AR094054A1 - 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma - Google Patents
6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la mismaInfo
- Publication number
- AR094054A1 AR094054A1 ARP130104787A ARP130104787A AR094054A1 AR 094054 A1 AR094054 A1 AR 094054A1 AR P130104787 A ARP130104787 A AR P130104787A AR P130104787 A ARP130104787 A AR P130104787A AR 094054 A1 AR094054 A1 AR 094054A1
- Authority
- AR
- Argentina
- Prior art keywords
- inden
- chloro
- compound
- formula
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 abstract 6
- ANNOOGSNJGTWOR-UHFFFAOYSA-N 3-bromo-6-chloroinden-1-one Chemical compound ClC1=CC=C2C(Br)=CC(=O)C2=C1 ANNOOGSNJGTWOR-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001543 aryl boronic acids Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- RGAOXVRFQQHTQY-URRYIOODSA-N (3s)-6-chloro-3-(2,3,4,5,6-pentadeuteriophenyl)-2,3-dihydroinden-1-one Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[C@H]1C2=CC=C(Cl)C=C2C(=O)C1 RGAOXVRFQQHTQY-URRYIOODSA-N 0.000 abstract 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 1
- SMSGJDOJSQHQIW-UHFFFAOYSA-N 6-chloro-2,3-dihydroinden-1-one Chemical compound ClC1=CC=C2CCC(=O)C2=C1 SMSGJDOJSQHQIW-UHFFFAOYSA-N 0.000 abstract 1
- VBFPHOYPKVNWMJ-RALIUCGRSA-N 6-chloro-3-(2,3,4,5,6-pentadeuteriophenyl)inden-1-one Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1C1=CC(=O)C2=CC(Cl)=CC=C12 VBFPHOYPKVNWMJ-RALIUCGRSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- 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
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La presente da a conocer el compuesto 6-cloro-3-(fenil-d₅)-inden-1-ona de fórmula (1) y vías de síntesis para obtener el compuesto de fórmula (1). En un aspecto adicional la presente describe el uso de un compuesto de fórmula (1) para la síntesis de (S)-6-cloro-3-(fenil-d₅)-indan-1-ona. Reivindicación 2: Un proceso para la producción del compuesto de fórmula (1), por el cual se obtiene el compuesto de fórmula (1) mediante la reacción de 3-bromo-6-cloro-inden-1-ona con un ácido arilborónico o un éster arilborónico. Reivindicación 3: El proceso de acuerdo con la reivindicación 2 en el cual el ácido arilborónico o éster arilborónico es 4,4,5,5-tetrametil-2-d₅-fenil-[1,3,2] dioxaborolano. Reivindicación 4: El proceso de acuerdo con las reivindicaciones 1 ó 2 que comprende los siguientes pasos a) se agrega 2,2-azo-bis-isobutironitrilo y N-bromosuccinimida a una solución que comprende 6-cloro-1-indanona; b) se agrega trietilamina a la solución del paso a) para obtener 3-bromo-6-cloro-inden-1-ona; c) se separa 3-bromo-6-cloro-inden-1-ona y se la hace reaccionar con 4,4,5,5-tetrametil-2-d₅-fenil-[1,3,2]dioxaborolano en presencia de un catalizador apropiado y una base para obtener el compuesto de fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201200811 | 2012-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR094054A1 true AR094054A1 (es) | 2015-07-08 |
Family
ID=59295365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130104787A AR094054A1 (es) | 2012-12-19 | 2013-12-17 | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9309165B2 (es) |
| EP (1) | EP2943460B1 (es) |
| JP (1) | JP6290921B2 (es) |
| KR (1) | KR102212096B1 (es) |
| CN (1) | CN104955796B (es) |
| AR (1) | AR094054A1 (es) |
| AU (1) | AU2013366693B2 (es) |
| BR (1) | BR112015014384A2 (es) |
| CA (1) | CA2893224C (es) |
| CL (1) | CL2015001720A1 (es) |
| CY (1) | CY1122715T1 (es) |
| DK (1) | DK2943460T3 (es) |
| HR (1) | HRP20200385T1 (es) |
| IL (1) | IL239097A (es) |
| LT (1) | LT2943460T (es) |
| MX (1) | MX365707B (es) |
| PL (1) | PL2943460T3 (es) |
| PT (1) | PT2943460T (es) |
| RS (1) | RS59982B1 (es) |
| RU (1) | RU2681221C2 (es) |
| SG (1) | SG11201504437SA (es) |
| SI (1) | SI2943460T1 (es) |
| SM (1) | SMT202000131T1 (es) |
| WO (1) | WO2014096151A2 (es) |
| ZA (1) | ZA201504405B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3135656T3 (en) | 2011-06-20 | 2019-04-23 | H Lundbeck As | DEUTERATED 1-PIPERAZINO-3-PHENYL INDANES FOR TREATMENT OF schizophrenia |
| CN104628630B (zh) * | 2015-03-16 | 2017-01-18 | 哈尔滨工业大学 | 一种茚衍生物1‑吡啶基‑2‑溴茚及其合成方法 |
| CN104892492A (zh) * | 2015-06-18 | 2015-09-09 | 哈尔滨工业大学 | 一种茚衍生物1-吡啶基-6-甲基茚及其合成方法 |
