HU191209B - Process for preparing 4h-furo/3,2-b/indole derivatives with antiallergic activity - Google Patents
Process for preparing 4h-furo/3,2-b/indole derivatives with antiallergic activity Download PDFInfo
- Publication number
- HU191209B HU191209B HU831341A HU134183A HU191209B HU 191209 B HU191209 B HU 191209B HU 831341 A HU831341 A HU 831341A HU 134183 A HU134183 A HU 134183A HU 191209 B HU191209 B HU 191209B
- Authority
- HU
- Hungary
- Prior art keywords
- furo
- indole
- phenyl
- pharmaceutically acceptable
- carboxylic acid
- Prior art date
Links
- 230000003266 anti-allergic effect Effects 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 150000002475 indoles Chemical class 0.000 title abstract 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- HOOUZIRMRBQJEQ-UHFFFAOYSA-N 4h-furo[3,2-b]indole Chemical class N1C2=CC=CC=C2C2=C1C=CO2 HOOUZIRMRBQJEQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract 2
- 239000002184 metal Substances 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 17
- 150000002825 nitriles Chemical class 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 230000029936 alkylation Effects 0.000 claims description 11
- 238000005804 alkylation reaction Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 9
- 150000003536 tetrazoles Chemical class 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- YUEDRIPQRRVFJV-UHFFFAOYSA-N 3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical class C1=2C(OCC)=C(C(O)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 YUEDRIPQRRVFJV-UHFFFAOYSA-N 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- YCXRJOZNRPGVCN-UHFFFAOYSA-N 3,7-dimethoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OC)=C(C(=O)NC3=NNN=N3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 YCXRJOZNRPGVCN-UHFFFAOYSA-N 0.000 claims description 5
- LTNCFABAGCHHCV-UHFFFAOYSA-N 3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical class C1=2C(OC)=C(C(O)=O)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 LTNCFABAGCHHCV-UHFFFAOYSA-N 0.000 claims description 5
- VFWAJXMRCXLCOW-UHFFFAOYSA-N 3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical class C1=2C(OCC)=C(C(O)=O)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 VFWAJXMRCXLCOW-UHFFFAOYSA-N 0.000 claims description 5
- FQUMPJZPUCNMHI-UHFFFAOYSA-N 3-ethoxy-7-methoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OCC)=C(C(=O)NC=3NN=NN=3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 FQUMPJZPUCNMHI-UHFFFAOYSA-N 0.000 claims description 4
- ZPWMFKICQTVLOU-UHFFFAOYSA-N 3-methoxy-4-methylfuro[3,2-b]indole-2-carboxylic acid Chemical compound C12=CC=CC=C2N(C)C2=C1OC(C(O)=O)=C2OC ZPWMFKICQTVLOU-UHFFFAOYSA-N 0.000 claims description 4
- UIUZYXSRFZINPJ-UHFFFAOYSA-N 3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylic acid Chemical class C1=2C(OC)=C(C(O)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 UIUZYXSRFZINPJ-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- NDGDVSWGNSXCMK-UHFFFAOYSA-N 3-ethoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OCC)=C(C(=O)NC=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 NDGDVSWGNSXCMK-UHFFFAOYSA-N 0.000 claims description 3
