SI3033327T1 - (-)-(2r,3s)-2-amino-3-hidroksi-3-piridin-4-il-1-pirolidin-1-il-propan- 1-on(l)-(+) tartratna sol ter metoda za njeno proizvodnjo in njena uporaba - Google Patents

(-)-(2r,3s)-2-amino-3-hidroksi-3-piridin-4-il-1-pirolidin-1-il-propan- 1-on(l)-(+) tartratna sol ter metoda za njeno proizvodnjo in njena uporaba Download PDF

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SI3033327T1
SI3033327T1 SI201430670T SI201430670T SI3033327T1 SI 3033327 T1 SI3033327 T1 SI 3033327T1 SI 201430670 T SI201430670 T SI 201430670T SI 201430670 T SI201430670 T SI 201430670T SI 3033327 T1 SI3033327 T1 SI 3033327T1
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salt
pyridin
hydroxy
amino
pyrrolidin
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SI201430670T
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Gyorgy F. Ambrus
Katherine C. Kurjan
Jacopo Zanon
Giovanna Libralon
Faveri Carla De
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Allergan, Inc.
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    • C07—ORGANIC CHEMISTRY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C55/02—Dicarboxylic acids
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    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid

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  • Health & Medical Sciences (AREA)
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Claims (15)

  1. (-)-(2R3S)-2-AMINO-3-HIDROKSI-3-PIRIDIN-4-IL-l-PIROLIDIN-l-IL-PROPAN-l-ON (L)-(+) TARTRATNA SOL TER METODA ZA NJENO PROIZVODNJO IN NJENA UPORABA Patentni zahtevki 1. (-)-(2i?,3S)-2-amino-3-hidroksi-3-piridin-4-il- \ -pirolidin-1 -il-propan-1 -on (L)-(+) tartratna sol.
  2. 2. Sol iz patentnega zahtevka 1, ki je kristalinična in ima po možnosti spekter rentgenske praškovne difrakcije z značilnimi vrhovi, izraženimi v stopinjah (2Θ), pri približno:
  3. 3. Sol iz patentnega zahtevka 1, ki je kristalinična in ima spekter rentgenske praškovne difrakcije z vrhovi, izraženimi v stopinjah (2Θ), pri približno: 7,61, 7,89,12,97,13,50,15,13, 15,19,15,38,16,23,16,71,16,83,17,05,19,76, 20,14, 20,43,20,76,21,00,22,77,22,86, 23,07,23,66, 24,58,24,90,25,11, 25,35,25,63,25,83, 26,33,27,09,28,08, 30,71, 31,02, 31,72,33,00 in 34,15.
  4. 4. Farmacevtska sestava, ki zajema tartratno sol iz katerega koli patentnega zahtevka od 1 do 3 in najmanj enega farmacevtsko sprejemljivega prenašalca.
  5. 5. Sol iz katerega koli patentnega zahtevka od 1 do 3 za uporabo pri metodi za zdravljenje bolečine pri sesalcih, pri čemer omenjena metoda zajema dovajanje terapevtsko učinkovite količine soli omenjenim sesalcem, ki jo potrebujejo.
  6. 6. Sol za uporabo iz patentnega zahtevka 5, pri čemer je omenjena bolečina kronična bolečina.
  7. 7. Sol iz katerega koli patentnega zahtevka od 1 do 3 za uporabo pri metodi za zdravljenje kognitivne motnje pri sesalcih, pri čemer omenjena metoda zajema dovajanje terapevtsko učinkovite količine soli omenjenim sesalcem, ki jo potrebujejo.
  8. 8. Sol za uporabo iz patentnega zahtevka 7, pri čemer je kognitivna motnja izbrana iz skupine, ki jo sestavljajo agnozija, amnezija, afazija, apraksija, delirij, demenca in učna motnja; ali pri čemer je kognitivna motnja izbrana iz skupine, ki jo sestavljajo demenca pri aidsu, Binswangerjeva bolezen, demenca z Lewyjevimi telesci, frontotemporalna demenca, blaga kognitivna motnja, multiinfarktna demenca, Pickova bolezen, semantična demenca, senilna demenca in vaskulama demenca; ali pri čemer je kognitivna motnja povezana z nevrodegenerativno boleznijo, poškodbo možganov, psihijatričnimi motnjami ali kronično bolečino.
  9. 9. Sol za uporabo iz patentnega zahtevka 8, pri čemer je učna motnja izbrana iz skupine, ki jo sestavljajo Aspergeijev sindrom, motnja pomanjkanja pozornosti, motnja pomanjkanja pozornosti s hiperaktivnostjo, avtizem, otroška dezintegrativna motnja in Rettov sindrom.
  10. 10. Sol za uporabo iz patentnega zahtevka 8, pri čemer je afazija progresivna netekoča afazija.
  11. 11. Sol za uporabo iz patentnega zahtevka 8, pri čemer je nevrodegenerativna bolezen izbrana iz skupine, ki jo sestavljajo Alzheimerjeva bolezen, kortikobazalna degeneracija, Creutzfeldt-Jakobova bolezen, frontotemporalna lobama degeneracija, Huntingtonova bolezen, multipla skleroza, hidrocefalus z običajnim tlakom, kronični organski možganski sindrom, Parkinsonova bolezen, Pickova bolezen, progresivna supranukleama paraliza in senilna demenca (Alzheimerjevega tipa).
  12. 12. Sol za uporabo iz patentnega zahtevka 8, pri čemer je poškodba možganov izbrana iz skupine, ki jo sestavljajo kronični subduralni hematom, pretres možganov, intracerebralna krvavitev, encefalitis, meningitis, septikemija, zastrupitev z mamili in zloraba mamil, ali pri čemer so psihiatrične motnje izbrane iz skupine, ki jo sestavljajo tesnobne motnje, disociativne motnje, motnje razpoloženja, shizofrenija ter somatoformne in namišljene motnje.
  13. 13. Postopek za pripravo (-)-(2i?,35)-2-amino-3-hidroksi-3-piridin-4-il-l-pirolidin-l-il-propan-l-on (L)-(+) tartratne soli, pri čemer omenjeni postopek zajema: (a) Reagiranje etil izocianoacetata s pirolidinom za proizvodnjo intermediata 1, ki nato reagira s 4-piridinkarboksialdehidom za proizvodnjo intermediata 2, pri čemer je intermediat 2 hidroliziran (+/-)-DL-freo-2-amino-3 -hidroksi-3-piridin-4-il-1 -pirolidin-1 -il-propan-1 -on dihidroklorid; (b) Ločevanje omenjenega (+/-)-DL-/reo-2-amino-3-hidroksi-3-piridin-4-il-1 -pirolidin-1-il-propan-1-on dihidroklorida v prisotnosti di-p-toluil-L-vinske kisline za proizvodnjo (-)-(2R,3S)-2-amino-3-hidroksi-3-piridin-4-il-l -pirolidin-1 -il-propan-1 -on di-p-toluoil-L-tartrata; (c) Pretvarjanje omenjenega (-)-(2i?,3S)-2-amino-3-hidroksi-3-piridin-4-il-l-pirolidin-1-il-propan-1-on di-p-toluoil-L-tartrata v prisotnosti L-vinske kisline v surovo (-)-(2R,3 S)-2-amino-3 -hidroksi-3 -piridin-4-il-1 -pirolidin-1 -il-propan-1 -on (L)-(+) tartratno sol; in (d) Kristalizacijo omenjene surove (-)-(2i?,3S)-2-amino-3-hidroksi-3-piridin-4-il-l-pirolidin-1-il-propan-1-on (L)-(+) tartratne soli v prisotnosti ustreznega topila za proizvodnj o prečiščene (-)-(2R,3 S)-2-amino-3 -hidroksi-3 -piridin-4-il-1 -pirolidin-1 -il-propan-1-on (L)-(+) tartratne soli.
  14. 14. Postopek iz patentnega zahtevka 13, pri čemer v koraku (a) intermediat 1 ni izoliran in ima strukturo
    ali pri čemer v koraku (a) intermediat 2 ni izoliran in ima strukturo
    ali pri čemer v koraku (d) omenjeno ustrezno topilo zajema metanol.
  15. 15. (-)-(2i?,3<S)-2-amino-3-hidroksi-3-piridin-4-il-1 -pirolidin-1 -il-propan-1 -on (L)-(+) tartratna sol, izdelana po postopku iz patentnega zahtevka 13.
SI201430670T 2013-08-15 2014-08-14 (-)-(2r,3s)-2-amino-3-hidroksi-3-piridin-4-il-1-pirolidin-1-il-propan- 1-on(l)-(+) tartratna sol ter metoda za njeno proizvodnjo in njena uporaba SI3033327T1 (sl)

