JPS6254105B2 - - Google Patents

Info

Publication number: JPS6254105B2
Authority: JP; Japan
Prior art keywords: group; acid; hydrogen atom; atom; carbon atoms
Prior art date: 1978-05-24
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

JP54062779A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54154758A (en

Inventor

Fuigara Fuorukaa

Rainaa Georuku

Riideru Rihiaruto

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.)

Takeda GmbH

Original Assignee

Byk Gulden Lomberg Chemische Fabrik GmbH

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.)

1978-05-24

Filing date

1979-05-23

Publication date

1987-11-13

1979-05-23 Application filed by Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH

1979-12-06 Publication of JPS54154758A publication Critical patent/JPS54154758A/ja

1987-11-13 Publication of JPS6254105B2 publication Critical patent/JPS6254105B2/ja

Status Granted legal-status Critical Current

Links

125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
150000001875 compounds Chemical class 0.000 claims description 57
239000002253 acid Chemical class 0.000 claims description 56
229910052801 chlorine Inorganic materials 0.000 claims description 55
-1 2-hydroxyethoxy Chemical group 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 54
125000001309 chloro group Chemical group Cl* 0.000 claims description 52
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 28
238000000034 method Methods 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
RFBFZTAOPICSHT-UHFFFAOYSA-N acetic acid;n-phenylthiophen-2-amine Chemical class CC(O)=O.C=1C=CC=CC=1NC1=CC=CS1 RFBFZTAOPICSHT-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
AELILMBZWCGOSB-UHFFFAOYSA-N 2-[4-(2,6-dichloroanilino)thiophen-3-yl]acetic acid Chemical compound OC(=O)CC1=CSC=C1NC1=C(Cl)C=CC=C1Cl AELILMBZWCGOSB-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
ACBYDMGMWUOHHV-UHFFFAOYSA-N 2-(3-anilinothiophen-2-yl)acetic acid Chemical class S1C=CC(NC=2C=CC=CC=2)=C1CC(=O)O ACBYDMGMWUOHHV-UHFFFAOYSA-N 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
238000003797 solvolysis reaction Methods 0.000 claims description 10
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000002843 carboxylic acid group Chemical group 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
238000000354 decomposition reaction Methods 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
235000011054 acetic acid Nutrition 0.000 claims description 2
230000000144 pharmacologic effect Effects 0.000 claims description 2
TXFQJRFOGGSJCI-UHFFFAOYSA-N 2-(3-aminothiophen-2-yl)acetic acid Chemical class NC=1C=CSC=1CC(O)=O TXFQJRFOGGSJCI-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
230000008018 melting Effects 0.000 description 53
238000002844 melting Methods 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
241001465754 Metazoa Species 0.000 description 22
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 20
239000003814 drug Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
229940079593 drug Drugs 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
241000699670 Mus sp. Species 0.000 description 11
239000013543 active substance Substances 0.000 description 11
239000000284 extract Substances 0.000 description 11
230000003110 anti-inflammatory effect Effects 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
238000003756 stirring Methods 0.000 description 10
238000012360 testing method Methods 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
230000001754 anti-pyretic effect Effects 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
235000008504 concentrate Nutrition 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CPSPZBZRRLXMSY-UHFFFAOYSA-N 2-[4-(2,6-dichloroanilino)thiophen-3-yl]acetonitrile Chemical compound ClC1=CC=CC(Cl)=C1NC1=CSC=C1CC#N CPSPZBZRRLXMSY-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
