CA2352765A1 - Hapten-carrier conjugates for treating and preventing nicotine addiction - Google Patents

Hapten-carrier conjugates for treating and preventing nicotine addiction Download PDF

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Publication number
CA2352765A1
CA2352765A1 CA002352765A CA2352765A CA2352765A1 CA 2352765 A1 CA2352765 A1 CA 2352765A1 CA 002352765 A CA002352765 A CA 002352765A CA 2352765 A CA2352765 A CA 2352765A CA 2352765 A1 CA2352765 A1 CA 2352765A1
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CA
Canada
Prior art keywords
antibody
hapten
conjugate
administering
carrier
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002352765A
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French (fr)
Other versions
CA2352765C (en
Inventor
Sofiane Ennifar
Ali Ibrahim Fattom
Robert B. Naso
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Nabi Biopharmaceuticals Inc
Original Assignee
Nabi
Sofiane Ennifar
Ali Ibrahim Fattom
Robert B. Naso
Nabi Biopharmaceuticals
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Application filed by Nabi, Sofiane Ennifar, Ali Ibrahim Fattom, Robert B. Naso, Nabi Biopharmaceuticals filed Critical Nabi
Publication of CA2352765A1 publication Critical patent/CA2352765A1/en
Application granted granted Critical
Publication of CA2352765C publication Critical patent/CA2352765C/en
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/0013—Therapeutic immunisation against small organic molecules, e.g. cocaine, nicotine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A61K47/646—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/44—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material not provided for elsewhere, e.g. haptens, metals, DNA, RNA, amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/505—Medicinal preparations containing antigens or antibodies comprising antibodies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
    • A61K2039/6031—Proteins
    • A61K2039/6037—Bacterial toxins, e.g. diphteria toxoid [DT], tetanus toxoid [TT]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
    • A61K2039/6031—Proteins
    • A61K2039/6068—Other bacterial proteins, e.g. OMP
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/975—Kit
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S436/00—Chemistry: analytical and immunological testing
    • Y10S436/815—Test for named compound or class of compounds
    • Y10S436/816—Alkaloids, amphetamines, and barbiturates
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/807—Hapten conjugated with peptide or protein

Abstract

Novel hapten-carrier conjugates are capable of inducing the production of antibodies, in vivo, that specifically bind to nicotine. These conjugates comprise a nicotine hapten conjugated to an immunogenic carrier protein. The novel conjugates preserve the chirality of nicotine in its native (S)-(-) state, and have good stability properties. The conjugates are useful in formulating vaccines for active immunization, that are used to prevent and treat nicotine addiction. The antibodies raised in response to the nicotine hapten-carrier conjugate are used for passive immunization. These antibodies are administered for prevention and treatment of nicotine addiction.

Claims (35)

1. A hapten-carrier conjugate of the following formula:

wherein m is 1 to 2500, n is 0 to 12, y is 1 to 12, X is selected from the group consisting of NH-CO, CO-NH, CO-NH-NH, NH-NH-CO, NH-CO-NH, CO-NH-NH-CO, and S-S;
Y is selected from the group consisting of NH-CO, CO-NH, CO-NH-NH, NH-NH-CO, NH-CO-NH, CO-NH-NH-CO, and S-S, and the -(CH2)n-X-(CH2)y-Y- moiety is bonded to the 3', 4' or 5' position.
2. The conjugate of claim 1, wherein m is 11 to 17, n is 1, y is 2, X is NH-CO, Y is CO-NH, wherein the carrier protein is exoprotein A and the -(CH2 )n-X-(CH2)y-Y- is bonded to the 3' position.
3. The conjugate of claim 1, wherein m is 11 to 17, n is 1, y is 2, X is NH-CO, Y is CO-NH, wherein the carrier protein is exoprotein A and the -(CH2 )n-X-(CH2)y-Y- is bonded to the 4' position.
4. The conjugate of claim 1, wherein m is 11 to 17, n is 1, y is 2, X is NH-CO, Y is CO-NH, wherein the carrier protein is exoprotein A and the -(CH2)n-X-(CH2)Y-Y- is bonded to the 5' position.
5. The conjugate of claim 1, wherein m is selected from the group consisting of 1 to 20 and 1 to 200.
6. A hapten-carrier conjugate of the following formula:

