FI62301C - Analogifoerfarande foer framstaellning av farmakologiskt aktiva imidazolderivat - Google Patents
Analogifoerfarande foer framstaellning av farmakologiskt aktiva imidazolderivat Download PDFInfo
- Publication number
- FI62301C FI62301C FI1261/74A FI126174A FI62301C FI 62301 C FI62301 C FI 62301C FI 1261/74 A FI1261/74 A FI 1261/74A FI 126174 A FI126174 A FI 126174A FI 62301 C FI62301 C FI 62301C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- imidazolylmethylthio
- ethylamino
- pyrimidone
- lower alkyl
- Prior art date
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- 238000009313 farming Methods 0.000 title 1
- 230000000144 pharmacologic effect Effects 0.000 title 1
- -1 5-imidazolyl ring Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229930194542 Keto Natural products 0.000 claims description 2
- 241001061127 Thione Species 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
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- 230000000694 effects Effects 0.000 description 9
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- 238000001816 cooling Methods 0.000 description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 7
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- 238000010992 reflux Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
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- WVISNVMELKXLPM-UHFFFAOYSA-N 5-ethyl-4-methyl-2-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethylamino]-1H-pyrimidin-6-one dihydrochloride Chemical compound Cl.Cl.O=C1C(CC)=C(C)NC(NCCSCC2=C(NC=N2)C)=N1 WVISNVMELKXLPM-UHFFFAOYSA-N 0.000 description 2
- ONXSJKJUFVKYFZ-UHFFFAOYSA-N 6-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylamino]-1h-pyrimidin-2-one Chemical compound N1=CNC(CSCCNC2=NC(=O)NC=C2)=C1C ONXSJKJUFVKYFZ-UHFFFAOYSA-N 0.000 description 2
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- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CMBUCVSPXQXRCF-UHFFFAOYSA-N [I-].C[NH+]1C=NC(C1)=O Chemical compound [I-].C[NH+]1C=NC(C1)=O CMBUCVSPXQXRCF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 231100001252 long-term toxicity Toxicity 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2106373 | 1973-05-03 | ||
| GB2106373A GB1419994A (en) | 1973-05-03 | 1973-05-03 | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| GB3555173 | 1973-07-26 | ||
| GB3555173 | 1973-07-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI62301B FI62301B (fi) | 1982-08-31 |
| FI62301C true FI62301C (fi) | 1982-12-10 |
Family
ID=26255089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1261/74A FI62301C (fi) | 1973-05-03 | 1974-04-24 | Analogifoerfarande foer framstaellning av farmakologiskt aktiva imidazolderivat |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3932644A (cs) |
| JP (1) | JPS5855145B2 (cs) |
| AU (1) | AU477220B2 (cs) |
| BE (1) | BE814032A (cs) |
| CA (1) | CA1041108A (cs) |
| CH (1) | CH605917A5 (cs) |
| DE (1) | DE2421548A1 (cs) |
| ES (1) | ES425936A1 (cs) |
| FI (1) | FI62301C (cs) |
| FR (1) | FR2227869B1 (cs) |
| GB (1) | GB1419994A (cs) |
| HU (1) | HU168863B (cs) |
| IE (1) | IE40014B1 (cs) |
| IL (1) | IL44526A (cs) |
| IN (1) | IN138721B (cs) |
| NL (1) | NL7404811A (cs) |
| SE (1) | SE416299B (cs) |
| SU (1) | SU719500A3 (cs) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4578459A (en) * | 1973-05-03 | 1986-03-25 | Smithkline & French Laboratories Limited | Heterocyclic alkylaminoheterocycles |
| JPS5239976U (cs) * | 1975-09-12 | 1977-03-22 | ||
| US4145546A (en) | 1975-10-02 | 1979-03-20 | Smith Kline & French Laboratories Limited | 4-Pyrimidone compounds |
| US4218452A (en) | 1975-10-02 | 1980-08-19 | Smith Kline & French Laboratories Limited | Substituted 4-pyrimidone compounds, compositions and methods of use |
| IN146736B (cs) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
| US4216318A (en) * | 1975-12-29 | 1980-08-05 | Smith Kline & French Laboratories Limited | Heterocyclic alkyl 4-pyrimidones |
