GB1249492A - New aryloxyalkanoic acid and salts thereof - Google Patents
New aryloxyalkanoic acid and salts thereofInfo
- Publication number
- GB1249492A GB1249492A GB47167/68A GB4716768A GB1249492A GB 1249492 A GB1249492 A GB 1249492A GB 47167/68 A GB47167/68 A GB 47167/68A GB 4716768 A GB4716768 A GB 4716768A GB 1249492 A GB1249492 A GB 1249492A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pentyl
- prepared
- acid
- biphenylyloxy
- ethyl
- 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
- 150000003839 salts Chemical class 0.000 title abstract 5
- 239000002253 acid Substances 0.000 title abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 4
- 229910052708 sodium Inorganic materials 0.000 abstract 4
- 239000011734 sodium Substances 0.000 abstract 4
- 239000000543 intermediate Substances 0.000 abstract 3
- RGMMREBHCYXQMA-UHFFFAOYSA-N 2-hydroxyheptanoic acid Chemical compound CCCCCC(O)C(O)=O RGMMREBHCYXQMA-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 abstract 1
- WEAFBPWCYVGTAB-UHFFFAOYSA-N 2-(4-phenylphenoxy)heptanoic acid Chemical compound C1=CC(OC(CCCCC)C(O)=O)=CC=C1C1=CC=CC=C1 WEAFBPWCYVGTAB-UHFFFAOYSA-N 0.000 abstract 1
- YVTMVUAFKLSFJY-UHFFFAOYSA-N 2-cyano-2-(4-phenylphenoxy)heptanoic acid Chemical compound C1(=CC=C(C=C1)OC(C(=O)O)(C#N)CCCCC)C1=CC=CC=C1 YVTMVUAFKLSFJY-UHFFFAOYSA-N 0.000 abstract 1
- YRKANMSVJZVSLB-UHFFFAOYSA-N 2-pentyl-2-(4-phenylphenoxy)propanedioic acid Chemical compound C1(=CC=C(C=C1)OC(C(=O)O)(C(=O)O)CCCCC)C1=CC=CC=C1 YRKANMSVJZVSLB-UHFFFAOYSA-N 0.000 abstract 1
- 101100188555 Arabidopsis thaliana OCT6 gene Proteins 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- PSOUETBRCHLRNY-UHFFFAOYSA-N diethyl 2-bromo-2-pentylpropanedioate Chemical compound CCCCCC(Br)(C(=O)OCC)C(=O)OCC PSOUETBRCHLRNY-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- VRCFFPJTGBDVAA-UHFFFAOYSA-N ethyl 2-(4-phenylphenoxy)heptanoate Chemical compound C(C)OC(C(CCCCC)OC1=CC=C(C=C1)C1=CC=CC=C1)=O VRCFFPJTGBDVAA-UHFFFAOYSA-N 0.000 abstract 1
- AZRBWVKLYGQVTI-UHFFFAOYSA-N ethyl 2-bromo-2-cyanoheptanoate Chemical compound C(C)OC(C(C#N)(CCCCC)Br)=O AZRBWVKLYGQVTI-UHFFFAOYSA-N 0.000 abstract 1
- GNCLPIAYAPQPOU-UHFFFAOYSA-N ethyl 2-bromoheptanoate Chemical compound CCCCCC(Br)C(=O)OCC GNCLPIAYAPQPOU-UHFFFAOYSA-N 0.000 abstract 1
- HONATTAEGBOECL-UHFFFAOYSA-N ethyl 2-cyano-2-(4-phenylphenoxy)heptanoate Chemical compound C1(=CC=C(C=C1)OC(C(=O)OCC)(C#N)CCCCC)C1=CC=CC=C1 HONATTAEGBOECL-UHFFFAOYSA-N 0.000 abstract 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 1
- OKMWRBGVXIVCNF-UHFFFAOYSA-N ethyl 2-cyanoheptanoate Chemical compound CCCCCC(C#N)C(=O)OCC OKMWRBGVXIVCNF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
Classifications
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,249,492. Aryloxyalkanoic acid derivative. J. R. GEIGY A.G. 4 Oct., 1968 [6 Oct., 1967], No. 47167/68. Heading C2C. Novel 2-(4-biphenylyloxy)-heptanoic acid (I) and its salts with organic and inorganic bases are prepared (a) by hydrolysing a functional derivative of the acid; (b) decarboxylating (4 - biphenylyloxy) - n - pentyl - malonic acid or a functional derivative thereof; or (c) reacting an alkali metal salt of p-phenylphenol with a salt of an ester of 2-hydroxyheptanoic acid (the hydroxy group being esterified) and where desired in (a), (b) or (c) forming the salt by conventional methods. Intermediates isolated are 2-(4-biphenylyloxy)- heptanoic acid ethyl ester, prepared from sodium p-phenylphenate and 2-bromoheptanoic acid ethyl ester; ethyl 2-n-pentyl-2-cyano-acetate, prepared from ethyl cyanoacetate, metallic sodium and n-pentyl bromide; ethyl 2-n-pentyl- 2-bromo-2-cyano-acetate, prepared from the previous intermediate by bromination; ethyl 2- (4 - biphenylyloxy) - 2 - n - pentyl - 2 - cyanoacetate prepared by reacting the appropriate 2-bromo derivative with sodium p-phenylphenate; 2 - (4 - biphenylyloxy) - 2 - n - pentyl- 2-cyano acetic acid, prepared by hydrolysis of the ethyl ester; 2-(4-biphenylyloxy)-heptanoic acid nitrile, prepared by decarboxylation of the former intermediate; and diethyl-(4-diphenylyloxy)-n-pentyl-malonate, prepared from sodium p-phenyl-phenate and diethyl n-pentyl-bromomalonate. Pharmaceutical compositions comprise a compound (I) or a salt thereof in conjunction with a suitable excipient for oral or rectal administration and exhibit hypolipemic activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1402967A CH501575A (en) | 1967-10-06 | 1967-10-06 | Process for the preparation of a new aryloxyalkanoic acid and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1249492A true GB1249492A (en) | 1971-10-13 |
