C4-carboxylic acid-substituted tryptamine derivatives and methods of using
Disclosed are novel C 4 -carboxylic acid-substituted tryptamine derivative compounds and pharmaceutical and recreational drug formulations containing the same. The pharmaceutical formulations may be used to treat brain neurological disorders.
1. A method of synthesizing a chemical compound having chemical formula (I):
wherein R 4 is a carboxylic acid moiety or a derivative thereof, wherein the carboxylic acid moiety or derivative thereof has the chemical formula (II):
wherein the method involves:
reacting a chemical compound having chemical formula (III):
with an acyl chloride having the chemical formula (IV):
under reaction conditions sufficient to form the compound having chemical formula (I), wherein in chemical formula (II) and chemical formula (IV) R 4a are identical and R 4a is a substituted phenyl group, a heteroaryl group, a substituted heteroaryl group,
an amine group, or a substituted amine group,
wherein
the substituted phenyl group is selected from, (i) a trifluoromethylated phenyl group, (ii) a trifluoromethoxy phenyl group, (iii) a phenyl group in which two substituents on the phenyl group are joined together to form an additional 5-7-membered carbocyclic or heterocyclic ring, and (iv) a phenyl group substituted with an alkoxy group, a substituted alkoxy group, an acetamidyl group, an alkoxycarbonyl group, or a substituted heteroaryl-carbonyl group (heteroaryl-O—C(═O)—),
and
wherein in chemical formula (I) and chemical formula (III) R 3a are identical, R 3b are identical, and R 3a and R 3b are each independently a hydrogen atom, an alkyl group, or aryl group.
2. A method according to claim 1 , wherein the substituted heteroaryl group is a substituted pyridine group.
3. A method according to claim 1 , wherein the compound having chemical formula (I) is a compound having chemical formula C(V):
the compound having formula (III) is a compound having chemical formula A(I):
and
the compound having formula (IV) is a compound having chemical formula B(I):
4. A method according to claim 3 , wherein the compound having chemical formula A(I) and the compound having chemical formula B(I) are reacted in the presence of a base selected from triethylamine (Et 3 N) and N,N-diisopropylethylamine (DIPEA).
5. A method of synthesizing a chemical compound having chemical formula C(VI):
wherein the method involves:
reacting a chemical compound having chemical formula A(I):
with an acyl chloride having chemical formula B(I):
under reaction conditions sufficient to form the compound having chemical formula C(VI).
6. A method according to claim 5 , wherein the compound having chemical formula A(I) and the compound having chemical formula B(III) are reacted in the presence of a base selected from triethylamine (Et 3 N) and N,N-diisopropylethylamine (DIPEA).
7. A method according to claim 1 , wherein the compound having chemical formula (I) is a compound having formula C(VII):
the compound having formula (III) is a compound having chemical formula A(I):
and
the compound having formula (IV) is a compound having chemical formula B(IV):
8. A method according to claim 7 , wherein the compound having chemical formula A(I) and the compound having chemical formula B(IV) are reacted in the presence of a base selected from triethylamine (Et 3 N) and N,N-diisopropylethylamine (DIPEA).
9. A method according to claim 1 , wherein the compound having chemical formula (I) is a compound having formula C(XLIII):
the compound having formula (III) is a compound having chemical formula A(I):
and
the compound having formula (IV) is a compound having chemical formula B(VI):
10. A method according to claim 9 , wherein the compound having chemical formula A(I) and the compound having chemical formula B(VI) are reacted in the presence of a base selected from triethylamine (Et 3 N) and N,N-diisopropylethylamine (DIPEA).
11. A method of synthesizing a chemical compound having chemical formula C(I):
wherein the method involves:
reacting a chemical compound having chemical formula A(I):
with an acyl chloride having chemical formula B(VII):
under reaction conditions sufficient to form the compound having chemical formula C(I).
12. A method according to claim 11 , wherein the compound having chemical formula A(I) and the compound having chemical formula B(VII) are reacted in the presence of a base selected from triethylamine (Et 3 N) and N,N-diisopropylethylamine (DIPEA).
13. A method according to claim 1 , wherein
the compound having chemical formula (I) is a compound having formula C(XX):
the compound having formula (III) is a compound having chemical formula A(I):
and
the compound having formula (IV) is a compound having chemical formula B(VIII):
14. A method according to claim 13 , wherein the compound having chemical formula A(I) and the compound having chemical formula B(VII) are reacted in the presence of a base selected from triethylamine (Et 3 N) and N,N-diisopropylethylamine (DIPEA).
15. A method according to claim 1 , wherein the alkoxycarbonyl group is a methoxycarbonyl (CH 3 OC(═O)—).
16. A method according to claim 2 , wherein the substituted pyridine group is selected from (i) an O-alkylated pyridine group, (ii) an O-arylated pyridine group, and (iii) a halogenated pyridine group.