US 11,739,054 B2
Methods and compositions for substance use disorder vaccine formulations and uses thereof
Kim Janda, Rancho Dominguez, CA (US); Sam On Ho, Rancho Dominguez, CA (US); and Gary Fujii, Rancho Dominguez, CA (US)
Assigned to MOLECULAR EXPRESS, INC., Rancho Dominguez, CA (US)
Filed by MOLECULAR EXPRESS, INC., Rancho Dominguez, CA (US)
Filed on Dec. 21, 2020, as Appl. No. 17/129,712.
Application 17/129,712 is a continuation of application No. 16/621,224, abandoned, previously published as PCT/US2018/036904, filed on Jun. 11, 2018.
Claims priority of provisional application 62/517,973, filed on Jun. 11, 2017.
Prior Publication US 2021/0107862 A1, Apr. 15, 2021
Int. Cl. C07C 233/54 (2006.01); A61P 25/30 (2006.01); A61K 39/00 (2006.01); A61K 39/385 (2006.01)
CPC C07C 233/54 (2013.01) [A61K 39/0013 (2013.01); A61K 39/385 (2013.01); A61P 25/30 (2018.01); A61K 2039/55505 (2013.01); A61K 2039/55555 (2013.01); A61K 2039/55561 (2013.01); A61K 2039/6012 (2013.01); A61K 2039/6037 (2013.01); A61K 2039/627 (2013.01)] 9 Claims
 
1. A method of stimulating an immune response to methamphetamine, comprising:
immunizing an animal by administering to the animal a conjugate comprising one or more compounds having a general formula:

OG Complex Work Unit Chemistry
wherein
R1 is —(O—CH2—CH2)p—, wherein p is 1 to 6, or R1 is an optionally substituted C1-6 alkyl, wherein substitution(s) are independently selected from the group consisting of —NO2, —NH2, —OH, ═O, —COOR′ where R′ is H or lower alkyl, —CH2OH, and —CONH2,
R2 is peptide of m amino acid residues, an alkylene oxide of m alkylene oxide monomers, or (CH2)m, where m=2 to 6; and
R3 is selected from the group consisting of a protected or unprotected maleimide, alkyl halide, aryl halide, alpha-haloacyl, pyridyl disulfide, aldehyde, ketone, carboxyl, thiol, thioester, disulfide, N-hydroxy-succinimide, or cyclic thiolactone,
or salts thereof, wherein the one or more compounds or salts thereof are covalently bound through R3 on the compound(s) to a corresponding coupling site on a protein, polypeptide, detectable label, nucleic acid, or solid phase to provide the conjugate.