DE3537768A1 - Neue 4-(3-thienyl)phenyl-alcancarbonsaeuren und deren derivate als entzuendungshemmende und antiarthritische arzneimittel - Google Patents
Neue 4-(3-thienyl)phenyl-alcancarbonsaeuren und deren derivate als entzuendungshemmende und antiarthritische arzneimittelInfo
- Publication number
- DE3537768A1 DE3537768A1 DE19853537768 DE3537768A DE3537768A1 DE 3537768 A1 DE3537768 A1 DE 3537768A1 DE 19853537768 DE19853537768 DE 19853537768 DE 3537768 A DE3537768 A DE 3537768A DE 3537768 A1 DE3537768 A1 DE 3537768A1
- Authority
- DE
- Germany
- Prior art keywords
- thienyl
- phenyl
- methyl
- hydrogen
- acids
- 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.)
- Granted
Links
- -1 4- (3-THIENYL) PHENYL Chemical class 0.000 title claims description 51
- 239000002253 acid Substances 0.000 title claims description 31
- 150000007513 acids Chemical class 0.000 title claims description 20
- 230000002456 anti-arthritic effect Effects 0.000 title description 3
- 230000002757 inflammatory effect Effects 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 13
- ZGWSBZQVHPJFNR-UHFFFAOYSA-N 2-(4-thiophen-3-ylphenyl)acetonitrile Chemical compound C1=CC(CC#N)=CC=C1C1=CSC=C1 ZGWSBZQVHPJFNR-UHFFFAOYSA-N 0.000 claims description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- PFLCZHOSQMPCMN-UHFFFAOYSA-N 2-(4-thiophen-3-ylphenyl)propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CSC=C1 PFLCZHOSQMPCMN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- BUVVMCSDRGHLCC-UHFFFAOYSA-N 2-(4-thiophen-3-ylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CSC=C1 BUVVMCSDRGHLCC-UHFFFAOYSA-N 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- CCUJJVAQFMGIJO-UHFFFAOYSA-N 3-[4-(bromomethyl)phenyl]thiophene Chemical compound C1=CC(CBr)=CC=C1C1=CSC=C1 CCUJJVAQFMGIJO-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CUJNFQBKPBMRPZ-UHFFFAOYSA-N 2-(4-thiophen-3-ylphenyl)propan-1-ol Chemical compound S1C=C(C=C1)C1=CC=C(C=C1)C(CO)C CUJNFQBKPBMRPZ-UHFFFAOYSA-N 0.000 claims description 4
- HNCPAJPMBWXHEH-UHFFFAOYSA-N 3-(4-methylphenyl)thiophene Chemical compound C1=CC(C)=CC=C1C1=CSC=C1 HNCPAJPMBWXHEH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- RLWPMJJQDMPZIF-UHFFFAOYSA-N N-hydroxy-2-(4-thiophen-3-ylphenyl)propanamide Chemical compound S1C=C(C=C1)C1=CC=C(C=C1)C(C(=O)NO)C RLWPMJJQDMPZIF-UHFFFAOYSA-N 0.000 claims description 3
- 150000003983 crown ethers Chemical class 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- GOKGNUMKBYWRIA-UHFFFAOYSA-N 5-[(4-thiophen-3-ylphenyl)methyl]-2h-tetrazole Chemical compound C=1C=C(C2=CSC=C2)C=CC=1CC=1N=NNN=1 GOKGNUMKBYWRIA-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 3
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229960002895 phenylbutazone Drugs 0.000 description 13
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 229960000905 indomethacin Drugs 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- WINXAKJYORVNHU-UHFFFAOYSA-N methyl 2-(4-thiophen-3-ylphenyl)propanoate Chemical compound C1=CC(C(C)C(=O)OC)=CC=C1C1=CSC=C1 WINXAKJYORVNHU-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000001754 anti-pyretic effect Effects 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate 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
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8525881A GB2181728B (en) | 1985-10-21 | 1985-10-21 | 4-(3-thienyl)phenylalkanoic acids and derivatives and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3537768A1 true DE3537768A1 (de) | 1987-04-30 |
Family
ID=10586988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853537768 Granted DE3537768A1 (de) | 1985-10-21 | 1985-10-24 | Neue 4-(3-thienyl)phenyl-alcancarbonsaeuren und deren derivate als entzuendungshemmende und antiarthritische arzneimittel |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH672128A5 (enExample) |
| DE (1) | DE3537768A1 (enExample) |
| FR (1) | FR2589156B3 (enExample) |
| GB (1) | GB2181728B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6617351B1 (en) | 1998-07-31 | 2003-09-09 | Eli Lilly And Company | Amide, carbamate, and urea derivatives |
| PE20000942A1 (es) * | 1998-07-31 | 2000-09-28 | Lilly Co Eli | Derivados de amida, carbamato y urea |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2711585A1 (de) * | 1976-03-24 | 1977-09-29 | Lipha | 2-eckige klammer auf 4-thenoyl-(3')- phenyl eckige klammer zu -propionsaeure und deren salze, verfahren zu deren herstellung und sie enthaltende arzneimittel |
| DE2850485B2 (de) * | 1977-11-21 | 1981-01-08 | Toyama Chemical Co. Ltd., Tokio | 2- {4- [3-Methyl-thienyl (2)] -phenyl} -propionsäure, pharmazeutisch verträgliches Salz derselben, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von rheumatischen Schmerzzuständen und Entzündungen |
| DE3229752A1 (de) * | 1981-08-11 | 1983-07-21 | Laboratorios Madaus Cerafarm, S.A., Barcelona | 5'-substituierte 2-(3'-thienyl)-propionsaeuren |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6574940D0 (pt) * | 1964-11-27 | 1973-08-07 | Merck & Co Inc | Processo para fazer acidos fenil-aceticos |
-
1985
- 1985-10-21 GB GB8525881A patent/GB2181728B/en not_active Expired - Fee Related
- 1985-10-24 CH CH458385A patent/CH672128A5/de not_active IP Right Cessation
- 1985-10-24 DE DE19853537768 patent/DE3537768A1/de active Granted
- 1985-10-25 FR FR8515895A patent/FR2589156B3/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2711585A1 (de) * | 1976-03-24 | 1977-09-29 | Lipha | 2-eckige klammer auf 4-thenoyl-(3')- phenyl eckige klammer zu -propionsaeure und deren salze, verfahren zu deren herstellung und sie enthaltende arzneimittel |
| DE2850485B2 (de) * | 1977-11-21 | 1981-01-08 | Toyama Chemical Co. Ltd., Tokio | 2- {4- [3-Methyl-thienyl (2)] -phenyl} -propionsäure, pharmazeutisch verträgliches Salz derselben, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von rheumatischen Schmerzzuständen und Entzündungen |
| DE3229752A1 (de) * | 1981-08-11 | 1983-07-21 | Laboratorios Madaus Cerafarm, S.A., Barcelona | 5'-substituierte 2-(3'-thienyl)-propionsaeuren |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8525881D0 (en) | 1985-11-27 |
| GB2181728B (en) | 1990-01-24 |
| GB2181728A (en) | 1987-04-29 |
| CH672128A5 (enExample) | 1989-10-31 |
| FR2589156A1 (fr) | 1987-04-30 |
| FR2589156B3 (fr) | 1988-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |