KR20160101012A - 신규 조성물 - Google Patents
신규 조성물 Download PDFInfo
- Publication number
- KR20160101012A KR20160101012A KR1020167018428A KR20167018428A KR20160101012A KR 20160101012 A KR20160101012 A KR 20160101012A KR 1020167018428 A KR1020167018428 A KR 1020167018428A KR 20167018428 A KR20167018428 A KR 20167018428A KR 20160101012 A KR20160101012 A KR 20160101012A
- Authority
- KR
- South Korea
- Prior art keywords
- composition
- azabicyclo
- less
- naphthalen
- hexane
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 163
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- HKHCSWPSUSWGLI-CABCVRRESA-N (1r,5s)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC([C@@]34CNC[C@H]4C3)=CC=C21 HKHCSWPSUSWGLI-CABCVRRESA-N 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 239000012730 sustained-release form Substances 0.000 claims abstract description 21
- 238000013268 sustained release Methods 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 38
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- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 37
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 36
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 20
- -1 hydroxypropoxy Chemical group 0.000 claims description 19
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims description 10
- 235000019359 magnesium stearate Nutrition 0.000 claims description 10
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920003084 Avicel® PH-102 Polymers 0.000 claims description 2
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- 229920003096 Methocel™ K100M Polymers 0.000 claims description 2
- 229920003095 Methocel™ K15M Polymers 0.000 claims description 2
- 229920003094 Methocel™ K4M Polymers 0.000 claims description 2
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- 229920002472 Starch Polymers 0.000 claims description 2
- 229960000913 crospovidone Drugs 0.000 claims description 2
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940049654 glyceryl behenate Drugs 0.000 claims description 2
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- 239000000594 mannitol Substances 0.000 claims description 2
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- 229940033134 talc Drugs 0.000 claims description 2
- 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 abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- ACVMJAJGCQUPKX-LIOBNPLQSA-N (1r,5s)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1=CC=CC2=CC([C@@]34CNC[C@H]4C3)=CC=C21 ACVMJAJGCQUPKX-LIOBNPLQSA-N 0.000 description 10
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- 239000003185 4 aminobutyric acid B receptor stimulating agent Substances 0.000 description 2
- QRDSDKAGXMWBID-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexane Chemical compound C1CCN2CC21 QRDSDKAGXMWBID-UHFFFAOYSA-N 0.000 description 2
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- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
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- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
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- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
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- 229960002464 fluoxetine Drugs 0.000 description 1
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- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 1
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- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
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- 239000004050 mood stabilizer Substances 0.000 description 1
- 229940127237 mood stabilizer Drugs 0.000 description 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 description 1
- 210000001009 nucleus accumben Anatomy 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- DQMZLTXERSFNPB-UHFFFAOYSA-N primidone Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NCNC1=O DQMZLTXERSFNPB-UHFFFAOYSA-N 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
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- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- 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
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K9/2004—Excipients; Inactive ingredients
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- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
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- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
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- A—HUMAN NECESSITIES
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Neurology (AREA)
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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| US201361913886P | 2013-12-09 | 2013-12-09 | |
| US61/913,886 | 2013-12-09 | ||
| PCT/US2014/069416 WO2015102826A1 (en) | 2013-12-09 | 2014-12-09 | Novel compositions |