- WZCCJHJBIGMHLJ-UHFFFAOYSA-N 3-methoxy-4-methyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound O1C=2C3=CC=CC=C3N(C)C=2C(OC)=C1C(=O)NC1=NN=NN1 WZCCJHJBIGMHLJ-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical group NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 3
- 229940008406 diethyl sulfate Drugs 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- JOINTFUOXCQRLQ-UHFFFAOYSA-N 3-ethoxy-4-phenyl-2-(2h-tetrazol-5-yl)furo[3,2-b]indole Chemical compound C1=2C(OCC)=C(C=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 JOINTFUOXCQRLQ-UHFFFAOYSA-N 0.000 claims description 2
- 101001062098 Homo sapiens RNA-binding protein 14 Proteins 0.000 claims description 2
- 102100029250 RNA-binding protein 14 Human genes 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- SKQDAKUPRAMWKY-UHFFFAOYSA-N methyl 3-ethoxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OCC)=C(C(=O)OC)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 SKQDAKUPRAMWKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical group OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- DCEMUONUJXUSHM-UHFFFAOYSA-N 3,7-dimethoxy-4-phenyl-2-(2h-tetrazol-5-yl)furo[3,2-b]indole Chemical compound C1=2C(OC)=C(C=3NN=NN=3)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 DCEMUONUJXUSHM-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 8
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 230000007815 allergy Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 238000001953 recrystallisation Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000012043 crude product Substances 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000427 antigen Substances 0.000 description 6
- 102000036639 antigens Human genes 0.000 description 6
- 108091007433 antigens Proteins 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- NPEIRKVWYZPQHS-UHFFFAOYSA-N ethyl 3-methoxy-4-methylfuro[3,2-b]indole-2-carboxylate Chemical compound C12=CC=CC=C2N(C)C2=C1OC(C(=O)OCC)=C2OC NPEIRKVWYZPQHS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000012431 wafers Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 2
- JWJAOYGHEABQSH-UHFFFAOYSA-N 3-ethoxy-4-phenylfuro[3,2-b]indole-2-carbonitrile Chemical compound C1=2C(OCC)=C(C#N)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 JWJAOYGHEABQSH-UHFFFAOYSA-N 0.000 description 2
- FWOGNFJKYGQZOW-UHFFFAOYSA-N 3-methoxy-4-methylfuro[3,2-b]indole-2-carbonitrile Chemical compound C12=CC=CC=C2N(C)C2=C1OC(C#N)=C2OC FWOGNFJKYGQZOW-UHFFFAOYSA-N 0.000 description 2
- UOCRBEBVQFQIKZ-UHFFFAOYSA-N 3-methoxy-4-phenyl-n-(2h-tetrazol-5-yl)furo[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OC)=C(C(=O)NC=3NN=NN=3)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 UOCRBEBVQFQIKZ-UHFFFAOYSA-N 0.000 description 2
- HORCQVXSANZLAY-UHFFFAOYSA-N 3-methoxy-4-phenylfuro[3,2-b]indole-2-carbonitrile Chemical compound C1=2C(OC)=C(C#N)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 HORCQVXSANZLAY-UHFFFAOYSA-N 0.000 description 2
- BKFIBMISQJZFFP-UHFFFAOYSA-N 3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxamide Chemical compound C1=2C(OC)=C(C(N)=O)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 BKFIBMISQJZFFP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 150000001483 arginine derivatives Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000008297 liquid dosage form 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
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- SQGMODLFBXUZFC-UHFFFAOYSA-N methyl 3-ethoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OCC)=C(C(=O)OC)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 SQGMODLFBXUZFC-UHFFFAOYSA-N 0.000 description 2
- LBJWKXZFFSDGRE-UHFFFAOYSA-N methyl 3-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OC)=C(C(=O)OC)OC=2C2=CC=CC=C2N1C1=CC=CC=C1 LBJWKXZFFSDGRE-UHFFFAOYSA-N 0.000 description 2
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- 238000011067 equilibration Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- QBYZWKQETPWEPB-UHFFFAOYSA-N ethyl 3-(2-ethoxy-2-oxoethoxy)-1-methylindole-2-carboxylate Chemical compound C1=CC=C2C(OCC(=O)OCC)=C(C(=O)OCC)N(C)C2=C1 QBYZWKQETPWEPB-UHFFFAOYSA-N 0.000 description 1
- WCYURHXDMXGKQD-UHFFFAOYSA-N ethyl 3-hydroxy-1-methylindole-2-carboxylate Chemical compound C1=CC=C2N(C)C(C(=O)OCC)=C(O)C2=C1 WCYURHXDMXGKQD-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- PPYPKYLOIVTCHE-UHFFFAOYSA-N methyl 3,7-dimethoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(OC)=C(C(=O)OC)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 PPYPKYLOIVTCHE-UHFFFAOYSA-N 0.000 description 1
- SNBBSWPBQYKAKK-UHFFFAOYSA-N methyl 3-(2-methoxy-2-oxoethoxy)-1-phenylindole-2-carboxylate Chemical compound C12=CC=CC=C2C(OCC(=O)OC)=C(C(=O)OC)N1C1=CC=CC=C1 SNBBSWPBQYKAKK-UHFFFAOYSA-N 0.000 description 1
- ODWPOBLOANXRFF-UHFFFAOYSA-N methyl 3-hydroxy-7-methoxy-4-phenylfuro[3,2-b]indole-2-carboxylate Chemical compound C1=2C(O)=C(C(=O)OC)OC=2C2=CC(OC)=CC=C2N1C1=CC=CC=C1 ODWPOBLOANXRFF-UHFFFAOYSA-N 0.000 description 1
- XRYUQPQOMXOEGO-UHFFFAOYSA-N methyl 5-methoxy-2-(n-(2-methoxy-2-oxoethyl)anilino)benzoate Chemical compound C=1C=C(OC)C=C(C(=O)OC)C=1N(CC(=O)OC)C1=CC=CC=C1 XRYUQPQOMXOEGO-UHFFFAOYSA-N 0.000 description 1
- PHFUJJYLQGKDEJ-UHFFFAOYSA-N methyl 5-methoxy-3-(2-methoxy-2-oxoethoxy)-1-phenylindole-2-carboxylate Chemical compound C12=CC=C(OC)C=C2C(OCC(=O)OC)=C(C(=O)OC)N1C1=CC=CC=C1 PHFUJJYLQGKDEJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- QDMPKKFNRFFSNK-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)formamide Chemical compound O=CNC1=NN=NN1 QDMPKKFNRFFSNK-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36944882A | 1982-04-19 | 1982-04-19 | |
| US06/456,121 US4503236A (en) | 1982-04-19 | 1983-01-10 | Antiallergic 4Hfuro[3,2-b]indoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU191209B true HU191209B (en) | 1987-01-28 |
Family
ID=27004584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU831341A HU191209B (en) | 1982-04-19 | 1983-04-18 | Process for preparing 4h-furo/3,2-b/indole derivatives with antiallergic activity |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4503236A (OSRAM) |
| EP (1) | EP0092380B1 (OSRAM) |
| KR (1) | KR870000933B1 (OSRAM) |
| AR (1) | AR240457A1 (OSRAM) |
| AU (1) | AU556487B2 (OSRAM) |
| CA (1) | CA1194880A (OSRAM) |
| DE (1) | DE3375396D1 (OSRAM) |
| DK (1) | DK157025C (OSRAM) |
| ES (1) | ES521563A0 (OSRAM) |
| FI (1) | FI77246C (OSRAM) |
| GR (1) | GR78343B (OSRAM) |
| HU (1) | HU191209B (OSRAM) |
| IE (1) | IE54834B1 (OSRAM) |
| IL (1) | IL68192A (OSRAM) |
| NO (1) | NO159600C (OSRAM) |
| NZ (1) | NZ203908A (OSRAM) |
| PH (1) | PH18914A (OSRAM) |
