NO834637L - Fremgangsmaate ved fremstilling av nye tieno(2,3-6)-pyrrolderivater - Google Patents
Fremgangsmaate ved fremstilling av nye tieno(2,3-6)-pyrrolderivaterInfo
- Publication number
- NO834637L NO834637L NO834637A NO834637A NO834637L NO 834637 L NO834637 L NO 834637L NO 834637 A NO834637 A NO 834637A NO 834637 A NO834637 A NO 834637A NO 834637 L NO834637 L NO 834637L
- Authority
- NO
- Norway
- Prior art keywords
- residue
- compounds
- pyrrole
- methyl
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- MYTYHLDSYLKPSF-UHFFFAOYSA-N 6h-thieno[2,3-b]pyrrole Chemical class C1=CSC2=C1C=CN2 MYTYHLDSYLKPSF-UHFFFAOYSA-N 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 150000001299 aldehydes Chemical group 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- -1 cyano, carboxy Chemical group 0.000 abstract description 3
- 208000000094 Chronic Pain Diseases 0.000 abstract description 2
- 230000001154 acute effect Effects 0.000 abstract description 2
- 208000005298 acute pain Diseases 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 208000002193 Pain Diseases 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- UFXHPFAOYHEIMJ-UHFFFAOYSA-N (4-chlorophenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=CC=C(Cl)C=C1 UFXHPFAOYHEIMJ-UHFFFAOYSA-N 0.000 description 3
- KDZWAECTZBCGTB-UHFFFAOYSA-N 2-(4-benzoyl-3-methylthieno[2,3-b]pyrrol-6-yl)propanoic acid Chemical compound C1=2C(C)=CSC=2N(C(C(O)=O)C)C=C1C(=O)C1=CC=CC=C1 KDZWAECTZBCGTB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MDLKWDQMIZRIBY-UHFFFAOYSA-N 1-(dimethylamino)ethanol Chemical class CC(O)N(C)C MDLKWDQMIZRIBY-UHFFFAOYSA-N 0.000 description 2
- 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
- WPBLWCGQUGOFPH-UHFFFAOYSA-N 4-(4-chlorobenzoyl)-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylic acid Chemical compound C1=2C(C)=C(C(O)=O)SC=2NC(C(O)=O)=C1C(=O)C1=CC=C(Cl)C=C1 WPBLWCGQUGOFPH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- DHIJTAXELAKZLR-UHFFFAOYSA-N diethyl 3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylate Chemical compound CC1=C(C(=O)OCC)SC2=C1C=C(C(=O)OCC)N2 DHIJTAXELAKZLR-UHFFFAOYSA-N 0.000 description 2
- YJFJOUUMGTZERN-UHFFFAOYSA-N diethyl 4-(4-chlorobenzoyl)-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C=1NC=2SC(C(=O)OCC)=C(C)C=2C=1C(=O)C1=CC=C(Cl)C=C1 YJFJOUUMGTZERN-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 2
- 229960001650 glafenine Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FQZKTZUIIUFJOO-UHFFFAOYSA-N (2,6-dichlorophenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=C(Cl)C=CC=C1Cl FQZKTZUIIUFJOO-UHFFFAOYSA-N 0.000 description 1
- YKTHDKVTIWHUHW-UHFFFAOYSA-N (2-chlorophenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=CC=CC=C1Cl YKTHDKVTIWHUHW-UHFFFAOYSA-N 0.000 description 1
- BFCXJOVPIDPAPP-UHFFFAOYSA-N (2-methylphenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=CC=CC=C1C BFCXJOVPIDPAPP-UHFFFAOYSA-N 0.000 description 1
