On March 24, 2005, Le Grand, Darren Mark published a patent.COA of Formula: C9H11Cl2NO The title of the patent was Preparation of 1,3-disubstituted azetidine derivatives for use as CCR-3 receptor antagonists in the treatment of inflammatory and allergic diseases. And the patent contained the following:
Compounds of formula I and II [Ar = Ph optionally substituted by one or more substituents selected from halo, C1-C8-alkyl, cyano, nitro; X1 = S, S(O), S(O)2; X2 = C(O), O, CH2, S, S(O), S(O)2; m = 1, 2, 3, 4; R1 = H, C1-C8-alkyl optionally substituted; Q = C(Rb)(Rc) where Rb and Rc are independently C1-C8-alkyl or Rb and Rc together form a C3-C10-cycloalkyl; Y = O, S; R2 = H, C1-C8-alkyl, C3-C10-cycloalkyl; R3 = C1-C8-alkyl substituted by Ph, phenoxy, acyloxy, naphthyl, or R3 is C3-C10-cycloalkyl optionally having a benzo group, a heterocyclic group] were prepared and are useful for treating conditions that are mediated by CCR-3, for example an inflammatory or allergic condition, particularly an inflammatory or obstructive airways disease. E.g., 1-benzhydryl-3-(4-chlorophenylsulfanyl)azetidine was oxidized with MCPBA, and treated with 1-chloroethoxycarbonyl chloride to give 3-(4-chlorobenzenesulfinyl)azetidine. Reaction of the latter with [(S)-1-(tert-butyldiphenylsilanyloxymethyl)-3-iodopropyl]carbamic acid tert-Bu ester gave [(S)-1-(tert-butyldiphenylsilanyloxymethyl)-3-[3-(4-chlorophenylsulfinyl)azetidin-1-yl]propyl]carbamic acid tert-Bu ester. The latter was desilylated, then treated with TFA to give (S)-2-amino-4-[3-(4-chlorobenzenesulfinyl)azetidin-1-yl]butan-1-ol. Reaction of the latter with 3,5-dimethoxyphenyl isocyanate resulted in 1-[(S)-3-[3-(4-chlorobenzenesulfinyl)azetidin-1-yl]-1-hydroxymethylpropyl]-3-(3,5-dimethoxyphenyl)urea. The experimental process involved the reaction of 3-(4-Chlorophenoxy)azetidine hydrochloride(cas: 490021-97-1).COA of Formula: C9H11Cl2NO
The Article related to inflammatory allergic disease treatment azetidine derivative preparation, azetidine derivative preparation ccr3 receptor antagonist, Heterocyclic Compounds (One Hetero Atom): 4-Membered Rings and other aspects.COA of Formula: C9H11Cl2NO
Referemce:
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