# US 11,077,104 B2 · Pharmaceutical compositions comprising POH derivatives

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- Number: US 11,077,104 B2
- Document ID: US11077104B2
- Status: Granted
- Kind: B2
- Application number: 16/123,729
- Filed: 2018-09-06
- Published: 2019-09-12
- Granted: 2021-08-03
- Earliest claimed: 2010-08-27
- Assignees: NeOnc Technologies, Inc.
- Applicants: NeOnc Technologies, Inc.
- Inventors: Thomas Chen; Daniel Levin; Satish Pupalli
- Web page: https://patentgrep.com/patent/US11077104B2

## CPC

- A61K 31/495: having six-membered rings with two {or more} nitrogen atoms as the only ring heteroatoms, e.g. piperazine {or tetrazines}(A61K31/48 takes precedence {; with three nitrogen atoms A61K31/53})
- A61K 9/0043: {Nose}
- A61K 31/045: Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K 31/4015: having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
- A61K 31/415: 1,2-Diazoles
- A61K 31/4188: condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/54: the modifying agent being an organic compound
- A61K 47/542: {Carboxylic acids, e.g. a fatty acid or an amino acid}
- A61K 47/543: {Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine}
- A61N 5/10: X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy (A61N5/01 takes precedence)
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07B 59/00: Introduction of isotopes of elements into organic compounds {; Labelled organic compounds per se}
- C07C 33/14: containing six-membered rings
- C07D 207/26: 2-Pyrrolidones
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 487/04: Ortho-condensed systems
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07C 2601/16: the ring being unsaturated
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides for a derivative of monoterpene or sesquiterpene, such as a perillyl alcohol derivative. For example, the perillyl alcohol derivative may be a perillyl alcohol carbamate. The perillyl alcohol derivative may be perillyl alcohol conjugated with a therapeutic agent such as a chemotherapeutic agent. The present invention also provides for a method of treating a disease such as cancer, comprising the step of delivering to a patient a therapeutically effective amount of a derivative of monoterpene (or sesquiterpene). The route of administration may vary, and can include, inhalation, intranasal, oral, transdermal, intravenous, subcutaneous or intramuscular injection.

## Claims

### Claim 1

A method for treating a tumor of the central nervous system in a mammal, comprising the step of administering to the mammal a therapeutically effective amount of a perillyl alcohol carbamate, wherein the perillyl alcohol carbamate comprises perillyl alcohol conjugated with rolipram and wherein a tumor of the central nervous system is selected from the group consisting of glioblastoma and astrocytoma.

### Claim 2 (depends on 1)

The method of claim 1, wherein the perillyl alcohol carbamate is administered using a nasal delivery device.

### Claim 3 (depends on 1)

The method of claim 1, further comprising the step of treating the mammal with radiation.

### Claim 4 (depends on 1)

The method of claim 1, further comprising the step of delivering to the mammal a chemotherapeutic agent.

### Claim 5 (depends on 1)

The method of claim 1, wherein the perillyl alcohol carbamate is 4-(3-cyclopentyloxy-4-methoxy phenyl)-2-oxo-pyrrolidine-1-carboxylic acid 4-isopropenyl cyclohex-1-enylmethyl ester.

### Claim 6 (depends on 2)

The method of claim 2, wherein the nasal delivery device is selected from the group consisting of an intranasal inhaler, an intranasal spray device, an atomizer, a nebulizer, a metered dose inhaler (MDI), a pressurized dose inhaler, an insufflator, a unit dose container, a pump, a dropper, a nasal spray bottle, a squeeze bottle and a bi-directional device.

### Claim 7

A method for inhibiting or decreasing growth of a tumor cell of the nervous central system, the method comprising contacting the tumor cell with an effective amount of a perillyl alcohol carbamate, wherein the perillyl alcohol carbamate perillyl alcohol conjugated with rolipram and wherein the tumor cell is selected from the group consisting of glioblastoma and astrocytoma.

### Claim 8 (depends on 7)

The method of claim 7, wherein the perillyl alcohol carbamate is 4-(3-cyclopentyloxy-4-methoxy phenyl)-2-oxo-pyrrolidine-1-carboxylic acid 4-isopropenyl cyclohex-1-enylmethyl ester.