SlideShare a Scribd company logo
Intellectual Property Project
Brittney Blackburne
CHE 243-300
4/29/14
 Dronabinol is “medical
marijuana”
 Aka
'Tetrahydrocannabinol'
(THC)
 Antimietic
 Taken orally
 Side effects
 Brand names
 Marinol®
What is Dronabinol?
What does it treat?
 Nausea/vomiting
 Motion sickness
 Appetite
 Cancer effects
 Side effects from
other drugs
Chemistry of Dronabinol
 Molecular Formula: C21H30O2
 Molecular Weight: 314.4617
 Solubility: Soluble in ethanol
 Boiling point: 157 °C
 Other notes: Very low toxicity.
Chemical found naturally in cannabis.
Represses neurotransmitters in the
brain.
Patent Information
 Name of Patent: Synthetic route to dronabinol
 Purpose: To determine a novel synthetic route for creating the compound
dronabinol, which can be distributed as an antiemetic.
 Patent Number: 7,323,576
 Inventors: Souza; Fabio E. S. (Mississauga, CA), Field; Jason E. (Mississauga,
CA), Pan; Ming (Mississauga, CA), Ramjit; Navindra J. (Mississauga, CA),
Tharmanathan; Tharsika (Markham, CA), Jende-Tindall; Tracey (Aurora, CA)
 Assignee: Alphora Research Inc. (Mississauga, Ontario, CA)
 Date of Filing: October 1, 2004
 Date Patent Expires: October 1, 2024
Patent Information
 Seven Dependent Claims
 Two independent claims:
 1. A process for preparing Dronabinol by esterifying cis-(1R,2S)-2-hydroxy-4-
methylcyclohex-3-ene carboxylic acid to form a lower alkyl ester. Then, subjecting the
lower alkyl ester to a nucleophilic addition reaction with an appropriate
organometallic compound to form cis-(3S,4R)-1-methyl-3-hydroxy-4-(2-hydroxyprop-2-
yl) cyclohex-1-ene. Finally, reacting said product with olivetol (1,3-dihydroxy-5-n-
pentylbenzene).
Patent Information
 Seven Dependent Claims
 Two independent claims:
 1. A process for preparing Dronabinol by esterifying cis-(1R,2S)-2-hydroxy-4-
methylcyclohex-3-ene carboxylic acid to form a lower alkyl ester. Then, subjecting the
lower alkyl ester to a nucleophilic addition reaction with an appropriate
organometallic compound to form cis-(3S,4R)-1-methyl-3-hydroxy-4-(2-hydroxyprop-2-
yl) cyclohex-1-ene. Finally, reacting said product with olivetol (1,3-dihydroxy-5-n-
pentylbenzene).
Patent Information
 2. A process of preparing dronabinol, which comprises the successive steps of: (a)
reacting 2-methyl-3-butyn-2-ol with acetic anhydride under acidic conditions, followed
by transition metal catalyzed rearrangement, to obtain 1-acetoxy-3-methyl-1,3-
butadiene; (b) subjecting the product to Diels-Alder reaction with methyl acrylate to
form methyl 2-acetoxy-4-methyl cyclohex-3-ene carboxylate; (c) isolating the racemic
cis isomer of product from (b) by crystallization; (d) converting this carboxylate to
racemic cis-2-hydroxy-4-methylcyclohex-3-ene carboxylic acid; (e) resolving the racemic
mixture to obtain significantly enantiomerically enriched cis-2-hydroxy-4-
methylcyclohex-3-ene carboxylic acid; (f) esterifying the resolved product from (e) to
form a lower alkyl ester (g) reacting the lower alkyl ester with a methyl magnesium
halide to form cis-menth-1-ene-3,8-diol; (h) reacting product from (g) with olivetol to
form 1,3-dihydroxy-2-[(1R,6R)-6-(2-hydroxyprop-2-yl)-3-methylcyclohex-2-en-1-y- l]-5-n-
pentylbenzene; and (i) cyclizing the product from (h) to obtain dronabinol.
Questions?
Sources
 US Patent Office
 Medline Plus
 Pubchem

