GB1420802A - Substituted geranyl acetic acids and pharmaceutical compositions thereof - Google Patents
Substituted geranyl acetic acids and pharmaceutical compositions thereofInfo
- Publication number
- GB1420802A GB1420802A GB2894073A GB2894073A GB1420802A GB 1420802 A GB1420802 A GB 1420802A GB 2894073 A GB2894073 A GB 2894073A GB 2894073 A GB2894073 A GB 2894073A GB 1420802 A GB1420802 A GB 1420802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- condensation product
- cyanoacetate
- acids
- geranylacetic
- 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
Links
- -1 geranyl acetic acids Chemical class 0.000 title abstract 3
- 235000011054 acetic acid Nutrition 0.000 title 1
- 239000008194 pharmaceutical composition Chemical class 0.000 title 1
- 239000007859 condensation product Substances 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 4
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 3
- 239000012279 sodium borohydride Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- WIHSFNRKGXNWNK-NTCAYCPXSA-N (4e)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid Chemical compound CC(C)=CCC\C(C)=C\CC(C(O)=O)C1CCCCC1 WIHSFNRKGXNWNK-NTCAYCPXSA-N 0.000 abstract 1
- HPOYZGTYWKRTPU-DHZHZOJOSA-N (4e)-5,9-dimethyldeca-4,8-dienoic acid Chemical class CC(C)=CCC\C(C)=C\CCC(O)=O HPOYZGTYWKRTPU-DHZHZOJOSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- CXGASOOHQODCNR-JXMROGBWSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienyl]propanedioic acid Chemical class CC(C)=CCC\C(C)=C\CC(C(O)=O)C(O)=O CXGASOOHQODCNR-JXMROGBWSA-N 0.000 abstract 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 abstract 1
- 229940043350 citral Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- CNARYHFSSZYVQJ-SDNWHVSQSA-N diethyl 2-[(2e)-3,7-dimethylocta-2,6-dienyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C\C=C(/C)CCC=C(C)C CNARYHFSSZYVQJ-SDNWHVSQSA-N 0.000 abstract 1
- BRSWMPIPCHQQHE-KNTRCKAVSA-N diethyl 2-cyclohexyl-2-[(2e)-3,7-dimethylocta-2,6-dienyl]propanedioate Chemical compound CC(C)=CCCC(/C)=C/CC(C(=O)OCC)(C(=O)OCC)C1CCCCC1 BRSWMPIPCHQQHE-KNTRCKAVSA-N 0.000 abstract 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 abstract 1
- 230000006127 geranylation Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
- C07C57/28—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings containing an adamantane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27168772A | 1972-07-14 | 1972-07-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1420802A true GB1420802A (en) | 1976-01-14 |
Family
ID=23036632
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2894073A Expired GB1420802A (en) | 1972-07-14 | 1973-06-19 | Substituted geranyl acetic acids and pharmaceutical compositions thereof |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS4943917A (enrdf_load_stackoverflow) |
AU (1) | AU5677773A (enrdf_load_stackoverflow) |
BE (1) | BE802155A (enrdf_load_stackoverflow) |
CA (1) | CA970365A (enrdf_load_stackoverflow) |
DE (1) | DE2335067A1 (enrdf_load_stackoverflow) |
FR (1) | FR2192826B1 (enrdf_load_stackoverflow) |
GB (1) | GB1420802A (enrdf_load_stackoverflow) |
ZA (1) | ZA734022B (enrdf_load_stackoverflow) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4289786A (en) | 1978-11-28 | 1981-09-15 | Kuraray Co., Ltd. | Farnesylacetic acid ester derivatives |
US8575386B2 (en) | 2006-06-15 | 2013-11-05 | Givaudan S.A. | Fragrance compounds |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0501237D0 (en) * | 2005-01-21 | 2005-03-02 | Givaudan Sa | Organic compounds |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL130627C (enrdf_load_stackoverflow) * | 1961-05-26 |
-
1973
- 1973-06-12 CA CA173,830A patent/CA970365A/en not_active Expired
- 1973-06-12 AU AU56777/73A patent/AU5677773A/en not_active Expired
- 1973-06-13 ZA ZA734022A patent/ZA734022B/xx unknown
- 1973-06-19 GB GB2894073A patent/GB1420802A/en not_active Expired
- 1973-07-10 DE DE19732335067 patent/DE2335067A1/de active Pending
- 1973-07-10 BE BE133329A patent/BE802155A/xx unknown
- 1973-07-13 FR FR7325724A patent/FR2192826B1/fr not_active Expired
- 1973-07-14 JP JP48079755A patent/JPS4943917A/ja active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4289786A (en) | 1978-11-28 | 1981-09-15 | Kuraray Co., Ltd. | Farnesylacetic acid ester derivatives |
US8575386B2 (en) | 2006-06-15 | 2013-11-05 | Givaudan S.A. | Fragrance compounds |
US9057041B2 (en) | 2006-06-15 | 2015-06-16 | Givaudan, S.A. | Fragrance compounds |
US9447364B2 (en) | 2006-06-15 | 2016-09-20 | Givaudan S.A. | Fragrance compounds |
US9585362B2 (en) | 2006-06-15 | 2017-03-07 | Givaudan S.A. | Fragrance compounds |
Also Published As
Publication number | Publication date |
---|---|
FR2192826A1 (enrdf_load_stackoverflow) | 1974-02-15 |
ZA734022B (en) | 1974-09-25 |
FR2192826B1 (enrdf_load_stackoverflow) | 1977-07-01 |
CA970365A (en) | 1975-07-01 |
BE802155A (fr) | 1973-11-05 |
DE2335067A1 (de) | 1974-01-31 |
AU5677773A (en) | 1974-12-12 |
JPS4943917A (enrdf_load_stackoverflow) | 1974-04-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLE | Entries relating assignments, transmissions, licences in the register of patents | ||
PCNP | Patent ceased through non-payment of renewal fee |