ES2643557T3 - Procedimientos de producción de molindona y sus sales - Google Patents
Procedimientos de producción de molindona y sus sales Download PDFInfo
- Publication number
- ES2643557T3 ES2643557T3 ES13714783.1T ES13714783T ES2643557T3 ES 2643557 T3 ES2643557 T3 ES 2643557T3 ES 13714783 T ES13714783 T ES 13714783T ES 2643557 T3 ES2643557 T3 ES 2643557T3
- Authority
- ES
- Spain
- Prior art keywords
- reaction
- sumo
- molindone
- salts
- production procedures
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title description 3
- KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 title 1
- 229960004938 molindone Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 102100026940 Small ubiquitin-related modifier 1 Human genes 0.000 description 8
- 101710081623 Small ubiquitin-related modifier 1 Proteins 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZVJBPHMCBRHVEV-UHFFFAOYSA-N 2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(C)=NO ZVJBPHMCBRHVEV-UHFFFAOYSA-N 0.000 description 1
- KKJVJCIOIRIFFK-UHFFFAOYSA-N 3-hydroxyiminopentan-2-one Chemical compound CCC(=NO)C(C)=O KKJVJCIOIRIFFK-UHFFFAOYSA-N 0.000 description 1
- 108010053481 Antifreeze Proteins Proteins 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 102100024542 Small ubiquitin-related modifier 2 Human genes 0.000 description 1
- 101710081711 Small ubiquitin-related modifier 2 Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
- C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Description
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ETAPA DE PREPARACIÓN DE SUMO-1
[0072] Los procedimientos de preparación de SUMO-1 utilizados para la preparación de SUMO-2 son conocidos en la técnica. SUMO-1 se puede preparar, por ejemplo, a través de la reacción de 2,3-pentanodiona con clorhidrato de hidroxilamina en presencia de una base (Reacción 5). Reacción 5:
[0073] Generalmente, la regioselectividad de la reacción de 2,3-pentanodiona con hidroxilamina a SUMO-1 no es alta, lo que da lugar a la formación del isómero de SUMO-1 2,3-pentanodiona-3-oxima y 2,3-pentanodiona-2,3
20 dioxima, junto con el producto SUMO-1 2,3-pentanodiona-2-oxima deseado.
[0074] Se descubrió inesperadamente que la regioselectividad de esta reacción se puede optimizar a través del control cuidadoso de las condiciones de reacción, tales como la naturaleza y la cantidad del agente alcalinizante, pH, disolventes, temperatura y una secuencia de dosificación.
25 [0075] El proceso de Reacción 5 puede llevarse a cabo a valores de pH que van de 4,5 a 9,5.
[0076] En una realización, la reacción 5 tiene lugar a valores de pH que van de 4,5 a 8. En otra realización, la reacción tiene lugar a valores de pH en el intervalo de 8 a 9,5.
30 [0077] La base, útil para establecer el pH necesario se puede seleccionar entre hidróxido de litio (LiOH), hidróxido sódico (NaOH), hidróxido de potasio (KOH), carbonato de litio (Li2CO3), carbonato de potasio (K2CO3) , carbonato de sodio (Na2CO3), y combinaciones de los mismos. La base se puede emplear en las cantidades de 1,0-3,0 eq, por ejemplo, en la cantidad de 1,05 a 1,5 eq o de 1,05 a 2,0 eq.
35 [0078] En una realización de preparación de SUMO-1, la base se selecciona entre NaOH, KOH y combinaciones de los mismos. En otra realización, la base se selecciona entre Li2CO3, K2CO3, Na2CO3, y combinaciones.
[0079] En aún otra realización, la base es Na2CO3, que puede usarse en las cantidades de 1 a 3 equivalentes. En
40 una variación de esta realización, se utilizó carbonato de sodio en la cantidad de aproximadamente 1,0 equivalentes. En una variación adicional de esta realización, se utilizó carbonato de sodio en la cantidad de 1,1 equivalentes. En otra variación, se usó carbonato de sodio en la cantidad de 1,2 equivalentes.
