JP2014520140A5 - - Google Patents
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- Publication number
- JP2014520140A5 JP2014520140A5 JP2014516459A JP2014516459A JP2014520140A5 JP 2014520140 A5 JP2014520140 A5 JP 2014520140A5 JP 2014516459 A JP2014516459 A JP 2014516459A JP 2014516459 A JP2014516459 A JP 2014516459A JP 2014520140 A5 JP2014520140 A5 JP 2014520140A5
- Authority
- JP
- Japan
- Prior art keywords
- deuterium
- compound
- hydrogen
- compound according
- formula
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 62
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 47
- 229910052805 deuterium Inorganic materials 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 description 22
- 238000000034 method Methods 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 201000000980 schizophrenia Diseases 0.000 description 7
- 0 CC(C)(CN(C1)[C@](C[C@]2c3c(*)c(*)c(*)c(*)c3*)c3c2ccc(Cl)c3)N(C(*)(*)*)C1(*)I Chemical compound CC(C)(CN(C1)[C@](C[C@]2c3c(*)c(*)c(*)c(*)c3*)c3c2ccc(Cl)c3)N(C(*)(*)*)C1(*)I 0.000 description 6
- 150000001975 deuterium Chemical group 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 3
- SXFBQAMLJMDXOD-UHFFFAOYSA-N (+)-hydrogentartrate bitartrate salt Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O SXFBQAMLJMDXOD-UHFFFAOYSA-N 0.000 description 2
- IIISHLMCTDMUHH-UHFFFAOYSA-N 2-bromo-5-chlorobenzaldehyde Chemical compound ClC1=CC=C(Br)C(C=O)=C1 IIISHLMCTDMUHH-UHFFFAOYSA-N 0.000 description 2
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 2
- 208000020925 Bipolar disease Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 229960004372 aripiprazole Drugs 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 229960004170 clozapine Drugs 0.000 description 2
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 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 2
- 229960005017 olanzapine Drugs 0.000 description 2
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 2
- 229950009875 osanetant Drugs 0.000 description 2
- DZOJBGLFWINFBF-UMSFTDKQSA-N osanetant Chemical compound C([C@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UMSFTDKQSA-N 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 229960004431 quetiapine Drugs 0.000 description 2
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 2
- 229960001534 risperidone Drugs 0.000 description 2
- 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 2
- 229960000652 sertindole Drugs 0.000 description 2
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 229960000607 ziprasidone Drugs 0.000 description 2
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 2
- RFAPOGMFZTYBEW-UHFFFAOYSA-N 1,2,2-trimethylpiperazine Chemical compound CN1CCNCC1(C)C RFAPOGMFZTYBEW-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 208000019568 Shared Paranoid disease Diseases 0.000 description 1
- 208000028810 Shared psychotic disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161498651P | 2011-06-20 | 2011-06-20 | |
| US61/498,651 | 2011-06-20 | ||
| US201161537103P | 2011-09-21 | 2011-09-21 | |
| US61/537,103 | 2011-09-21 | ||
| PCT/IB2012/001386 WO2012176066A1 (en) | 2011-06-20 | 2012-06-19 | Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014520140A JP2014520140A (ja) | 2014-08-21 |
| JP2014520140A5 true JP2014520140A5 (enExample) | 2014-10-02 |
| JP5668177B2 JP5668177B2 (ja) | 2015-02-12 |
Family
ID=46682855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014516459A Active JP5668177B2 (ja) | 2011-06-20 | 2012-06-19 | 統合失調症の治療のための重水素化１−ピペラジノ−３−フェニルインダン |
Country Status (40)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2719145T3 (es) | 2011-06-20 | 2019-07-08 | H Lundbeck As | 1-Piperazino-3-fenil-indanos deuterados para el tratamiento de la esquizofrenia |
| AR094054A1 (es) * | 2012-12-19 | 2015-07-08 | H Lundbeck As | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
