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AR072163A1 - Derivados de arilpirrolidinil y piperidinil-cetonas, composiciones farmaceuticas que los contienen, un metodo para el tratamiento o la prevencion de enfermedades y el uso del compuesto para la fabricacion de medicamentos - Google Patents

Derivados de arilpirrolidinil y piperidinil-cetonas, composiciones farmaceuticas que los contienen, un metodo para el tratamiento o la prevencion de enfermedades y el uso del compuesto para la fabricacion de medicamentos

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Publication number
AR072163A1
AR072163A1 ARP090102188A ARP090102188A AR072163A1 AR 072163 A1 AR072163 A1 AR 072163A1 AR P090102188 A ARP090102188 A AR P090102188A AR P090102188 A ARP090102188 A AR P090102188A AR 072163 A1 AR072163 A1 AR 072163A1
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Argentina
Prior art keywords
phenyl
chloro
methanone
pyrrolidin
piperidin
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Application number
ARP090102188A
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English (en)
Inventor
Ann Marie Madera
Ryan Craig Schoenfeld
Robert James Weikert
Clara Jeou Jen Lin
Pravin Iyer
Matthew C Lucas
Kerem Erol Ozboya
Original Assignee
Hoffmann La Roche
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Publication of AR072163A1 publication Critical patent/AR072163A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • 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
    • 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
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Los compuestos de la presente invencion son utiles para el tratamiento de enfermedades asociadas con la inhibicion de la reabsorcion de monoaminas. Tales como esquizofrenia, psicosis, alzheimer, ataques de p nico, trastornos de ingestion de comidas, obesidad, anorexia y bulimia. Reivindicacion 1: Un compuesto de la formula 1: en la que: R1 es: 4-cloro-3-metil-fenilo; 2-amino-3, 4-dicloro-fenilo); 3, 4-dicloro-fenilo; 4-cloro-3-(3,3-dimetil-butoxi)-fenilo; 3-benciloxi-4-cloro-fenilo; 7-fluor-1H-indol-5-ilo; 4-amino-3-cloro-5-trifluormetil-fenilo; 4-cloro-3-(4-fluor-fenoxi) -fenilo; 4-cloro-3-(2-fluor-fenoxi)-fenilo; 3-benciloxi-4-cloro-fenilo; 4-cloro-3-(3,3-dimetil-butoxi)-fenilo; 4-cloro-2-fenoxi-fenilo; 4-cloro-3-(tetrahidro-piran-4-ilmetoxi)-fenilo; 4-cloro-3-trifluormetoxi-fenilo; 4-cloro-3-fenilsulfanil-fenilo; 3-bencenosulfonil-4-cloro-fenilo; 4-cloro-3-(2-fluor-fenoxi)-fenilo; 4-cloro-3- (4-fluor-fenoxi)-fenilo; 4-cloro-3-fenoxi-fenilo; 4-bromo-3-fenoxi-fenilo; 4-amino-3-cloro-5-fluor-fenilo; 4-amino-3-cloro-fenilo; 4-cloro-3-(4-trifluormetil-fenoxi)-fenilo; 3-cloro-4-metil-fenilo; naftalen-2-ilo; 4-cloro-2-fenoxi-fenilo; fenilo; 3-cloro-4-metilamino-fenilo; 4-cloro-3-fenoxi-fenilo; 4-cloro-3-(2H-pirazol-3-il)-fenilo; 4-cloro-3-(metil-fenil-amino)-fenilo; 1H-indol-5-ilo; 4-cloro-3-piridin-3-il-fenilo; 3-bromo-4-imidazol-1-il-fenilo; o 4-cloro-3-imidazol-1-il-fenilo; R2 es: 3-(3,3-dimetil-butil)-pirrolidin-3-ilo; (R)-3-isobutil-pirrolidin-3-ilo; (1R,2S,4S)-2-butil-7-aza-biciclo[2.2.1]hept-2-ilo; 3-(2-metoxi-2-metil-propil)-pirrolidin-3-ilo; 3-propil-pirrolidin-3-ilo; 3-isobutil-pirrolidin-3-ilo; 