IP Library Granted Patent US 10,975,111
Granted Patent B2
US 10,975,111 · App. 16/452,858 · Granted Apr 13, 2021

Cardiopathy-reducing phosphodiester lipids

Inventors: James McChesney (Etta, MS); Annie Bouchard (Stoke, CA); Saravanan Kappusamy (Bangalore, IN); John Kallikat Augustine (Bangalore, IN); Daniel Emil Levy (San Mateo, CA)
Assignee: Signpath Pharma, Inc.
C07F9/09A61P9/00C07F9/65515A61K45/06
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,975,111
App. No.
16/452,858
Granted
Apr 13, 2021
Kind
B2
Abstract

The present invention includes compound having the following structural formula:

Claims (40)

1. A compound of Formula I,

wherein,

R 1 is a C 1 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

R 2 is a C 1 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

R 3 is

R 4 is H or a pharmaceutically acceptable cation, wherein incorporation of said pharmaceutically acceptable cation results in a salt;

R 5 is a saturated C 1 -C 10 branched or unbranched hydrocarbon optionally substituted with one or more groups selected from OH, OAc, OMe, NH 2 , NHAc, NHMe, N(Me) 2 , SH, CN, COOH, CONH 2 , Cl, Br and I;

R 6 is a saturated C 1 -C 10 branched or unbranched hydrocarbon optionally substituted with one or more groups selected from OH, OAc, OMe, NH 2 , NHAc, NHMe, N(Me) 2 , SH, CN, COOH, CONH 2 , Cl, Br and I;

R 7 is a C 5 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

R 8 is either H or a C 0 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

X is a direct linkage, CH 2 , O or NH;

Y is a direct linkage, CH 2 , O or NH; and,

Each stereogenic center is independently R, S or racemic.

2. The compound of claim 1 , wherein R 4 is H, Li, Na, K, Mg, Ca, Zn, Cs, ammonium or tetraalkylammonium.

3. The compound of claim 1 , wherein the compound is selected from at least one of:

4. The compound of claim 1 , wherein the compound is a single entity, a solvate, a hydrate, a crystal, an amorphous solid, a liquid or an oil.

5. A pharmaceutical composition comprising a compound of Formula I and a pharmaceutically acceptable diluent or carrier

wherein,

R 1 is a C 1 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

R 2 is a C 1 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

R 3 is

R 4 is H or a pharmaceutically acceptable cation, wherein incorporation of said pharmaceutically acceptable cation results in a salt;

R 5 is a saturated C 1 -C 10 branched or unbranched hydrocarbon optionally substituted with one or more groups selected from OH, OAc, OMe, NH 2 , NHAc, NHMe, N(Me) 2 , SH, CN, COOH, CONH 2 , Cl, Br and I;

R 6 is a saturated C 1 -C 10 branched or unbranched hydrocarbon optionally substituted with one or more groups selected from OH, OAc, OMe, NH 2 , NHAc, NHMe, N(Me) 2 , SH, CN, COOH, CONH 2 , Cl, Br and I;

R 7 is a C 0 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

R 8 is either H or a C 0 -C 20 branched or unbranched hydrocarbon possessing 0-10 double bonds, 0-10 triple bonds or a combination of 0-10 double and triple bonds;

X is a direct linkage, CH 2 , O or NH;

Y is a direct linkage, CH 2 , O or NH; and,

each stereogenic center is independently R, S or racemic.

6. The pharmaceutical composition of claim 5 , wherein R 4 of the compound of Formula I is H, Li, Na, K, Mg, Ca, Zn, Cs, ammonium or tetraalkylammonium.

7. The pharmaceutical composition of claim 5 , wherein the compound of Formula I is selected from one or more of:

8. The pharmaceutical composition of claim 5 , wherein the compound of Formula I exists as a single entity, a solvate, a hydrate, a crystal, an amorphous solid, a liquid or an oil.

9. The pharmaceutical composition of claim 5 , wherein the pharmaceutical composition further comprises one or more agents that induce a cardiopathy as a side effect.

