On January 21, 2010, Lee, Eun Kyung; Schoenfeld, Ryan Craig; Weikert, Robert James published a patent.Name: Ethyl 3-fluoro-2-methylbenzoate The title of the patent was Indole and indazole derivatives as monoamine reuptake inhibitors and their preparation, pharmaceutical compositions and use in the treatment of depression and anxiety. And the patent contained the following:
The invention discloses indole and indazole derivatives of formula I and their pharmaceutically acceptable salts, which are useful for treatment of diseases associated with monoamine deficiency. Also provided are pharmaceutical compositions, methods of using, and methods of preparing the compounds Compounds of formula I wherein A is CH, CR2 and N; Q is CH, CR1 and N; X is CH2, CH(OH) and CO; Y is (CHR5)0-2 and O(CHR5)0-2; Z1 is CH, N and CR3; Z2 is CH, S and CR3; B is (CH)0-1; R1 and R2 are independently CN, CONH2, SO2H, SO2-lower alkyl, halo, lower (halo)alkyl and lower alkoxy; R3 is lower (halo)alkyl, lower alkoxy, halo, CN, CONH2 and derivatives, NHSO2H, NHSO2-lower alkyl, and NH2 and derivatives; R4 is heterocycloalkyl and NH2 and derivatives; R5 is H, lower (hydroxy)alkyl, lower alkoxy and lower haloalkyl; with the proviso that if X is CO, Y is O(CH2)2, A, B, Q, Z1 and Z2 are CH, R1 and R3 are absent, R4 is NH(C(CH3)3), then R2 is a substitute; and their pharmaceutically acceptable salts and esters thereof, are claimed. Example compound II was prepared by a multi-step procedure starting from 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (procedure given). All the invention compounds were evaluated for their monoamine reuptake inhibitory activity. From the assay, it was determined that II exhibited the pKi values of 5.93, 6.41 and 6.95 against SERT, NEt and DAT, resp. The experimental process involved the reaction of Ethyl 3-fluoro-2-methylbenzoate(cas: 114312-57-1).Name: Ethyl 3-fluoro-2-methylbenzoate
The Article related to indole indazole preparation monoamine reuptake inhibitor treatment depression anxiety, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Name: Ethyl 3-fluoro-2-methylbenzoate
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