[0080] Como se descubrió que la temperatura más baja de la reacción conduce a una mejor selectividad, la
45 Reacción 5 tiene lugar ventajosamente a una temperatura de 5ºC a 20ºC. En una realización, la reacción tiene lugar a una temperatura de 5ºC a 0ºC. En otra realización, la temperatura es de 0ºC a -15ºC. En aún otra realización, la temperatura se establece para que sea de -5ºC a -10ºC.
[0081] Además, la adición de un agente anti-congelación para bajar el punto de congelación de la solución es
50 beneficiosa para la reacción. El agente anti-congelación se puede seleccionar entre haluros de metales alcalinos y alcalinotérreos, tales como cloruro de sodio (NaCl), cloruro de potasio (KCl), cloruro de calcio (CaCl2), cloruro de magnesio (MgCl2), y similares.
[0082] Los disolventes útiles para la reacción de Reacción 5 se seleccionan del grupo que consiste en agua, metil
55 butil terciario éter (MTBE), metanol, etanol, isopropanol, tetrahidrofurano (THF), acetonitrilo, piridina, éter etílico, ácido acético y combinaciones de los mismos. Los siguientes disolventes pueden añadirse adicionalmente para proporcionar propiedades anti-congelación: glicerol, etilenglicol, propilenglicol, dietilenglicol y combinaciones de los mismos.
60 [0083] Se puede obtener un alto rendimiento de SUMO-1, por encima del 90%, a través de la realización de las realizaciones descritas anteriormente de Reacción 5, con cantidades reducidas de impurezas generadas en el producto.
[0084] Los siguientes compuestos fueron identificados como potenciales subproductos resultantes de la Reacción 5: 65
13
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261701007P | 2012-09-14 | 2012-09-14 | |
| US201261701007P | 2012-09-14 | ||
| PCT/US2013/032142 WO2014042688A1 (en) | 2012-09-14 | 2013-03-15 | Methods of producing molindone and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2643557T3 true ES2643557T3 (es) | 2017-11-23 |
Family
ID=48050289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13714783.1T Active ES2643557T3 (es) | 2012-09-14 | 2013-03-15 | Procedimientos de producción de molindona y sus sales |
Country Status (8)
| Country | Link |
|---|---|
| US (6) | US8957206B2 (es) |
| EP (3) | EP2895175B1 (es) |
| JP (4) | JP6133427B2 (es) |
| AU (3) | AU2013316119B2 (es) |
| CA (3) | CA3170247A1 (es) |
| ES (1) | ES2643557T3 (es) |
| MX (4) | MX379124B (es) |
| WO (1) | WO2014042688A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6133427B2 (ja) * | 2012-09-14 | 2017-05-24 | スパーナス ファーマシューティカルズ インコーポレイテッド | モリンドン及びその塩の製造方法 |
| CN107011237B (zh) * | 2016-01-27 | 2020-04-21 | 合肥立方制药股份有限公司 | 一种改进的吗茚酮的合成方法 |
| US10752586B1 (en) | 2019-02-16 | 2020-08-25 | Lupin Limited | Process for preparation of molindone |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467755A (en) * | 1966-05-11 | 1969-09-16 | Endo Lab | Compositions and methods for producing sedation and tranquilization with substituted 4,5,6,7- tetrahydro-4-oxindoles |
| US3491093A (en) * | 1967-11-29 | 1970-01-20 | Endo Lab | Derivatives of 5 aminomethyl-4,5,6,7-tetrahydro-4-oxoindoles |
