Source: https://patents.justia.com/patent/10285995
Timestamp: 2019-08-19 07:49:15
Document Index: 221600994

Matched Legal Cases: ['§ 120', '§ 120', '§ 120', '§ 120', '§ 120', '§ 120', 'Application No. 21', 'Application No. 21']

US Patent for Compositions and methods for reducing body fat Patent (Patent # 10,285,995 issued May 14, 2019) - Justia Patents Search
Justia Patents US Patent for Compositions and methods for reducing body fat Patent (Patent # 10,285,995)
Oct 23, 2017 - Topokine Therapeutics, Inc.
The present application is a continuation of and claims priority under 35 U.S.C. § 120 to U.S. application Ser. No. 15/243,641, filed Aug. 22, 2016, now U.S. Pat. No. 9,795,614, which is a continuation of and claims priority under 35 U.S.C. § 120 to U.S. application Ser. No. 14/838,049, filed Aug. 27, 2015, now U.S. Pat. No. 9,421,215, which is a continuation of and claims priority under 35 U.S.C. § 120 to U.S. application Ser. No. 14/504,788, filed Oct. 2, 2014, now U.S. Pat. No. 9,144,574, which is a continuation of and claims priority under 35 U.S.C. § 120 to U.S. application Ser. No. 14/180,074, filed Feb. 13, 2014, now U.S. Pat. No. 8,877,807, which is a continuation of and claims priority under 35 U.S.C. § 120 to U.S. application Ser. No. 12/652,968, filed Jan. 6, 2010, now U.S. Pat. No. 8,829,050, which is a continuation of and claims priority under 35 U.S.C. § 120 to U.S. application Ser. No. 11/712,839, filed Mar. 1, 2007, now U.S. Pat. No. 7,666,912, which claims the benefit of and priority to U.S. Provisional Patent Application Ser. No. 60/785,360, filed Mar. 23, 2006, and U.S. Provisional Patent Application Ser. No. 60/844,337, filed Sep. 13, 2006, the entire disclosures of which are incorporated by reference herein for all purposes.
In certain embodiments, the compound can be cyclopentane heptenol-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane N,N-dimethylheptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenyl methoxide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenyl ethoxide-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenylamide-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenylamide-5-cis-2-(3α-hydroxy-4-trifluoromethylphenoxy-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane N-isopropyl heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane N-methyl heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenol-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-butenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenamide-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-butenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; and/or cyclopentane heptenol-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)3, 5-dihydroxy, [1α, 2β, 3α, 5α].
and their 9- and/or 11- and/or 15-esters. Furthermore, an embodiment of the present invention utilizes bimatoprost, also referred to as cyclopentane N-ethyl heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3,5-dihydroxy, [1α, 2β, 3α, 5α] (see U.S. Pat. No. 6,403,649), or (Z)-7-[(1 R,2 R,3 R,5 S)-3, 5-Dihydroxy-2-[1 E,3 S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-N-ethylheptenamide, the compound represented by formula IV
In addition, the following compounds may be used in the pharmaceutical compositions and the methods of treatment of the present invention: cyclopentane heptenol-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane N,N-dimethylheptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenyl methoxide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenyl ethoxide-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenylamide-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenylamide-5-cis-2-(3α-hydroxy-4-trifluoromethylphenoxy-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane N-isopropyl heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane N-methyl heptenamide-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenol-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-butenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; cyclopentane heptenamide-5-cis-2-(3α-hydroxy-4-meta-chlorophenoxy-1-trans-butenyl)-3, 5-dihydroxy, [1α, 2β, 3α, 5α]; and cyclopentane heptenol-5-cis-2-(3α-hydroxy-5-phenyl-1-trans-pentenyl)3, 5-dihydroxy, [1α, 2β, 3α, 5α].
Method. In all cases the vehicle is a compatible ointment, such as petrolatum, with a final bimatoprost concentration of 0%, 0.003%, 0.03%, or 0.3%. A fixed amount of ointment, for example 1 gram, is applied daily in a thin film over a uniform surface area of the abdominal skin of each animal. Each animal is randomized to a daily application of a dose of topical bimatoprost or vehicle alone. On a weekly basis, total body mass of each animal is determined on a scale. Total body fat is estimated by any of the several methods established for this purpose, for example, water displacement (Dahms et al. (1982) J NUTR. 112: 398-400), isotopic dilution (Culebras et al. (1977) J. PHYSIOL. 232: R60-65), Total Body Electrical Conductance (TOBEC) (Baer et al. (1993) PHYSIOL. BEHAV. 53: 1195-99), Dual-Energy X-Ray Absorptiometry (DEXA) (Bertin et al. (1998) J NUTRITION 128: 1550-54), or Nuclear Magnetic Resonance (NMR) (Kunnecke et al. (2004) OBES RES. 12: 1604-15). Animals are maintained and monitored in this fashion for six months, at which point they are sacrificed.