10. The pharmaceutical composition of claim 9 , wherein one or more agents that induces a cardiopathy as a side effect is selected from at least one of: Albuterol, Alfuzosin, Amantadine, Amiodarone, Amisulpride, Amitriptyline, Amoxapine, Amphetamine, Anagrelide, Apomorphine, Arformoterol, Aripiprazole, Arsenic trioxide, Astemizole, Atazanavir, Atomoxetine, Azithromycin, Bedaquiline, Bepridil, Bortezomib, Bosutinib, Chloral hydrate, Chloroquine, Chlorpromazine, Ciprofloxacin, Cisapride, Citalopram, Clarithromycin, Clomipramine, Clozapine, Cocaine, Curcumin, Crizotinib, Dabrafenib, Dasatinib, Desipramine, Dexmedetomidine, Dexmethylphenidate, Dextroamphetamine, Amphetamine, Dihydroartemisinin and Piperaquine, Diphenhydramine, Disopyramide, Dobutamine, Dofetilide, Dolasetron, Domperidone, Dopamine, Doxepin, Dronedarone, Droperidol, Ephedrine, Epinephrine, Adrenaline, Eribulin, Erythromycin, Escitalopram, Famotidine, Felbamate, Fenfluramine, Fingolimod, Flecainide, Fluconazole, Fluoxetine, Formoterol, Foscarnet, Fosphenytoin, Furosemide, Frusemide, Galantamine, Gatifloxacin, Gemifloxacin, Granisetron, Halofantrine, Haloperidol, Hydrochlorothiazide, Ibutilide, Iloperidone, Imipramine, Melipramine, Indapamide, Isoproterenol, Isradipine, Itraconazole, Ivabradine, Ketoconazole, Lapatinib, Levalbuterol, Levofloxacin, Levomethadyl, Lisdexamfetamine, Lithium, Mesoridazine, Metaproterenol, Methadone, Methamphetamine, Methylphenidate, Midodrine, Mifepristone, Mirabegron, Mirtazapine, Moexipril/HCTZ, Moxifloxacin, Nelfinavir, Nicardipine, Nilotinib, Norepinephrine, Norfloxacin, Nortriptyline, Ofloxacin, Olanzapine, Ondansetron, Oxytocin, Paliperidone, Paroxetine, Pasireotide, Pazopanib, Pentamidine, Perflutren lipid microspheres, Phentermine, Phenylephrine, Phenylpropanolamine, Pimozide, Posaconazole, Probucol, Procainamide, Promethazine, Protriptyline, Pseudoephedrine, Quetiapine, Quinidine, Quinine sulfate, Ranolazine, Rilpivirine, Risperidone, Ritodrine, Ritonavir, Roxithromycin, Salbutamol, Salmeterol, Saquinavir, Sertindole, Sertraline, Sevoflurane, Sibutramine, Solifenacin, Sorafenib, Sotalol, Sparfloxacin, Sulpiride, Sunitinib, Tacrolimus, Tamoxifen, Telaprevir, Telavancin, Telithromycin, Terbutaline, Terfenadine, Tetrabenazine, Thioridazine, Tizanidine, Tolterodine, Toremifene, Trazodone, Trimethoprim-Sulfa, Trimipramine, Vandetanib, Vardenafil, Vemurafenib, Venlafaxine, Voriconazole, Vorinostat, or Ziprasidone.

11. The pharmaceutical composition of claim 5 , wherein the pharmaceutical composition further comprises one or more excipients, binders, anti-adherents, coatings, disintegrants, fillers, flavors, dyes, colors, glidants, lubricants, preservatives, sorbents, sweeteners, derivatives thereof, or combinations thereof.

12. The pharmaceutical composition of claim 11 , wherein the binder is selected from the group consisting of hydroxypropylmethylcellulose, ethyl cellulose, povidone, acrylic and methacrylic acid co-polymers, pharmaceutical glaze, gums, and milk derivatives.

13. The pharmaceutical composition of claim 5 , wherein the pharmaceutical composition comprises a compound of Formula I in an amount per unit dose of between about 1 mg and about 1 gram per unit dose.

14. The pharmaceutical composition of claim 5 , wherein the pharmaceutical composition is a formulation for oral, sublingual, transdermal, suppository, intrathecal, enteral, parenteral, intravenous, intraperitoneal, cutaneous, subcutaneous, topical, pulmonary, rectal, vaginal, or intramuscular administration.

15. The pharmaceutical composition of claim 14 , wherein the formulation for oral administration is a tablet, capsule, caplet, pill, powder, troche, lozenge, slurry, liquid solution, suspension, emulsion, elixir or oral thin film (OTF).

16. The pharmaceutical composition of claim 15 , wherein the formulation is a solid form, a solution, a suspension, or a soft gel form.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2019
From: MCCHESNEY, JAMES; BOUCHARD, ANNIE; KAPPUSAMY, SARAVANAN; KALLIKAT AUGUSTINE, JOHN; LEVY, DANIEL EMIL
To: SIGNPATH PHARMA INC.
Reel/Frame 049917/0789 →
Continuity (2)
Provisional Application 62690196 · Jun 26, 2018
Related Publication 20190389888A1 · Dec 26, 2019
Cited By (1)
US 12,617,809