| US3646042A (en) | 1970-02-09 | 1972-02-29 | Velsicol Chemical Corp | Certain n-phenyl n-lower-alkyl-pyridine carboxamides and derivatives thereof |
| US4016281A (en) * | 1975-02-22 | 1977-04-05 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Tetralone and indanone compounds |
| US4065453A (en) | 1976-11-01 | 1977-12-27 | Endo Laboratories, Inc. | Levorotatory molindone and the use as an antidepressant |
| US4707484A (en) * | 1986-11-25 | 1987-11-17 | Hoffmann-La Roche Inc. | Substituted piperidinomethylindolone and cyclopent(b)indolone derivatives |
| US5114936A (en) * | 1990-08-23 | 1992-05-19 | Hoechst-Roussel Pharmaceuticals Incorporated | 6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5h)-ones and -ols, compositions and pharmaceutical use |
| US5180834A (en) * | 1990-08-23 | 1993-01-19 | Hoechst-Roussel Pharmaceuticals Incorporated | 6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5h)-ones |
| JP2804364B2 (ja) * | 1990-10-31 | 1998-09-24 | 三井化学株式会社 | オキシム類の製造方法 |
| JP4169562B2 (ja) | 2002-10-09 | 2008-10-22 | 横浜ゴム株式会社 | タイヤ成形用金型及び空気入りタイヤ |
| NZ569317A (en) * | 2005-12-29 | 2010-08-27 | Toyama Chemical Co Ltd | Novel arylamidine derivative, salt thereof and antifungal agent containing those |
| JP2007217353A (ja) * | 2006-02-17 | 2007-08-30 | Sankyo Agro Kk | １，２，３，４−テトラヒドロキノリン化合物 |
| JP6133427B2 (ja) * | 2012-09-14 | 2017-05-24 | スパーナス ファーマシューティカルズ インコーポレイテッド | モリンドン及びその塩の製造方法 |
-
2013
- 2013-03-15 JP JP2015531913A patent/JP6133427B2/ja not_active Expired - Fee Related
- 2013-03-15 CA CA3170247A patent/CA3170247A1/en active Pending
- 2013-03-15 EP EP13714783.1A patent/EP2895175B1/en active Active
- 2013-03-15 EP EP22177217.1A patent/EP4074691A1/en not_active Withdrawn
- 2013-03-15 MX MX2017015078A patent/MX379124B/es unknown
- 2013-03-15 EP EP17180165.7A patent/EP3290403A3/en not_active Withdrawn
- 2013-03-15 WO PCT/US2013/032142 patent/WO2014042688A1/en not_active Ceased
- 2013-03-15 MX MX2017015076A patent/MX382345B/es unknown
- 2013-03-15 AU AU2013316119A patent/AU2013316119B2/en active Active
- 2013-03-15 MX MX2017015070A patent/MX379125B/es unknown
- 2013-03-15 US US13/834,097 patent/US8957206B2/en active Active
- 2013-03-15 ES ES13714783.1T patent/ES2643557T3/es active Active
- 2013-03-15 CA CA3111577A patent/CA3111577C/en active Active
- 2013-03-15 CA CA2884179A patent/CA2884179C/en active Active
- 2013-03-15 MX MX2015003237A patent/MX356357B/es active IP Right Grant
-
2015
- 2015-01-29 US US14/608,262 patent/US9562011B2/en active Active
-
2016
- 2016-11-30 US US15/365,566 patent/US9802893B2/en active Active
-
2017
- 2017-03-13 JP JP2017047064A patent/JP6324567B2/ja not_active Expired - Fee Related
- 2017-07-27 AU AU2017208312A patent/AU2017208312B2/en active Active
- 2017-10-03 US US15/723,515 patent/US10081595B2/en active Active
-
2018
- 2018-02-09 JP JP2018021784A patent/JP2018090604A/ja active Pending
- 2018-08-21 US US16/107,836 patent/US10676432B2/en active Active
-
2019
- 2019-02-26 JP JP2019032306A patent/JP2019108351A/ja active Pending
- 2019-05-09 AU AU2019203270A patent/AU2019203270B2/en active Active
-
2020
- 2020-04-30 US US16/863,020 patent/US11117862B2/en active Active
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