GB1489359A - Alicyclic carboxamides having physiological cooling activity - Google Patents

Alicyclic carboxamides having physiological cooling activity

Info

Publication number
GB1489359A
GB1489359A GB50801/76A GB5080176A GB1489359A GB 1489359 A GB1489359 A GB 1489359A GB 50801/76 A GB50801/76 A GB 50801/76A GB 5080176 A GB5080176 A GB 5080176A GB 1489359 A GB1489359 A GB 1489359A
Authority
GB
United Kingdom
Prior art keywords
group
carbon atoms
prepared
alkyl
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB50801/76A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wilkinson Sword Ltd
Original Assignee
Wilkinson Sword Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wilkinson Sword Ltd filed Critical Wilkinson Sword Ltd
Priority to GB50801/76A priority Critical patent/GB1489359A/en
Publication of GB1489359A publication Critical patent/GB1489359A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/413—Saturated compounds containing a keto group being part of a ring of a seven- to twelve-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1489359 Cycloalkane-carboxamides WILKINSON SWORD Ltd 11 Dec 1974 [12 Dec 1973] 50801/76 Divided out of 1471894 Heading C2C Novel compounds I n is 0 or an integer of from 2-6 inclusive; R is C 1 -C 5 alkyl; x is an integer of from 1-3, with the proviso that at least one R group is in a 1-, 2- or 3-position relative to the carboxamide group, the values of R, n and x being such that the total number of carbon atoms provided by the R groups and the carbocycle to which they are attached is from 8-14, preferably 8-12 and that when x is 2 or 3, each R is the same or different; and R<SP>11</SP>, when taken separately, is H or C 1 -C 10 alkyl; R<SP>111</SP>, when taken separately, is H, C 1 -C 10 alkyl, hydroxy C 1 -C 10 alkyl, or alkoxycarbonylalkyl of up to 8 carbon atoms, with the proviso that when R<SP>11</SP> is H, R<SP>111</SP> may also be cycloalkyl of up to 8 carbon atoms, phenyl or substituted phenyl containing alkyl, hydroxy or methoxy substituents and a total of up to 10 carbon atoms; and R<SP>11</SP> and R<SP>111</SP>, when taken together represent an alkylene group of up to 8 carbon atoms, the carbon atom chain of which may optionally be interrupted by an oxygen atom; with the provisos that: (i) where n is 0 and x is 2, with one R group being isopropyl in the 1-position and the other R group being in the 2-position, then said other R group contains at least 2 carbon atoms, when R<SP>11</SP> is H and R<SP>111</SP> is phenyl; and (ii) where n is 0 and x is 2, with one R group being isopropyl in the 3-position and the other R group being in the 1-position, then said other R group contains at least 2 carbon atoms, when R<SP>11</SP> and R<SP>111</SP> are both ethyl, are prepared by conversion of the corresponding acid to the amide by conventional procedures. 2 - Isopropylcycloheptone - carboxylic acid is prepared by reacting a Schiffs base of cycloheptanone with isoPrI and acid hydrolysis to give 2-isopropylcycloheptanone which undergoes a Grignard reaction with EtOCH 2 MgCl followed by treatment with Ag 2 O/HCOOH; 2,6,6 - trimethylcycloheptane-carboxylic acid is similarly prepared from 2,6,6-trimethylcycloheptanone. 1-Ethyl-cyclooctanecarboxylic acid is prepared by ethylation of cyclooctane nitrile followed by hydrolysis. 1-Isopropyl-2-methylcyclopentonecarboxylic acid is prepared by hydrolysis of the corresponding ethyl ester which is obtained by hydrogenation of the corresponding cyclopentene prepared by dehydration of ethyl 2 - hydroxyl - 1 - iso - propyl- 2 - methyl - cyclopentane - carboxylate which in turn is prepared by a Grignard reaction between MeMgI and 2 - isopropyl - 2 - carbethoxycyclopentanone.
GB50801/76A 1974-12-11 1974-12-11 Alicyclic carboxamides having physiological cooling activity Expired GB1489359A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB50801/76A GB1489359A (en) 1974-12-11 1974-12-11 Alicyclic carboxamides having physiological cooling activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB50801/76A GB1489359A (en) 1974-12-11 1974-12-11 Alicyclic carboxamides having physiological cooling activity

Publications (1)

Publication Number Publication Date
GB1489359A true GB1489359A (en) 1977-10-19

Family

ID=10457420

Family Applications (1)

Application Number Title Priority Date Filing Date
GB50801/76A Expired GB1489359A (en) 1974-12-11 1974-12-11 Alicyclic carboxamides having physiological cooling activity

Country Status (1)

Country Link
GB (1) GB1489359A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006084246A2 (en) * 2005-02-04 2006-08-10 Senomyx, Inc. Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers
JP2007517493A (en) * 2003-08-06 2007-07-05 セノミックス、インコーポレイテッド Novel flavors, flavor modifiers, taste agents, taste enhancers, umami and sweet taste agents, and / or their enhancers and uses
US7842324B2 (en) 2005-06-15 2010-11-30 Senomyx, Inc. Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers
US8784782B2 (en) 2005-02-04 2014-07-22 Senomyx, Inc. Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions
US9072313B2 (en) 2006-04-21 2015-07-07 Senomyx, Inc. Comestible compositions comprising high potency savory flavorants, and processes for producing them

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8735081B2 (en) 2003-08-06 2014-05-27 Senomyx, Inc. T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds
US9459250B2 (en) 2003-08-06 2016-10-04 Senomyx, Inc. Use of T1R3 venus flytrap region polypeptide to screen for taste modulators
US11268952B2 (en) 2003-08-06 2022-03-08 Firmenich Incorporated Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
JP2007330268A (en) * 2003-08-06 2007-12-27 Senomyx Inc New flavor, flavor modifier, tastant, taste enhancer, delicious and sweet testant and/or enhancer and use thereof
US10352929B2 (en) 2003-08-06 2019-07-16 Senomyx, Inc. T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds
US10060909B2 (en) 2003-08-06 2018-08-28 Senomyx, Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US7888470B2 (en) 2003-08-06 2011-02-15 Senomyx, Inc. Chimeric T1R taste receptor polypeptides and nucleic acid sequences encoding and cell lines that express said chimeric T1R polypeptides
US8895050B2 (en) 2003-08-06 2014-11-25 Senomyx, Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
JP2007517493A (en) * 2003-08-06 2007-07-05 セノミックス、インコーポレイテッド Novel flavors, flavor modifiers, taste agents, taste enhancers, umami and sweet taste agents, and / or their enhancers and uses
US7476399B2 (en) 2003-08-06 2009-01-13 Senomyx Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US8124121B2 (en) 2003-08-06 2012-02-28 Senomyx, Inc. Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
US8968708B2 (en) 2005-02-04 2015-03-03 Senomyx, Inc. Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions
WO2006084246A3 (en) * 2005-02-04 2007-01-25 Senomyx Inc Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers
US8784782B2 (en) 2005-02-04 2014-07-22 Senomyx, Inc. Compounds comprising linked heteroaryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions
WO2006084246A2 (en) * 2005-02-04 2006-08-10 Senomyx, Inc. Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers
US7842324B2 (en) 2005-06-15 2010-11-30 Senomyx, Inc. Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers
US9072313B2 (en) 2006-04-21 2015-07-07 Senomyx, Inc. Comestible compositions comprising high potency savory flavorants, and processes for producing them

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19941210