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US201361866155P 2013-08-15 2013-08-15
PCT/US2014/051007 WO2015023816A1 (en) 2013-08-15 2014-08-14 (-)-(2r,3s)-2-amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one (l)-(+) tartrate salt, its method of production and use
EP14755535.3A EP3033327B1 (en) 2013-08-15 2014-08-14 (-)-(2r,3s)-2-amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one (l)-(+) tartrate salt, its method of production and use

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CN105555765B (zh) 2013-08-15 2018-05-25 阿勒根公司 (-)-(2r,3s)-2-氨基-3-羟基-3-吡啶-4-基-1-吡咯烷-1-基-丙-1-酮(l)-(+)酒石酸盐、其制备方法及用途
US9992703B2 (en) * 2016-04-04 2018-06-05 Cisco Technology, Inc. Insertion of management packet into a deterministic track
WO2023154450A2 (en) * 2022-02-11 2023-08-17 Gilgamesh Pharmaceuticals, Inc. (ampa-pam)-nmda receptor antagonist combination therapy for treatment of mental conditions and disorders

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US5545745A (en) * 1994-05-23 1996-08-13 Sepracor, Inc. Enantioselective preparation of optically pure albuterol
AU2002348261A1 (en) * 2001-11-26 2003-06-10 Genzyme Corporation Diastereoselective synthesis of udp-glucose : n-acylsphingosine glucosyltransferase inhibitors
ATE549020T1 (de) * 2005-01-26 2012-03-15 Allergan Inc Pharmazeutische zusammensetzungen enthaltend 1- benzyl-1- hydroxy-2,3-diamino-propylamine, 3- benzyl-3 hydroxy-2-amino-propionsäureamide und verwandte verbindungen als analgetika
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WO2008011483A2 (en) * 2006-07-19 2008-01-24 Allergan, Inc. Methods for treating chronic pain using 1- (hetero) aryl-1-hydroxy 2,3-diamino-propyl amines and related compounds
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WO2008109286A1 (en) * 2007-03-06 2008-09-12 Allergan, Inc. Methods for treating cognitive disorders using 1-aryl-1-hydroxy-2,3-diamino-propyl amines, 1-heteroaryl-1-hydroxy-2,3-diamino-propyl amines and related compounds
WO2008109285A1 (en) * 2007-03-06 2008-09-12 Allergan, Inc. Methods for treating cognitive disorders
CN105555765B (zh) 2013-08-15 2018-05-25 阿勒根公司 (-)-(2r,3s)-2-氨基-3-羟基-3-吡啶-4-基-1-吡咯烷-1-基-丙-1-酮(l)-(+)酒石酸盐、其制备方法及用途

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ES2664749T3 (es) 2018-04-23
US9242935B2 (en) 2016-01-26
JP6486358B2 (ja) 2019-03-20
DK3033327T3 (en) 2018-04-16
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HUE036381T2 (hu) 2018-07-30
CN105555765B (zh) 2018-05-25
US9540328B2 (en) 2017-01-10
NO2960430T3 (sl) 2018-01-06
EP3033327B1 (en) 2018-01-03
HK1224292A1 (zh) 2017-08-18
EP3336079A1 (en) 2018-06-20
CN108794386B (zh) 2021-06-22
CA2921385A1 (en) 2015-02-19
US20160347712A1 (en) 2016-12-01
CN108794386A (zh) 2018-11-13
PT3033327T (pt) 2018-04-04
US20150051253A1 (en) 2015-02-19

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