Family
ID=4397336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47167/68A Expired GB1249492A (en) | 1967-10-06 | 1968-10-04 | New aryloxyalkanoic acid and salts thereof |
Country Status (10)
| Country | Link |
|---|---|
| AT (3) | AT282607B (en) |
| BE (1) | BE721973A (en) |
| BR (1) | BR6802881D0 (en) |
| CH (2) | CH501575A (en) |
| DE (1) | DE1801312A1 (en) |
| ES (4) | ES358828A1 (en) |
| FR (2) | FR1596597A (en) |
| GB (1) | GB1249492A (en) |
| IL (1) | IL30817A0 (en) |
| NL (1) | NL6813908A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120467A (en) * | 1983-09-10 | 1992-06-09 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anisotropic compounds and liquid crystal mixtures |
| US5252252A (en) * | 1983-09-10 | 1993-10-12 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Anisotropic compounds and liquid crystal mixtures |
| WO2004099168A3 (en) * | 2003-04-30 | 2005-02-24 | Inst For Pharm Discovery Inc | Substituted carboxylic acids |
| WO2008033931A1 (en) * | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Para-xylylene carboxylic acids and isothiazolones useful as protein tyrosine phosphatases (ptps) in particular ptp-ib |
-
1967
- 1967-10-06 CH CH1402967A patent/CH501575A/en not_active IP Right Cessation
- 1967-10-06 CH CH239570A patent/CH542806A/en not_active IP Right Cessation
-
1968
- 1968-09-27 NL NL6813908A patent/NL6813908A/xx unknown
- 1968-10-04 AT AT764869A patent/AT282607B/en not_active IP Right Cessation
- 1968-10-04 ES ES358828A patent/ES358828A1/en not_active Expired
- 1968-10-04 ES ES358827A patent/ES358827A1/en not_active Expired
- 1968-10-04 DE DE19681801312 patent/DE1801312A1/en active Pending
- 1968-10-04 BR BR202881/68A patent/BR6802881D0/en unknown
- 1968-10-04 ES ES358826A patent/ES358826A1/en not_active Expired
- 1968-10-04 GB GB47167/68A patent/GB1249492A/en not_active Expired
- 1968-10-04 ES ES358825A patent/ES358825A1/en not_active Expired
- 1968-10-04 IL IL30817A patent/IL30817A0/en unknown
- 1968-10-04 AT AT765069A patent/AT282608B/en not_active IP Right Cessation
- 1968-10-04 AT AT968268A patent/AT282604B/en not_active IP Right Cessation
- 1968-10-07 FR FR1596597D patent/FR1596597A/fr not_active Expired
- 1968-10-07 BE BE721973D patent/BE721973A/xx unknown
-
1969
- 1969-01-03 FR FR183176A patent/FR8267M/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120467A (en) * | 1983-09-10 | 1992-06-09 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anisotropic compounds and liquid crystal mixtures |
| US5252252A (en) * | 1983-09-10 | 1993-10-12 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Anisotropic compounds and liquid crystal mixtures |
| WO2004099168A3 (en) * | 2003-04-30 | 2005-02-24 | Inst For Pharm Discovery Inc | Substituted carboxylic acids |
| US7358364B2 (en) | 2003-04-30 | 2008-04-15 | The Institute For Pharmaceutical Discovery Llc | Substituted carboxylic acids |
| AU2004236173B2 (en) * | 2003-04-30 | 2008-07-03 | The Institutes For Pharmaceutical Discovery, Llc | Substituted carboxylic acids |
| WO2008033931A1 (en) * | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Para-xylylene carboxylic acids and isothiazolones useful as protein tyrosine phosphatases (ptps) in particular ptp-ib |
Also Published As
| Publication number | Publication date |
|---|---|
| ES358827A1 (en) | 1970-06-01 |
| FR1596597A (en) | 1970-06-22 |
| BR6802881D0 (en) | 1973-02-22 |
| CH501575A (en) | 1971-01-15 |
| ES358828A1 (en) | 1970-06-01 |
| IL30817A0 (en) | 1968-12-26 |
| NL6813908A (en) | 1969-04-09 |
| AT282608B (en) | 1970-07-10 |
| BE721973A (en) | 1969-04-08 |
| AT282607B (en) | 1970-07-10 |
| DE1801312A1 (en) | 1969-05-08 |
| FR8267M (en) | 1970-10-26 |
| AT282604B (en) | 1970-07-10 |
| ES358825A1 (en) | 1970-06-01 |
| CH542806A (en) | 1973-10-15 |
| ES358826A1 (en) | 1970-06-01 |
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