More Related Content

Viewers also liked

Searching for Inorganic Organometallic Substances in Reaxys 2013
Searching for Inorganic Organometallic Substances in Reaxys 2013Searching for Inorganic Organometallic Substances in Reaxys 2013
Searching for Inorganic Organometallic Substances in Reaxys 2013
Reaxys
 
Masters Research Summary
Masters Research SummaryMasters Research Summary
Masters Research SummaryPeter Vednor
 
Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...
Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...
Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...
Ashik Biswas
 
Green Oxidative catalyst
Green Oxidative catalystGreen Oxidative catalyst
Green Oxidative catalystEdwin Lozano
 
Article on Ernst Otto Fischer
Article on Ernst Otto FischerArticle on Ernst Otto Fischer
Article on Ernst Otto Fischer
rita martin
 
LGRAUX_Research summary
LGRAUX_Research summaryLGRAUX_Research summary
LGRAUX_Research summaryLionel Graux
 
Alkylation
AlkylationAlkylation
Alkylation
adeeba2
 
Mechanistic aspects of C-C cross coupling reaction
Mechanistic aspects of C-C cross coupling reactionMechanistic aspects of C-C cross coupling reaction
Mechanistic aspects of C-C cross coupling reaction
Rashmi Gaur
 
Ph.D. Thesis overview_
Ph.D. Thesis overview_Ph.D. Thesis overview_
Ph.D. Thesis overview_Raj K Das
 
Inorganic and organometallic chemistry: The Reaxys solution_may24_cf
Inorganic and organometallic chemistry: The Reaxys solution_may24_cfInorganic and organometallic chemistry: The Reaxys solution_may24_cf
Inorganic and organometallic chemistry: The Reaxys solution_may24_cf
Ann-Marie Roche
 
1 organometallic chemistry
1   organometallic chemistry1   organometallic chemistry
1 organometallic chemistry
Sirod Judin
 
Nanocatalysts in Refining & Petrochemical Processes
Nanocatalysts in Refining & Petrochemical ProcessesNanocatalysts in Refining & Petrochemical Processes
Nanocatalysts in Refining & Petrochemical Processes
Gerard B. Hawkins
 
Chemistry of benzene
Chemistry of benzeneChemistry of benzene
Chemistry of benzeneKandarp Vyas
 
Selective Catalytic Reduction of NOx
Selective Catalytic Reduction of NOxSelective Catalytic Reduction of NOx
Selective Catalytic Reduction of NOx
badcrackcherry
 
Organic compound
Organic compoundOrganic compound
Organic compound
Ahura1
 
heck reaction, suzuki coupling and sharpless epoxidation
heck reaction, suzuki coupling and sharpless epoxidationheck reaction, suzuki coupling and sharpless epoxidation
heck reaction, suzuki coupling and sharpless epoxidation
VISHAL PATIL
 

Viewers also liked (18)

rajkdas_CV
rajkdas_CVrajkdas_CV
rajkdas_CV
 
Searching for Inorganic Organometallic Substances in Reaxys 2013
Searching for Inorganic Organometallic Substances in Reaxys 2013Searching for Inorganic Organometallic Substances in Reaxys 2013
Searching for Inorganic Organometallic Substances in Reaxys 2013
 
Masters Research Summary
Masters Research SummaryMasters Research Summary
Masters Research Summary
 
Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...
Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...
Design,Synthesis, and carbon- heteroatom coupling reactions of organometallic...
 
