John E. Cabaj
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Senior Scientist
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John designs and develops processes for manufacturing active pharmaceutical ingredients (APIs) including steroids, vitamin D analogs, retinoids, cannabinoids and other drug candidates in Cedarburg Hauser Pharmaceuticals' cGMP environment.
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Past Experience | Education | Publications | Patents
Past Experience
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| Aldrich Chemical Company |
| Scientist |
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| Types of Projects: |
- Developed and executed the multiple step synthesis of pharmaceuticals and pharmaceutical intermediates in a cGMP setting.
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| Pharmacia and Upjohn |
| Scientist |
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| Types of Projects: |
- Designed and developed processes for the large scale manufacture of pharmaceuticals and pharmaceutical candidates.
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Education
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| University of Wisconsin - Madison |
| MS Chemistry, 1988 |
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| Scientific Advisor: Professor Edwin Vedejs |
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| Description of important work: |
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Under the direction of Professor Edwin Vedejs, John's research resulted in the development of a method to stereoselectively synthesize trisubstituted olefins via phosphole ylides.
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| University of Wisconsin - Madison |
| B.S. Chemistry, 1986 |
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| Scientific Advisor: Professor Stephen Nelsen |
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| Description of important work: |
- John's undergraduate research, directed by Professor Stephen Nelsen, involved the preparation of organic compounds for mechanistic study.
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Publications
Summary List of Publications
Click on any of the titles below to view the abstract, detailed listing and a link to the complete text on the site which owns the copyright for the article. You may be required to have a membership for the site you are linked to in order to see the complete text.
| Large-Scale Preparation of (+)-p-Menth-2-ene-1,8-diol, a Key Intermediate in the Synthesis of delta-9-Tetrahydrocannabinol. |
View Abstract |
| Development of a Commercial Process to Produce Oxandrolone. |
View Abstract |
| Use of a delta 1-Piperidine for the Synthesis of a Differentially Protected Diamine Intermediate for the Preparation of the Iron Siderophore Desferrioxamine. |
View Abstract |
| Bromine-Mediated Addition of Nucleophiles to the Electron-Rich Pyrimidine Subunit of Tirilazad. |
View Abstract |
| Wittig Ethylidenation of Ketones: Reagent Control of Z/E Selectivity. |
View Abstract |
| An Effective Method for the Preparation of 21-Chlorosteroids Using the Vilsmeier Reagent. |
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| Large-Scale Preparation of (+)-p-Menth-2-ene-1,8-diol, a Key Intermediate in the Synthesis of delta-9-Tetrahydrocannabinol. |
Organic Process Research and Development (January 5,2009)
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| Abstract: |
| A manufacturing-scale process for the preparation of p-menth-2-ene-1,8-diol, a key intermediate for the preparation of delta-9-THC, was developed. The process entails a large scale olefin migration/epoxidation and hydrolytic epoxide opening in organic solvent. The water soluble product is isolated without the need for exhaustive extraction. |
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| Detailed Listing: |
| “Large-Scale Preparation of (+)-p-Menth-2-ene-1,8-diol, a Key Intermediate in the Synthesis of delta-9-Tetrahydrocannabinol.” Cabaj, J. E.; Lukesh, J. M.; Pariza, R. P.; Zizelman, P. M. Org. Process Res. Dev. 2009, 13, 358. |
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| View complete text |
Summary List of Publications | Top
| Development of a Commercial Process to Produce Oxandrolone. |
| Organic Process Research and Development (April 20,2007) |
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| Abstract: |
| A manufacturing scale process for the preparation of the anabolic steroid Oxandrolone was developed. Key elements include: the bromination of methylandrostanolone with perbromide to give the 2-bromoketone in ca. 80% yield with minimal dehydration, subsequent elimination of the bromide with Li2CO3/LiBr to give the 2-enone in ca. 70% yield with minimal formation of methyltestosterone, and an ozonolysis procedure to give the penultimate intermediate in ca. 90% yield. The overall yield from methylandrostanolone to Oxandrolone using the described process was 45% as compared to the original Searle yield of 8%. |
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| Detailed Listing: |
| “Development of a Commercial Process to Produce Oxandrolone.” Cabaj, J. E.; Kairys, D.; Benson, T. R. Org. Process Res. Dev. 2007, 11, 378. |
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| View complete text |
Summary List of Publications | Top
Summary List of Publications | Top
Summary List of Publications | Top
Summary List of Publications | Top
Summary List of Publications | Top
Patents
Summary List of Patents
* You will find the abstracts from John's patents below along with a link to the complete text on the appropriate office patent websites.
| Preparation of Amides of Retinoic Acid via Mixed Anhydride and Mixed Carbonate Intermediates. (US 7,321,064) |
View Abstract |
| Methods and Intermediates for the Synthesis of delta-9-Tetrahydrocannabinol. (US 20070287843) |
View Abstract |
| Process to Prepare Tolterodine. (US 5,922,914) |
View Abstract |
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| Preparation of Amides of Retinoic Acid via Mixed Anhydride and Mixed Carbonate Intermediates. |
| United States Patent #7,321,064 (January 22, 2008) |
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| Abstract: |
| Processes for preparing amides of retinoic acid are disclosed. Intermediates useful in the preparation of amides of retinoic acid are also disclosed. In one version of the invention, fenretinide is produced via activation of retinoic acid (tretinoin) via its corresponding mixed anhydride or mixed carbonate followed by reaction of the activated intermediate with 4-aminophenol. Other amides of retinoic acid and isomers of retinoic acid, such as the 9-cis-form or 13-cis-form can also be made by this invention. |
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| Detailed Listing: |
| “Preparation of Amides of Retinoic Acid via Mixed Anhydride and Mixed Carbonate Intermediates.” Cabaj, J. E.; Hutchison, J., U. S. Patent 7,321,064 (January 2008). |
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| View complete text |
Summary List of Patents | Top
| Methods and Intermediates for the Synthesis of delta-9-Tetrahydrocannabinol. |
| United States Patent Application #US 20070287843 (December 13, 2007) |
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| Abstract: |
| Processes are disclosed for the synthesis of Delta-9 tetrahydrocannabinol which result in an improved Y-THC/Y-THC ratio, and intermediates are disclosed that may be used in the synthesis of Delta-9 tetrahydrocannabinol such that improved Y-THCIY-THC ratios are achieved. The intermediates may be cyclic compounds prepared from 2-Carene. There is also provided a scaleable process for the preparation of (+)-p-menth-2-ene-1,8-diol, another intermediate used in the synthesis of delta-9-tetrahydrocannibinol. |
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| Detailed Listing: |
| “Methods and Intermediates for the Synthesis of delta-9-Tetrahydrocannabinol.” Cabaj, J. E.; Pariza, R.; Lukesh, J., U. S. Patent Application 2007/0287843 (December 2007). |
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| View complete text |
Summary List of Patents | Top
| Process to Prepare Tolterodine. |
| United States Patent #5,922,914 (July 13, 1999) |
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| Abstract: |
| Disclosed is a novel intermediate, 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-ol (IV) ##STR1## and an improved process for the preparation of tolterodine. |
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| Detailed Listing: |
| “Process to Prepare Tolterodine.” Gage, J. R.; Cabaj, J. E. U. S. Patent 5,922,914 (May 1999). |
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| View complete text |
Summary List of Patents | Top
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