# US 7,407,648 B2 · Merocyanine derivatives for cosmetic use

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- Number: US 7,407,648 B2
- Document ID: US7407648B2
- Status: Granted
- Kind: B2
- Application number: 10/520,840
- Filed: 2003-07-01
- Published: 2005-11-17
- Granted: 2008-08-05
- Earliest claimed: 2002-07-10
- Assignees: Ciba Specialty Chemicals Corporation
- Inventors: Barbara Wagner; Thomas Ehlis; Kai Eichin
- Web page: https://patentgrep.com/patent/US7407648B2

## CPC

- C07D 239/54: as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- A61K 8/4906: {with one nitrogen as the only hetero atom}
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- C07C 255/30: containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same unsaturated acyclic carbon skeleton
- C07C 255/31: having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
- C07D 207/20: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 231/36: with hydrocarbon radicals, substituted by hetero atoms, attached in position 4
- C07D 263/14: with radicals substituted by oxygen atoms
- C07D 277/10: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 295/145: with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D 295/155: with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 319/06: not condensed with other rings
- C07C 2601/16: the ring being unsaturated
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The use is described of merocyanine derivatives of formula (1), wherein R1 and R2 are each independently of the other hydrogen; C1-C22alkyl; cyclo-C3C8alkyl; or unsubstituted or C1-C5alkyl- or C1-C5alkoxy-substituted C6-C20aryl; orl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or, interrupted by —O— or by —NH—; R3 is a cyano group; —COOR5; —CONHR5; —COR5; or —SO2R5; R4 is a cyano group; —COOR6; —CONHR6; —COR6; or —SO2R6; R5 and R6 are each independently of the other C1-C22alkyl; or unsubstituted or C1-C5alkyl substituted C6-C20aryl; or R3 and R4 together or R5 and R6 together form in a 5- to 7-membered, monocyclic, carbocyclic or heterocyclic ring; Z1, and Z2 are each independently of the other a —(CH2)n— group which is uninterrupted or interrupted by —O—, —S—, or by —NR7—, and/or is unsubstituted or substituted by C1-C5alkyl; R7 is (ClC5alkyl; 1 is from 1 to 4; m is from 1 to 7; n is from 1 to 4; when n=2, R1, R5 or R6 is a bivalent alkyl group; or R1, and R2 together with the 2 nitrogen atoms linking them form a —(CH2)m— ring; when n=3, R1, R5 or R6 is a trivalent alkyl group; when n=4, R1, R5 or R6 is a tetravalent alkyl group; and R1, and R2 in formula (1) are not simultaneously hydrogen, in protecting human and animal hair and skin from UV radiation.

## Claims

### Claim 1

A method of protecting human and animal hair or skin from UV radiation, which comprises contacting said hair or skin with an effective UV-protective amount of a compound of formula
wherein
R1 and R2 are each independently of the other hydrogen; C1-C22alkyl; cyclo-C3-C8alkyl; or unsubstituted or C1-C6alkyl- or C1-C6alkoxy-substituted C6-C20aryl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is a cyano group; —COOR5; —CONHR5; —COR5; —SO2R5; or —CONR1R5;
R4 is a cyano group; —COOR6; —CONHR6; —COR6; —SO2R6; or —CONR2R6;
R5 and R6 are each independently of the other C1-C22alkyl; cyclo-C3-C8alkyl; or unsubstituted or C1-C6alkyl-substituted C6-C20aryl;
or R3 and R4 together or R5 and R6 together form a 5- to 7-membered, monocyclic, carbocyclic or heterocyclic ring;
Z1 and Z2 are each independently of the other a —(CH2)1— group which is uninterrupted or interrupted by —O—, —S—, or by —NR7—, and/or is unsubstituted or substituted by C1-C6alkyl;
R7 is C1-C5alkyl;
l is a number from 1 to 4;
m is a number from 1 to 7;
n is a number from 1 to 4;
when n=2, R1, R5 or R6 is a bivalent alkyl group; or R1 and R2 together with the 2 nitrogen atoms linking them form a —(CH2)m— ring;
when n=3, R1, R5 or R6 is a trivalent alkyl group;
when n=4, R1, R5 or R6 is a tetravalent alkyl group; and
R1 and R2 in formula (1) are not simultaneously hydrogen.

### Claim 2 (depends on 1)

A method according to claim 1, relating to a compound of formula (1) or (2a)
wherein
R1 and R2 are each independently of the other hydrogen; C1-C22alkyl; or unsubstituted or C1-C5alkyl- or C1-C5alkoxy-substituted C6-C20aryl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is a cyano group; —COOR5; —CONHR5; —COR5; or —SO2R5;
R4 is a cyano group; —COOR6; —CONHR6; —COR6; or —SO2R6;
R5 and R6 are each independently of the other C1-C22alkyl; or unsubstituted or C1-C5alkyl-substituted C6-C20aryl;
or R5 and R6 together form a 5- to 7-membered, monocyclic, carbocyclic or heterocyclic ring;
Z1 and Z2 are each independently of the other a —(CH2)l— group which is uninterrupted or interrupted by —O—, —S—, or by —NR7—, and/or is unsubstituted or substituted by C1-C5alkyl;
R7 is C1-C5alkyl;
l is a number from 1 to 4;
m is a number from 1 to 7;
n is a number from 1 to 4;
when n=2, R1, R5 or R6 is a bivalent alkyl group; or R1 and R2 together with the 2 nitrogen atoms linking them form a —(CH2)m— ring;
when n=3, R1, R5 or R6 is a trivalent alkyl group;
when n=4, R1, R5 or R6 is a tetravalent alkyl group; and
R1 and R2 in formula (1) are not simultaneously hydrogen.