wherein n is 0 to 12, j is 1 to 1000, k is 1 to 20, and E is an amino acid-containing matrix.
7. The hapten-carrier conjugate of claim 6, wherein the matrix is poly-L-glutamic acid.
8. An antibody produced in response to the hapten-carrier conjugate of claim 1.
9. A functional fragment of the antibody of claim 8.
10. The antibody of claim 8, which is a monoclonal antibody.
11. The antibody of claim 8, which is a polyclonal antibody.
12. An antibody produced in response to the hapten-carrier conjugate of claim 6.
13. A functional fragment of the antibody of claim 12.
14. The antibody of claim 12, which is a monoclonal antibody.
15. The antibody of claim 12, which is a polyclonal antibody.
16. A method of treating nicotine addiction in a patient in need of such treatment comprising administering a therapeutically effective amount of the hapten-carrier conjugate of claim 1.
17. A method of treating nicotine addiction in a patient in need of such treatment comprising administering a therapeutically effective amount of the antibody of claim 8.
18. A method of preventing nicotine addiction in a patient in need of such prevention, comprising administering a therapeutically effective amount of the hapten-carrier conjugate of claim 1.
19. A method of preventing nicotine addiction in a patient in need of such treatment comprising administering a therapeutically effective amount of the antibody of claim 8.
20. The method of claim 16, further comprising administering a compound that is useful in the treatment of addiction.
21. A method of treating nicotine addiction in a patient in need of such treatment comprising administering a therapeutically effective amount of the hapten-carrier conjugate of claim 6.
22. The method of claim 21, further comprising administering a compound that is useful in the treatment of addiction.
23. A method of treating nicotine addiction in a patient in need of such treatment comprising administering a therapeutically effective amount of the antibody of claim 12.
24. A method of preventing nicotine addiction in a patient in need of such prevention, comprising administering a therapeutically effective amount of the hapten-carrier conjugate of claim 6.
25. A method of preventing nicotine addiction in a patient in need of such treatment comprising administering a therapeutically effective amount of the antibody of claim 12.
26. A process for producing an antibody, comprising immunizing a host mammal with the hapten-carrier conjugate of claim 1.
27. The process of claim 26, wherein the antibody is monoclonal.
28. The process of claim 26, wherein the antibody is polyclonal.
29. A process for producing an antibody, comprising immunizing a host mammal with the hapten-carrier conjugate of claim 6.
30. The process of claim 29, wherein the antibody is monoclonal.
31. The process of claim 29, wherein the antibody is polyclonal.
32. A vaccine composition comprising at least one conjugate of claim 1.
33. A vaccine composition comprising at least one conjugate of claim 6.
34. A kit for determining the presence of nicotine in a sample, comprising an antibody of claim 8.
35. A kit for determining the presence of nicotine in a sample, comprising an antibody of claim 12.
CA2352765A 1998-12-01 1999-12-01 Hapten-carrier conjugates for treating and preventing nicotine addiction Expired - Fee Related CA2352765C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/201,800 1998-12-01
US09/201,800 US6232082B1 (en) 1998-12-01 1998-12-01 Hapten-carrier conjugates for treating and preventing nicotine addiction
PCT/US1999/028272 WO2000032239A1 (en) 1998-12-01 1999-12-01 Hapten-carrier conjugates for treating and preventing nicotine addiction

Publications (2)

Publication Number Publication Date
CA2352765A1 true CA2352765A1 (en) 2000-06-08
CA2352765C CA2352765C (en) 2011-02-15

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ID=22747358

Family Applications (1)

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CA2352765A Expired - Fee Related CA2352765C (en) 1998-12-01 1999-12-01 Hapten-carrier conjugates for treating and preventing nicotine addiction

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US (7) US6232082B1 (en)
EP (3) EP2324855A1 (en)
JP (2) JP4971542B2 (en)
KR (1) KR100656836B1 (en)
CN (2) CN100586481C (en)
AT (1) ATE279211T1 (en)
AU (1) AU763001B2 (en)
BR (1) BR9915852A (en)
CA (1) CA2352765C (en)
DE (1) DE69921178T2 (en)
DK (1) DK1135166T3 (en)
EA (1) EA004956B1 (en)
ES (1) ES2229800T3 (en)
HK (3) HK1042428B (en)
HU (1) HUP0104365A3 (en)
IL (2) IL143474A0 (en)
ME (1) MEP34208A (en)
MX (1) MXPA01005511A (en)
NO (1) NO331998B1 (en)
NZ (1) NZ512103A (en)
PL (1) PL199253B1 (en)
PT (1) PT1135166E (en)
RS (1) RS51273B (en)
TR (1) TR200102411T2 (en)
WO (1) WO2000032239A1 (en)
ZA (1) ZA200104477B (en)

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