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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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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Landscapes
- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Oncology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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- Medicinal Preparation (AREA)
Applications Claiming Priority (11)
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| US201261624292P | 2012-04-14 | 2012-04-14 | |
| US201261624291P | 2012-04-14 | 2012-04-14 | |
| US201261624293P | 2012-04-14 | 2012-04-14 | |
| US61/624,292 | 2012-04-14 | ||
| US61/624,293 | 2012-04-14 | ||
| US61/624,291 | 2012-04-14 | ||
| US201261671713P | 2012-07-14 | 2012-07-14 | |
| US201261671723P | 2012-07-14 | 2012-07-14 | |
| US61/671,723 | 2012-07-14 | ||
| US61/671,713 | 2012-07-14 | ||
| PCT/US2013/036514 WO2013155505A1 (en) | 2012-04-14 | 2013-04-14 | Organic compounds |
Publications (1)
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| CA2870303A1 true CA2870303A1 (en) | 2013-10-17 |
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| PL2262505T3 (pl) | 2008-03-12 | 2015-04-30 | Intra Cellular Therapies Inc | Podstawione heterocykliczne skondensowane gamma-karboliny w postaci stałej |
| US8598119B2 (en) | 2008-05-27 | 2013-12-03 | Intra-Cellular Therapies, Inc. | Methods and compositions 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 |
| US10039813B2 (en) | 2012-02-07 | 2018-08-07 | Massachusetts Institute Of Technology | Use of antagonists of ghrelin or ghrelin receptor to prevent or treat stress-sensitive psychiatric illness |
| WO2013155504A1 (en) * | 2012-04-14 | 2013-10-17 | Intra-Cellular Therapies, Inc. | Novel methods |
| WO2014145192A1 (en) | 2013-03-15 | 2014-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| 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 |
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| MX388258B (es) | 2014-04-04 | 2025-03-19 | Intra Cellular Therapies Inc | Gamma-carbolinas fusionadas con heterociclos sustituidas con deuterio. |
| AU2015240526A1 (en) * | 2014-04-04 | 2016-11-24 | Intra-Cellular Therapies, Inc. | Organic compounds |
| 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 |
| US10179776B2 (en) | 2014-06-09 | 2019-01-15 | Intra-Cellular Therapies, Inc. | Compounds and methods of use to treat schizophrenia |
| US10317418B2 (en) | 2015-02-24 | 2019-06-11 | Massachusetts Institute Of Technology | Use of ghrelin or functional ghrelin receptor agonists to prevent and treat stress-sensitive psychiatric illness |
| WO2016205631A1 (en) * | 2015-06-17 | 2016-12-22 | Massachusetts Institute Of Technology | Serotonin 2c receptor antagonists to prevent and treat stress-related trauma disorders |
| PT3407888T (pt) | 2016-01-26 | 2021-03-19 | Intra Cellular Therapies Inc | Compostos de piridopirroloquinoxalina, suas composições e utilizações |
| JP6686168B2 (ja) * | 2016-03-25 | 2020-04-22 | 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． | 有機化合物 |
| JP2019510039A (ja) | 2016-03-28 | 2019-04-11 | 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 |
| 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 |
| JP6997718B2 (ja) | 2016-03-28 | 2022-01-18 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規共結晶 |
| EP3525763B1 (en) | 2016-10-12 | 2025-03-05 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
| US10906906B2 (en) | 2016-12-29 | 2021-02-02 | Intra-Cellular Therapies, Inc. | Organic compounds |
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| 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 |
| US11433253B2 (en) | 2017-02-15 | 2022-09-06 | The Regents Of The University Of California | Light therapy system and methods of use |
| CN116327770B (zh) * | 2017-03-24 | 2025-10-31 | 细胞内治疗公司 | 新组合物和方法 |
| CN110636845A (zh) * | 2017-04-10 | 2019-12-31 | 雷迪博士实验室有限公司 | 卢美哌隆对甲苯磺酸盐的无定形形式和固体分散体 |
| IL272252B2 (en) * | 2017-07-26 | 2024-03-01 | Intra Cellular Therapies Inc | Derivatives of substituted heterocycle fused gamma-carbolines, pharmaceutical compositions comnprising them and their use in treatment |
| BR112020001666A2 (pt) * | 2017-07-26 | 2020-07-21 | Intra-Cellular Therapies, Inc. | compostos orgânicos |
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|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180418 |