IP Library Granted Patent US 12,091,386
Granted Patent B2
US 12,091,386 · App. 17/500,680 · Granted Sep 17, 2024

D-amphetamine compounds, compositions, and processes for making and using the same

Inventors: Sven Guenther (Coralville, IA); Guochen Chi (Coralville, IA); Travis Mickle (Kissimme, FL)
Assignee: ZEVRA THERAPEUTICS, INC.
C07D213/79A61K9/0019A61K9/0043A61K31/4458A61K31/4545A61K47/55C07D213/80C07D213/81C07D401/06C07D413/06A61K9/0053A61K9/02
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Quick Facts
Patent No.
US 12,091,386
App. No.
17/500,680
Granted
Sep 17, 2024
Kind
B2
Abstract

Disclosed are d-amphetamine compounds and compositions comprising at least one organic acid covalently bound to d-amphetamine, having the structure of a salt thereof, a derivative thereof, or a combination thereof. Methods of making and using the same are also disclosed.

Claims (20)

1. A compound having a structure selected from the group consisting of:

2. A compound having a structure selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 2 , wherein the pharmaceutically acceptable salt is selected from the group consisting of an acetate, L-aspartate, besylate, bicarbonate, carbonate, D-camsylate, L-camsylate, citrate, edisylate, formate, fumarate, gluconate, hydrobromide/bromide, hydrochloride/chloride, D-lactate, L-lactate, D,L-lactate, D,L-malate, L-malate, mesylate, pamoate, phosphate, succinate, sulfate, bisulfate, D-tartrate, L-tartrate, D,L-tartrate, meso-tartrate, benzoate, gluceptate, D-glucuronate, hybenzate, isethionate, malonate, methylsulfate, 2-napsylate, nicotinate, nitrate, orotate, stearate, tosylate, thiocyanate, acefyllinate, aceturate, aminosalicylate, ascorbate, borate, butyrate, camphorate, camphocarbonate, decanoate, hexanoate, cholate, cypionate, dichloroacetate, edentate, ethyl sulfate, furate, fusidate, galactarate, galacturonate, gallate, gentisate, glutamate, glutarate, glycerophosphate, heptanoate, hydroxybenzoate, hippurate, phenylpropionate, iodide, xinafoate, lactobionate, laurate, maleate, mandelate, methanesulfonate, myristate, napadisilate, oleate, oxalate, palmitate, picrate, pivalate, propionate, pyrophosphate, salicylate, salicyl sulfate, sulfosalicylate, tannate, terephthalate, thiosalicylate, tribrophenate, valerate, valproate, adipate, 4-acetamidobenzoate, camsylate, octanoate, estolate, esylate, glycolate, thiocyanate, undecylenate, sodium, potassium, calcium, magnesium, zinc, aluminum, lithium, cholinate, lysinium, ammonium, troethamine, and a mixture thereof.

4. A composition comprising the compound of claim 1 .

5. A composition comprising the compound of claim 2 or pharmaceutically acceptable salt of the compound.

6. The composition of claim 4 , wherein the composition is formulated for oral administration or suppository administration.

7. The composition of claim 5 , wherein the composition is formulated for oral administration or suppository administration.

8. The composition of claim 6 , wherein the composition formulated for oral administration is in a dosage form selected from the group consisting of solid form, a tablet, a capsule, a caplet, a soft gel, a suppository, a troche, a lozenge, an oral powder, a solution, a syrup, an oral film, a thin strip, a slurry, an emulsion, an elixir, and a suspension.

9. The composition of claim 7 , wherein the composition formulated for oral administration is in a dosage form selected from the group consisting of solid form, a tablet, a capsule, a caplet, a soft gel, a suppository, a troche, a lozenge, an oral powder, a solution, a syrup, an oral film, a thin strip, a slurry, an emulsion, an elixir, and a suspension.

10. The composition of claim 8 , wherein the composition further comprises one or more excipients, wherein the excipients are selected from the group consisting of antiadherents, binders, coatings, disintegrants, fillers, flavors, dyes, colors, glidants, lubricants, preservatives, sorbents, sweeteners, derivatives thereof, and combinations thereof.

11. The composition of claim 9 , wherein the composition further comprises one or more excipients, wherein the excipients are selected from the group consisting of antiadherents, binders, coatings, disintegrants, fillers, flavors, dyes, colors, glidants, lubricants, preservatives, sorbents, sweeteners, derivatives thereof, and combinations thereof.

12. The composition of claim 10 , wherein the binder is selected from the group consisting of hydroxypropylmethyl cellulose, ethyl cellulose, povidone, acrylic and methacrylic acid co-polymers, pharmaceutical glaze, gums, and milk derivatives.

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

14. The composition of claim 4 , wherein the compound is present in an amount per unit dose of between about 0.1 mg and about 2000 mg per unit dose.

15. The composition of claim 5 , wherein the compound is present in an amount per unit dose of between about 0.1 mg and about 2000 mg per unit dose.

16. The composition of claim 4 , wherein the composition further comprises one or more of methylphenidate, aripiprazole, atomoxetine, baclofen, clonidine, desipramine, dihydrotetrabenazine, guanfacine, haloperidol, levetiracetam, mecamylamine, etoclopramide, olanzapine, ondansetron, pergolide, pimozide, pramipexole, risperidone, selegiline, sulpiride, tetrabenazine, topiramate, ziprasidone, or one or more of additional amphetamine, or any combination thereof and/or one or more additional pharmacological substance selected from the group consisting of stimulants, anti-depressants, combinations thereof and prodrugs thereof.

17. The composition of claim 5 , wherein the composition further comprises one or more of methylphenidate, aripiprazole, atomoxetine, baclofen, clonidine, desipramine, dihydrotetrabenazine, guanfacine, haloperidol, levetiracetam, mecamylamine, etoclopramide, olanzapine, ondansetron, pergolide, pimozide, pramipexole, risperidone, selegiline, sulpiride, tetrabenazine, topiramate, ziprasidone, or one or more of additional amphetamine, or any combination thereof and/or one or more additional pharmacological substance selected from the group consisting of stimulants, anti-depressants, combinations thereof and prodrugs thereof.

18. A kit comprising individual doses of a therapeutically effective amount of a composition comprising the compound of claim 1 .

19. A kit comprising individual doses of a therapeutically effective amount of a composition comprising the compound of claim 2 .

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Mar 13, 2026
From: ALTER DOMUS (US) LLC
To: ZEVRA THERAPEUTICS, INC.
Reel/Frame 075080/0907 →
SECURITY INTEREST Recorded Apr 8, 2024
From: ZEVRA THERAPEUTICS, INC.
To: ALTER DOMUS (US) LLC
Reel/Frame 067040/0637 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2023
From: GUENTHER, SVEN; CHI, GUOCHEN; MICKLE, TRAVIS
To: KEMPHARM, INC.
Reel/Frame 064387/0095 →
CHANGE OF NAME Recorded Jul 26, 2023
From: KEMPHARM, INC.
To: ZEVRA THERAPEUTICS, INC.
Reel/Frame 064388/0285 →
Continuity (4)
Continuation 16667807 · Oct 29, 2019
Provisional Application 62800494 · Feb 2, 2019
Provisional Application 62752324 · Oct 29, 2018
Related Publication 20220064116A1 · Mar 3, 2022