Green Oxidative catalyst
Green Oxidative catalystGreen Oxidative catalyst
Green Oxidative catalyst
 
Article on Ernst Otto Fischer
Article on Ernst Otto FischerArticle on Ernst Otto Fischer
Article on Ernst Otto Fischer
 
LGRAUX_Research summary
LGRAUX_Research summaryLGRAUX_Research summary
LGRAUX_Research summary
 
Alkylation
AlkylationAlkylation
Alkylation
 
Mechanistic aspects of C-C cross coupling reaction
Mechanistic aspects of C-C cross coupling reactionMechanistic aspects of C-C cross coupling reaction
Mechanistic aspects of C-C cross coupling reaction
 
organic
organicorganic
organic
 
Ph.D. Thesis overview_
Ph.D. Thesis overview_Ph.D. Thesis overview_
Ph.D. Thesis overview_
 
Inorganic and organometallic chemistry: The Reaxys solution_may24_cf
Inorganic and organometallic chemistry: The Reaxys solution_may24_cfInorganic and organometallic chemistry: The Reaxys solution_may24_cf
Inorganic and organometallic chemistry: The Reaxys solution_may24_cf
 
1 organometallic chemistry
1   organometallic chemistry1   organometallic chemistry
1 organometallic chemistry
 
Nanocatalysts in Refining & Petrochemical Processes
Nanocatalysts in Refining & Petrochemical ProcessesNanocatalysts in Refining & Petrochemical Processes
Nanocatalysts in Refining & Petrochemical Processes
 
Chemistry of benzene
Chemistry of benzeneChemistry of benzene
Chemistry of benzene
 
Selective Catalytic Reduction of NOx
Selective Catalytic Reduction of NOxSelective Catalytic Reduction of NOx
Selective Catalytic Reduction of NOx
 
Organic compound
Organic compoundOrganic compound
Organic compound
 
heck reaction, suzuki coupling and sharpless epoxidation
heck reaction, suzuki coupling and sharpless epoxidationheck reaction, suzuki coupling and sharpless epoxidation
heck reaction, suzuki coupling and sharpless epoxidation
 

Similar to Intellectual Property (BB) ODP

A convenient synthesis of some diarylurea and thiourea derivatives as antimic...
A convenient synthesis of some diarylurea and thiourea derivatives as antimic...A convenient synthesis of some diarylurea and thiourea derivatives as antimic...
A convenient synthesis of some diarylurea and thiourea derivatives as antimic...
Alexander Decker
 
Proline catalyzed aldol reaction
Proline catalyzed aldol reactionProline catalyzed aldol reaction
Proline catalyzed aldol reaction
Debtanu Chakraborty
 
A optimized process for the synthesis of a key starting material for etodolac...
A optimized process for the synthesis of a key starting material for etodolac...A optimized process for the synthesis of a key starting material for etodolac...
A optimized process for the synthesis of a key starting material for etodolac...
IOSR Journals
 
“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...
“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...
“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...
BRNSS Publication Hub
 
Synthetic Reagents & Applications in Organic Chemistry
Synthetic Reagents & Applications in Organic ChemistrySynthetic Reagents & Applications in Organic Chemistry
Synthetic Reagents & Applications in Organic Chemistry
Ajay Kumar
 
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...
inventionjournals
 
Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...
Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...
Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...
Alexander Decker
 
Ea24804807
Ea24804807Ea24804807
Ea24804807
IJERA Editor
 
Synthesis Of Hetero-cyclic Drugs
Synthesis Of Hetero-cyclic DrugsSynthesis Of Hetero-cyclic Drugs
Synthesis Of Hetero-cyclic Drugs
Nirali Mistry
 
Natural insecticides .pptx
Natural insecticides .pptxNatural insecticides .pptx
Natural insecticides .pptx
pravin bendle
 
A convenient new and efficient commercial synthetic route for dasatinib (Spry...
A convenient new and efficient commercial synthetic route for dasatinib (Spry...A convenient new and efficient commercial synthetic route for dasatinib (Spry...
A convenient new and efficient commercial synthetic route for dasatinib (Spry...
Ratnakaram Venkata Nadh
 
