DK2352497T3 - Fremgangsmåde til fremstilling af delta-9-thc-aminosyreestere - Google Patents

Fremgangsmåde til fremstilling af delta-9-thc-aminosyreestere Download PDF

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Publication number
DK2352497T3
DK2352497T3 DK09824226.6T DK09824226T DK2352497T3 DK 2352497 T3 DK2352497 T3 DK 2352497T3 DK 09824226 T DK09824226 T DK 09824226T DK 2352497 T3 DK2352497 T3 DK 2352497T3
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amino acid
thc
allyl formate
derivative
formate derivative
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DK09824226.6T
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Mahmoud A Elsohly
Waseem Gul
Soumyajit Majumdar
Michael A Repka
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Univ Mississippi
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • A61K9/0051—Ocular inserts, ocular implants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • 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
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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]
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
    • B08B13/00—Accessories or details of general applicability for machines or apparatus for cleaning
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
    • B08B3/00—Cleaning by methods involving the use or presence of liquid or steam
    • B08B3/02—Cleaning by the force of jets or sprays
    • B08B3/026—Cleaning by making use of hand-held spray guns; Fluid preparations therefor
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
    • B08B2203/00—Details of cleaning machines or methods involving the use or presence of liquid or steam
    • B08B2203/02—Details of machines or methods for cleaning by the force of jets or sprays
    • B08B2203/0264—Splash guards

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Claims (5)

1. Fremgangsmåde til fremstilling af en A9-tetrahydrocannabinolaminosyreesterforbindelse med formlen
hvor Ri er
ved en fremgangsmåde som vist i følgende skema I
hvilken fremgangsmåde omfatter trinnene, der går ud på: 1) at fremstille allylformatderivatet af aminosyren, 2) at omsætte allylformatderivatet af aminosyren med THC, og 3) at afbeskytte THC-allylformatderivatet af aminosyren.
2. Fremgangsmåde til fremstilling af en Ay-tctrahydrocannabinolaminosyrcesterforb in delse med formlen
hvor Ri er
hvor R2 er
or
hvor grupperne Ri og R2 er bundet til hinanden for at danne en peptidbinding, ved en fremgangsmåde som vist i følgende skema I
hvilken fremgangsmåde omfatter trinnene, der går ud på: 1) at fremstille allylformatderivatet af aminosyren, 2) at omsætte allylformatderivatet af aminosyren med THC, 3) at afbeskytte THC-allylformatderivatet af aminosyren, 4) at omsætte allylformatderivatet af den anden aminosyre med THC-aminosyre, og 5) at afbeskytte allylformatderivatet for at danne diaminosyrederivatet af THC.
3. Fremgangsmåde til fremstilling af en Ay-tctrahydrocannabinolaminosyrcestcrforbindelsc med formlen
hvor Ri er
hvor R2 er
or
hvor R3 er
or
hvor grupperne Ri og R2 og grupperne R2 og R3 er bundet til hinanden for at danne en peptidbinding, ved en fremgangsmåde som vist i følgende skema I
og som omfatter trinnene, der går ud på: 1) at fremstille allylformatderivatet af aminosyren, 2) at omsætte allylformatderivatet af aminosyren med THC, 3) at afbeskytte THC-allylformatderivatet af aminosyren, 4) at omsætte allylformatderivatet af den anden aminosyre med THC-aminosyre, 5) at afbeskytte THC-aminosyren, der er koblet til allylformatderivatet af aminosyren, 6) at omsætte allylformatderivatet af den tredje aminosyre med THC-diaminosyre, og 7) at afbeskytte allylformatderivatet for at danne triaminosyrederivatet af THC.
4. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 3, som endvidere omfatter at fremstille hcmisuccinatcmc og hemigluturateme af cn Δ9- tetrahydrocannabinolaminosyreesterforbindelse ifølge et hvilket som helst af kravene 1 til 3 ved at omsætte forbindelsen med ravsyreanhydrid eller glutarsyreanhydrid i nærværelse af en basisk katalysator efterfulgt af oprensningen af reaktionsblandingen.
5. Fremgangsmåde ifølge krav 4, hvor den basiske katalysator er en blanding af dimethylaminopyridin og triethylamin.
DK09824226.6T 2008-10-31 2009-11-02 Fremgangsmåde til fremstilling af delta-9-thc-aminosyreestere DK2352497T3 (da)

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US11016508P 2008-10-31 2008-10-31
PCT/US2009/062998 WO2010051541A2 (en) 2008-10-31 2009-11-02 Compositions containing delta-9-thc-amino acid esters and process of preparation

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US (2) US8809261B2 (da)
EP (1) EP2352497B1 (da)
JP (1) JP5739344B2 (da)
AU (1) AU2009308665B2 (da)
CA (1) CA2741862C (da)
DK (1) DK2352497T3 (da)
ES (1) ES2622582T3 (da)
HK (1) HK1158517A1 (da)
HU (1) HUE032158T2 (da)
PL (1) PL2352497T3 (da)
WO (1) WO2010051541A2 (da)

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JP5739344B2 (ja) 2015-06-24
WO2010051541A3 (en) 2010-07-08
CA2741862A1 (en) 2010-05-06
JP2012507568A (ja) 2012-03-29
US20150045282A1 (en) 2015-02-12
AU2009308665A1 (en) 2010-05-06
AU2009308665B2 (en) 2015-10-22
US20110275555A1 (en) 2011-11-10
US8809261B2 (en) 2014-08-19
ES2622582T3 (es) 2017-07-06
HK1158517A1 (zh) 2012-07-20
HUE032158T2 (en) 2017-09-28
EP2352497B1 (en) 2017-02-22
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