| PT3679018T (pt) | 2017-09-07 | 2022-04-05 | Otsuka Pharma Co Ltd | Processo industrial de monoalquilação de um nitrogénio de piperidina em derivados de piperidina com alquilo deuterado |
| EP3873885A1 (en) * | 2018-10-29 | 2021-09-08 | H. Lundbeck A/S | Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts |
| US11535600B2 (en) | 2018-12-03 | 2022-12-27 | H. Lundbeck A/S | Prodrugs of 4-((1R,3S)-6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1R,3S)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1H-inden-1-yl)-2,2-dimethyl-1-(methyl-d3)piperazine |
| EA202191731A1 (ru) * | 2018-12-21 | 2021-10-28 | Консерт Фармасьютикалз, Инк. | Дейтерированные формы и производные волинансерина |
| CN113518771A (zh) * | 2019-03-13 | 2021-10-19 | 大塚制药株式会社 | 向含有仲胺的化合物的胺部分导入氘代低级烷基的方法 |
| CN117164518A (zh) * | 2022-05-26 | 2023-12-05 | 四川大学 | 一种制备氘代咪唑类化合物的方法 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ196284A (en) | 1980-02-29 | 1983-12-16 | Kefalas As | 1-piperazino-3-phenylindane derivatives:pharmaceutical compositions |
| GB8427125D0 (en) | 1984-10-26 | 1984-12-05 | Lundbeck & Co As H | Organic compounds |
| HU198005B (en) | 1984-12-04 | 1989-07-28 | Sandoz Ag | Process for producing mevqlolakton, derivatives, its indene-analogues and pharmaceutical compositions containing them |
| DK286990D0 (da) | 1990-12-04 | 1990-12-04 | Lundbeck & Co As H | Indanderivater |
| DK55192D0 (da) | 1992-04-28 | 1992-04-28 | Lundbeck & Co As H | 1-piperazino-1,2-dihydroindenderivater |
| US6221335B1 (en) | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| JP3696884B2 (ja) | 1994-03-25 | 2005-09-21 | アイソテクニカ、インコーポレーテッド | ジュウテリウム化による薬物の効能の増強 |
| WO1999015524A1 (en) | 1997-09-23 | 1999-04-01 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives |
| US6350786B1 (en) | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
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| UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| CA2536073A1 (en) | 2003-08-18 | 2005-02-24 | H. Lundbeck A/S | Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine |
| TWI388550B (zh) * | 2003-08-18 | 2013-03-11 | Lundbeck & Co As H | 反-４-（（１ｒ，３ｓ）-６-氯-３-苯基二氫茚-１-基）-１，２，２-三甲基哌之琥珀酸氫鹽和丙二酸氫鹽及其作為醫藥品之用途 |
| RU2366654C2 (ru) | 2004-06-08 | 2009-09-10 | ЭнЭсЭйБи, ФИЛИАЛ АФ НЕУРОСЕРЧ СВИДЕН АБ, СВЕРИЙЕ | Новые дизамещенные фенилпиперидины/пиперазины в качестве модуляторов допаминовой нейротрансмиссии |
| AU2005251909A1 (en) | 2004-06-08 | 2005-12-22 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | New disubstituted phenylpiperidines as modulators of dopamine and serotonin neurotransmission |
| JP2008530039A (ja) | 2005-02-16 | 2008-08-07 | ハー・ルンドベック・アクチエゼルスカベット | トランス−１−（（１ｒ，３ｓ）−６−クロロ−３−フェニルインダン−１−イル）−３，３−ジメチルピペラジンの酒石酸塩およびリンゴ酸塩 |
| TWI453198B (zh) | 2005-02-16 | 2014-09-21 | Lundbeck & Co As H | 製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s）-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法 |
| TWI376373B (en) | 2005-02-16 | 2012-11-11 | Lundbeck & Co As H | Crystalline base of a pharmaceutical compound |
| JP5301991B2 (ja) | 2005-07-29 | 2013-09-25 | コンサート ファーマシューティカルズ インコーポレイテッド | 新規なベンゾ［ｄ］［１，３］−ジオキソール誘導体 |
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| HUE027865T2 (en) | 2005-12-01 | 2016-11-28 | Auspex Pharmaceuticals Inc | Substituted phenyl ethylamines with serotonergic and / or norepinephrine activity |
| JP4986462B2 (ja) | 2006-01-27 | 2012-07-25 | シャープ株式会社 | 太陽電池ストリングおよびその製造方法、ならびに、その太陽電池ストリングを用いる太陽電池モジュール |
| TW200819426A (en) | 2006-08-31 | 2008-05-01 | Lundbeck & Co As H | Novel indane compounds |
| WO2008086158A1 (en) | 2007-01-04 | 2008-07-17 | Smithkline Beecham Corporation | Benzodihydroquinazoline as pi3 kinase inhibitors |
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| SI2003120T1 (sl) | 2007-06-12 | 2010-03-31 | Concert Pharmaceuticals Inc | Azapeptidni derivati kot inhibitorji hiv proteaze |