STUDY OF FOLLOWING OFFICIAL COMPOUNDS
STUDY OF FOLLOWING OFFICIAL COMPOUNDSSTUDY OF FOLLOWING OFFICIAL COMPOUNDS
STUDY OF FOLLOWING OFFICIAL COMPOUNDS
Mr.S.SEETARAM SWAMY
 
Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...
Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...
Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...
IOSR Journals
 
Molecules 22-00357
Molecules 22-00357Molecules 22-00357
Molecules 22-00357
elshimaa eid
 
Synthesis, characterization, antimicrobial
Synthesis, characterization, antimicrobialSynthesis, characterization, antimicrobial
Synthesis, characterization, antimicrobial
Alexander Decker
 
11.synthesis, characterization, antimicrobial
11.synthesis, characterization, antimicrobial11.synthesis, characterization, antimicrobial
11.synthesis, characterization, antimicrobialAlexander Decker
 
Synthesis Of Lidocaine Lab Report
Synthesis Of Lidocaine Lab ReportSynthesis Of Lidocaine Lab Report
Synthesis Of Lidocaine Lab Report
Michelle Singh
 
An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...
An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...
An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...
inventionjournals
 
Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...
Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...
Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...
IJAEMSJORNAL
 
ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...
ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...
ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...
tanveercdr
 

Similar to Intellectual Property (BB) ODP (20)

A convenient synthesis of some diarylurea and thiourea derivatives as antimic...
A convenient synthesis of some diarylurea and thiourea derivatives as antimic...A convenient synthesis of some diarylurea and thiourea derivatives as antimic...
A convenient synthesis of some diarylurea and thiourea derivatives as antimic...
 
Proline catalyzed aldol reaction
Proline catalyzed aldol reactionProline catalyzed aldol reaction
Proline catalyzed aldol reaction
 
A optimized process for the synthesis of a key starting material for etodolac...
A optimized process for the synthesis of a key starting material for etodolac...A optimized process for the synthesis of a key starting material for etodolac...
A optimized process for the synthesis of a key starting material for etodolac...
 
“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...
“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...
“Synthesis, Characterization, and Antipsychotic Evaluation of Some Aryl Piper...
 
Synthetic Reagents & Applications in Organic Chemistry
Synthetic Reagents & Applications in Organic ChemistrySynthetic Reagents & Applications in Organic Chemistry
Synthetic Reagents & Applications in Organic Chemistry
 
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...
Synthesis And Antibacterial Activity Of 3-[(3-Phenyl-5-Thioxo-1, 5-Dihydro-4h...
 
Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...
Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...
Novel approach to synthesis of pentofurano nucleoside assisted natural phosph...
 
Ea24804807
Ea24804807Ea24804807
Ea24804807
 
Synthesis Of Hetero-cyclic Drugs
Synthesis Of Hetero-cyclic DrugsSynthesis Of Hetero-cyclic Drugs
Synthesis Of Hetero-cyclic Drugs
 
Natural insecticides .pptx
Natural insecticides .pptxNatural insecticides .pptx
Natural insecticides .pptx
 
A convenient new and efficient commercial synthetic route for dasatinib (Spry...
A convenient new and efficient commercial synthetic route for dasatinib (Spry...A convenient new and efficient commercial synthetic route for dasatinib (Spry...
A convenient new and efficient commercial synthetic route for dasatinib (Spry...
 
STUDY OF FOLLOWING OFFICIAL COMPOUNDS
STUDY OF FOLLOWING OFFICIAL COMPOUNDSSTUDY OF FOLLOWING OFFICIAL COMPOUNDS
STUDY OF FOLLOWING OFFICIAL COMPOUNDS
 
Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...
Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...
Synthesis and Characterization O-, M- and Para-Toluyl Thiourea Substituted Pa...
 