| JP2021520382A (ja) * | 2018-04-06 | 2021-08-19 | ハー・ルンドベック・アクチエゼルスカベット | ２，２−ジメチルピペラジンの調製方法 |
| EP3873885A1 (en) * | 2018-10-29 | 2021-09-08 | H. Lundbeck A/S | Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts |
| WO2020114853A1 (en) | 2018-12-03 | 2020-06-11 | 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-((1/r,3s)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1h-inden-1-yl)-2,2-dimethy-1-(methyl-d3)piperazine |
| KR102051783B1 (ko) * | 2019-09-02 | 2019-12-03 | 부산대학교 산학협력단 | 3,10-이치환 벤조풀벤 유도체의 신규 합성방법 |
| CN116251081A (zh) * | 2021-12-09 | 2023-06-13 | 复旦大学 | 3-芳基茚酮类化合物及其药物用途 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU198005B (en) * | 1984-12-04 | 1989-07-28 | Sandoz Ag | Process for producing mevqlolakton, derivatives, its indene-analogues and pharmaceutical compositions containing them |
| DE19538218A1 (de) * | 1995-10-13 | 1997-04-17 | Bayer Ag | Cyclopentan-1,3-dion-Derivate |
| JP2001517666A (ja) * | 1997-09-23 | 2001-10-09 | 藤沢薬品工業株式会社 | チアゾール誘導体 |
| SE9904850D0 (sv) * | 1999-12-30 | 1999-12-30 | Pharmacia & Upjohn Ab | Novel process and intermediates |
| US7767683B2 (en) * | 2003-08-18 | 2010-08-03 | H. Lundbeck A/S | Hydrogen succinate salts of trans-4-((1R, 3S)-6-chloro-3-phenylindan-1-YL)-1,2,2-trimethylpiperazine and the use as a medicament |
| RU2366654C2 (ru) * | 2004-06-08 | 2009-09-10 | ЭнЭсЭйБи, ФИЛИАЛ АФ НЕУРОСЕРЧ СВИДЕН АБ, СВЕРИЙЕ | Новые дизамещенные фенилпиперидины/пиперазины в качестве модуляторов допаминовой нейротрансмиссии |
| 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 |
| 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 |
| WO2008086158A1 (en) * | 2007-01-04 | 2008-07-17 | Smithkline Beecham Corporation | Benzodihydroquinazoline as pi3 kinase inhibitors |
| 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 |
| KR101149529B1 (ko) * | 2009-09-11 | 2012-05-25 | 한국화학연구원 | 인덴온 유도체 및 이를 포함하는 약학적 조성물 |
| JP5941410B2 (ja) | 2010-11-09 | 2016-06-29 | 株式会社カネカ | ハロゲン化インデノン類及びそれを用いた光学活性インダノン類又は光学活性インダノール類の製造方法 |
| CA2823103A1 (en) | 2011-01-07 | 2012-07-12 | H. Lundbeck A/S | Method for resolution 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 |
| DK3135656T3 (en) * | 2011-06-20 | 2019-04-23 | H Lundbeck As | DEUTERATED 1-PIPERAZINO-3-PHENYL INDANES FOR TREATMENT OF schizophrenia |
-
2013
- 2013-12-17 AR ARP130104787A patent/AR094054A1/es active IP Right Grant
- 2013-12-19 AU AU2013366693A patent/AU2013366693B2/en active Active
- 2013-12-19 PL PL13811511T patent/PL2943460T3/pl unknown
- 2013-12-19 PT PT138115118T patent/PT2943460T/pt unknown
- 2013-12-19 RU RU2015123308A patent/RU2681221C2/ru active
- 2013-12-19 DK DK13811511.8T patent/DK2943460T3/da active
- 2013-12-19 CN CN201380065995.3A patent/CN104955796B/zh active Active
- 2013-12-19 EP EP13811511.8A patent/EP2943460B1/en active Active
- 2013-12-19 JP JP2015548555A patent/JP6290921B2/ja active Active
- 2013-12-19 BR BR112015014384A patent/BR112015014384A2/pt not_active IP Right Cessation
- 2013-12-19 HR HRP20200385TT patent/HRP20200385T1/hr unknown
- 2013-12-19 CA CA2893224A patent/CA2893224C/en active Active
- 2013-12-19 SM SM20200131T patent/SMT202000131T1/it unknown
- 2013-12-19 SG SG11201504437SA patent/SG11201504437SA/en unknown
- 2013-12-19 US US14/653,318 patent/US9309165B2/en active Active
- 2013-12-19 SI SI201331680T patent/SI2943460T1/sl unknown
- 2013-12-19 LT LTEP13811511.8T patent/LT2943460T/lt unknown
- 2013-12-19 WO PCT/EP2013/077314 patent/WO2014096151A2/en not_active Ceased
- 2013-12-19 RS RS20200220A patent/RS59982B1/sr unknown
- 2013-12-19 MX MX2015007727A patent/MX365707B/es active IP Right Grant
- 2013-12-19 KR KR1020157015940A patent/KR102212096B1/ko active Active
-
2015
- 2015-05-31 IL IL239097A patent/IL239097A/en active IP Right Grant
- 2015-06-18 CL CL2015001720A patent/CL2015001720A1/es unknown
- 2015-06-18 ZA ZA2015/04405A patent/ZA201504405B/en unknown
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2020
- 2020-03-05 CY CY20201100198T patent/CY1122715T1/el unknown
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Legal Events
| Date | Code | Title | Description |
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| FG | Grant, registration |