| US20090062303A1 (en) | 2007-08-29 | 2009-03-05 | Protia, Llc | Deuterium-enriched ziprasidone |
| JP2011519873A (ja) | 2008-05-07 | 2011-07-14 | ハー・ルンドベック・アクチエゼルスカベット | 認知欠損を治療する方法 |
| CA2732613A1 (en) | 2008-10-03 | 2010-04-08 | H. Lundbeck A/S | Oral formulation |
| EP2349336B1 (en) | 2008-10-28 | 2017-11-22 | Agency For Science, Technology And Research | Mesoporous material excipients for poorly aqueous soluble ingredients |
| EP2362865A2 (en) | 2008-10-28 | 2011-09-07 | Concert Pharmaceuticals Inc. | Deuterated 2-propylpentanoic acid compounds |
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| TW201102370A (en) | 2009-07-07 | 2011-01-16 | Lundbeck & Co As H | Manufacture of 4-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-1,2,2-trimethyl-piperazine and 1-((1R,3S)-6-chloro-3-phenyl-indan-1-yl)-3,3-dimethyl piperazine |
| US8557994B2 (en) | 2009-07-27 | 2013-10-15 | Daljit Singh Dhanoa | Deuterium-enriched pyridinonecarboxamides and derivatives |
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| WO2012137225A1 (en) | 2011-04-08 | 2012-10-11 | Sphaera Pharma Pvt. Ltd | Substituted methylformyl reagents and method of using same to modify physicochemical and/or pharmacokinetic properties of compounds |
| ES2719145T3 (es) | 2011-06-20 | 2019-07-08 | H Lundbeck As | 1-Piperazino-3-fenil-indanos deuterados para el tratamiento de la esquizofrenia |
| AU2013326850B2 (en) | 2012-10-04 | 2017-09-21 | Inhibikase Therapeutics, Inc. | Novel compounds, their preparation and their uses |
| AR094054A1 (es) | 2012-12-19 | 2015-07-08 | H Lundbeck As | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
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2012
- 2012-06-19 ES ES16179882T patent/ES2719145T3/es active Active
- 2012-06-19 LT LTEP12748046.5T patent/LT2720989T/lt unknown
- 2012-06-19 LT LTEP16179882.2T patent/LT3135656T/lt unknown
- 2012-06-19 AP AP2013007338A patent/AP3310A/xx active
- 2012-06-19 HR HRP20161348TT patent/HRP20161348T1/hr unknown
- 2012-06-19 JO JOP/2012/0161A patent/JO3128B1/ar active
- 2012-06-19 GE GEAP201213350A patent/GEP201706655B/en unknown
- 2012-06-19 MY MYPI2021002383A patent/MY196998A/en unknown
- 2012-06-19 CN CN201280029731.8A patent/CN103649019B/zh active Active
- 2012-06-19 SM SM20190179T patent/SMT201900179T1/it unknown
- 2012-06-19 PE PE2015000596A patent/PE20150928A1/es active IP Right Grant
- 2012-06-19 JP JP2014516459A patent/JP5668177B2/ja active Active
- 2012-06-19 EP EP19151618.6A patent/EP3508468B1/en active Active
- 2012-06-19 RS RS20160916A patent/RS55304B1/sr unknown
- 2012-06-19 KR KR1020137033717A patent/KR101879474B1/ko active Active
- 2012-06-19 PL PL16179882T patent/PL3135656T3/pl unknown
- 2012-06-19 CA CA2837820A patent/CA2837820C/en active Active
- 2012-06-19 KR KR1020187018343A patent/KR101939546B1/ko active Active
- 2012-06-19 PH PH1/2013/502598A patent/PH12013502598A1/en unknown
- 2012-06-19 AR ARP120102179 patent/AR086987A1/es active IP Right Grant
- 2012-06-19 AU AU2012273657A patent/AU2012273657B2/en active Active
- 2012-06-19 SI SI201231582T patent/SI3135656T1/sl unknown
- 2012-06-19 ES ES12748046.5T patent/ES2601213T3/es active Active
- 2012-06-19 EA EA201490045A patent/EA024651B1/ru not_active IP Right Cessation
- 2012-06-19 PL PL12748046T patent/PL2720989T3/pl unknown
- 2012-06-19 EP EP12748046.5A patent/EP2720989B1/en active Active
- 2012-06-19 PT PT16179882T patent/PT3135656T/pt unknown
- 2012-06-19 ME MEP-2019-93A patent/ME03375B/me unknown
- 2012-06-19 RS RS20190429A patent/RS58546B1/sr unknown
- 2012-06-19 BR BR112013031702-7A patent/BR112013031702B1/pt active IP Right Grant
- 2012-06-19 WO PCT/IB2012/001386 patent/WO2012176066A1/en not_active Ceased
- 2012-06-19 HU HUE16179882A patent/HUE044043T2/hu unknown
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