- OHSOGPHHVKJFPU-UHFFFAOYSA-N (3-chlorophenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=CC=CC(Cl)=C1 OHSOGPHHVKJFPU-UHFFFAOYSA-N 0.000 description 1
- TYOQDEZZRSQYLK-UHFFFAOYSA-N (3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)-phenylmethanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=CC=CC=C1 TYOQDEZZRSQYLK-UHFFFAOYSA-N 0.000 description 1
- AWZHKDJBLLZFLI-UHFFFAOYSA-N (4-fluorophenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=2C(C)=CSC=2NC=C1C(=O)C1=CC=C(F)C=C1 AWZHKDJBLLZFLI-UHFFFAOYSA-N 0.000 description 1
- JBJLWIJYWJAPCP-UHFFFAOYSA-N (4-methoxyphenyl)-(3-methyl-6h-thieno[2,3-b]pyrrol-4-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CNC2=C1C(C)=CS2 JBJLWIJYWJAPCP-UHFFFAOYSA-N 0.000 description 1
- ZACLMESRUMHIAM-UHFFFAOYSA-N 2-(4-acetyl-3-methylthieno[2,3-b]pyrrol-6-yl)acetic acid Chemical compound S1C=C(C)C2=C1N(CC(O)=O)C=C2C(=O)C ZACLMESRUMHIAM-UHFFFAOYSA-N 0.000 description 1
- WUMVUVNFZIRREA-UHFFFAOYSA-N 2-[4-(2-chlorobenzoyl)-3-methylthieno[2,3-b]pyrrol-6-yl]acetic acid Chemical compound C1=2C(C)=CSC=2N(CC(O)=O)C=C1C(=O)C1=CC=CC=C1Cl WUMVUVNFZIRREA-UHFFFAOYSA-N 0.000 description 1
- FUJBWZNKOBVXJY-UHFFFAOYSA-N 2-[4-(2-chlorobenzoyl)-3-methylthieno[2,3-b]pyrrol-6-yl]propanoic acid Chemical compound C1=2C(C)=CSC=2N(C(C(O)=O)C)C=C1C(=O)C1=CC=CC=C1Cl FUJBWZNKOBVXJY-UHFFFAOYSA-N 0.000 description 1
- LXKCNIIFYQNVRT-UHFFFAOYSA-N 2-[4-(4-chlorobenzoyl)-3-methylthieno[2,3-b]pyrrol-6-yl]acetic acid Chemical compound C1=2C(C)=CSC=2N(CC(O)=O)C=C1C(=O)C1=CC=C(Cl)C=C1 LXKCNIIFYQNVRT-UHFFFAOYSA-N 0.000 description 1
- YZYZKXALSMPQQA-UHFFFAOYSA-N 4-(2,6-dichlorobenzoyl)-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylic acid Chemical compound C1=2C(C)=C(C(O)=O)SC=2NC(C(O)=O)=C1C(=O)C1=C(Cl)C=CC=C1Cl YZYZKXALSMPQQA-UHFFFAOYSA-N 0.000 description 1
- MXULMQSASOKTQL-UHFFFAOYSA-N 4-(2-chlorobenzoyl)-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylic acid Chemical compound C1=2C(C)=C(C(O)=O)SC=2NC(C(O)=O)=C1C(=O)C1=CC=CC=C1Cl MXULMQSASOKTQL-UHFFFAOYSA-N 0.000 description 1
- XAFLGJWVPRLOLQ-UHFFFAOYSA-N 4-acetyl-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylic acid Chemical compound S1C(C(O)=O)=C(C)C2=C1NC(C(O)=O)=C2C(=O)C XAFLGJWVPRLOLQ-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- BKLYKHSVDXVNIL-UHFFFAOYSA-N diethyl 4-(2,6-dichlorobenzoyl)-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C=1NC=2SC(C(=O)OCC)=C(C)C=2C=1C(=O)C1=C(Cl)C=CC=C1Cl BKLYKHSVDXVNIL-UHFFFAOYSA-N 0.000 description 1
- RXRZLUFTTMOUFE-UHFFFAOYSA-N diethyl 4-(2-chlorobenzoyl)-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C=1NC=2SC(C(=O)OCC)=C(C)C=2C=1C(=O)C1=CC=CC=C1Cl RXRZLUFTTMOUFE-UHFFFAOYSA-N 0.000 description 1
- HMNMPXYXZFKDEU-UHFFFAOYSA-N diethyl 4-acetyl-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylate Chemical compound S1C(C(=O)OCC)=C(C)C2=C1NC(C(=O)OCC)=C2C(C)=O HMNMPXYXZFKDEU-UHFFFAOYSA-N 0.000 description 1
