On January 26, 2017, Kane, John L., Jr.; Barberis, Claude; Czekaj, Mark; Erdman, Paul; Giese, Barret; Kothe, Michael; Le, Tieu-Binh; Liu, Jinyu; Ma, Liang; Metz, Markus; Patel, Vinod; Scholte, Andrew; Shum, Patrick; Wei, Limli published a patent.Formula: C7H6F3NO The title of the patent was Preparation of nitrogen heterocycles as colony stimulating factor-1 receptor (CSF-1R) inhibitors. And the patent contained the following:
Compounds I [A = (CR1R2)n; M = (CR4R5)m; n is 0, 1, 2, 3, 4 or 5; m is 1, 2, 3 or 4; X1 is C, N or CR7, X2, X3, X4, X5, X6 and X7 are each independently selected from N, NR7 or CR7;]. [Wherein: each R7 is independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, C2-10-alkylnyl, (C1-10-alkyl)NH, (C1-0-alkyl)2N, (C2-10-alkynyl)NH, C(:O), (C1-10-alkyl)-CO2-, (C1-10-alkyl)-CO2H, (C3-10-cycloalkyl)-CO2H, C1-10-alkoxy, R8-(C1-10-alkyl), R8-(C3-10-cycloalkyl), NR8R9, etc.;]. [Wherein: R8 and R9 are each independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, COOH, (C1-10-alkyl)CO2H, etc.; or, R8 and R9 are taken together to form a 3 to 10 member cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring;]. [X8 and X9 are each independently selected from N or C; T1, T2 and T3 is each independently selected from are each independently selected from N or CR10; wherein: each R10 is independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, C2-10-alkylnyl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C2-10-alkynyl)NH, C(:O), (C1-10-alkyl)-CO2-, (C1-10-alkyl)-CO2H, (C3-10-cycloalkyl)-CO2H, C1-10-alkoxy, etc.;]. [Y1 is O, S, NR12 or CR12R13; wherein: R12 is absent or R12 and R13 are each independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, (C1-10-alkyl)CO2H, (C3-10-cycloalkyl)CO2H, C1-10-alkoxy, etc,;]. [R1 together with the carbon to which it is attached to form a carbonyl and R2 is absent; or, R1 and R2 are each independently selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, C1-10-alkoxy, etc.;]. [R4 is selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, C1-10-alkoxy, etc.; or, R4 and R5 can be taken together with the carbon to which they are attached to form a 3 to 10 member ring;]. [R5 is absent or selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, C1-10-alkoxy, etc.;]. [R6 is selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, C2-10-alkynyl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C2-10-alkynyl)NH, C(:O), etc.;]. [R3 is N or CR16; wherein: R16 is selected from the group consisting of H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, (C1-10-alkyl)-CO2H,(C3-10-cycloalkyl)-CO2H, C1-10-alkoxy, etc.;]. [When m is 1, R16 and R4 are taken together with the carbons to which they are attached to form a compound; wherein the dashed lines represent optional double bonds;] and II [p is 0, 1, 2, 3, 4 or 5; Z = (CZ1)p; Z1 is each independently selected from H, halogen, C1-10-alkyl, C2-9-heteroalkyl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C2-10-alkynyl)NH, C1-10-alkoxy or NH2;]. [Y2 is O, S, NR17, or CR17R18, wherein R17 is absent, or R17 and R18 are each independently selected from H, C1-10-alkyl, C3-10-cycloalkyl, C2-9-heterocycloalkyl, C6-14-aryl, C2-9-heteroaryl, (C1-10-alkyl)NH, (C1-10-alkyl)2N, (C1-3-alkynyl)NH, (C1-10-alkyl)-CO2-, etc.;], or the pharmaceutically acceptable salt thereof, are described. Compounds I and II are useful as colony stimulating factor-1 receptor inhibitors (“”CSF-1R inhibitors””). Thus, 4-(1-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-1H-benzo[d]imidazol-5-yl)-2-methylbut-3-yn-2-amine (III) was prepared and tested for CSF-1R inhibition [c-FMS IC50 = 0.005 μM; Phospho c-FMS IC50 = 0,053 μM]. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Formula: C7H6F3NO
The Article related to colony stimulating factor receptor inhibitors heterocyclic compound preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C7H6F3NO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts