Jon C Antilla

US Patent:

7799934, Sep 21, 2010

Filed:

Jun 30, 2008

Appl. No.:

12/215837

Inventors:

Jon C. Antilla - Tampa FL, US
Emily B. Rowland - Tampa FL, US
Gerald B. Rowland - Tampa FL, US

Assignee:

University of South Florida - Tampa FL

International Classification:

C07D 203/04

US Classification:

548954

Abstract:

A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst.

US Patent:

8513452, Aug 20, 2013

Filed:

Jun 2, 2011

Appl. No.:

13/151705

Inventors:

Jon Clarence Antilla - Tampa FL, US
Pankaj Jain - Tampa FL, US

Assignee:

University of South Florida - Tampa FL

International Classification:

C07F 9/12

US Classification:

558 86, 558 73

Abstract:

A method synthesizing homoallylic or homopropargylic alcohols was developed to react aldehydes with allyl boronates, such as allylboronic acid pinacol ester, or allenylborates in the presence of a catalytic amount of a chiral binaphthyl-derived chiral phosphoric acid. The method showed enhanced enantiocontrol and chemical yield, which increased with lower temperatures. A large series of aldehydes were tested under these catalytic conditions and wide successful substrate scope was found, including aryl, heteroaryl, aromatic aldehydes, heteroaryl aldehydes, α,β-unsaturated aldehydes and aliphatic aldehydes, and alkyl aldehydes. Likewise, the use of crotyl boronates (E and Z) were successfully reacted with aryl aldehydes under the conditions to allow for highly enantio- and diasteo-selective crotylation.

US Patent:

20110201688, Aug 18, 2011

Filed:

Apr 20, 2011

Appl. No.:

13/090828

Inventors:

Keith Pennypacker - Wesley Chapel FL, US
Javier Cuevas - Lutz FL, US
Jon Antilla - Tampa FL, US

Assignee:

UNIVERSITY OF SOUTH FLORIDA - Tampa FL

International Classification:

A61K 31/155
C07C 279/18
C07C 277/06
A61P 9/10

US Classification:

514634, 564238, 564239

Abstract:

1,3 di-o-tolylguanidine (DTG) was examined as anti-stroke drug with a broad therapeutic window. DTG activates sigma 1 and 2 receptors. Administration of DTG at 24 hours post-stroke to rats reduces neurodegeneration by 85%; this is the only pharmacological agent that has been used successfully at this delayed timepoint. Treatment with DTG provides protection of neurons exposed to hypoxia and blocks activation of immune cells that are responsible for delayed neurodegeneration associated with stroke. Disclosed is an altered DTG structure, placing a bromide at the para position to increase tissue penetrance and efficacy. Results show that N,N′-di-p-bromophenyl guanidine protects cultured neurons under hypoxic conditions but is more potent than DTG. Moreover, N,N′-di-p-bromophenyl guanidine is as least as efficacious as DTG in treating rats 24 hours after experimental stroke.

US Patent:

20160151311, Jun 2, 2016

Filed:

Feb 4, 2016

Appl. No.:

15/015796

Inventors:

Keith R. Pennypacker - Wesley Chapel FL, US
Alison Willing - Tampa FL, US
Javier Cuevas - Lutz FL, US
Jon C. Antilla - Tampa FL, US

Assignee:

University of South Florida - Tampa FL

International Classification:

A61K 31/155

Abstract:

A method of treating stroke by administration of a novel sigma agonist is presented. Twenty-four hours after MCAO, systemic administration of several novel sigma agonists including: Bromo-DTG; Chloro-DTG; N,N′-di-1-Naphthylguanidine hydrochloride (NAGH); N,N′-di-p-Nitrophenylguanidine HCL (NAD) or vehicle were injected subcutaneously daily for 3 days. Rats treated with Bromo-DTG and Chloro-DTG had no significant improvements in any of the motor or cognitive tests while NAGH treated rats showed improved vertical movement and had significantly less motor asymmetry and bias than vehicle treated rats. Sigma receptor agonist NAGH also was found to exert its long-term neuroprotective effects by preserving both gray matter and white matter tracts. Both NAD and NAGH, when administered 24 hours after experimental stroke, reduced neural damage and enhanced behavioral recovery thirty days later which suggests that NAGH and NAD potentially extend the therapeutic window of stroke several fold over the current treatments.

US Patent:

20150051291, Feb 19, 2015

Filed:

Nov 3, 2014

Appl. No.:

14/531296

Inventors:

Keith R. Pennypacker - Wesley Chapel FL, US
Alison Willing - Tampa FL, US
Javier Cuevas - Lutz FL, US
Jon C. Antilla - Tampa FL, US

Assignee:

UNIVERSITY OF SOUTH FLORIDA - Tampa FL

International Classification:

C07C 279/18

US Classification:

514634, 564238

Abstract:

A composition and method of treating stroke by administration of a novel sigma agonist is presented. Twenty-four hours after MCAO, systemic administration of several novel sigma agonists including: Bromo-DTG; Chloro-DTG; N,N′-di-1-Naphthylguanidine hydrochloride (NAGH); N,N′-di-p-Nitrophenylguanidine HCL (NAD) or vehicle were injected subcutaneously daily for 3 days. Rats treated with Bromo-DTG and Chloro-DTG had no significant improvements in any of the motor or cognitive tests while NAGH treated rats showed improved vertical movement and had significantly less motor asymmetry and bias than vehicle treated rats. Sigma receptor agonist NAGH also was found to exert its long-term neuroprotective effects by preserving both gray matter and white matter tracts. Both NAD and NAGH, when administered 24 hours after experimental stroke, reduced neural damage and enhanced behavioral recovery thirty days later which suggests that NAGH and NAD potentially extend the therapeutic window of stroke several fold over the current treatments.