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| KR20160101012A true KR20160101012A (ko) | 2016-08-24 |
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| US (3) | US9839627B2 (enExample) |
| EP (1) | EP3080080A4 (enExample) |
| JP (1) | JP2017502948A (enExample) |
| KR (1) | KR20160101012A (enExample) |
| CN (1) | CN106029637A (enExample) |
| AU (1) | AU2014374259A1 (enExample) |
| CA (1) | CA2936108A1 (enExample) |
| WO (2) | WO2015089111A1 (enExample) |
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| EP1915146A4 (en) | 2005-07-27 | 2010-06-02 | Dov Pharmaceutical Inc | NOVEL 1-ARYL-3-AZABICYCLO [3.1.0] HEXANEES. PREPARATION AND USE FOR THE TREATMENT OF NEUROPSYCHIATRIC DISEASES |
| US20140206740A1 (en) | 2011-07-30 | 2014-07-24 | Neurovance, Inc. | Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters |
| CA2936108A1 (en) * | 2013-12-09 | 2015-07-09 | Neurovance, Inc. | Novel compositions |
| LT3597189T (lt) | 2015-06-17 | 2022-07-11 | Otsuka America Pharmaceutical, Inc. | Kristaliniai junginia |
| WO2018119291A1 (en) * | 2016-12-21 | 2018-06-28 | Otsuka America Pharmaceutical, Inc. | Synthetic methods |
| CN120441453A (zh) | 2018-04-26 | 2025-08-08 | 株式会社Api | 芳香族腈化合物的制造方法 |
| KR20220088777A (ko) | 2019-10-29 | 2022-06-28 | 가부시키가이샤 에이피아이 코포레이션 | 고순도 2-나프틸아세토니트릴 및 이의 제조 방법 |
| IL303767A (en) | 2021-02-23 | 2023-08-01 | Otsuka Pharma Co Ltd | Pharmaceutical formulations of centrapadin, and methods for its preparation and use |
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| EP1874298A4 (en) | 2005-03-08 | 2009-08-05 | Dov Pharmaceutical Inc | METHOD AND COMPOSITIONS FOR THE PREPARATION, FORMULATION AND USE OF 1-ARYL-3-AZABICYCLO [3,1,0] HEXANES |
| US20070082939A1 (en) | 2005-07-26 | 2007-04-12 | Lippa Arnold S | Methods and compositions for the treatment of neuropathies and related disorders |
| EP1915146A4 (en) | 2005-07-27 | 2010-06-02 | Dov Pharmaceutical Inc | NOVEL 1-ARYL-3-AZABICYCLO [3.1.0] HEXANEES. PREPARATION AND USE FOR THE TREATMENT OF NEUROPSYCHIATRIC DISEASES |
| US20090041844A1 (en) * | 2006-02-10 | 2009-02-12 | Boehringer Ingelheim International Gmbh | Modified Release Formulation |
| NZ573174A (en) * | 2006-06-01 | 2012-01-12 | Msd Consumer Care Inc | Sustained release pharmaceutical dosage form containing phenylephrine |
| US20080058535A1 (en) * | 2006-07-25 | 2008-03-06 | Zhengming Chen | Methods and compositions for production, formulation and use of 1 aryl-3-azabicyclo[3.1.0]hexanes |
| US20110034565A1 (en) * | 2008-04-18 | 2011-02-10 | University College Dublin, National University Of Ireland, Dublin | Psycho-pharmaceuticals |
| EP2646019A4 (en) | 2010-12-03 | 2014-05-21 | Euthymic Bioscience Inc | PREPARATION AND USE OF (+) - 1- (3,4-DICHLOROPHENYL) -3-AZABICYCLO- [3.1.0] HEXANE IN THE TREATMENT OF DISEASES AFFECTED BY MONOAMINE-TYPE NEUROTRANSMITTERS |
| US9085562B2 (en) * | 2011-03-03 | 2015-07-21 | Vanderbilt University | 6-alkyl-N-(pyridin-2-yl)-4-aryloxypicolinamide analogs as mGluR5 negative allosteric modulators and methods of making and using the same |
| US20140206740A1 (en) * | 2011-07-30 | 2014-07-24 | Neurovance, Inc. | Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters |
| EP2819516B1 (en) * | 2011-07-30 | 2019-12-25 | Otsuka America Pharmaceutical, Inc. | Use of (1r,5s)-(+)-1-(naphthalen-2-yl)-3-azabicyclo{3.1.0}hexane in the treatment of conditions affected by monoamine neurotransmitters |
| US20140228421A1 (en) | 2011-09-07 | 2014-08-14 | Anthony McKinney | Methods For Inhibiting Native And Promiscuous Uptake Of Monoamine Neurotransmitters |
| CA2936108A1 (en) * | 2013-12-09 | 2015-07-09 | Neurovance, Inc. | Novel compositions |
| LT3597189T (lt) | 2015-06-17 | 2022-07-11 | Otsuka America Pharmaceutical, Inc. | Kristaliniai junginia |
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2014
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- 2014-12-09 JP JP2016539110A patent/JP2017502948A/ja not_active Withdrawn
- 2014-12-09 KR KR1020167018428A patent/KR20160101012A/ko not_active Withdrawn
- 2014-12-09 US US15/102,871 patent/US9839627B2/en active Active
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- 2014-12-09 US US15/102,949 patent/US20160303077A1/en not_active Abandoned
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2022
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Also Published As
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|---|---|
| EP3080080A1 (en) | 2016-10-19 |
| WO2015102826A1 (en) | 2015-07-09 |
| US20220347157A1 (en) | 2022-11-03 |
| US9839627B2 (en) | 2017-12-12 |
| JP2017502948A (ja) | 2017-01-26 |
| US20160303077A1 (en) | 2016-10-20 |
| EP3080080A4 (en) | 2017-08-16 |
| AU2014374259A1 (en) | 2016-07-21 |
| WO2015089111A1 (en) | 2015-06-18 |
| US20160303076A1 (en) | 2016-10-20 |
| CN106029637A (zh) | 2016-10-12 |
| CA2936108A1 (en) | 2015-07-09 |
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