3-etil-pirrolidin-3-ilo; (R)-3-(3-metil-butil)-pirrolidin-3-ilo; (S)-3-(3-metil-butil)-pirrolidin-3-ilo; (S)-3-isobutil-pirrolidin-3-ilo; (S)-3-(3,3-dimetil-butil)-pirrolidin-3-ilo; (R)-3-(3,3-dimetil-butil)-pirrolidin-3-ilo; (S)-3-propil-pirrolidin-3-ilo; (R)-3-propil-pirrolidin-3-ilo; (R)-2-propil-pirrolidin-2-il)-metanona; 4-(1-metil-ciclopropilmetil)-piperidin-4-ilo; 4-isobutil-piperidin-4-ilo; 4-propil-piperidin-4-ilo; 4-(2-metoxi-2-metil-propil)-piperidin-4-ilo; 4-(3-metil-butil)-piperidin-4-ilo; 4-ciclopentilmetil-piperidin-4-ilo; 4-(tetrahidro-piran-4-ilmetil)-piperidin-4-ilo; 4-(tetrahidro-furan-2-ilmetil)-piperidin-4-ilo; 4-(3,4-dicloro-bencil)-piperidin-4-ilo; (1R,2S,5R)-2-isobutil-8-aza-biciclo[3.2.1]oct-2-ilo; (1R,2R,5R)-2-etil-8-aza-biciclo[3.2.1]oct-2-ilo; (1R,2S,5R)-2-etil-8-aza-biciclo[3.2.1]oct-2-ilo; 3-propil-piperidin-3-ilo; (1R, 2R, 5R)-2-propil-8-aza-biciclo [3.2.1] oct-2-ilo; (1R, 2R, 5R)-2-etil-8-metil-8-aza-biciclo[3,2.1]oct-2-ilo; (1R, 2R, 5R)-2-butil-8-metil-8-aza-biciclo[3.2.1]oct-2-ilo; 3-(3,3-dimetil-butil)-piperidin-3-ilo; (S)-3-(3,3-dimetil-butil)-piperidin-3-ilo; o (R)-3-(3,3-dimetil-butil)-piperidin-3-il]-metanona; y dicho compuesto se elige entre el grupo formado por: (4-cloro-3-metil-fenil)-[3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; (2-amino-3,4-dicloro-fenil)-((R)-3-isobutil-pirrolidin-3-il)-metanona; ((1R, 2S, 4S)-2-butil-7-aza-biciclo[2.2.1]hept-2-il)-(3,4-di-cloro-fenil)-metanona; [4-cloro-3-(3,3-dimetil-butoxi)-fenil]-[3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; (3-benciloxi-4-cloro-fenil)-[3-(3,3-dimetil butil)-Pirrolidin-3-il]-metanona; (7-fluor-1H-indol-5-il)-[3-(2-metoxi-2-metil-propil)-pirrolidin-3-il]-metanona; (4-amino-3-cloro-5-trifluormetil-fenil)-[3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; [4-cloro-3-(4-fluor-fenoxi)-fenil]-[3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; [4-cloro-3-(2-fluor-fenoxi)-fenil]-[3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; (3-benciloxi-4-cloro-fenil)-(3-propil-pirrolidin-3-il)-metanona; [4-cloro-3-(3,3-dimetil-butoxi)-fenil]-(3-propil-pirrolidin-3-il)-metanona; (4-cloro-2-fenoxi-fenil)-(3-isobutil-pirrolidin-3-il)-metanona; [4-cloro-3-(tetrahidro-piran-4-ilmetoxi)-fenil]-(3-propil-pirrolidin-3-il)-metanona; (4-cloro-3-trifluormetoxi-fenil)-(3-propil-pirrolidin-3-il metanona; (4-cloro-3-fenilsulfanil-fenil)-(3-propil-pirrolidin-3-il)-metanona; (3-bencenosulfonil-4-cloro-fenil)-(3-propil-pirrolidin-3-il)-metanona; [4-cloro-3-(2-fluor-fenoxi)-fenil]-(3-propil-pirrolidin-3-il)-metanona; [4-cloro-3-(4-fluor-fenoxi)-fenil]-(3-propil-pirrolidin-3-il)-metanona; (4-cloro-3-fenoxi-fenil)-(3-etil-pirrolidin-3-il)-metanona; (4-bromo-3-fenoxi-fenil)-(3-propil-pirrolidin-3-il)-metanona; (4-amino-3-cloro-5-fluor-fenil)-[(R)-3-(3-metil-butil)-pirrolidin-3-il]-metanona; (4-amino-3-cloro-5-fluor-fenil)-[(S)-3-(3-metil-butil)-pirrolidin-3-il]-metanona; (4-amino-3-cloro-5-fluor-fenil)-((S)-3-isobutil-pirrolidin-3-il)-metanona; (4-amino-3-cloro-5-fluor-fenil)-((R)-3-isobutil-pirrolidin-3-il)-metanona; (4-amino-3-cloro-5-fluor-fenil)-[(S)-3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; (4-amino-3-cloro-5-fluor-fenil)-[(R)-3-(3,3-dimetil-butil)