- QSZWCYZOFXHQDW-UHFFFAOYSA-N diethyl 4-benzoyl-3-methyl-6h-thieno[2,3-b]pyrrole-2,5-dicarboxylate Chemical compound CCOC(=O)C=1NC=2SC(C(=O)OCC)=C(C)C=2C=1C(=O)C1=CC=CC=C1 QSZWCYZOFXHQDW-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- HOXMUFDZGGNNEA-UHFFFAOYSA-N ethyl 5-acetamido-4-cyano-3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(NC(C)=O)=C(C#N)C=1C HOXMUFDZGGNNEA-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 208000008423 pleurisy Diseases 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 125000003259 prostaglandin group Chemical group 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000000472 traumatic effect Effects 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8221090A FR2537974A1 (fr) | 1982-12-16 | 1982-12-16 | Nouveaux derives de thieno (2,3-b) pyrrole, leur procede de preparation et les compositions pharmaceutiques les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO834637L true NO834637L (no) | 1984-06-18 |
Family
ID=9280166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834637A NO834637L (no) | 1982-12-16 | 1983-12-15 | Fremgangsmaate ved fremstilling av nye tieno(2,3-6)-pyrrolderivater |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4608384A (ja) |
| EP (1) | EP0114014B1 (ja) |
| JP (1) | JPS59118788A (ja) |
| KR (1) | KR840007004A (ja) |
| AT (1) | ATE27277T1 (ja) |
| AU (1) | AU2245883A (ja) |
| CA (1) | CA1212380A (ja) |
| DD (1) | DD259193A5 (ja) |
| DE (1) | DE3371632D1 (ja) |
| DK (1) | DK577483A (ja) |
| ES (1) | ES8501766A1 (ja) |
| FR (1) | FR2537974A1 (ja) |
| GR (1) | GR79477B (ja) |
| IL (1) | IL70457A (ja) |
| MA (1) | MA19977A1 (ja) |
| NO (1) | NO834637L (ja) |
| OA (1) | OA07612A (ja) |
| PH (1) | PH19425A (ja) |
| PT (1) | PT77826B (ja) |
| ZA (1) | ZA839341B (ja) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2554819B1 (fr) * | 1983-11-10 | 1986-05-16 | Adir | Nouveaux derives de thieno (2,3-b) pyrrole, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| JP3091297B2 (ja) * | 1992-01-10 | 2000-09-25 | 住友製薬株式会社 | ピロリジン誘導体およびその製造方法 |
| FR2733750B1 (fr) * | 1995-05-03 | 1997-06-13 | Synthelabo | Derives de l'acide gamma-oxo-alpha-(phenylmethyl)-5,6- dihydro-4h-thieno(3,4-c)pyrrole-5-butanoique, leur preparation et leur application en therapeutique |
| GB9716657D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9803226D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| GB9803228D0 (en) * | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| GB9902455D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902453D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902461D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902459D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902452D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB0000625D0 (en) | 2000-01-13 | 2000-03-01 | Zeneca Ltd | Chemical compounds |
| AU2001280461A1 (en) * | 2000-08-04 | 2002-02-18 | Eli Lilly And Company | Substituted pyrrole compounds and their use as spla2 inhibitors |
