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WO2013119304A3 - Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof - Google Patents

Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof Download PDF

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Publication number
WO2013119304A3
WO2013119304A3 PCT/US2012/066379 US2012066379W WO2013119304A3 WO 2013119304 A3 WO2013119304 A3 WO 2013119304A3 US 2012066379 W US2012066379 W US 2012066379W WO 2013119304 A3 WO2013119304 A3 WO 2013119304A3
Authority
WO
WIPO (PCT)
Prior art keywords
deuterium
enriched
perillyl alcohol
alcohol
iso
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.)
Ceased
Application number
PCT/US2012/066379
Other languages
French (fr)
Other versions
WO2013119304A2 (en
Inventor
Thomas Chen
Daniel Levin
Satish Pupalli
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.)
Neonc Technologies Inc
Original Assignee
Neonc Technologies 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
Priority claimed from US13/566,731 external-priority patent/US8916545B2/en
Priority to CA2856403A priority Critical patent/CA2856403A1/en
Priority to CN201280057166.6A priority patent/CN103946202A/en
Priority to KR20147016865A priority patent/KR20150000469A/en
Priority to JP2014542593A priority patent/JP2015502352A/en
Priority to US14/359,366 priority patent/US20160039731A1/en
Application filed by Neonc Technologies Inc filed Critical Neonc Technologies Inc
Priority to EP12867815.8A priority patent/EP2782894A4/en
Priority to BR112014012180A priority patent/BR112014012180A2/en
Priority to HK15101876.0A priority patent/HK1201253A1/en
Publication of WO2013119304A2 publication Critical patent/WO2013119304A2/en
Publication of WO2013119304A3 publication Critical patent/WO2013119304A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • A61N2005/1092—Details
    • A61N2005/1098—Enhancing the effect of the particle by an injected agent or implanted device

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Radiology & Medical Imaging (AREA)
  • Neurosurgery (AREA)
  • Pathology (AREA)
  • Neurology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention, provides for a deuterium-enriched monoterpene or sesquiterpene such as perillyl alcohol, or a deuterium-enriched isomer or analog of monoterpenes or sesquiterpenes, such as isoperillyl alcohol. The present invention also provides for a deuterium-enriched derivative of a monoterpene or sesquiterpene, such as a perillyl alcohol carbamate, or a deuterium-enriched derivative of an isomer or analog of a monoterpene or sesquiterpene, such as an isoperillyl alcohol carbamate. The deuterium-enriched derivative may be perillyl alcohol or isoperillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The present invention also provides for a method of treating a disease such as cancer, comprising the step of delivering to a patient a therapeutically effective amount of a deuterium-enriched compound.
PCT/US2012/066379 2010-08-27 2012-11-21 Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof Ceased WO2013119304A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
HK15101876.0A HK1201253A1 (en) 2011-11-21 2012-11-21 Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof
CN201280057166.6A CN103946202A (en) 2011-11-21 2012-11-21 Pharmaceutical composition comprising deuterium-enriched perillyl alcohol, isoperillyl alcohol and derivatives thereof
KR20147016865A KR20150000469A (en) 2011-11-21 2012-11-21 Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof
JP2014542593A JP2015502352A (en) 2011-11-21 2012-11-21 Pharmaceutical composition comprising deuterium fortified perillyl alcohol, isoperylyl alcohol, and derivatives thereof
US14/359,366 US20160039731A1 (en) 2010-08-27 2012-11-21 Pharmaceutical Compositions Comprising Deuterium-Enriched Perillyl Alcohol, Iso-Perillyl Alcohol and Derivatives Thereof
CA2856403A CA2856403A1 (en) 2011-11-21 2012-11-21 Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof
EP12867815.8A EP2782894A4 (en) 2011-11-21 2012-11-21 PHARMACEUTICAL COMPOSITIONS COMPRISING DEUTERIUM-ENRICHED PERILYL ALCOHOL AND DERIVATIVES THEREOF
BR112014012180A BR112014012180A2 (en) 2011-11-21 2012-11-21 pharmaceutical compositions comprising perilyl alcohol, iso-perilyl alcohol and its enriched deuterium derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201161562105P 2011-11-21 2011-11-21
US61/562,105 2011-11-21
US13/566,731 2012-08-03
US13/566,731 US8916545B2 (en) 2010-08-27 2012-08-03 Pharmaceutical compositions comprising POH derivatives