-pirrolidin-3-il]-metanona; (4-amino-3-cloro-fenil)-((R)-3-isobutil-pirrolidin-3-il)-metanona; (4-amino-3-cloro-fenil)-((S)-3-isobutil-pirrolidin-3-il)-metanona; (4-cloro-3-fenoxi-fenil)-((S)-3-propil-pirrolidin-3-il)-metanona; (4-cloro-3-fenoxi-fenil)-((R)-3-propil-pirrolidin-3-il)-metanona; (4-cloro-3-fenoxi-fenil)-(3-isobutil-pirrolidin-3-il)-metanona; [4-cloro-3-(4-trifluormetil-fenoxi)-fenil]-(3-propil-pirrolidin-3-il)-metanona; (4-cloro-3-fenoxi-fenil)-((R)-2-propil-pirrolidin-2-il)-metanona; (3,4-dicloro-fenil)-[4-(metil-ciclopropilmetil)-piperidin-4-il]-metanona; (3-cloro-4-metil-fenil)-(4-isobutil-piperidin-4-il)-metanona; naftalen-2-il-(4-propil-piperidin-4-il)-metanona; (3,4-dicloro-fenil)-[4-(2-metoxi-2-metil-propil)-piperidin-4-il]-metanona; (3-cloro-4-metil-fenil)-[4-(3-metil-butil)-piperidin-4-il]-metanona; (4-ciclopentilmetil-piperidin-4-il)-(3,4-dicloro-fenil)-metanona; (4-cloro-2-fenoxi-fenil)-(4-propil-piperidin-4-il)-metanona; (3,4-dicloro-fenil)-[4-(tetrahidro-piran-4-ilmetil)-piperidin-4-il]-metanona; (3,4-dicloro-fenil)-[4-(tetrahidro-furan-2-ilmetil)-piperidin-4-il]-metanona; [4-(3,4-dicloro-bencil)-piperidin-4-il]-fenil-metanona; (3-cloro-4-metilamino-fenil)-(4-isobutil-piperidin-4-il)-metanona; (4-cloro-3-fenoxi-fenil)-(4-isobutil-piperidin-4-il)-metanona; (4-cloro-3-fenoxi-fenil)-(4-propil-piperidin-4-il)-metanona; (3,4-dicloro-fenil)-((1R, 2S, 5R)-2-isobutil-8-aza-biciclo-[3.2.1]oct-2-il)-metanona; (3,4-dicloro-fenil)-((1R, 2R, 5R)-2-etil-8-aza-biciclo[3.2.1]-oct-2-il)-metanona; (3,4-dicloro-fenil)-((1R, 2S, 5R)-2-etil-8-aza-biciclo[3.2.1]-oct-2-il)-metanona; [4-cloro-3-(2H-pirazol-3-il)-fenil]-(3-propil-piperidin-3-il)-metanona; [4-cloro-3-(metil-fenil-amino)-fenil]-(3-propil-piperidin-3-il)-metanona; (1H-indol-5-il)-((1R, 2R, 5R)-2-propil-8-aza-biciclo[3.2.1]oct-2-il)-metanona; (3,4-dicloro-fenil)-((1R, 2R, 5R)-2-etil-8-metil-8-aza-biciclo-[3.2.1]oct-2-il)-metanona; ((1R, 2R, 5R)-2-butil-8-metil-8-aza-biciclo[3.2.1]oct-2-il)-(3,4-dicloro-fenil)-metanona; (4-cloro-3-piridin-3-il-fenil)-(3-propil-piperidin-3-il)-metanona; (3,4-dicloro-fenil)-[3-(3,3-dimetil-butil)-piperidin-3-il]-metanona; (3-bromo-4-imidazol-1-il-fenil)-(3-propil-piperidin-3-il)-metanona; (4-cloro-3-imidazol-1-il-fenil)-(3-propil-piperidin-3-il)-metanona; (3, 4-dicloro-fenil)-(5)-3-(3,3-dimetil-butil)-piperidin-3-il)-metanona; y (3,4-dicloro-fenil)-[(R)-3-(3,3-dimetil-butil)-piperidin-3-il]-metanona.
ARP090102188A 2008-06-18 2009-06-17 Derivados de arilpirrolidinil y piperidinil-cetonas, composiciones farmaceuticas que los contienen, un metodo para el tratamiento o la prevencion de enfermedades y el uso del compuesto para la fabricacion de medicamentos AR072163A1 (es)

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US10421696B2 (en) 2014-12-18 2019-09-24 California Institute Of Technology Enantioselective synthesis of α-quaternary mannich adducts by palladium-catalyzed allylic alkylation
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US11214568B2 (en) 2018-10-18 2022-01-04 California Institute Of Technology Gem-disubstituted pyrrolidines, piperazines, and diazepanes, and compositions and methods of making the same
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