International Flavors & Fragrances Inc.

Merck Sharp + Dohme Corp.

Tao Pei

Mark Lawrence Dewis

Garry Conklin

David O Agyemang

Zhiguo Jake Song

Michelle E Huber

Adam Jan Janczuk

Michael Vernie Cossette

John S Wai

Peter D Williams

Catherine Marie Smith

Feng Xu

Guy R Humphrey

Shankar Venkatraman

Wayne J Thompson

Dai-Shi Su

Mark W Embrey

Peter Emmanuel Maligres

Tao Wang

Thorsten E Fisher

Laura Marie Artino

Jingjun Yin

David C Dubost

Kathryn Bardsley

Thumplasseril V John

Markus A Eckert

Neil A Strotman

Neil C Da Costa

Michael Shevlin

Jan Herman Colstee

Richard C A Isaacs

Richard G Ball

Dietrich P Steinhuebel

Matthew L Maddess

Eric J Choi

Neil Campbell

Sarah L Trice

Garry Conkiln

The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams from the intermediates. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. HCV NS3 inhibitory compounds have therapeutic and research applications.

Process and intermediates for preparing macrolactams

Compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: wherein X, X, Y, R, R, Rand Rare defined herein. The compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset or progression of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se (or as hydrates or solvates thereof) or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Processes for making compounds of Formula I and intermediates thereof are also described.

HIV integrase inhibitors

Alkyldienamides compounds suitable for use as flavoring agents are disclosed. The compounds are used as flavors since they possess umami characteristics or other desirable organoleptic properties. The disclosed compounds are defined by the structure set forth below: 

Alkyldienamides exhibiting taste and sensory effect in flavor compositions

The present invention relates to novel compounds having sweet, salt or umami taste enhancement qualities. These compounds have the structure:  where Ris H or methyl;Ris selected from the group consisting of H, C1-C4 alkyl, alkenyl;Ris selected from the group consisting of H, phenyl, C1-C10 straight or branched chain alkyl, alkenyl, alkynyl, alkyldienyl, acyclic or containing no more than one ring, which contains no more than a total of five heteroatoms selected from F, O, S, N, and P; and if R&#x2550;H, Rand Rtaken together can represent cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl, which contains no more than two of each heteroatom selected from N, O, and S;or if R, Rand Rtaken together can represent one, or two aromatic rings, which contain no more than three of each heteroatom selected from F, N, S, and O.Ris selected from the group consisting of H, methyl or ethyl;Ris selected from the group consisting of H, methyl and ethyl;Ris selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;except for in the case of structurewhen if R&#x2550;H or methyl and R&#x2550;H or methyl, Ras described above and phenyl;or when R, R, and Rtaken together can be equal to Ris selected from the group consisting C1-C4 alkyl, or alkenyl.

Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions

Saturated and unsaturated compounds having sweet, salt or umami taste enhancement qualities. The compounds have the structure:  cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;

Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions

Compounds suitable for use as flavoring agents are disclosed. The compounds are used as flavors since they possess umami characteristics or other desirable organoleptic properties. The disclosed compounds are defined by the structure set forth below:  where X is selected from the group consisting of H, methyl, ethyl, n-propyl, and isopropyl; Y is selected from the group consisting of methyl, ethyl, cyclopropyl, isopropyl, n-propyl, n-butyl, sec-butyl, isobutyl, 2-methylbutyl, allyl, cyclobutyl, cyclopentyl, CHCH(OH)CH, CH(CH)CHOH, CHC(CH)OH, CHCHOH, CHCOCH, geranyl, neryl; or X and Y together form the structures  Ris selected from the group consisting of methyl and H; Ris selected from the group consisting of methyl and H; 

The present invention relates to thioester compounds and the incorporation and use of the new chemical entities as flavor and fragrance chemicals.

Thioester compounds and their use in fragrance or flavor applications

The present invention is directed to novel compounds and a process for augmenting or imparting a flavor enhancement effect or modifying the perception of one or more of the five basic taste qualities sweet, sour, salt, bitter and umami, to a foodstuff, chewing gum, medicinal product, toothpaste, alcoholic beverage, aqueous beverage, snack, sauce or soup comprising the step of adding to a foodstuff, chewing gum, medicinal product, toothpaste, alcoholic beverage, aqueous beverage, snack, sauce or soup a flavor enhancement or modification of basic taste quality augmenting, enhancing or imparting quantity and concentration of at least one N-substituted unsaturated alkyl amide defined according to the structures: 

Saturated and unsaturated compounds having sweet, salt or umami taste enhancement qualities. The compounds have the structure: where R&#x2550;H or methyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;

Described are mixtures of at least four of the alkadienamides defined according to the structure: wherein R represents C-Cn-alkyl; Ris 2-methyl-1-propyl and Ris hydrogen, or Rand Rtaken together is a moiety having the formula wherein n is 4 or 5, or compositions containing substantial concentrations of such mixtures, prepared according to novel processes: (a) extraction of a ground substantially dried fruit of one of thespecies,Linn or; (b) natural product-forming synthesis; or (c) synthetic product-forming synthesis. Also described are uses of the thus-formed products for augmenting, enhancing or imparting an aroma, taste, chemesthetic effect and/or antibacterial effect in or to a consumable material and/or in the oral cavity and/or on the mammalian epidermis.

Conjugated dienamides, methods of production thereof, compositions containing same and uses thereof

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Morganville, NJ, United States of America

Tao Pei