CA3111577C - Methods of producing molindone and its salts - Google Patents

Methods of producing molindone and its salts Download PDF

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Publication number
CA3111577C
CA3111577C CA3111577A CA3111577A CA3111577C CA 3111577 C CA3111577 C CA 3111577C CA 3111577 A CA3111577 A CA 3111577A CA 3111577 A CA3111577 A CA 3111577A CA 3111577 C CA3111577 C CA 3111577C
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CA
Canada
Prior art keywords
sumo
molindone
reaction
acid
stage
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
Application number
CA3111577A
Other languages
English (en)
French (fr)
Other versions
CA3111577A1 (en
Inventor
Martin HANBAUER
Zarghun Nazir
Peter Hildebrand
Attilia Figini
Likan Liang
Tiziano FUMAGALLI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Supernus Pharmaceuticals Inc
Original Assignee
Supernus Pharmaceuticals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Supernus Pharmaceuticals Inc filed Critical Supernus Pharmaceuticals Inc
Priority to CA3170247A priority Critical patent/CA3170247A1/en
Publication of CA3111577A1 publication Critical patent/CA3111577A1/en
Application granted granted Critical
Publication of CA3111577C publication Critical patent/CA3111577C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • 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)
CA3111577A 2012-09-14 2013-03-15 Methods of producing molindone and its salts Active CA3111577C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3170247A CA3170247A1 (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261701007P 2012-09-14 2012-09-14
US61/701,007 2012-09-14
CA2884179A CA2884179C (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2884179A Division CA2884179C (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3170247A Division CA3170247A1 (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts

Publications (2)

Publication Number Publication Date
CA3111577A1 CA3111577A1 (en) 2014-03-20
CA3111577C true CA3111577C (en) 2023-01-31

Family

ID=48050289

Family Applications (3)

Application Number Title Priority Date Filing Date
CA3111577A Active CA3111577C (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts
CA2884179A Active CA2884179C (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts
CA3170247A Pending CA3170247A1 (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts

Family Applications After (2)

Application Number Title Priority Date Filing Date
CA2884179A Active CA2884179C (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts
CA3170247A Pending CA3170247A1 (en) 2012-09-14 2013-03-15 Methods of producing molindone and its salts

Country Status (8)

Country Link
US (6) US8957206B2 (enExample)
EP (3) EP3290403A3 (enExample)
JP (4) JP6133427B2 (enExample)
AU (3) AU2013316119B2 (enExample)
CA (3) CA3111577C (enExample)
ES (1) ES2643557T3 (enExample)
MX (4) MX379124B (enExample)
WO (1) WO2014042688A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
CN101351204B (zh) * 2005-12-29 2011-01-12 富山化学工业株式会社 芳脒衍生物及其盐、以及含有它们的抗真菌药
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

Also Published As

Publication number Publication date
AU2019203270A1 (en) 2019-05-30
US20200262789A1 (en) 2020-08-20
US20170101377A1 (en) 2017-04-13
EP4074691A1 (en) 2022-10-19
EP3290403A2 (en) 2018-03-07
AU2013316119B2 (en) 2017-05-04
MX379125B (es) 2025-03-10
EP2895175A1 (en) 2015-07-22
AU2017208312A1 (en) 2017-08-17
MX379124B (es) 2025-03-11
US9802893B2 (en) 2017-10-31
MX356357B (es) 2018-05-25
US8957206B2 (en) 2015-02-17
US9562011B2 (en) 2017-02-07
CA3170247A1 (en) 2014-03-20
JP2018090604A (ja) 2018-06-14
US20140081020A1 (en) 2014-03-20
US20180029982A1 (en) 2018-02-01
JP6133427B2 (ja) 2017-05-24
ES2643557T3 (es) 2017-11-23
EP3290403A3 (en) 2018-03-21
AU2013316119A1 (en) 2015-04-02
US11117862B2 (en) 2021-09-14
MX2015003237A (es) 2016-02-05
CA3111577A1 (en) 2014-03-20
CA2884179C (en) 2021-05-04
CA2884179A1 (en) 2014-03-20
JP2015534551A (ja) 2015-12-03
JP2019108351A (ja) 2019-07-04
AU2019203270B2 (en) 2020-07-09
AU2017208312B2 (en) 2019-02-14
JP6324567B2 (ja) 2018-05-16
JP2017141247A (ja) 2017-08-17
MX382345B (es) 2025-03-13
EP2895175B1 (en) 2017-07-12
US10081595B2 (en) 2018-09-25
US20190218179A1 (en) 2019-07-18
US20150141645A1 (en) 2015-05-21
US10676432B2 (en) 2020-06-09
WO2014042688A1 (en) 2014-03-20

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