### Claim 3 (depends on 1)

A method according to claim 1, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is a cyano group; —COOR5; —CONHR5; —COR5; or —SO2R5;
R4 is a cyano group; —COOR6; —CONHR6; —COR6; or —SO2R6;
R5 and R6 are each independently of the other C1-C22alkyl; or C6-C20aryl; and
Z is as defined in claim 1.

### Claim 4 (depends on 1)

A method Use according to claim 1, wherein
R3 is a cyano group; and
R4 is —CONHR6; and
R6 is C1-C22alkyl; or C6-C20aryl.

### Claim 5 (depends on 1)

A method according to claim 1, wherein
R6 is C4-C20alkyl.

### Claim 6 (depends on 1)

A method according to claim 1, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is —COOR5;
R4 is a cyano group; —COOR6; or —SO2R6;
R5 and R6 are each independently of the other C1-C22alkyl; or C6-C20aryl; and
m is from 1 to 7.

### Claim 7 (depends on 6)

A method according to claim 6, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is —COOR5;
R4 is —COOR6;
R5 and R6 are each independently of the other C1-C22alkyl; or C6-C20aryl; and
m is from 1 to 7.

### Claim 8 (depends on 6)

A method according to claim 6, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is —COOR5;
R4 is a cyano group;
R5 is C1-C22alkyl; or C6-C20aryl; and
m is from 1 to 7.

### Claim 9 (depends on 6)

A method according to claim 6, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is —COOR5;
R4 is —SO2R6;
R5 and R6 are each independently of the other C1-C22alkyl; or C6-C20aryl; and
m is from 1 to 7.

### Claim 10 (depends on 1)

A method according to claim 1, which comprises using a compound of formula
wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the 2 nitrogen atoms linking them form a —(CH2)m— ring;
X is —O—; or —NH—;
Z2 is a —(CH2)l— group which is uninterrupted or interrupted by —O—, —S—, or by —NR7—, and/or is unsubstituted or substituted by C1-C6alkyl; and
n is a number from 1 to 3.

### Claim 11 (depends on 10)

A method according to claim 10, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form the radical

### Claim 12 (depends on 1)

A method according to claim 1, which comprises using a compound of formula
wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is a cyano group; —COOR5; —CONHR5; —COR5; or —SO2R5; and
R5 and R6 are each independently of the other C1-C22alkyl; or C6-C20aryl.

### Claim 13 (depends on 12)

A method according to claim 12, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form the radical

### Claim 14 (depends on 1)

A method according to claim 1, which comprises using a compound of formula
wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is a cyano group; —COOR5; —CONHR5; —COR5; or —SO2R5; and
R5 is C1-C22alkyl; or C6-C20aryl.

### Claim 15 (depends on 14)

A method according to claim 14, wherein
R1 and R2 are each independently of the other C1-C22alkyl; or R1 and R2 together with the nitrogen atom linking them form the radical

### Claim 16 (depends on 1)

A method according to claim 1, wherein
Z1 or Z2 is an atom grouping which results in the formation of an oxazolidine ring, a pyrrolidine ring or a thiazolidine ring.

### Claim 17 (depends on 16)

A method according to claim 16, wherein the compound corresponds to formula
wherein
R8 and R9 are each independently of the other hydrogen; or C1-C5alkyl;
Y is —O—; —S—; or —CH2—;
R1 is hydrogen; C1-C22alkyl; cyclo-C3-C8alkyl; or unsubstituted or C1-C6alkyl- or C1-C6alkoxy-substituted C6-C20aryl; or R1 and R2 together with the nitrogen atom linking them form a —(CH2)m— ring which is uninterrupted or interrupted by —O— or by —NH—;
R3 is a cyano group; —COOR5; —CONHR5; —COR5; or —SO2R5; —CONR1R5;
R4 is a cyano group; —COOR6; —CONHR6; —COR6; or —SO2R6; —CONR2R6;
R5 and R6 are each independently of the other C1-C22alkyl; cyclo-C3-C8alkyl; or unsubstituted or C1-C6alkyl-substituted C6-C20aryl;
or R3 and R4 together or R5 and R6 together form a 5- to 7-membered, monocyclic, carbocyclic or heterocyclic ring; and
n is a number from 1 to 4.

### Claim 18 (depends on 17)

A method according to claim 17, wherein
R1 is C1-C12alkyl;
R3 is a cyano group; —COOR5; —COR5; or —SO2R5;
R4 is —COR6; or —COOR6;
R5 and R6 are each independently of the other unsubstituted or C1-C5alkyl- or C1-C5alkoxy-substituted C6-C20aryl.

### Claim 19 (depends on 1)

A cosmetic preparation comprising at least one or more compounds of formula (1) or (2) according to claim 1 with cosmetically acceptable carriers or adjuvants.