1. A method for reducing fat in the body of a subject, the method comprising administering to the skin of the subject a compound of Formula (I): or a pharmaceutically acceptable salt thereof, wherein:
the dashed bonds represent a single or double bond which can be in the cis or trans configuration;
A is alkylene or alkenylene radical having from two to six carbon atoms, which radical may be interrupted by one or more oxide radicals and substituted with one or more hydroxy, oxo, alkyloxy, or alkylcarboxy groups, wherein the alkyl radical is from one to six carbon atoms;
B is a cycloalkyl radical having from three to seven carbon atoms or an aryl radical selected from the group consisting of hydrocarbyl aryl and heteroaryl radicals having from four to ten carbon atoms in which a heteroatom may be selected from the group consisting of nitrogen, oxygen and sulfur atoms;
X is a radical selected from the group consisting of —OR4 and —N(R4)2, wherein R4 is hydrogen, a lower alkyl radical having from one to six carbon atoms,
R5 is a lower alkyl radical having from one to six carbon atoms;
Z is ═O or represents two hydrogen radicals;
one of R1 and R2 is ═O, —OH, or —O(CO)R6, and the other one is —OH or —O(CO)R6; or R1 is ═O and R2 is H;
R6 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to 20 carbon atoms, or —(CH2)mR7 in which m is 0-10 and R7 is cycloalkyl radical having from three to seven carbon atoms, or a hydrocarbyl aryl or heteroaryl radical.
2. The method of claim 1, wherein the compound is of Formula (II): or a pharmaceutically acceptable salt thereof, wherein:
x is 0 or 1; provided that x and y are not both 1;
Y is a radical selected from the group consisting of alkyl, halo, nitro, amino, thiol, hydroxy, alkyloxy, alkylcarboxy, and halosubstituted alkyl, wherein said alkyl radical comprises from one to six carbon atoms;
R3 is ═O, —OH or —O(CO)R6.
3. The method of claim 2, wherein the compound is of Formula (III): or a pharmaceutically acceptable salt thereof.
4. The method of claim 2, wherein the compound is of Formula (V): or a pharmaceutically acceptable salt thereof;
wherein Y1 is —Cl or trifluoromethyl.
5. The method of claim 4, wherein said compound is of Formula (VI): or a pharmaceutically acceptable salt thereof.
6. The method of claim 1, wherein Z is ═O; and X is —OR4 or —N(R4)2.
7. The method of claim 2, wherein R1, R2, and R3 are —OH.
8. The method of claim 2, wherein y is 0; and x is 1.
9. The method of claim 2, wherein y is 1; and x is 0.
10. The method of claim 2, wherein n is 0.
11. The method of claim 2, wherein n is 1.
12. The method of claim 2, wherein Y1 is trifluoromethyl.
13. The method of claim 1, wherein the administering is by topical application to the skin, injection into the skin, or implantation of a depot comprising the compound.
14. The method of claim 1, wherein the compound is administered to a localized area selected from the group consisting of the abdomen, chest, buttocks, hips, thighs, legs, knees, arms, chin, neck, face, and combinations thereof.
15. The method of claim 1, wherein the compound is administered to the skin of the face of the subject.
16. The method of claim 1, wherein the compound is delivered in an ointment, lotion, cream, patch, or transdermal system.
17. The method of claim 1, wherein the method is performed as an adjunct to a cosmetic or surgical procedure.
18. The method of claim 1, wherein the subject is a human having undesired fat.
19. The method of claim 1, wherein the compound is administered as a pharmaceutical composition, wherein the concentration of the compound is between 0.001% to about 1.0% (w/v), inclusive.
20. The method of claim 1, wherein the compound is administered in a sustained-release formulation.
21. The method of claim 1, provided that when B is not substituted with a pendant heteroatom-containing radical and Z is ═O, then X is not —OR4.
22. The method of claim 2, wherein Z is ═O; and X is —OR4 or —N(R4)2.
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Patent Publication Number: 20180104255
Application Number: 15/790,630