IP Library Granted Patent US 11,311,504
Granted Patent B2
US 11,311,504 · App. 16/502,651 · Granted Apr 26, 2022

Pharmaceutical composition comprising (1R,4R)-6′- fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano- [3,4,b ]indol] -4-amine and paracetamol or propacetamol

Inventors: Stefanie Frosch (Aachen, DE); Klaus Linz (Rheinbach, DE); Klaus Schiene (Juechen, DE)
Assignee: PARK THERAPEUTICS, INC.
A61K31/167A61K31/223A61K31/407
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 11,311,504
App. No.
16/502,651
Granted
Apr 26, 2022
Kind
B2
Abstract

The invention relates to a pharmaceutical composition comprising a first pharmacologically active ingredient selected from (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine and the physiologically acceptable salts thereof, and a second pharmacologically active ingredient selected from paracetamol and propacetamol.

Claims (28)

1. A pharmaceutical composition comprising:

a first pharmacologically active ingredient which is (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine or a physiologically acceptable salt thereof; and

a second pharmacologically active ingredient which is paracetamol or propacetamol,

wherein the first pharmacologically active ingredient and the second pharmacologically active ingredient are present in the pharmaceutical composition at a weight ratio such that the first pharmacologically active ingredient and the second pharmacologically active ingredient will exert a synergistic therapeutic effect when the pharmaceutical composition is administered to a patient.

2. The pharmaceutical composition according to claim 1 , wherein the first pharmacologically active ingredient is

(1 r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine hydrochloride,

(1 r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine hemicitrate, or

(1 r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine maleate.

3. The pharmaceutical composition according to claim 1 , wherein the second pharmacologically active ingredient is paracetamol.

4. The pharmaceutical composition according to claim 1 , wherein a relative weight ratio of the first pharmacologically active ingredient to the second pharmacologically active ingredient is 1:30 to 1:1,000,000.

5. A method for treating pain comprising administering to a patient the pharmaceutical composition according to claim 1 .

6. The method according to claim 5 , wherein the pain is at least one of peripheral pain, central pain, musculoskeletal pain, acute pain, subacute pain, chronic pain, moderate to severe pain, neuropathic pain, psychogenic pain, nociceptive pain, mixed pain, lower back pain, visceral pain, headache pain, post-operative (post-surgical) pain, pain associated with cancer, and inflammatory pain.

7. A pharmaceutical dosage form comprising the pharmaceutical composition according to claim 1 .

8. The pharmaceutical dosage form according to claim 7 , wherein the first pharmacologically active ingredient is present at 10 to 1,200 μg.

9. The pharmaceutical dosage form according to claim 7 , wherein the second pharmacologically active ingredient is present at 100 to 8,000 mg.

10. The pharmaceutical dosage form according to claim 7 , wherein the first pharmacologically active ingredient is present in the dosage form in a dosage that is within a range of from 1:20 to 20:1 of an amount which is equieffective to a dosage of the second pharmacologically active ingredient contained in the dosage form.

11. The pharmaceutical dosage form according to claim 7 , wherein the pharmaceutical dosage form is adapted for oral administration, intravenous administration, intraperitoneal administration, transdermal administration, intrathecal administration, intramuscular administration, intranasal administration, transmucosal administration, subcutaneous administration, or rectal administration.

12. The pharmaceutical dosage form according to claim 7 , wherein the pharmaceutical dosage form provides under in vitro conditions immediate release or controlled release of at least one of the first pharmacologically active ingredient and the second pharmacologically active ingredient.

13. A kit comprising:

a first pharmaceutical dosage form comprising a first pharmacologically active ingredient selected from the group consisting of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine or a physiologically acceptable salt thereof; and

a second pharmaceutical dosage form comprising a second pharmacologically active ingredient selected from the group consisting of paracetamol or propacetamol;

wherein the first pharmacologically active ingredient and the second pharmacologically active ingredient are present in the kit at a weight ratio such that the first pharmacologically active ingredient and the second pharmacologically active ingredient will exert a synergistic therapeutic effect when they are both administered to a patient.

14. The kit according to claim 13 , wherein the first pharmaceutical dosage form and the second pharmaceutical dosage form are adapted for simultaneous or sequential administration.

15. The kit according to claim 14 , wherein the first pharmaceutical dosage form and the second pharmaceutical dosage form are adapted for administration by the same pathway of administration.

16. The kit according to claim 14 , wherein the first pharmaceutical dosage form and the second pharmaceutical dosage form are adapted for administration by a different pathway of administration.

17. A pharmaceutical composition comprising a synergistic combination of:

(1) a first pharmacologically active ingredient which is (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine or a physiologically acceptable salt thereof; and

(2) a second pharmacologically active ingredient which is paracetamol or propacetamol.

Assignments (3)
CHANGE OF NAME Recorded May 21, 2025
From: PARK THERAPEUTICS, INC.
To: ADNEURIS THERAPEUTICS, INC.
Reel/Frame 071349/0825 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE ASSIGNMENT PREVIOUSLY RECORDED PREVIOUSLY RECORDED AT REEL: 068713 FRAME: 0499. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 24, 2024
From: TRIS PHARMA, INC.; PARK THERAPEUTICS, INC.
To: PROVIDENT BANK
Reel/Frame 070760/0864 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2021
From: GRÜNENTHAL GMBH
To: PARK THERAPEUTICS, INC.
Reel/Frame 057212/0157 →
Priority Claims (1)
EP 12003897 · May 18, 2012 · regional
Continuity (4)
Continuation 15726761 · Oct 6, 2017
Continuation 13892969 · May 13, 2013
Provisional Application 61648732 · May 18, 2012
Related Publication 20190350884A1 · Nov 21, 2019