# US 5,703,104 A · Cyclic amides and derivatives thereof

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- Number: US 5,703,104 A
- Document ID: US5703104A
- Status: Granted
- Kind: A
- Application number: 08/674,843
- Filed: 1996-07-03
- Granted: 1997-12-30
- Earliest claimed: 1996-07-03
- Assignees: Durham Pharmaceuticals LLC
- Inventors: James V. Peck; Gevork Minaskanian; Mark C. Sleevi
- Web page: https://patentgrep.com/patent/US5703104A

## CPC

- A61K 8/49: containing heterocyclic compounds
- A61K 8/4913: {having five membered rings, e.g. pyrrolidone carboxylic acid}
- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61P 39/00: General protective or antinoxious agents
- A61Q 17/00: Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- C07D 207/36: Oxygen or sulfur atoms
- C07D 233/70: One oxygen atom
- C07D 233/74: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
- C07D 263/26: with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
- C07D 263/42: attached in position 5
- C07D 263/44: Two oxygen atoms
- C07D 277/34: Oxygen atoms
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds, topical compositions and methods useful for preventing the penetration of toxic chemicals through the skin of a mammal are disclosed. The compounds of the invention provide an enhanced barrier for the skin of a mammal to further inhibit or decrease the passage of bioactive agents through the skin of a mammal either from the outside environment into the systems of said mammal or from the mammal into the outside environment.

## Claims

### Claim 1

A compound having one of Formulae I-IV: ##STR4## and pharmaceutically acceptable salts and esters thereof; wherein
R is a C.sub.6-20 hydrocarbyl radical;
X is one of --CH.sub.2 --, --NH--, --O-- or --S--.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R is a straight chain alkyl radical containing 6 to 20 carbon atoms.

### Claim 3 (depends on 2)

The compound of claim 2 wherein R is a straight chain alkyl radical containing 10 or 11 carbon atoms.

### Claim 4 (depends on 1)

The compound of claim 1 which is one of: ##STR5##

### Claim 5 (depends on 1)

A topical pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier or diluent.

### Claim 6 (depends on 1)

A method for decreasing the percutaneous absorption of toxic chemicals through the skin of a mammal comprising
applying to the stratum corneum of the skin of a mammal in need thereof a compound of claim 1 in an amount effective to decrease the percutaneous absorption of said toxic chemicals.

### Claim 7 (depends on 1)

A method for increasing the stability of lipid bilayers in mammalian skin in order to decrease passage of bioactive agents through the skin of a mammal, said method comprising
applying to the stratum corneum of the skin of a mammal in need thereof a compound of claim 1 in an amount effective to decrease passage of bioactive agents through said lipid bilayers.

### Claim 8 (depends on 6, 7)

The method of either claim 6 or 7 wherein said mammal is a human.

### Claim 9 (depends on 6, 7)

The method of either claim 6 or 7 wherein said bioactive agent is water.