专利号:US-2007287843-A1 优先权日:2004-04-07 标题 :Methods and Intermediates for the Synthesis of Delta-9 Tetrahydrocannabinol 发明人:CABAJ JOHN E; PARIZA RICHARD J; LUKESH JULIE M 权利人:CABAJ JOHN E; PARIZA RICHARD J; LUKESH JULIE M 摘要:Processes are disclosed for the synthesis of Delta-9 tetrahydrocannabinol which result in an improved Y-THC/Y-THC ratio, and intermediates are disclosed that may be used in the synthesis of Delta-9 tetrahydrocannabinol such that improved Y-THCIY-THC ratios are achieved. The intermediates may be cyclic compounds prepared from 2-Carene. There is also provided a scaleable process for the preparation of (+)-p-menth-2-ene-1,8-diol, another intermediate used in the synthesis of delta-9-tetrahydrocannibinol.
专利号:US-11046978-B2 优先权日:2016-03-16 标 题:Synthesis of isoprenoids and derivatives 发明人:GONZALEZ RAMON; CLOMBURG JAMES M; CHEONG SEOKJUNG 权利人:UNIV RICE WILLIAM M 摘要:This disclosure generally relates to the use of enzyme combinations or recombinant microbes comprising same to make isoprenoid precursors, isoprenoids and derivatives thereof including prenylated aromatic compounds. Novel metabolic pathways exploiting Claisen, aldol, and acyioin condensations are used instead of the natural mevalonate (MVA) pathway or 1-deoxy-d-xylulose 5-phosphate (DXP) pathways for generating isoprenoid precursors such as isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), and geranyl pyrophosphate (GPP). These pathways have the potential for better carbon and or energy efficiency than native pathways. Both decarboxylative and non-carboxylative condensations are utilized, enabling product synthesis from a number of different starting compounds. These condensation reactions serve as a platform for the synthesis of isoprenoid precursors when utilized in combination with a variety of metabolic pathways and enzymes for carbon rearrangement and the addition/removal of functional groups. Isoprenoid alcohols are key intermediary products for the production of isoprenoid precursors in these novel synthetic metabolic pathways.
专利号:US-4895922-A 优先权日:1988-05-05 标 题 :Low temperature synthesis of polyesteramides 发明人:OGATA NAOYA 权利人:GOODYEAR TIRE & RUBBER 摘要:This invention disclosed a process for the synthesis of polyesteramides. By utilizing the phosphorus containing catalyst systems of the present invention, such polyesteramides can be synthesized at relatively low temperatures. The present invention specifically discloses a process for the synthesis of a polyesteramide which comprises polymerizing at least one diamine, at least one diol, and at least one dicarboxylic acid in the presence of (1) at least one acid acceptor; (2) at least one halogenated organic compound; and (3) at least one phosphorus containing compound selected from the group consisting of (a) triphenylphosphine, (b) triphenylphosphine oxide, (c) triphenylphosphine sulfide, (d) polymeric agents having pendant diphenylphosphine groups, (e) silicon-phosphorus compositions which contain at least one divalent oxygen atom which is bonded directly to a tetravalent silicon atom and a trivalent or pentavalent phosphorus atom; (f) compounds with the structural formula (C 6 H 5 ) 3 P=N-R, wherein R is a hydrogen atom or an alkyl group containing from 1 to 10 carbon atoms; and (g) compounds with the structural formula (C 6 H 5 )PR 1 R 2 wherein R 1 and R 2 can be the same or different, wherein R 1 is selected from the group consisting of alkyl groups containing from 1 to 10 carbon atoms and phenyl groups, and wherein R 2 is an alkyl group containing from 1 to 10 carbon atoms.
专利号:US-2020079715-A1 优先权日:2018-09-06 标题 :2-position modification for synthesis of resorcinol scaffolding 发明人:DAVIS ROBERT; BLACK JACOB; SMELTZER THOMAS; COLVIN SEAN 权利人:CANOPY HOLDINGS LLC 摘要:A resorcinol with modifications at the 2-position is provided. The reactant resorcinol may have a variety of functional groups at each of the 1, 3, and 5 position such as a hydroxide, a lower alkyl group, a phenyl, a substituted phenyl, a lower alkenyl, or a lower alkynyl sp 2 carbon group (e.g., substituted phenyl, vinyl), sp (e.g., alkyne), hydrogen. The resorcinol is modified at the 2-position with a nucleophile or an electrophile. The resulting resorcinol may serve as a stable intermediate for the synthesis of cannabinoid or cannabinoid derivatives.
专利号:US-11434217-B2 优先权日:2017-12-29 标 题 :Method for synthesis of lobaric acid and analog thereof 发明人:YIM JOUNG HAN; KIM IL-CHAN; HAN SE JONG; YOUN UI JOUNG; LEE HONG KUM; LEE JUN HYUCK; KIM TAI KYOUNG; YEO KWON JOO 权利人:KOREA INST OCEAN SCI & TECH; KOREA INSTITUTE OF OCEAN SCIENCE AND TECH 摘要:The present invention can synthesize lobaric acid and four analogues thereof, which are five phenolic lichen metabolites isolated from an extract of the Antarctic lichen Stereocaulon alpinum and selectively inhibit PTP1B, by a simple, economic and efficient chemical synthesis method.
专利号:US-12264143-B2 优先权日:2020-12-17 标 题:Synthesis of cannabinoids and cannabinoid precursors, and related compounds, formulations, and methods of use 发明人:SAMMIS GLENN M; ROGGEN MARKUS 权利人:NALU BIO INC 摘要:Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((−)-trans-Δ9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.
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合成参考文献
参考文献:10.1371/journal.pone.0021917 摘要:Brents LK, Reichard EE, Zimmerman SM, Moran JH, Fantegrossi WE, Prather PL. Phase I Hydroxylated Metabolites of the K2 Synthetic Cannabinoid JWH-018 Retain In Vitro and In Vivo Cannabinoid 1 Receptor Affinity and Activity. PLoS ONE. 2011 Jul 06;6(7):e21917. doi: 10.1371/journal.pone.0021917.