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| US4649138A (en) * | 1976-05-14 | 1987-03-10 | Smithkline & French Laboratories Limited | Pharmaceutical compositions |
| US4378365A (en) * | 1976-05-14 | 1983-03-29 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions |
| NZ186511A (en) * | 1977-03-19 | 1980-11-14 | Smith Kline French Lab | 3-substituted alkylamino-6-substituted alkyl-1,2,4-triazin-5-ones and pharmaceutical compositions 3-substituted thio-1,2,4-triazin-5-ones |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| ZA782129B (en) | 1977-04-20 | 1979-03-28 | Ici Ltd | Hertocyclic derivatives |
| US4539207A (en) * | 1978-02-13 | 1985-09-03 | Smith Kline & French Laboratories Limited | Pyrimidine compounds |
| IN151188B (cs) * | 1978-02-13 | 1983-03-05 | Smith Kline French Lab | |
| AU527202B2 (en) * | 1978-04-11 | 1983-02-24 | Smith Kline & French Laboratories Limited | 2-aminopyrimidones |
| AR228941A1 (es) * | 1978-04-26 | 1983-05-13 | Glaxo Group Ltd | Procedimiento para preparar nuevos derivados de 3,5-diamino-1,2,4-triazol que son activos contra receptores histaminicos |
| DE2963363D1 (en) | 1978-05-24 | 1982-09-09 | Ici Plc | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4584384A (en) * | 1978-05-30 | 1986-04-22 | Smith Kline & French Laboratories Limited | Nitro pyrroles |
| ZA792608B (en) * | 1978-05-30 | 1980-06-25 | Smith Kline French Lab | Nitro compounds |
| ZA792607B (en) * | 1978-05-30 | 1980-07-30 | Smith Kline French Lab | Nitro compounds |
| IL57415A (en) * | 1978-05-30 | 1984-08-31 | Smith Kline French Lab | Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them |
| PT69886A (en) * | 1978-07-15 | 1979-08-01 | Smith Kline French Lab | Process for preparing isoureas and isothioureas |
| ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
| US4374836A (en) | 1978-10-16 | 1983-02-22 | Imperial Chemical Industries Ltd. | Antisecretory heterocyclic derivatives, process for their manufacture and pharmaceutical compositions containing them |
| US4496567A (en) * | 1978-11-13 | 1985-01-29 | Smith Kline & French Laboratories Limited | Phenyl alkylaminopyrimidones |
| EP0014057B1 (en) | 1979-01-18 | 1985-01-02 | Imperial Chemical Industries Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| US4521418A (en) * | 1979-02-21 | 1985-06-04 | Smith Kline & French Laboratories Limited | Guanidinothiazolyl derivatives |
| US4256743A (en) * | 1979-02-22 | 1981-03-17 | President And Fellows Of Harvard College | Inhibition of bone resorption with H1 -blocking antihistamines |
| PH18379A (en) * | 1979-03-02 | 1985-06-19 | Glaxo Group Ltd | Triazole acylamines and pharmaceutical compositions thereof |
| JPS55120571A (en) * | 1979-03-02 | 1980-09-17 | Glaxo Group Ltd | Heterocyclic derivative |
| AU531142B2 (en) * | 1979-04-04 | 1983-08-11 | Smith Kline & French Laboratories Limited | 2 amino- pyimindones |
| DE3067564D1 (en) * | 1979-10-22 | 1984-05-24 | Glaxo Group Ltd | 1,2,4-triazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing them |
| IL61233A (en) * | 1979-10-24 | 1984-08-31 | Smith Kline French Lab | Guanidino thiazolylalkylamino(alkylthioalkylamino)nitro pyrroles,process for their preparation and pharmaceutical compositions containing them |
| IL61234A (en) * | 1979-10-24 | 1984-03-30 | Smith Kline French Lab | Guanidino thiazolyl alkylamino(alkylthioalkylamino)nitrotetrahydropyridines,process for preparing them and pharmaceutical compositions containing them |
| CH655104A5 (fr) * | 1980-02-28 | 1986-03-27 | Glaxo Group Ltd | Derives heterocycliques triazoliques, procedes pour leur preparation et compositions pharmaceutiques les comportant. |
| ZW21281A1 (en) * | 1980-10-01 | 1981-11-18 | Smith Kline French Lab | Amine derivatives |
| US4439609A (en) * | 1980-10-01 | 1984-03-27 | Smith Kline & French Laboratories Limited | Pyridines |
| US4352933A (en) * | 1981-02-06 | 1982-10-05 | Smithkline Beckman Corporation | Chemical methods and intermediates for preparing substituted pyrimidinones |
