On July 24, 2014, Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; Yuan, Shendong published a patent.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the patent was N-Heteroaryl carbamates as lysophosphatidic acid receptor antagonists and their preparation. And the patent contained the following:
Compounds of formula I, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided. Compounds of formula I wherein one of and B is acetylene and the other is (un)substituted 6- to 11-membered aryl, (un)substituted 5- to 11- membered heteroaryl, (un)substituted 4- to 11-membered heterocyclyl and (un)substituted 4- to 11-membered carbocyclyl; G is (un)substituted 6- to 11-membered aryl, (un)substituted 5- to 11- membered heteroaryl, (un)substituted 5- to 11-membered heterocyclyl and (un)substituted 5- to 11-membered carbocyclyl; D is OH, CO2H and derivatives, CONH2 and derivatives, azolyl, etc.; E is (un)substituted 6- to 10-membered arylene, (un)substituted 3- to 11-membered carbocyclyl, (un)substituted 3- to 11-membered heterocyclyl and (un)substituted 5- to 10-membered heteroarylene; J is (CR4R5)0-3; K is (CR2’R3′)n; M is (CR2R3)m; n and m are independently 0 – 3, provided that the sum of m + n is equal or greater than 1; L1 and L2 are independently a bond, CH2, CC, etc.; L3 is azolyl, thienyl, aminosulfonyl, etc.; L5 is single bond, CH=CH, CC, etc.; dashed bonds are single and double bonds; each Y is independently absent CR9, C(R9)2, N and NH, provided that only one of Y can be absent; R2, R2′, R3 and R3′ are independently H, halo, alkyl, haloalkyl, etc.; R4, R5 and R9 are independently H and (un)substituted alkyl; R4R5 or two adjacent R9 can be taken together to form (un)substituted cycloalkyl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their LPA antagonistic activity. From the assay, it was determined that compound II exhibited EC50 value in the range of greater than or equal to 50 nM and less than or equal to 500 nM. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate
The Article related to heteroaryl carbamate preparation lysophosphatidic acid receptor antagonist, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of Methyl 2-(6-bromo-1H-indol-3-yl)acetate
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles