiai Chemical Industry Co | Derivados de 5h-1,3,4-tiadiazolo-(3,2-a)-pirimidin-5-ona y nuevo compuesto fungicida agricola-horticola que contiene dicho derivado. |
| FI95572C (fi) | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| US5114976A (en) | 1989-01-06 | 1992-05-19 | Norden Michael J | Method for treating certain psychiatric disorders and certain psychiatric symptoms |
| ATE94384T1 (de) | 1989-04-14 | 1993-10-15 | Merz & Co Gmbh & Co | Verwendung von adamantan-derivaten zur praevention und behandlung der cerebralen ischaemie. |
| US5538739A (en) | 1989-07-07 | 1996-07-23 | Sandoz Ltd. | Sustained release formulations of water soluble peptides |
| IT1271352B (it) | 1993-04-08 | 1997-05-27 | Boehringer Ingelheim Italia | Derivati dell'indolo utili nel trattamento dei disturbi del sistema nervoso centrale |
| DE69434258T2 (de) | 1993-11-19 | 2006-01-19 | Janssen Pharmaceutica N.V. | Mikroverkapselte 1,2-benzazole |
| US5576460A (en) | 1994-07-27 | 1996-11-19 | Massachusetts Institute Of Technology | Preparation of arylamines |
| US5648539A (en) | 1996-02-29 | 1997-07-15 | Xerox Corporation | Low temperature arylamine processes |
| US5648542A (en) | 1996-02-29 | 1997-07-15 | Xerox Corporation | Arylamine processes |
| US5654482A (en) | 1996-02-29 | 1997-08-05 | Xerox Corporation | Triarylamine processes |
| US5847166A (en) | 1996-10-10 | 1998-12-08 | Massachusetts Institute Of Technology | Synthesis of aryl ethers |
| US5723671A (en) | 1997-01-30 | 1998-03-03 | Xerox Corporation | Arylamine processes |
| US5705697A (en) | 1997-01-30 | 1998-01-06 | Xerox Corporation | Arylamine processes |
| US5723669A (en) | 1997-01-30 | 1998-03-03 | Xerox Corporation | Arylamine processes |
| TWI242011B (en) | 1997-03-31 | 2005-10-21 | Eisai Co Ltd | 1,4-substituted cyclic amine derivatives |
| US6323366B1 (en) | 1997-07-29 | 2001-11-27 | Massachusetts Institute Of Technology | Arylamine synthesis |
| GB2328686B (en) | 1997-08-25 | 2001-09-26 | Sankio Chemical Co Ltd | Method for producing arylamine |
| US6395939B1 (en) | 1997-10-06 | 2002-05-28 | Massachusetts Institute Of Technology | Diaryl ether condensation reactions |
| US6235936B1 (en) | 1998-02-26 | 2001-05-22 | Massachusetts Institute Of Technology | Metal-catalyzed arylations of hydrazines, hydrazones, and related substrates |
| EP1058678B1 (en) | 1998-02-26 | 2002-12-11 | Massachusetts Institute of Technology | Metal-catalyzed arylations and vinylations of hydrazines, hydrazones, hydroxylamines and oximes |
| US5902901A (en) | 1998-05-07 | 1999-05-11 | Xerox Corporation | Arylamine processes |
| US6307087B1 (en) | 1998-07-10 | 2001-10-23 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| JP5035813B2 (ja) | 1998-07-10 | 2012-09-26 | マサチューセッツ インスティテュート オブ テクノロジー | 金属用のリガンドおよびそれらに基づいて改善された金属触媒法 |
| US6395916B1 (en) | 1998-07-10 | 2002-05-28 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US7223879B2 (en) | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US20010008942A1 (en) | 1998-12-08 | 2001-07-19 | Buchwald Stephen L. | Synthesis of aryl ethers |
| EP1140012B1 (en) | 1998-12-17 | 2004-03-03 | Alza Corporation | Conversion of liquid filled gelatin capsules into controlled release systems by multiple coatings |
| PE20010052A1 (es) | 1999-04-23 | 2001-01-27 | Upjohn Co | Compuestos de azepinindol tetraciclico como agonistas o antagonistas del receptor de 5-ht |
| US6407092B1 (en) | 1999-04-23 | 2002-06-18 | Pharmacia & Upjohn Company | Tetracyclic azepinoindole compounds |
| US6713471B1 (en) | 1999-06-15 | 2004-03-30 | Bristol-Myers Squibb Pharma Company | Substituted heterocycle fused gamma-carbolines |
| US7071186B2 (en) * | 1999-06-15 | 2006-07-04 | Bristol-Myers Squibb Pharma Co. | Substituted heterocycle fused gamma-carbolines |
| CN1370176A (zh) | 1999-06-15 | 2002-09-18 | 布里斯托尔-迈尔斯斯奎布药品公司 | 取代的杂环稠合γ－咔啉 |
| US6541639B2 (en) | 2000-07-26 | 2003-04-01 | Bristol-Myers Squibb Pharma Company | Efficient ligand-mediated Ullmann coupling of anilines and azoles |
| BR0116429A (pt) | 2000-12-20 | 2006-05-09 | Bristol Myers Squibb Co | piridoindóis substituìdos como agonistas e antagonistas da serotonina |
| US6849619B2 (en) | 2000-12-20 | 2005-02-01 | Bristol-Myers Squibb Company | Substituted pyridoindoles as serotonin agonists and antagonists |
| CN1854128B (zh) | 2001-04-24 | 2012-05-16 | 麻省理工学院 | 铜-催化的碳-杂原子键和碳-碳键的形成 |
| CA2453537A1 (en) | 2001-08-08 | 2003-02-20 | Pharmacia & Upjohn Company | Therapeutic 1h-pyrido¬4,3-b|indoles |
| US20050232995A1 (en) | 2002-07-29 | 2005-10-20 | Yam Nyomi V | Methods and dosage forms for controlled delivery of paliperidone and risperidone |
| PL210119B1 (pl) | 2002-07-29 | 2011-12-30 | Alza Corp | Lek do leczenia stanu wrażliwego na paliperidon |
| KR20050032107A (ko) | 2002-08-02 | 2005-04-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 구리를 촉매로 한 탄소-헤테로원자 결합 및 탄소-탄소결합 형성방법 |
| US7223870B2 (en) | 2002-11-01 | 2007-05-29 | Pfizer Inc. | Methods for preparing N-arylated oxazolidinones via a copper catalyzed cross coupling reaction |
| AU2003287433A1 (en) | 2002-11-01 | 2004-06-07 | Oregon Health And Science University | Treatment of hyperkinetic movement disorder with donepezil |
| US7109339B2 (en) | 2002-12-19 | 2006-09-19 | Bristol-Myers Squibb Company | Substituted tricyclic gamma-carbolines as serotonin receptor agonists and antagonists |
| SI1587789T1 (sl) | 2003-01-16 | 2009-02-28 | Acadia Pharm Inc | Selektivni inverzni agonisti serotoninskega 2A/2Creceptorja kot terapevtiki za nevrodegenerativne bolezni |
| US7462641B2 (en) | 2003-07-21 | 2008-12-09 | 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 |
| JP2005259113A (ja) | 2004-02-12 | 2005-09-22 | Ricoh Co Ltd | プロセス編集装置、プロセス管理装置、プロセス編集プログラム、プロセス管理プログラム、記録媒体、プロセス編集方法及びプロセス管理方法 |
| CA2564018A1 (en) | 2004-03-05 | 2005-10-13 | Pharma C S.A. | 8-phenoxy-.gamma. carboline derivatives |
| US7592454B2 (en) | 2004-04-14 | 2009-09-22 | Bristol-Myers Squibb Company | Substituted hexahydro-pyridoindole derivatives as serotonin receptor agonists and antagonists |
| ES2367868T3 (es) | 2004-09-20 | 2011-11-10 | Mount Sinai School Of Medicine | Uso de memantina (namenda) para tratar el autismo, la compulsividad y la impulsividad. |
| WO2006032999A1 (en) * | 2004-09-21 | 2006-03-30 | Pfizer Products Inc. | N-methyl hydroxyethylamine useful in treating cns conditions |
| MX2007006896A (es) | 2004-12-15 | 2007-06-26 | Hoffmann La Roche | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador 1 de glicina (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| WO2006133261A2 (en) * | 2005-06-06 | 2006-12-14 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR101805914B1 (ko) | 2007-03-12 | 2017-12-06 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| WO2009017836A1 (en) | 2007-08-01 | 2009-02-05 | Medivation Neurology, Inc. | Methods and compositions for treating schizophrenia using antipsychotic combination therapy |
| EP2262502A4 (en) * | 2008-02-05 | 2011-12-28 | Clera Inc | Compositions and methods for alleviating depression or improving cognition |
| PL2262505T3 (pl) | 2008-03-12 | 2015-04-30 | Intra Cellular Therapies Inc | Podstawione heterocykliczne skondensowane gamma-karboliny w postaci stałej |
| JP6106361B2 (ja) | 2008-05-27 | 2017-03-29 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 睡眠障害および他の障害のための方法および組成物 |
| 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 |
| ES2727815T3 (es) | 2012-04-14 | 2019-10-18 | Intra Cellular Therapies Inc | Tratamiento del TEPT y de trastornos del control de impulsos |
| US10011602B2 (en) | 2012-07-06 | 2018-07-03 | The University Of Melbourne | Immunological reagents and uses therefor |
| PL2968320T3 (pl) | 2013-03-15 | 2021-05-17 | Intra-Cellular Therapies, Inc. | Związki organiczne |
| US9161061B2 (en) | 2013-03-15 | 2015-10-13 | Pictech Management Limited | Data storage and exchange device for color space encoded images |
| AU2014360452C1 (en) | 2013-12-03 | 2019-05-16 | Intra-Cellular Therapies, Inc. | Novel methods |
| KR20170012210A (ko) | 2014-04-04 | 2017-02-02 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| WO2015154030A1 (en) | 2014-04-04 | 2015-10-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2015191554A1 (en) | 2014-06-09 | 2015-12-17 | Intra-Cellular Therapies, Inc. | Compounds and methods of use to treat schizophrenia |
| IL309536B2 (en) | 2016-01-26 | 2025-07-01 | Intra Cellular Therapies Inc | Pharmaceutical preparation for injection containing (Sa10, Rb6)-3-)8-(4-fluorophenoxy)propyl)-b6, 7, 8, 9, 10, 10a- hexahydro-H1- pyrido[3',4' :4,5]pyrrolo[1,2,3 -de]quinoxalin-2(H3)-one |
| US10688097B2 (en) | 2016-03-25 | 2020-06-23 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP2019513143A (ja) | 2016-03-28 | 2019-05-23 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規塩類および結晶 |
| 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 |
| JP7132939B2 (ja) | 2017-03-24 | 2022-09-07 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規組成物および方法 |
| EP3658145A4 (en) | 2017-07-26 | 2021-04-21 | Intra-Cellular Therapies, Inc. | ORGANIC COMPOUNDS |
| US11427587B2 (en) | 2017-07-26 | 2022-08-30 | Intra-Cellular Therapies, Inc. | Organic compounds |
-
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