Detail of "5318-27-4"

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Preparation of 6-aminoindole and 7-amino-1,2,3,4-tetrahydroquinoline derivatives as non-peptidic neuropeptide Y (NPY) Y2 receptor inhibitors

Preparation of 6-aminoindole and 7-amino-1,2,3,4-tetrahydroquinoline derivatives as non-peptidic neuropeptide Y (NPY) Y2 receptor inhibitors. Carruthers, Nicholas I.There are some reagents like 5318-27-4 is used in this study.; Chai, Wenying; Dax, Scott L.; Jablonowski, Jill A.; Li, Xiaobing; Lovenberg, Timothy W.; Murray, William V.; Rudolph, Dale A.; Seierstad, Mark; Youngman, Mark A. (USA ). U.S. Pat. Appl. Publ. US 2005070534 A1 31 Mar 2005,34 pp. (English). (United States of America). CODEN: USXXCO. CLASS: ICM: A61K031-541. ICS: A61K031-5377; A61K031-496; A61K031-52; A61K031-497; C07D473-02; C07D417-02; C07D413-02; C07D043-02. APPLICATION: US 2004-949055 24 Sep 2004. PRIORITY: US 2003-2003/PV505462 24 Sep 2003. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 1 The title compds. (I) [wherein the fused pyrrolidine ring optionally contains a single carbon- carbon double bond or a single carbon ring member adjacent to the nitrogen is optionally :O substituted; n = 1, 2; m = 0,1, 2; Y1 = each C0-5 alkylene, alkenylene, alkynylene, or acylene -CH(CONRfRg)-, -CH(CO2C1-4 alkyl)- (where Rf, Rg = H or C1-4 alkyl); Y2 = H, Ph, C4-8 cycloalkyl, or C4-8 cycloalkenyl, wherein each ring optionally substituted; Y3 = -CH2-, carbonyl or sulfone; Y4 = (un)substituted C2-7 alkyl, C2-7 alkenyl, C2-7 alkynyl or C3-7 cycloalkyl; Y5 = each (un)substituted Ph, furanyl, thiophenyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholinyl, dithianyl, thiomorpholinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, naphthalenyl, quinolonyl, purinyl, indolyl, benzofuranyl; R1 = H CORa, SO2Ra (where Ra = H, each (un)substituted C1-5 alkyl, C1-5 alkenyl, C1-5 alkynyl, or C1-5 acyl); R2, R3 = H, each (un)substituted C1-5 alkyl, C1-5 alkenyl, or C1-5 alkynyl, or R2 and R3 may be taken together with the nitrogen of R3 attachment to form piperidine or pyrrolidine or azepine] and enantiomers, diastereomers, hydrates, solvates and pharmaceutically acceptable salts, esters and amides thereof are prepd. These compds. are novel non-peptidic NPY Y2 receptor inhibitors and useful in treating or preventing anxiolytic disorders or depression, injured mammalian nerve tissue, conditions responsive to treatment through administration of a neurotrophic factor, neurol. disorders, bone loss, substance related disorders, obesity, or an obesity-related disorder. They are also useful in modulating endocrine functions, particularly endocrine functions controlled by the pituitary and hypothalamic glands, and are therefore useful in the treatment or prevention of inovulation and infertility. Thus, to a soln. of 1-[6-(1-benzylpiperidin-4-ylamino)-2,3-dihydroindol-1-yl]ethanone > (250 mg, 0.72 mmol) in CH2Cl2 (10 mL) was added cinnamoyl chloride (160 mg, 0.93 mmol) and triethylamine (TEA, 0.30 mL, 2.2 mmol). The mixt. was stirred at 25° for 16 h to give, after purifn. by preparative TLC (PTLC, 20% EtOAc/CH2Cl2) to give 290 mg (85%) trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-N-(1-benzylpiperidin-4-yl)-3 -phenylacrylamide (II). II and trans-N-(1-acetyl-2,3-dihydro-1H-indol-6-yl)-3-(3-cyanophenyl)-N-[1-(2-c yclopentylethyl)piperidin-4-yl]acrylamide in vitro inhibited the binding of [125I]PYY to KAN-Ts endogenously expressing Y2 receptor with IC50 4.0 and 0.1 mM, resp. .