Molecules 22-00357
Molecules 22-00357Molecules 22-00357
Molecules 22-00357
 
Synthesis, characterization, antimicrobial
Synthesis, characterization, antimicrobialSynthesis, characterization, antimicrobial
Synthesis, characterization, antimicrobial
 
11.synthesis, characterization, antimicrobial
11.synthesis, characterization, antimicrobial11.synthesis, characterization, antimicrobial
11.synthesis, characterization, antimicrobial
 
Synthesis Of Lidocaine Lab Report
Synthesis Of Lidocaine Lab ReportSynthesis Of Lidocaine Lab Report
Synthesis Of Lidocaine Lab Report
 
An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...
An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...
An Efficient Synthetic Approach Towards 4-Cyano-3-(Methylthio)-5-Oxo-2H-Pyraz...
 
Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...
Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...
Syntheses and Characterizations of Some New N-alkyl, Isoxazole and Dioxazole ...
 
ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...
ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...
ORGANOCATALYSED ENANTIOSELECTIVE CYCLIZATION REACTIONS FOR THE SYNTHESIS Of -...
 

Recently uploaded

Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...
Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...
Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...
University of Maribor
 
Leaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdfLeaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdf
RenuJangid3
 
Hemostasis_importance& clinical significance.pptx
Hemostasis_importance& clinical significance.pptxHemostasis_importance& clinical significance.pptx
Hemostasis_importance& clinical significance.pptx
muralinath2
 
NuGOweek 2024 Ghent - programme - final version
NuGOweek 2024 Ghent - programme - final versionNuGOweek 2024 Ghent - programme - final version
NuGOweek 2024 Ghent - programme - final version
pablovgd
 
(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...
(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...
(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...
Scintica Instrumentation
 
DMARDs Pharmacolgy Pharm D 5th Semester.pdf
DMARDs Pharmacolgy Pharm D 5th Semester.pdfDMARDs Pharmacolgy Pharm D 5th Semester.pdf
DMARDs Pharmacolgy Pharm D 5th Semester.pdf
fafyfskhan251kmf
 
bordetella pertussis.................................ppt
bordetella pertussis.................................pptbordetella pertussis.................................ppt
bordetella pertussis.................................ppt
kejapriya1
 
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.
Sérgio Sacani
 
What is greenhouse gasses and how many gasses are there to affect the Earth.
What is greenhouse gasses and how many gasses are there to affect the Earth.What is greenhouse gasses and how many gasses are there to affect the Earth.
What is greenhouse gasses and how many gasses are there to affect the Earth.
moosaasad1975
 
DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...
DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...
DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...
Wasswaderrick3
 
Unveiling the Energy Potential of Marshmallow Deposits.pdf
Unveiling the Energy Potential of Marshmallow Deposits.pdfUnveiling the Energy Potential of Marshmallow Deposits.pdf
Unveiling the Energy Potential of Marshmallow Deposits.pdf
Erdal Coalmaker
 
GBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram StainingGBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram Staining
Areesha Ahmad
 
Nutraceutical market, scope and growth: Herbal drug technology
Nutraceutical market, scope and growth: Herbal drug technologyNutraceutical market, scope and growth: Herbal drug technology
Nutraceutical market, scope and growth: Herbal drug technology
Lokesh Patil
 
Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.
Nistarini College, Purulia (W.B) India
 
general properties of oerganologametal.ppt
general properties of oerganologametal.pptgeneral properties of oerganologametal.ppt
general properties of oerganologametal.ppt
IqrimaNabilatulhusni
 
如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样
如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样
如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样
yqqaatn0
 
Mammalian Pineal Body Structure and Also Functions
Mammalian Pineal Body Structure and Also FunctionsMammalian Pineal Body Structure and Also Functions
Mammalian Pineal Body Structure and Also Functions
YOGESH DOGRA
 
Lateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensiveLateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensive
silvermistyshot
 
platelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptxplatelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptx
muralinath2
 
BLOOD AND BLOOD COMPONENT- introduction to blood physiology
BLOOD AND BLOOD COMPONENT- introduction to blood physiologyBLOOD AND BLOOD COMPONENT- introduction to blood physiology
BLOOD AND BLOOD COMPONENT- introduction to blood physiology
NoelManyise1
 

Recently uploaded (20)

Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...
Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...
Comparing Evolved Extractive Text Summary Scores of Bidirectional Encoder Rep...
 
Leaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdfLeaf Initiation, Growth and Differentiation.pdf
Leaf Initiation, Growth and Differentiation.pdf
 
Hemostasis_importance& clinical significance.pptx
Hemostasis_importance& clinical significance.pptxHemostasis_importance& clinical significance.pptx
Hemostasis_importance& clinical significance.pptx
 
NuGOweek 2024 Ghent - programme - final version
NuGOweek 2024 Ghent - programme - final versionNuGOweek 2024 Ghent - programme - final version
NuGOweek 2024 Ghent - programme - final version
 
(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...
(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...
(May 29th, 2024) Advancements in Intravital Microscopy- Insights for Preclini...
 
DMARDs Pharmacolgy Pharm D 5th Semester.pdf
DMARDs Pharmacolgy Pharm D 5th Semester.pdfDMARDs Pharmacolgy Pharm D 5th Semester.pdf
DMARDs Pharmacolgy Pharm D 5th Semester.pdf
 
bordetella pertussis.................................ppt
bordetella pertussis.................................pptbordetella pertussis.................................ppt
bordetella pertussis.................................ppt
 
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.
THE IMPORTANCE OF MARTIAN ATMOSPHERE SAMPLE RETURN.
 
What is greenhouse gasses and how many gasses are there to affect the Earth.
What is greenhouse gasses and how many gasses are there to affect the Earth.What is greenhouse gasses and how many gasses are there to affect the Earth.
What is greenhouse gasses and how many gasses are there to affect the Earth.
 
DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...
DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...
DERIVATION OF MODIFIED BERNOULLI EQUATION WITH VISCOUS EFFECTS AND TERMINAL V...
 
Unveiling the Energy Potential of Marshmallow Deposits.pdf
Unveiling the Energy Potential of Marshmallow Deposits.pdfUnveiling the Energy Potential of Marshmallow Deposits.pdf
Unveiling the Energy Potential of Marshmallow Deposits.pdf
 
GBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram StainingGBSN- Microbiology (Lab 3) Gram Staining
GBSN- Microbiology (Lab 3) Gram Staining
 
Nutraceutical market, scope and growth: Herbal drug technology
Nutraceutical market, scope and growth: Herbal drug technologyNutraceutical market, scope and growth: Herbal drug technology
Nutraceutical market, scope and growth: Herbal drug technology
 
Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.Nucleic Acid-its structural and functional complexity.
Nucleic Acid-its structural and functional complexity.
 
general properties of oerganologametal.ppt
general properties of oerganologametal.pptgeneral properties of oerganologametal.ppt
general properties of oerganologametal.ppt
 
如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样
如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样
如何办理(uvic毕业证书)维多利亚大学毕业证本科学位证书原版一模一样
 
Mammalian Pineal Body Structure and Also Functions
Mammalian Pineal Body Structure and Also FunctionsMammalian Pineal Body Structure and Also Functions
Mammalian Pineal Body Structure and Also Functions
 
Lateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensiveLateral Ventricles.pdf very easy good diagrams comprehensive
Lateral Ventricles.pdf very easy good diagrams comprehensive
 
platelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptxplatelets_clotting_biogenesis.clot retractionpptx
platelets_clotting_biogenesis.clot retractionpptx
 
BLOOD AND BLOOD COMPONENT- introduction to blood physiology
BLOOD AND BLOOD COMPONENT- introduction to blood physiologyBLOOD AND BLOOD COMPONENT- introduction to blood physiology
BLOOD AND BLOOD COMPONENT- introduction to blood physiology
 

