Detail of "626-99-3"

Reference

2,4-Pentadienoic acid derivatives having retinoid-like biological activity

2,4-Pentadienoic acid derivatives having retinoid-like biological activity. Vuligonda, Vidyasagar; Chandraratna, Roshantha A. (Allergan, USA). PCT Int. Appl. WO 9639374 A1 12 Dec 1996, 70 pp. DESIGNATED STATES: W: AL, AM, AT, AU, AZ, BB, BG, BR, BY, CA, CH, CN, CZ, DE, DK, EE, ES, FI, GB, GE, HU, IS, JP, KE, KG, KP, KR, KZ, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI; RW: AT, BE, BF, BJ, CF, CG, CH, CI, CM, DE, DK, ES, FI, FR, GA, GB, GR, IE, IT, LU, MC, ML, NL, PT, SE. (English). (World Intellectual Property Organization). CODEN: PIXXD2. CLASS: ICM: C07C069-618. ICS: C07C057-50; C07D311-58; C07D335-06; A61K031-38; A61K031-35; A61K031-23; A61K031-20. 161916-80-9 and 186134-51-0 which are cas registry numbers are also used here. APPLICATION: WO 1996-US8925 4 Jun 1996. PRIORITY: US 1995-466000 6 Jun 1995. DOCUMENT TYPE: Patent CA Section: 30 (Terpenes and Terpenoids) Section cross-reference(s): 1, 2, 25, 27, 63 Title compds. I (Z = Q, Q1; Y = cycloalkyl, cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R4, or Y = Ph, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, being optionally substituted with one or two R4 groups, the divalent Y radical being substituted by the Z and -CR1:CR1CR1:CR1 groups on adjacent carbons, X = S, O, NR5; n = 1 or 2; R1 and R2 independently are H, lower alkyl or fluoroalkyl; R3 is hydrogen, lower alkyl, Cl or Br; R4 is lower alkyl, fluoroalkyl or halogen; R5 is H or lower alkyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, or tri-lower alkylsily, where R7 is an alkyl, cycloalkyl or alkenyl group contg. 1 to 5 carbons, R8 is an alkyl group of 1 to 10 carbons, a cycloalkyl group of 5 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or R8 is Ph or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or Ph or lower alkylphenyl, R11 is lower alkyl, Ph or lower alkylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons), with retinoid biol. activity were prepd. Thus,3-methyl-2,3-methano-3-(5,5,8,8-tetramethyl-5,6,7,,8-tetrahydrona phthy-2-yl)propan-1-ol, prepd. in 5 steps from 2-ethynyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene, was oxidized to the aldehyde and treated with Et diethylphosphono-3-methyl-2(E)-butenoate followed by hydrolysis to give 3,7-dimethyl-6,7-methano-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaph thy-2-yl)-2(E),4(E)-heptadienoic acid (II). The holoreceptor transactivation assay EC50 (nanomolar) of II with the RXRa receptor subtype was 1.80. .

Metal-ammonia reduction and reductive alkylation of conjugated dienoic acids

Metal-ammonia reduction and reductive alkylation of conjugated dienoic acids. Birch, Arthur J.; Slobbe, Jacob (Res. Sch. Chem., Aust. Natl. Univ., Canberra, Aust.). Aust. J. Chem., 29(12), 2737-9 (English) 1976. CODEN: AJCHAS. DOCUMENT TYPE: Journal CA Section: 23 (Aliphatic Compounds) Conjugated dienoic acids are readily reduced or reductively alkylated with Li-NH3 to their trans-.beta.,.gamma.-unsatd. and trans-.alpha.-alkyl-.beta.,.gamma.-unsatd.In this experiment, several chemicals are used like 20515-19-9 and 626-99-3 derivs., resp. Competing protonation in the latter reaction detracts from its general use in synthesis. The protonation occurs by reaction of the dianion with the solvent. .