| PT (1) | PT76570B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4596814A (en) * | 1983-01-10 | 1986-06-24 | Warner-Lambert Company | Tetrazolyl- and carboxamidotetrazolyl-substituted 4H-furo[3,2-b] indoles and anti-allergic use thereof |
| US4748183A (en) * | 1986-06-13 | 1988-05-31 | Warner-Lambert Company | N-1H-tetrazol-5-yl-2-thiophene carboxamides, N-1H-tetrazol-5-yl-2-pyrrole carboxamides, N-1H-tetrazol-5-yl-2-furan carboxamides, and anti-allergic and anti-inflammatory use thereof |
| JPH04217684A (ja) * | 1990-05-30 | 1992-08-07 | Shionogi & Co Ltd | アルド−ス還元酵素阻害物質 |
| GB9110625D0 (en) * | 1991-05-16 | 1991-07-03 | Glaxo Group Ltd | Chemical compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1296469A (OSRAM) * | 1970-02-05 | 1972-11-15 | ||
| US4028383A (en) * | 1975-09-08 | 1977-06-07 | Warner-Lambert Company | Indolopyrones having antiallergic activity |
| DE2837236A1 (de) * | 1977-09-30 | 1979-04-05 | Warner Lambert Co | Indolopyrone und ihre verwendung |
-
1983
- 1983-01-10 US US06/456,121 patent/US4503236A/en not_active Expired - Lifetime
- 1983-03-21 IE IE612/83A patent/IE54834B1/en not_active IP Right Cessation
- 1983-03-22 IL IL68192A patent/IL68192A/xx unknown
- 1983-04-14 GR GR71084A patent/GR78343B/el unknown
- 1983-04-14 EP EP83302099A patent/EP0092380B1/en not_active Expired
- 1983-04-14 AU AU13511/83A patent/AU556487B2/en not_active Expired
- 1983-04-14 DE DE8383302099T patent/DE3375396D1/de not_active Expired
- 1983-04-15 KR KR1019830001595A patent/KR870000933B1/ko not_active Expired
- 1983-04-15 FI FI831272A patent/FI77246C/fi not_active IP Right Cessation
- 1983-04-15 PH PH28783A patent/PH18914A/en unknown
- 1983-04-18 NZ NZ203908A patent/NZ203908A/en unknown
- 1983-04-18 ES ES521563A patent/ES521563A0/es active Granted
- 1983-04-18 NO NO831364A patent/NO159600C/no not_active IP Right Cessation
- 1983-04-18 HU HU831341A patent/HU191209B/hu not_active IP Right Cessation
- 1983-04-18 DK DK169783A patent/DK157025C/da not_active IP Right Cessation
- 1983-04-19 PT PT76570A patent/PT76570B/pt unknown
- 1983-04-19 CA CA000426192A patent/CA1194880A/en not_active Expired
- 1983-04-19 AR AR292747A patent/AR240457A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0092380A3 (en) | 1984-05-30 |
| FI831272L (fi) | 1983-10-20 |
| NZ203908A (en) | 1985-12-13 |
| PT76570A (en) | 1983-05-01 |
| AR240457A1 (es) | 1990-03-30 |
| KR840004432A (ko) | 1984-10-15 |
| NO159600B (no) | 1988-10-10 |
| EP0092380A2 (en) | 1983-10-26 |
| IE54834B1 (en) | 1990-02-28 |
| AU556487B2 (en) | 1986-11-06 |
| CA1194880A (en) | 1985-10-08 |
| KR870000933B1 (ko) | 1987-05-11 |
| DE3375396D1 (en) | 1988-02-25 |
| IL68192A0 (en) | 1983-06-15 |
| PH18914A (en) | 1985-11-06 |
| IE830612L (en) | 1983-10-19 |
| DK157025C (da) | 1990-03-26 |
| DK169783A (da) | 1983-10-20 |
| ES8406486A1 (es) | 1984-07-01 |
| US4503236A (en) | 1985-03-05 |
| DK157025B (da) | 1989-10-30 |
| NO831364L (no) | 1983-10-20 |
| DK169783D0 (da) | 1983-04-18 |
| EP0092380B1 (en) | 1988-01-20 |
| FI77246B (fi) | 1988-10-31 |
| FI831272A0 (fi) | 1983-04-15 |
| FI77246C (fi) | 1989-02-10 |
| PT76570B (pt) | 1985-12-10 |
| NO159600C (no) | 1989-01-18 |
| GR78343B (OSRAM) | 1984-09-26 |
| AU1351183A (en) | 1983-10-27 |
| ES521563A0 (es) | 1984-07-01 |
| IL68192A (en) | 1985-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |