# US 2014/0155585 A1 · Haptens of risperidone and paliperidone

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- Number: US 2014/0155585 A1
- Document ID: US20140155585A1
- Status: Published application
- Kind: A1
- Application number: 13/970,673
- Filed: 2013-08-20
- Published: 2014-06-05
- Earliest claimed: 2012-08-21
- Assignees: Ortho-Clinical Diagnostics, Inc.; Janssen Pharmaceutica NV
- Applicants: Ortho-Clinical Diagnostics, Inc.; Janssen Pharmaceutica NV
- Inventors: Pieter Rik HASPESLAGH; Maarten VLIEGEN; Eric HRYHORENKO; Thomas R. DeCORY; Banumathi SANKARAN
- Web page: https://patentgrep.com/patent/US20140155585A1

## CPC

- C07K 16/44: against material not provided for elsewhere {, e.g. haptens, metals, DNA, RNA, amino acids}
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to compounds of Formula I, wherein R1 and R2 are defined in the specification, useful for the synthesis of novel conjugates and immunogens derived from risperidone and paliperidone. The invention also relates to conjugates of a risperidone or paliperidone hapten and a protein.

## Claims

### Claim 1

The compound of Formula I
wherein:
R1 is H, or OH;
R2 is O(CH2)rNH2,
O(CH2)rNHC(O)(CH2)mCO2H, or Z—(Y)p-G;
wherein:
Z is selected from the group consisting of:
—N(R4)—, —O—, —S—, -heteroalkyl-;
R4 is H, an alkyl group, cycloalkyl group, aralkyl group or substituted or unsubstituted aryl group;
Y is an organic spacer group;
G is a functional linking group capable of binding to a carrier;
p is 0, or 1;
r is 1, 2, 3, 4, or 5;
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.

### Claim 2 (depends on 1)

The compound of claim 1
wherein:
R1 is H, or OH;
R2 is O(CH2)rNH2,
O(CH2)rNHC(O)(CH2)mCO2H, or Z—(Y)p-G;
wherein:
Z is O;
Y is an organic spacer group;
G is a functional linking group capable of binding to a carrier;
p is 0, or 1;
r is 1, 2, 3, 4, or 5;
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.

### Claim 3 (depends on 1)

The compound of claim 1
wherein:
R1 is H, or OH;
R2 is O(CH2)rNH2,
O(CH2)rNHC(O)(CH2)mCO2H, or Z—(Y)p-G;
wherein:
Z is O(CH2)rNH;
Y is an organic spacer group;
G is a functional linking group capable of binding to a carrier;
p is 0, or 1;
r is 1, 2, 3, 4, or 5;
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.

### Claim 4 (depends on 3)

The compound of claim 3
wherein:
p is 1;
r is 2.
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.

### Claim 5 (depends on 3)

The compound of claim 3
wherein
R1 is H, or OH;
R2 is O(CH2)rNH2,
or
O(CH2)rNHC(O)(CH2)mCO2H;
wherein:
r is 2;
m is 1, 2, 3, or 4; and
n is 1, or 2.

### Claim 6 (depends on 5)

The compound of claim 5, wherein
R1 is H, or OH; and
R2 is O(CH2)rNH2, or
r is 2;
m is 1.

### Claim 7 (depends on 1)

The compound of claim 1, selected from the group consisting of

### Claim 8 (depends on 1)

A conjugate of a compound of claim 1 and an immunogenic carrier.

### Claim 9 (depends on 8)

The conjugate of claim 8, where said immunogenic carrier is a protein.

### Claim 10 (depends on 9)

The conjugate of claim 9, where said protein is keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

### Claim 11 (depends on 2)

A conjugate of the compound of claim 2 and an immunogenic carrier.

### Claim 12 (depends on 3)

A conjugate of the compound of claim 3 and an immunogenic carrier.

### Claim 13 (depends on 4)

A conjugate of the compound of claim 4 and an immunogenic carrier.

### Claim 14 (depends on 5)

A conjugate of the compound of claim 5 and an immunogenic carrier.

### Claim 15 (depends on 6)

A conjugate of the compound of claim 6 and an immunogenic carrier.

### Claim 16 (depends on 8)

The conjugate of claim 8 wherein the compound is

### Claim 17 (depends on 16)

The conjugate of claim 16, where said immunogenic carrier is a protein.

### Claim 18 (depends on 17)

The conjugate of claim 17, where said protein is keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

### Claim 19 (depends on 1)

A product made by the process of contacting a compound of claim 1 with an immunogenic carrier.

### Claim 20 (depends on 2)

A product made by the process of contacting a compound of claim 2 with an immunogenic carrier.

### Claim 21 (depends on 3)

A product made by the process of contacting the compound of claim 3 with an immunogenic carrier.

### Claim 22 (depends on 4)

A product made by the process of contacting the compound of claim 4 with an immunogenic carrier.

### Claim 23 (depends on 5)

A product made by the process of contacting the compound of claim 5 with an immunogenic carrier.

### Claim 24 (depends on 6)

A product made by the process of contacting the compound of claim 6 with an immunogenic carrier.

### Claim 25 (depends on 19)

The product of claim 19 wherein the immunogenic carrier is a protein.

### Claim 26 (depends on 25)

The product of claim 25 wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.

### Claim 27 (depends on 19)

The product of claim 19 wherein the compound is

### Claim 28 (depends on 27)

The product of claim 27 wherein the immunogenic carrier is a protein.

### Claim 29 (depends on 28)

The product of claim 28 wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.