JPS5929578B2 - 置換フエノキシ脂肪酸類を製造する方法 - Google Patents

置換フエノキシ脂肪酸類を製造する方法

Info

Publication number: JPS5929578B2
Authority: JP; Japan
Prior art keywords: group; formula; salts; halogen; lower alkyl
Prior art date: 1975-03-04
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

JP2679675A

Other languages

English (en)

Japanese (ja)

Other versions

JPS51101938A (ja

Inventor

孝紙谷

能久斉藤

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.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa Pharmaceutical Co 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.)

1975-03-04

Filing date

1975-03-04

Publication date

1984-07-21

1975-03-04 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1975-03-04 Priority to JP2679675A priority Critical patent/JPS5929578B2/ja

1975-05-22 Priority to GB2210075A priority patent/GB1503953A/en

1975-06-03 Priority to DK248875A priority patent/DK248875A/da

1975-06-04 Priority to FR7517497A priority patent/FR2273518A1/fr

1975-06-04 Priority to DE19752524865 priority patent/DE2524865A1/de

1975-06-04 Priority to AT424575A priority patent/AT354423B/de

1975-06-04 Priority to AU81855/75A priority patent/AU8185575A/en

1975-06-04 Priority to CH719775A priority patent/CH613940A5/xx

1975-06-04 Priority to CA228,557A priority patent/CA1050985A/en

1976-09-08 Publication of JPS51101938A publication Critical patent/JPS51101938A/ja

1984-07-21 Publication of JPS5929578B2 publication Critical patent/JPS5929578B2/ja

Status Expired legal-status Critical Current

Links

-1 phenoxy fatty acids Chemical class 0.000 title claims description 17
235000014113 dietary fatty acids Nutrition 0.000 title claims description 6
239000000194 fatty acid Substances 0.000 title claims description 6
229930195729 fatty acid Natural products 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
150000002989 phenols Chemical class 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical class CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 3
239000002585 base Substances 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
159000000003 magnesium salts Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
159000000001 potassium salts Chemical class 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZVNLRFIXKURKHJ-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylbutanoic acid Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1CNC1=CC=C(Cl)C=C1 ZVNLRFIXKURKHJ-UHFFFAOYSA-N 0.000 description 2
ZDEUJEHDUBUXNW-UHFFFAOYSA-N 4-[(4-chloroanilino)methyl]phenol Chemical compound C1=CC(O)=CC=C1CNC1=CC=C(Cl)C=C1 ZDEUJEHDUBUXNW-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
LWYLSIFFQWAXDO-UHFFFAOYSA-N 2-[4-[(4-chloro-n-methylanilino)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(Cl)C=CC=1N(C)CC1=CC=C(OC(C)(C)C(O)=O)C=C1 LWYLSIFFQWAXDO-UHFFFAOYSA-N 0.000 description 1
ZCCDFDBNRCYYSY-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CNC1=CC=C(Cl)C=C1 ZCCDFDBNRCYYSY-UHFFFAOYSA-N 0.000 description 1
ZEYJNGVEPKXOHX-UHFFFAOYSA-N 2-[4-[(4-chloroanilino)methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1CNC1=CC=C(Cl)C=C1 ZEYJNGVEPKXOHX-UHFFFAOYSA-N 0.000 description 1
JDYAFGNOBOFAJU-UHFFFAOYSA-N 2-[4-[(n-benzyl-4-chloroanilino)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CN(C=1C=CC(Cl)=CC=1)CC1=CC=CC=C1 JDYAFGNOBOFAJU-UHFFFAOYSA-N 0.000 description 1
XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
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 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000012971 dimethylpiperazine Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
ZZLPARSOINTZAZ-UHFFFAOYSA-N ethyl 2-[4-[(4-chloro-n-methylanilino)methyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1CN(C)C1=CC=C(Cl)C=C1 ZZLPARSOINTZAZ-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP2679675A 1974-06-04 1975-03-04 置換フエノキシ脂肪酸類を製造する方法 Expired JPS5929578B2 (ja)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
JP2679675A JPS5929578B2 (ja)	1975-03-04	1975-03-04	置換フエノキシ脂肪酸類を製造する方法
GB2210075A GB1503953A (en)	1974-06-04	1975-05-22	Substituted-phenyl substituted-alkyl ethers and the preparation thereof
DK248875A DK248875A (da)	1974-06-04	1975-06-03	Fremgangsmade til fremstilling af med substitueret phenyl substituerede alkylethere
FR7517497A FR2273518A1 (fr)	1974-06-04	1975-06-04	Ethers alkyliques substitues et phenyliques substitues et leurs procedes de preparation
DE19752524865 DE2524865A1 (de)	1974-06-04	1975-06-04	Durch substituiertes phenyl substituierte alkylaether, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
AT424575A AT354423B (de)	1975-03-04	1975-06-04	Verfahren zur herstellung von neuen aminoalkylphenoxyalkansaeuren, deren estern und salzen
AU81855/75A AU8185575A (en)	1974-06-04	1975-06-04	Substituted-phenyl substituted-alkyl ethers and the prep- aration thereof
CH719775A CH613940A5 (en)	1974-06-04	1975-06-04	Process for the preparation of alkyl ethers substituted by substituted phenyl
CA228,557A CA1050985A (en)	1974-06-04	1975-06-04	Substituted-phenyl substituted-alkyl ethers and the preparation thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2679675A JPS5929578B2 (ja)	1975-03-04	1975-03-04	置換フエノキシ脂肪酸類を製造する方法

Publications (2)

Publication Number	Publication Date
JPS51101938A JPS51101938A (ja)	1976-09-08
JPS5929578B2 true JPS5929578B2 (ja)	1984-07-21

Family

ID=12203271

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2679675A Expired JPS5929578B2 (ja)	1974-06-04	1975-03-04	置換フエノキシ脂肪酸類を製造する方法

Country Status (2)

Country	Link
JP (1)	JPS5929578B2 (de)
AT (1)	AT354423B (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6298193A (ja) *	1985-10-25	1987-05-07	Mayekawa Mfg Co Ltd	蓄熱槽を有する冷水循環装置
JPS63273788A (ja) *	1987-04-30	1988-11-10	Shimizu Constr Co Ltd	蓄熱槽

1975
- 1975-03-04 JP JP2679675A patent/JPS5929578B2/ja not_active Expired
- 1975-06-04 AT AT424575A patent/AT354423B/de not_active IP Right Cessation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6298193A (ja) *	1985-10-25	1987-05-07	Mayekawa Mfg Co Ltd	蓄熱槽を有する冷水循環装置
JPS63273788A (ja) *	1987-04-30	1988-11-10	Shimizu Constr Co Ltd	蓄熱槽

Also Published As

Publication number	Publication date
ATA424575A (de)	1979-06-15
AT354423B (de)	1979-01-10
JPS51101938A (ja)	1976-09-08

Publication	Publication Date	Title
KR940001774B1 (ko)	1994-03-05	치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법
GB2126580A (en)	1984-03-28	Heterocyclic oxyphenols
JPH0733729A (ja)	1995-02-03	Ｎ−シアノ−ｎ′−置換−アリールカルボキシイミダミド化合物の製造法
JPH04230263A (ja)	1992-08-19	ピリジンジカルボン酸化合物の製法
CS236668B2 (en)	1985-05-15	Manufacturing process of aralkylamides 2-substituted aminophenylalkancarboxyle and amino-3-pyridylalkancarboxyl acides
JPS5922711B2 (ja)	1984-05-28	ベンゾオキサゾリノン誘導体の製造法
JPS5929578B2 (ja)	1984-07-21	置換フエノキシ脂肪酸類を製造する方法
JPH0273075A (ja)	1990-03-13	ピペラジン誘導体およびその製造方法
JPH01156965A (ja)	1989-06-20	チオヒダントイン化合物
JP2709677B2 (ja)	1998-02-04	ホスホン酸ジエステル誘導体
DK157005B (da)	1989-10-30	Analogifremgangsmaade til fremstilling af 2-(4-benzyl-phenoxy)-alkansyrederivater
US3980643A (en)	1976-09-14	Novel piperazine- and homopiperazine-monoalkanol esters and a process of production thereof
US4172203A (en)	1979-10-23	Method for preparing dichloromethyl pyridines
JP2527961B2 (ja)	1996-08-28	安息香酸エステル誘導体及びその製造方法
GB2182927A (en)	1987-05-28	3-perfluoroalkyl-5-hydroxyisoxazoles
CA1055492A (en)	1979-05-29	Piperazine-and homopiperazine-monoalkanol esters and a process of production thereof
JPS593466B2 (ja)	1984-01-24	チカンアルキルチカンフエノキシカルボンサンルイオセイゾウスルホウホウ
JPS5927343B2 (ja)	1984-07-05	３−アミノイソオキサゾ−ル類の合成法
JPS5929575B2 (ja)	1984-07-21	置換フエノキシ脂肪酸類の製造法
JPS6216446A (ja)	1987-01-24	光学活性２−（４−ヒドロキシフエノキシ）プロピオン酸の製造方法
SU457211A3 (ru)	1975-01-15	Способ получени производных 1-фенокси -3-аминопропан-2-ола
JPS5929580B2 (ja)	1984-07-21	置換アミノアルキル置換フエノキシ脂肪酸類の製造法
JPS63104939A (ja)	1988-05-10	新規カプロン酸誘導体
JPS5929577B2 (ja)	1984-07-21	ジ置換アミノアルキル置換フエノキシ脂肪酸類の製造法
JPS6025425B2 (ja)	1985-06-18	置換フエノキシ脂肪酸類の合成法

JPS5929578B2 - 置換フエノキシ脂肪酸類を製造する方法 - Google Patents

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