Publications (2)

Publication Number Publication Date
WO2013119304A2 WO2013119304A2 (en) 2013-08-15
WO2013119304A3 true WO2013119304A3 (en) 2013-10-03

Family

ID=48948152

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/066379 Ceased WO2013119304A2 (en) 2010-08-27 2012-11-21 Pharmaceutical compositions comprising deuterium-enriched perillyl alcohol, iso-perillyl alcohol and derivatives thereof

Country Status (8)

Country Link
EP (1) EP2782894A4 (en)
JP (2) JP2015502352A (en)
KR (1) KR20150000469A (en)
CN (1) CN103946202A (en)
BR (1) BR112014012180A2 (en)
CA (1) CA2856403A1 (en)
HK (1) HK1201253A1 (en)
WO (1) WO2013119304A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104945335B (en) * 2014-03-27 2018-02-16 沈阳药科大学 Purple perilla aminated compounds and its preparation and application
CN104945334B (en) * 2014-03-27 2018-02-16 沈阳药科大学 Perilla alcohol derivant and its preparation and application
CN104945336B (en) * 2014-03-27 2018-02-16 沈阳药科大学 Perillic acid methyl esters nitrogen containing derivative and its preparation and application
CN104945333B (en) * 2014-03-27 2018-02-02 沈阳药科大学 Perilla alcohol analog and its preparation and application
CN111936125B (en) * 2018-02-08 2025-03-04 南加州大学 Methods of penetrating the blood-brain barrier
CN116789530A (en) * 2023-05-16 2023-09-22 杭州师范大学 Perilla alcohol phenol derivative and preparation method and application thereof

Citations (3)

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US20060014732A1 (en) * 2004-06-23 2006-01-19 Hofmann Robert F Use of targeted oxidative therapeutic formulation in treatment of burns
US20100168228A1 (en) * 2006-10-13 2010-07-01 Reliance Life Sciences Pvt. Ltd. Novel chemotherapeutic agents against inflammation and cancer
WO2012027693A2 (en) * 2010-08-27 2012-03-01 Neonc Technologies Inc. Pharmaceutical compositions comprising poh derivatives

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ES2387562T3 (en) * 2001-03-23 2012-09-26 Luitpold Pharmaceuticals, Inc. Conjugates fatty alcohol-medication
WO2003057193A1 (en) * 2001-12-11 2003-07-17 Dor Biopharma, Inc. Monoterpene compositions and uses thereof
BR0107262B1 (en) 2001-12-17 2014-04-22 Da Fonseca Clovis Orlando Pereira INHALORY PHARMACEUTICAL COMPOSITION
US7601355B2 (en) 2005-06-01 2009-10-13 Northwestern University Compositions and methods for altering immune function
EP2393488B1 (en) * 2009-02-06 2019-06-19 University Of Southern California Therapeutic compositions comprising monoterpenes
CN101979378B (en) * 2010-10-13 2012-06-27 中国科学院上海有机化学研究所 Method for synthesizing chiral gamma-lactam compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060014732A1 (en) * 2004-06-23 2006-01-19 Hofmann Robert F Use of targeted oxidative therapeutic formulation in treatment of burns
US20100168228A1 (en) * 2006-10-13 2010-07-01 Reliance Life Sciences Pvt. Ltd. Novel chemotherapeutic agents against inflammation and cancer
WO2012027693A2 (en) * 2010-08-27 2012-03-01 Neonc Technologies Inc. Pharmaceutical compositions comprising poh derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEN ET AL.: "Synthesis of Deuterium Labeled Perillyl Alcohol and Dual C-13 and Deuterium Labeled Perillic Acid, Major Metabolites of d-Limonene.", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. XXXIX, no. 5, 1997, XP055149706 *
See also references of EP2782894A4 *

Also Published As

Publication number Publication date
CA2856403A1 (en) 2013-08-15
CN103946202A (en) 2014-07-23
WO2013119304A2 (en) 2013-08-15
EP2782894A2 (en) 2014-10-01
EP2782894A4 (en) 2015-03-11
JP2015502352A (en) 2015-01-22
KR20150000469A (en) 2015-01-02
BR112014012180A2 (en) 2017-05-30
JP2018035148A (en) 2018-03-08
HK1201253A1 (en) 2015-08-28

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