| US6730694B1 (en) * | 2001-07-20 | 2004-05-04 | Eli Lilly And Company | sPLA2 inhibitors |
| JP2004035507A (ja) * | 2002-07-05 | 2004-02-05 | Nippon Soda Co Ltd | ピロール誘導体及びその製造方法 |
| US7196106B2 (en) * | 2002-11-05 | 2007-03-27 | Merck & Co., Inc | Cyanothiophene derivatives, compositions containing such compounds and methods of use |
| DK1648904T3 (da) * | 2003-07-31 | 2007-10-22 | Wyeth Corp | N-sulfonylheterocyclopyrrolalkylaminforbindelser som 5-hydroxytryptamin-6-ligander |
| WO2011100324A1 (en) * | 2010-02-09 | 2011-08-18 | Ironwood Pharmaceuticals Inc. | Cannabinoid receptor agonists |
-
1982
- 1982-12-16 FR FR8221090A patent/FR2537974A1/fr active Granted
-
1983
- 1983-12-12 US US06/560,419 patent/US4608384A/en not_active Expired - Fee Related
- 1983-12-14 KR KR1019830005937A patent/KR840007004A/ko not_active Application Discontinuation
- 1983-12-15 EP EP83402438A patent/EP0114014B1/fr not_active Expired
- 1983-12-15 IL IL70457A patent/IL70457A/xx not_active IP Right Cessation
- 1983-12-15 PH PH29982A patent/PH19425A/en unknown
- 1983-12-15 ES ES528088A patent/ES8501766A1/es not_active Expired
- 1983-12-15 AT AT83402438T patent/ATE27277T1/de not_active IP Right Cessation
- 1983-12-15 CA CA000443344A patent/CA1212380A/fr not_active Expired
- 1983-12-15 PT PT77826A patent/PT77826B/pt unknown
- 1983-12-15 OA OA58184A patent/OA07612A/xx unknown
- 1983-12-15 GR GR73254A patent/GR79477B/el unknown
- 1983-12-15 DE DE8383402438T patent/DE3371632D1/de not_active Expired
- 1983-12-15 AU AU22458/83A patent/AU2245883A/en not_active Abandoned
- 1983-12-15 NO NO834637A patent/NO834637L/no unknown
- 1983-12-15 ZA ZA839341A patent/ZA839341B/xx unknown
- 1983-12-15 DK DK577483A patent/DK577483A/da not_active Application Discontinuation
- 1983-12-16 MA MA20198A patent/MA19977A1/fr unknown
- 1983-12-16 DD DD83258084A patent/DD259193A5/de unknown
- 1983-12-16 JP JP58237747A patent/JPS59118788A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL70457A (en) | 1986-02-28 |
| FR2537974A1 (fr) | 1984-06-22 |
| DD259193A5 (de) | 1988-08-17 |
| ZA839341B (en) | 1984-07-25 |
| ES528088A0 (es) | 1984-12-16 |
| US4608384A (en) | 1986-08-26 |
| EP0114014A2 (fr) | 1984-07-25 |
| OA07612A (fr) | 1985-03-31 |
| EP0114014B1 (fr) | 1987-05-20 |
| DK577483A (da) | 1984-06-17 |
| PH19425A (en) | 1986-04-15 |
| AU2245883A (en) | 1984-06-21 |
| MA19977A1 (fr) | 1984-07-01 |
| DE3371632D1 (en) | 1987-06-25 |
| EP0114014A3 (en) | 1984-08-22 |
| FR2537974B1 (ja) | 1985-03-15 |
| ATE27277T1 (de) | 1987-06-15 |
| PT77826B (fr) | 1986-05-05 |
| CA1212380A (fr) | 1986-10-07 |
| ES8501766A1 (es) | 1984-12-16 |
| GR79477B (ja) | 1984-10-30 |
| DK577483D0 (da) | 1983-12-15 |
| KR840007004A (ko) | 1984-12-04 |
| IL70457A0 (en) | 1984-03-30 |
| PT77826A (fr) | 1984-01-01 |
| JPS59118788A (ja) | 1984-07-09 |
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