| US4439437A (en) * | 1981-04-28 | 1984-03-27 | Smith Kline & French Laboratories Limited | 2-[2-Thiazolyl or 2-guanidino-4-thiazolyl methylthioethyl(or butyl)amino]-3-(hydroxy or carboxy)pyridines, compositions containing same and method of use |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| US4525477A (en) * | 1981-12-02 | 1985-06-25 | Smith Kline & French Laboratories Limited | 2-Thiazolyl, isothiazolyl, oxazolyl and isoxazolyl alkylamino-3-nitro-heterocyclic compounds |
| EP0102026A3 (en) * | 1982-08-20 | 1984-05-16 | Hoechst Uk Limited | Thiazole derivatives |
| EP0104611A3 (en) * | 1982-09-28 | 1985-06-12 | Hoechst Uk Limited | Thiatriazine derivatives |
| JO1275B1 (en) * | 1982-12-03 | 1985-04-20 | هنري براون ثوماس | Chemical process |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| PT77856B (en) * | 1982-12-23 | 1986-04-16 | Smith Kline French Lab | Pyridine derivatives |
| EP0112704B1 (en) * | 1982-12-23 | 1987-10-07 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| GB8311443D0 (en) * | 1983-04-27 | 1983-06-02 | Smith Kline French Lab | Chemical compounds |
| GB8318638D0 (en) * | 1983-07-09 | 1983-08-10 | Smith Kline French Lab | Chemical compounds |
| GB8328907D0 (en) * | 1983-10-28 | 1983-11-30 | Smith Kline French Lab | Chemical compounds |
| GB8332091D0 (en) * | 1983-12-01 | 1984-01-11 | Smith Kline French Lab | Chemical compounds |
| GB9715814D0 (en) | 1997-07-25 | 1997-10-01 | Black James Foundation | Histamine H3 receptor ligands |
| GB2344588B (en) * | 1997-07-25 | 2001-11-14 | Black James Foundation | 1H-4(5)-substituted imidazole derivatives their preparation and their use as histamine H 3 receptor ligands |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758759A (fr) * | 1969-11-12 | 1971-05-10 | Merck & Co Inc | Pyridones anti-inflammatoires |
| US3853897A (en) * | 1971-07-16 | 1974-12-10 | Merck & Co Inc | Certain 1-substituted-3-amino-1(2h)pyridones |
-
1973
- 1973-05-03 GB GB2106373A patent/GB1419994A/en not_active Expired
-
1974
- 1974-03-26 IN IN664/CAL/74A patent/IN138721B/en unknown
- 1974-03-29 IL IL7444526A patent/IL44526A/xx unknown
- 1974-04-09 CA CA197,225A patent/CA1041108A/en not_active Expired
- 1974-04-09 NL NL7404811A patent/NL7404811A/xx not_active Application Discontinuation
- 1974-04-22 BE BE143479A patent/BE814032A/xx not_active IP Right Cessation
- 1974-04-24 FI FI1261/74A patent/FI62301C/fi active
- 1974-04-24 US US05/463,647 patent/US3932644A/en not_active Expired - Lifetime
- 1974-04-29 SE SE7405732A patent/SE416299B/xx unknown
- 1974-04-30 SU SU742021439A patent/SU719500A3/ru active
- 1974-04-30 JP JP49049242A patent/JPS5855145B2/ja not_active Expired
- 1974-04-30 FR FR7415085A patent/FR2227869B1/fr not_active Expired
- 1974-05-02 CH CH600174A patent/CH605917A5/xx not_active IP Right Cessation
- 1974-05-02 HU HUSI1399A patent/HU168863B/hu unknown
- 1974-05-03 ES ES74425936A patent/ES425936A1/es not_active Expired
- 1974-05-03 DE DE2421548A patent/DE2421548A1/de not_active Withdrawn
- 1974-05-03 IE IE949/74A patent/IE40014B1/xx unknown
- 1974-05-03 AU AU68598/74A patent/AU477220B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE814032A (fr) | 1974-10-22 |
| US3932644A (en) | 1976-01-13 |
| IL44526A (en) | 1979-05-31 |
| JPS5025565A (cs) | 1975-03-18 |
| NL7404811A (cs) | 1974-11-05 |
| DE2421548A1 (de) | 1974-11-21 |
| IE40014L (en) | 1974-11-03 |
| IE40014B1 (en) | 1979-02-28 |
| AU477220B2 (en) | 1976-10-21 |
| FI62301B (fi) | 1982-08-31 |
| HU168863B (cs) | 1976-07-28 |
| GB1419994A (en) | 1976-01-07 |
| ES425936A1 (es) | 1976-09-16 |
| JPS5855145B2 (ja) | 1983-12-08 |
| FR2227869B1 (cs) | 1978-07-21 |
| CA1041108A (en) | 1978-10-24 |
| IN138721B (cs) | 1976-03-20 |
| AU6859874A (en) | 1975-11-06 |
| FR2227869A1 (cs) | 1974-11-29 |
| IL44526A0 (en) | 1974-06-30 |
| SU719500A3 (ru) | 1980-02-29 |
| SE416299B (sv) | 1980-12-15 |
| CH605917A5 (cs) | 1978-10-13 |
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