NO781102L - Fremgangsmaate til fremstilling av cyklopropyl-6-dihydro-1,3-metyl-1-fenyl-5-okso-2,2h-tieno(2,3-2)-diazepin og salter derav - Google Patents
Fremgangsmaate til fremstilling av cyklopropyl-6-dihydro-1,3-metyl-1-fenyl-5-okso-2,2h-tieno(2,3-2)-diazepin og salter deravInfo
- Publication number
- NO781102L NO781102L NO781102A NO781102A NO781102L NO 781102 L NO781102 L NO 781102L NO 781102 A NO781102 A NO 781102A NO 781102 A NO781102 A NO 781102A NO 781102 L NO781102 L NO 781102L
- Authority
- NO
- Norway
- Prior art keywords
- cyclopropyl
- compound
- thieno
- diazepine
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006263 metalation reaction Methods 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- CWBXRPMPOBUVMH-UHFFFAOYSA-N 1-cyclopropylbutan-2-one Chemical compound CCC(=O)CC1CC1 CWBXRPMPOBUVMH-UHFFFAOYSA-N 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 206010052428 Wound Diseases 0.000 description 8
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 241000700159 Rattus Species 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- LPRBSWPDOZIDQE-UHFFFAOYSA-N 4-cyclopropylbutan-2-one Chemical compound CC(=O)CCC1CC1 LPRBSWPDOZIDQE-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- 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 2
- 238000000746 purification Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 101150046432 Tril gene Proteins 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- 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
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1358777 | 1977-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781102L true NO781102L (no) | 1978-10-03 |
Family
ID=10025687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781102A NO781102L (no) | 1977-03-31 | 1978-03-30 | Fremgangsmaate til fremstilling av cyklopropyl-6-dihydro-1,3-metyl-1-fenyl-5-okso-2,2h-tieno(2,3-2)-diazepin og salter derav |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4156009A (es) |
| JP (1) | JPS53121791A (es) |
| AR (1) | AR215171A1 (es) |
| AU (1) | AU3495678A (es) |
| BE (1) | BE865278A (es) |
| DD (2) | DD143777A5 (es) |
| DE (1) | DE2813996A1 (es) |
| DK (1) | DK135478A (es) |
| ES (2) | ES468382A1 (es) |
| FR (1) | FR2385721A1 (es) |
| GR (1) | GR62853B (es) |
| NL (1) | NL7803431A (es) |
| NO (1) | NO781102L (es) |
| PT (1) | PT67813A (es) |
| SE (1) | SE7803604L (es) |
| SU (1) | SU715027A3 (es) |
| ZA (1) | ZA781694B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0225554D0 (en) * | 2002-11-01 | 2002-12-11 | Syngenta Participations Ag | Chemical compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1256548A (es) * | 1968-12-10 | 1971-12-08 | ||
| CA927388A (en) * | 1970-02-17 | 1973-05-29 | Nakanishi Michio | Thieno (2,3-e)(1,4)diazepin-2-ones |
| US3806512A (en) * | 1970-09-03 | 1974-04-23 | Yoshitomi Pharmaceutical | 2-amino-3-pyridylcarbonylthiophene compounds |
| FI53214C (es) * | 1970-11-16 | 1978-03-10 | Sumitomo Chemical Co | |
| US3872089A (en) * | 1971-05-14 | 1975-03-18 | Hoffmann La Roche | Substituted thienodiazepines |
| GB1345998A (en) * | 1971-05-31 | 1974-02-06 | Yoshitomi Pharmaceutical | Thienodiazepine compounds and pharmaceutical compositions containining them |
| JPS5750794B2 (es) * | 1973-02-03 | 1982-10-28 | ||
| JPS5729472B2 (es) * | 1974-05-02 | 1982-06-23 |
-
1978
- 1978-03-16 FR FR7807697A patent/FR2385721A1/fr not_active Withdrawn
- 1978-03-23 PT PT67813A patent/PT67813A/pt unknown
- 1978-03-23 ZA ZA00781694A patent/ZA781694B/xx unknown
- 1978-03-23 GR GR55787A patent/GR62853B/el unknown
- 1978-03-24 BE BE2056799A patent/BE865278A/xx unknown
- 1978-03-27 JP JP3525278A patent/JPS53121791A/ja active Pending
- 1978-03-27 AR AR271535A patent/AR215171A1/es active
- 1978-03-27 US US05/890,410 patent/US4156009A/en not_active Expired - Lifetime
- 1978-03-28 DK DK135478A patent/DK135478A/da unknown
- 1978-03-29 DD DD78213659A patent/DD143777A5/de unknown
- 1978-03-29 DD DD78204460A patent/DD137108A5/xx unknown
- 1978-03-30 SU SU782594351A patent/SU715027A3/ru active
- 1978-03-30 SE SE7803604A patent/SE7803604L/xx unknown
- 1978-03-30 ES ES468382A patent/ES468382A1/es not_active Expired
- 1978-03-30 NO NO781102A patent/NO781102L/no unknown
- 1978-03-31 NL NL7803431A patent/NL7803431A/xx not_active Application Discontinuation
- 1978-03-31 DE DE19782813996 patent/DE2813996A1/de active Pending
- 1978-04-11 AU AU34956/78A patent/AU3495678A/en active Pending
-
1979
- 1979-01-25 ES ES477164A patent/ES477164A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU715027A3 (ru) | 1980-02-05 |
| DD143777A5 (de) | 1980-09-10 |
| GR62853B (en) | 1979-06-20 |
| BE865278A (fr) | 1978-09-25 |
| US4156009A (en) | 1979-05-22 |
| NL7803431A (nl) | 1978-10-03 |
| ZA781694B (en) | 1979-03-28 |
| PT67813A (fr) | 1978-04-01 |
| FR2385721A1 (fr) | 1978-10-27 |
| SE7803604L (sv) | 1978-10-01 |
| ES477164A1 (es) | 1979-10-16 |
| DK135478A (da) | 1978-10-01 |
| DE2813996A1 (de) | 1978-10-05 |
| AR215171A1 (es) | 1979-09-14 |
| ES468382A1 (es) | 1979-10-01 |
| AU3495678A (en) | 1979-10-18 |
| JPS53121791A (en) | 1978-10-24 |
| DD137108A5 (de) | 1979-08-15 |
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