206010061218 Inflammation Diseases 0.000 description 6
208000002193 Pain Diseases 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 6
235000012239 silicon dioxide Nutrition 0.000 description 6
239000000126 substance Substances 0.000 description 6
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
241000124008 Mammalia Species 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
DOWGQSKPFQDYIZ-UHFFFAOYSA-N [BH2-].[Na+] Chemical compound [BH2-].[Na+] DOWGQSKPFQDYIZ-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000002168 ethanoic acid esters Chemical class 0.000 description 5
235000019439 ethyl acetate Nutrition 0.000 description 5
239000000796 flavoring agent Substances 0.000 description 5
238000005755 formation reaction Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
239000002609 medium Substances 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
238000007127 saponification reaction Methods 0.000 description 5
239000000829 suppository Substances 0.000 description 5
239000003765 sweetening agent Substances 0.000 description 5
230000008961 swelling Effects 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
CAFPCOFXOKWMQF-UHFFFAOYSA-N 2-[3-(2,6-dichloroanilino)thiophen-2-yl]acetic acid Chemical compound S1C=CC(NC=2C(=CC=CC=2Cl)Cl)=C1CC(=O)O CAFPCOFXOKWMQF-UHFFFAOYSA-N 0.000 description 4
NJPJNXIMOMOYSG-UHFFFAOYSA-N 3-anilinothiophene-2-carboxylic acid Chemical compound S1C=CC(NC=2C=CC=CC=2)=C1C(=O)O NJPJNXIMOMOYSG-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229920000742 Cotton Polymers 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000005662 Paraffin oil Substances 0.000 description 4
206010037660 Pyrexia Diseases 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006136 alcoholysis reaction Methods 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
235000010418 carrageenan Nutrition 0.000 description 4
229920001525 carrageenan Polymers 0.000 description 4
235000013355 food flavoring agent Nutrition 0.000 description 4
235000003599 food sweetener Nutrition 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
230000026030 halogenation Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
VCESDBDLBWABPV-UHFFFAOYSA-N methyl 2-[4-(2,6-dichloroanilino)thiophen-3-yl]acetate Chemical compound COC(=O)CC1=CSC=C1NC1=C(Cl)C=CC=C1Cl VCESDBDLBWABPV-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000011160 research Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 3
XEHWUIYOKWYSSZ-UHFFFAOYSA-N 2-[4-(2,6-dimethylanilino)thiophen-3-yl]acetic acid Chemical compound CC1=CC=CC(C)=C1NC1=CSC=C1CC(O)=O XEHWUIYOKWYSSZ-UHFFFAOYSA-N 0.000 description 3
SFAPTSMWCKIVON-UHFFFAOYSA-N 2-[4-(2-chloro-3-methylanilino)thiophen-3-yl]acetic acid Chemical compound CC1=CC=CC(NC=2C(=CSC=2)CC(O)=O)=C1Cl SFAPTSMWCKIVON-UHFFFAOYSA-N 0.000 description 3
XXVYZRFDURSXOE-UHFFFAOYSA-N 2-[4-(2-chloro-6-methylanilino)thiophen-3-yl]acetic acid Chemical compound CC1=CC=CC(Cl)=C1NC1=CSC=C1CC(O)=O XXVYZRFDURSXOE-UHFFFAOYSA-N 0.000 description 3
WOAWQZULIHPWDB-UHFFFAOYSA-N 2-[5-chloro-4-(2-chloro-6-methylanilino)thiophen-3-yl]acetic acid Chemical compound CC1=CC=CC(Cl)=C1NC1=C(Cl)SC=C1CC(O)=O WOAWQZULIHPWDB-UHFFFAOYSA-N 0.000 description 3
LWRDXDNBYFQTCT-UHFFFAOYSA-N 4-(2-chloro-6-methylanilino)thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(Cl)=C1NC1=CSC=C1C(O)=O LWRDXDNBYFQTCT-UHFFFAOYSA-N 0.000 description 3
PPYVATYRURMAAX-UHFFFAOYSA-N 4-(chloromethyl)-n-(2-chloro-3-methylphenyl)thiophen-3-amine Chemical compound CC1=CC=CC(NC=2C(=CSC=2)CCl)=C1Cl PPYVATYRURMAAX-UHFFFAOYSA-N 0.000 description 3
UWKBHCAWRQRRGJ-UHFFFAOYSA-N 4-anilinothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1NC1=CC=CC=C1 UWKBHCAWRQRRGJ-UHFFFAOYSA-N 0.000 description 3
244000215068 Acacia senegal Species 0.000 description 3
235000006491 Acacia senegal Nutrition 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
240000001624 Espostoa lanata Species 0.000 description 3
235000009161 Espostoa lanata Nutrition 0.000 description 3
208000009386 Experimental Arthritis Diseases 0.000 description 3
229920000084 Gum arabic Polymers 0.000 description 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 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
235000019483 Peanut oil Nutrition 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
FOVFDFPBSQMFOO-UHFFFAOYSA-N [4-(2,6-dichloroanilino)thiophen-3-yl]methanol Chemical compound OCC1=CSC=C1NC1=C(Cl)C=CC=C1Cl FOVFDFPBSQMFOO-UHFFFAOYSA-N 0.000 description 3
235000010489 acacia gum Nutrition 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
239000002221 antipyretic Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
238000004061 bleaching Methods 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
230000002354 daily effect Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
QLSRSLGIQJGALU-UHFFFAOYSA-N ethyl 2-[3-(2,6-dichloroanilino)thiophen-2-yl]-2-oxoacetate Chemical compound S1C=CC(NC=2C(=CC=CC=2Cl)Cl)=C1C(=O)C(=O)OCC QLSRSLGIQJGALU-UHFFFAOYSA-N 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
PPECUTDHISTLTF-UHFFFAOYSA-N methyl 2-[5-chloro-4-(2-chloro-6-methylanilino)thiophen-3-yl]acetate Chemical compound COC(=O)CC1=CSC(Cl)=C1NC1=C(C)C=CC=C1Cl PPECUTDHISTLTF-UHFFFAOYSA-N 0.000 description 3
TUSSXVYKOOVOID-UHFFFAOYSA-N methyl 3-oxothiolane-2-carboxylate Chemical compound COC(=O)C1SCCC1=O TUSSXVYKOOVOID-UHFFFAOYSA-N 0.000 description 3
125000002560 nitrile group Chemical group 0.000 description 3
239000004006 olive oil Substances 0.000 description 3
235000008390 olive oil Nutrition 0.000 description 3
239000000312 peanut oil Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000004044 response Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000012453 sprague-dawley rat model Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
239000008399 tap water Substances 0.000 description 3
235000020679 tap water Nutrition 0.000 description 3
231100001274 therapeutic index Toxicity 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
YUZICJITAGPRGZ-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3h-thieno[3,4-b]pyrrol-2-one Chemical compound ClC1=CC=CC(Cl)=C1N1C2=CSC=C2CC1=O YUZICJITAGPRGZ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GHNAUCQJEAXYSE-UHFFFAOYSA-N 2-[3-(2,6-dichloroanilino)-4-methylthiophen-2-yl]-2-oxoacetic acid Chemical compound CC1=CSC(C(=O)C(O)=O)=C1NC1=C(Cl)C=CC=C1Cl GHNAUCQJEAXYSE-UHFFFAOYSA-N 0.000 description 2
SKEYXHHZIDZLJY-UHFFFAOYSA-N 2-[3-(2-chloro-6-methylanilino)thiophen-2-yl]acetic acid Chemical compound CC1=CC=CC(Cl)=C1NC1=C(CC(O)=O)SC=C1 SKEYXHHZIDZLJY-UHFFFAOYSA-N 0.000 description 2
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210000004872 soft tissue Anatomy 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
208000005801 spondylosis Diseases 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
229960002385 streptomycin sulfate Drugs 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000002700 tablet coating Substances 0.000 description 1
238000009492 tablet coating Methods 0.000 description 1
210000004341 tarsal joint Anatomy 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
229960001385 thiamine disulfide Drugs 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP6277979A 1978-05-24 1979-05-23 Phenylaminothiopheneacetic acid*its manufacture and drug containing it and having antiiinflammatory*sedative and antipyretic activity Granted JPS54154758A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH568778		1978-05-24

Publications (2)

Publication Number	Publication Date
JPS54154758A JPS54154758A (en)	1979-12-06
JPS6254105B2 true JPS6254105B2 (fr)	1987-11-13

Family

ID=4297692

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6277979A Granted JPS54154758A (en)	1978-05-24	1979-05-23	Phenylaminothiopheneacetic acidits manufacture and drug containing it and having antiiinflammatorysedative and antipyretic activity

Country Status (5)

Country	Link
JP (1)	JPS54154758A (fr)
BE (1)	BE876525A (fr)
GR (1)	GR67188B (fr)
PL (1)	PL123268B1 (fr)
ZA (1)	ZA792504B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1601663B1 (fr) *	2003-02-19	2008-12-10	Nycomed GmbH	Nitrate-esters de derives d'acide phenylaminothiophenacetique

1979
- 1979-04-18 GR GR58943A patent/GR67188B/el unknown
- 1979-05-22 ZA ZA792504A patent/ZA792504B/xx unknown
- 1979-05-22 PL PL1979215775A patent/PL123268B1/pl unknown
- 1979-05-23 JP JP6277979A patent/JPS54154758A/ja active Granted
- 1979-05-23 BE BE6/46844A patent/BE876525A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
PL123268B1 (en)	1982-10-30
GR67188B (fr)	1981-06-24
BE876525A (fr)	1979-11-23
JPS54154758A (en)	1979-12-06
ZA792504B (en)	1980-06-25
PL215775A1 (fr)	1980-07-01

Publication	Publication Date	Title
Goel et al.	1999	2-Substituted-3-(4-bromo-2-carboxyphenyl)-5-methyl-4-thiazolidinones as potential anti-inflammatory agents
KR840002434B1 (ko)	1984-12-27	이미다졸 유도체의 제조방법
JPH0153671B2 (fr)	1989-11-15
NO133669B (fr)	1976-03-01
JPH0251897B2 (fr)	1990-11-08
US4239901A (en)	1980-12-16	Pyrazol-1-ylphenylacetic acids
US3470195A (en)	1969-09-30	Phenyl and benzyl oxazole acetic acid compounds
US3933905A (en)	1976-01-20	(5-Oxo-10,11-dihydrodibenzo[a,d]-cyclohepten-2-yl)-alkanoic acids
EP0005559B1 (fr)	1981-11-04	Dérivés d'acide phénylaminothiophène-acétique, procédé pour leur préparation et médicaments les contenant
US3860636A (en)	1975-01-14	Substituted indenyl phosphonic acids having anti-inflammatory activity
EP0592664B1 (fr)	2000-07-05	Derives de diphenylthiazole ayant une activite antiinflammatoire
JP2000508638A (ja)	2000-07-11	新規のフランジアリールメチリデン誘導体、その製造方法及びその治療上の使用
GB2204037A (en)	1988-11-02	N-substituted 4-hydroxypyridine-3-carboxamides
JPS6254105B2 (fr)	1987-11-13
JPS5877849A (ja)	1983-05-11	ビフエニルアルキルカルボン酸エステル誘導体、その製造法及びこれを含む医薬
CA1139763A (fr)	1983-01-18	Procede d'obtention de nouveaux aryltrifluoroethanols
EP0083222B1 (fr)	1986-02-26	Acides quinoléinylacétiques et compositions pharmaceutiques les contenant
JPS6054285B2 (ja)	1985-11-29	シクロヘキサン誘導体を含有する医薬
DK154136B (da)	1988-10-17	Analogifremgangsmaade til fremstilling af 2-amino-3-benzoylphenylacetamider
JPH0859458A (ja)	1996-03-05	インダン誘導体を含有する高脂血症治療剤
US4042702A (en)	1977-08-16	Halogen pyrazole derivatives, a method for producing these halogen pyrazole derivatives, medicaments containing and methods of using them
US4087549A (en)	1978-05-02	Sulphonic acid containing indenyl derivatives
US3975437A (en)	1976-08-17	Dibenzo (a,d) cycloheptene derivatives
EP0011854B1 (fr)	1982-04-07	Dérivés de l'acide 4-(2'-pyridylamino)phényl-acétique, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et leur utilisation
FR2478640A1 (fr)	1981-09-25	Nouvelles thieno (2,3-d) pyridazinones-4 et thieno (2,3-d) pyridazinones-7, leur procede de preparation et leur therapeutique