US 12,129,222 B2
Production of bitter principle derivatives
Ralf Wyrwa, Rothenstein (DE); Claudia Rode, Jena (DE); Thomas Seemann, Bucha (DE); Lorenz Meinel, Wuerzburg (DE); Jennifer Ritzer, Estenfeld (DE); and Matthias Schnabelrauch, Jena (DE)
Assigned to Julius-Maximilians-Universitaet, Wuerzburg (DE)
Appl. No. 16/324,758
Filed by Julius-Maximilians-Universitaet Wuerzburg, Wuerzburg (DE)
PCT Filed Aug. 11, 2017, PCT No. PCT/EP2017/070450
§ 371(c)(1), (2) Date Feb. 11, 2019,
PCT Pub. No. WO2018/029347, PCT Pub. Date Feb. 15, 2018.
Claims priority of application No. 10 2016 009 766.3 (DE), filed on Aug. 11, 2016.
Prior Publication US 2019/0185416 A1, Jun. 20, 2019
Int. Cl. C07C 237/04 (2006.01); A61K 47/18 (2017.01); A61K 47/54 (2017.01); A61K 47/65 (2017.01); C07C 231/12 (2006.01); C07C 233/07 (2006.01); C07C 269/04 (2006.01)
CPC C07C 237/04 (2013.01) [A61K 47/186 (2013.01); A61K 47/54 (2017.08); A61K 47/65 (2017.08); C07C 231/12 (2013.01); C07C 233/07 (2013.01); C07C 269/04 (2013.01)] 3 Claims
 
1. A compound of general formula 1

OG Complex Work Unit Chemistry
wherein:
(i) X− represents halogenide, sulphate, benzoate, acetate, trifluoroacetate, hydroxide, saccharinate, or capsaicinate,
(ii) R1-R10 independently represent:
(a) hydrogen,
(b) halogen,
(c) C1-C5 alkyl,
(d) C1-C4 alkoxy,
(e) C1-C20 alkoxycarbonyl
(f) —NH—P or —O—P, wherein P is a hydrogen
or a residue consisting of 1-30 amino acids selected from the group consisting of D-amino acids, L-amino acids and unnatural amino acids, wherein said amino acids are optionally modified for coupling,
(g) —(Y)n—COOM with M=Na, K, or [N(R12)4]+, or
(h) —(Y)n—C(O)NR14R15, further wherein Y represents an organic residue selected from the group consisting of: —CH2, —CH(CH3)—, —CH2—CH2—, —(CH2)3—, —CH═CH—, —C≡C—, —O—CH2—CH2—, —O—CH2—CH2—O—CH2—CH2—, and —NH—CH2—CH2— and n=0 or 1,
(iii) R14 and R15 represent hydrogen, a C1-C12 alkyl, or a residue consisting of 1-30 amino acids selected from the group consisting of D-amino acids, L-amino acids and unnatural amino acids, and
(iv) at least one of the residues R1-R10 is a (a) —(Y)n—COOM or (b) —(Y)n—C(O)NR14R15, wherein Y, M, R14, and R15 are as defined above, and
(v) R11 and R12 independently represent hydrogen or a C1-C10 alkyl residue.