Intellectual Property (BB) ODP

  • 1. Intellectual Property Project Brittney Blackburne CHE 243-300 4/29/14
  • 2.  Dronabinol is “medical marijuana”  Aka 'Tetrahydrocannabinol' (THC)  Antimietic  Taken orally  Side effects  Brand names  Marinol® What is Dronabinol?
  • 3. What does it treat?  Nausea/vomiting  Motion sickness  Appetite  Cancer effects  Side effects from other drugs
  • 4. Chemistry of Dronabinol  Molecular Formula: C21H30O2  Molecular Weight: 314.4617  Solubility: Soluble in ethanol  Boiling point: 157 °C  Other notes: Very low toxicity. Chemical found naturally in cannabis. Represses neurotransmitters in the brain.
  • 5. Patent Information  Name of Patent: Synthetic route to dronabinol  Purpose: To determine a novel synthetic route for creating the compound dronabinol, which can be distributed as an antiemetic.  Patent Number: 7,323,576  Inventors: Souza; Fabio E. S. (Mississauga, CA), Field; Jason E. (Mississauga, CA), Pan; Ming (Mississauga, CA), Ramjit; Navindra J. (Mississauga, CA), Tharmanathan; Tharsika (Markham, CA), Jende-Tindall; Tracey (Aurora, CA)  Assignee: Alphora Research Inc. (Mississauga, Ontario, CA)  Date of Filing: October 1, 2004  Date Patent Expires: October 1, 2024
  • 6. Patent Information  Seven Dependent Claims  Two independent claims:  1. A process for preparing Dronabinol by esterifying cis-(1R,2S)-2-hydroxy-4- methylcyclohex-3-ene carboxylic acid to form a lower alkyl ester. Then, subjecting the lower alkyl ester to a nucleophilic addition reaction with an appropriate organometallic compound to form cis-(3S,4R)-1-methyl-3-hydroxy-4-(2-hydroxyprop-2- yl) cyclohex-1-ene. Finally, reacting said product with olivetol (1,3-dihydroxy-5-n- pentylbenzene).
  • 7. Patent Information  Seven Dependent Claims  Two independent claims:  1. A process for preparing Dronabinol by esterifying cis-(1R,2S)-2-hydroxy-4- methylcyclohex-3-ene carboxylic acid to form a lower alkyl ester. Then, subjecting the lower alkyl ester to a nucleophilic addition reaction with an appropriate organometallic compound to form cis-(3S,4R)-1-methyl-3-hydroxy-4-(2-hydroxyprop-2- yl) cyclohex-1-ene. Finally, reacting said product with olivetol (1,3-dihydroxy-5-n- pentylbenzene).
  • 8. Patent Information  2. A process of preparing dronabinol, which comprises the successive steps of: (a) reacting 2-methyl-3-butyn-2-ol with acetic anhydride under acidic conditions, followed by transition metal catalyzed rearrangement, to obtain 1-acetoxy-3-methyl-1,3- butadiene; (b) subjecting the product to Diels-Alder reaction with methyl acrylate to form methyl 2-acetoxy-4-methyl cyclohex-3-ene carboxylate; (c) isolating the racemic cis isomer of product from (b) by crystallization; (d) converting this carboxylate to racemic cis-2-hydroxy-4-methylcyclohex-3-ene carboxylic acid; (e) resolving the racemic mixture to obtain significantly enantiomerically enriched cis-2-hydroxy-4- methylcyclohex-3-ene carboxylic acid; (f) esterifying the resolved product from (e) to form a lower alkyl ester (g) reacting the lower alkyl ester with a methyl magnesium halide to form cis-menth-1-ene-3,8-diol; (h) reacting product from (g) with olivetol to form 1,3-dihydroxy-2-[(1R,6R)-6-(2-hydroxyprop-2-yl)-3-methylcyclohex-2-en-1-y- l]-5-n- pentylbenzene; and (i) cyclizing the product from (h) to obtain dronabinol.
  • 10. Sources  US Patent Office  Medline Plus  Pubchem