JPS6054318B2 - アロイル置換フエニル酢酸誘導体類の製造方法 - Google Patents

アロイル置換フエニル酢酸誘導体類の製造方法

Info

Publication number: JPS6054318B2
Authority: JP; Japan
Prior art keywords: formula; aroyl; acid; thenoyl; lower alkyl
Prior art date: 1972-10-24
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

JP59122200A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6041673A (ja

Inventor

ポール・アドリアン・ジヤン・ジヤンセン

ジヨルジユ・アンリ・ポール・フアン・デール

ヨゼフ・マルチン・ベーイ

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.)

Janssen Pharmaceutica NV

Original Assignee

Janssen Pharmaceutica NV

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.)

1972-10-24

Filing date

1984-06-15

Publication date

1985-11-29

1984-06-15 Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV

1985-03-05 Publication of JPS6041673A publication Critical patent/JPS6041673A/ja

1985-11-29 Publication of JPS6054318B2 publication Critical patent/JPS6054318B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims 3
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 16
-1 phenylacetic ester Chemical class 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 7
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000012360 testing method Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000000034 method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 7
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 7
238000011282 treatment Methods 0.000 description 7
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
150000005690 diesters Chemical class 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000000047 product Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000209094 Oryza Species 0.000 description 4
235000007164 Oryza sativa Nutrition 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
229960003424 phenylacetic acid Drugs 0.000 description 4
239000003279 phenylacetic acid Substances 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
206010003246 arthritis Diseases 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000010992 reflux Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
NLTRJPXIYKYMKT-UHFFFAOYSA-N (4-fluorophenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CS1 NLTRJPXIYKYMKT-UHFFFAOYSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
241000700157 Rattus norvegicus Species 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
RSUSQCKVKWHQFM-UHFFFAOYSA-N diethyl 2-methyl-2-[4-(thiophene-2-carbonyl)phenyl]propanedioate Chemical compound C1=CC(C(C)(C(=O)OCC)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 RSUSQCKVKWHQFM-UHFFFAOYSA-N 0.000 description 2
UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
XSYROCDSVGJVAW-UHFFFAOYSA-N ethyl 2-[4-(thiophene-2-carbonyl)phenyl]propanoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1C(=O)C1=CC=CS1 XSYROCDSVGJVAW-UHFFFAOYSA-N 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
210000003141 lower extremity Anatomy 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 2
230000008961 swelling Effects 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
LCZFQTKBLZXEMV-UHFFFAOYSA-N 2-[3-(dimethylamino)propoxy]-2-oxoacetic acid Chemical compound CN(C)CCCOC(=O)C(O)=O LCZFQTKBLZXEMV-UHFFFAOYSA-N 0.000 description 1
XSSMMNDGAZJDIQ-UHFFFAOYSA-N 2-[4-(thiophene-2-carbonyl)phenyl]butanoic acid Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1C(=O)C1=CC=CS1 XSSMMNDGAZJDIQ-UHFFFAOYSA-N 0.000 description 1
JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-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
239000005909 Kieselgur Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000186366 Mycobacterium bovis Species 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
238000001467 acupuncture Methods 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
150000001340 alkali metals Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000004075 alteration Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229940075894 denatured ethanol Drugs 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
210000002683 foot Anatomy 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
INOXCHKBMKWGLA-UHFFFAOYSA-N octyl 2-[4-(thiophene-2-carbonyl)phenyl]propanoate Chemical compound C1=CC(C(C)C(=O)OCCCCCCCC)=CC=C1C(=O)C1=CC=CS1 INOXCHKBMKWGLA-UHFFFAOYSA-N 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

JP59122200A 1972-10-24 1984-06-15 アロイル置換フエニル酢酸誘導体類の製造方法 Expired JPS6054318B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US30007972A	1972-10-24	1972-10-24
US300079		1972-10-24
US395877		1973-09-10

Publications (2)

Publication Number	Publication Date
JPS6041673A JPS6041673A (ja)	1985-03-05
JPS6054318B2 true JPS6054318B2 (ja)	1985-11-29

Family

ID=23157613

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59122200A Expired JPS6054318B2 (ja)	1972-10-24	1984-06-15	アロイル置換フエニル酢酸誘導体類の製造方法

Country Status (4)

Country	Link
JP (1)	JPS6054318B2 (fr)
KR (1)	KR780000730B1 (fr)
RO (1)	RO63632A2 (fr)
ZA (1)	ZA738203B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010500989A (ja) *	2006-08-15	2010-01-14	テックフィールズバイオケムカンパニーリミテッド	非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
JP2014043450A (ja) *	2013-10-08	2014-03-13	Techfields Biochem Co Ltd	非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
JP2016130241A (ja) *	2016-02-05	2016-07-21	テックフィールズバイオケムカンパニーリミテッド	非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ

1973
- 1973-10-23 ZA ZA00738203A patent/ZA738203B/xx unknown
- 1973-10-24 RO RO76419A patent/RO63632A2/fr unknown
- 1973-10-25 KR KR7301763A patent/KR780000730B1/ko not_active Expired
1984
- 1984-06-15 JP JP59122200A patent/JPS6054318B2/ja not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010500989A (ja) *	2006-08-15	2010-01-14	テックフィールズバイオケムカンパニーリミテッド	非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
JP2014043450A (ja) *	2013-10-08	2014-03-13	Techfields Biochem Co Ltd	非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ
JP2016130241A (ja) *	2016-02-05	2016-07-21	テックフィールズバイオケムカンパニーリミテッド	非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ

Also Published As

Publication number	Publication date
KR780000730B1 (en)	1978-12-30
RO63632A2 (fr)	1978-07-22
JPS6041673A (ja)	1985-03-05
ZA738203B (en)	1975-05-28

Publication	Publication Date	Title
IE49902B1 (en)	1986-01-08	4-substituted-3-hydroxy-3-pyrroline-2,5-dione compounds,process for their preparation and pharmaceutical compositions containing the same
JPS641456B2 (fr)	1989-01-11
JPS591711B2 (ja)	1984-01-13	５−テノイルピロ−ル酢酸誘導体の製造法
DE3107100A1 (de)	1982-09-09	Azaprostacycline, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
JPS5844668B2 (ja)	1983-10-04	ケツエキシシツテイカザイルイノセイホウ
US4221919A (en)	1980-09-09	Antiinflammatory substituted phenylacetic acids
DE2353357C2 (de)	1982-04-01	Aroylsubstituierte Phenylessigsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
JPH059424B2 (fr)	1993-02-04
US5288750A (en)	1994-02-22	Substituted β-diketones
JPS6131103B2 (fr)	1986-07-17
JPS6054318B2 (ja)	1985-11-29	アロイル置換フエニル酢酸誘導体類の製造方法
US4337353A (en)	1982-06-29	Novel carboxylic acids, benzoyl phenyl alkanoic acids and use thereof
US4116972A (en)	1978-09-26	Anti-inflammatory 1-oxo-isoindoline derivatives and processes for their preparation
JPS6054285B2 (ja)	1985-11-29	シクロヘキサン誘導体を含有する医薬
CH628014A5 (en)	1982-02-15	Gamma-aryl-gamma-oxoisovaleric acids having antiphlogistic and antalgic properties
JPS60104084A (ja)	1985-06-08	４Ｈ‐ベンゾ〔４，５〕シクロヘプタ〔１，２‐ｂ〕チオフエン誘導体
EP0155524A1 (fr)	1985-09-25	Composé omega-aryl-alkylthianyliques, leur procédé de préparation et produits pharmaceutiques les contenant
GB2027022A (en)	1980-02-13	Pyridoxine derivatives and their use
NO150878B (no)	1984-09-24	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 1-nafthyl-eddiksyrederivater
GB2113214A (en)	1983-08-03	New phenylacetic acid derivatives their preparation and compositions containing them
JPS62149672A (ja)	1987-07-03	４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体
US4187319A (en)	1980-02-05	Substituted benzaldehyde hypolipidemic agents
JPS6032763A (ja)	1985-02-19	新規な１１−オキソプロスタン酸誘導体ならびにその利用
US4066788A (en)	1978-01-03	Substituted benzaldehyde hypolipidemic agents
US4192884A (en)	1980-03-11	Substituted 4-(((thienyl)methyl)-amino)benzoic acids and a method for treating hypolipidemia

JPS6054318B2 - アロイル置換フエニル酢酸誘導体類の製造方法 - Google Patents

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