CA1125296A - Antisecretory oxadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them - Google Patents
Antisecretory oxadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing themInfo
- Publication number
- CA1125296A CA1125296A CA327,473A CA327473A CA1125296A CA 1125296 A CA1125296 A CA 1125296A CA 327473 A CA327473 A CA 327473A CA 1125296 A CA1125296 A CA 1125296A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- formula
- carbon atoms
- compound
- oxygen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004866 oxadiazoles Chemical class 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 7
- 230000001262 anti-secretory effect Effects 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 101100294106 Caenorhabditis elegans nhr-3 gene Chemical group 0.000 claims abstract description 6
- 101000989653 Homo sapiens Membrane frizzled-related protein Proteins 0.000 claims abstract 3
- 102100029357 Membrane frizzled-related protein Human genes 0.000 claims abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 3,4-dioxocyclobuten-1,2-diyl radical Chemical class 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 229960000520 diphenhydramine Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
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- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21738/78 | 1978-05-24 | ||
| GB2173878 | 1978-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1125296A true CA1125296A (en) | 1982-06-08 |
Family
ID=10167976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA327,473A Expired CA1125296A (en) | 1978-05-24 | 1979-05-11 | Antisecretory oxadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4338448A (en, 2012) |
| EP (1) | EP0006286B1 (en, 2012) |
| JP (1) | JPS54160377A (en, 2012) |
| AT (1) | ATE852T1 (en, 2012) |
| CA (1) | CA1125296A (en, 2012) |
| DE (1) | DE2962500D1 (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3069889D1 (en) * | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| DE3270716D1 (en) * | 1981-02-27 | 1986-05-28 | Ici Plc | Guanidino-substituted heterocyclic derivatives having histamine h-2 antagonist activity |
| EP0065823A1 (en) * | 1981-05-13 | 1982-12-01 | Imperial Chemical Industries Plc | Heterocyclic guanidines as histamine H-2 antagonists |
| US4526973A (en) * | 1981-05-18 | 1985-07-02 | Bristol-Myers Company | Chemical compounds |
| US4522943A (en) * | 1981-05-18 | 1985-06-11 | Bristol-Myers Company | Chemical compounds |
| US4772622A (en) * | 1983-03-25 | 1988-09-20 | Merck & Co., Inc. | 3,5-diamino-1,2,4-oxidiazoles as gastric secretion inhibitors |
| JPH0225908U (en, 2012) * | 1988-08-01 | 1990-02-20 | ||
| US5725756A (en) * | 1995-04-18 | 1998-03-10 | Center For Research, Inc. | In situ mitigation of coke buildup in porous catalysts with supercritical reaction media |
| 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1010231A (en) * | 1961-07-11 | 1965-11-17 | Jan Marcel Didier Aron Samuel | Substituted 3-phenyl-5-imino-4,5 dihydro-1,2,4-oxadiazoles, process for their manufacture and therapeutic compositions containing same |
| FR1575544A (en, 2012) * | 1967-11-09 | 1969-07-25 | ||
| GB1351025A (en) * | 1971-08-20 | 1974-04-24 | Aron Md Samuel J | Oxadiazol-5-yl biguanide derivatives method for their preparation and pharmaceutical compositions containing them |
-
1979
- 1979-05-02 AT AT79300755T patent/ATE852T1/de not_active IP Right Cessation
- 1979-05-02 DE DE7979300755T patent/DE2962500D1/de not_active Expired
- 1979-05-02 EP EP79300755A patent/EP0006286B1/en not_active Expired
- 1979-05-11 CA CA327,473A patent/CA1125296A/en not_active Expired
- 1979-05-24 JP JP6330379A patent/JPS54160377A/ja active Granted
-
1980
- 1980-08-01 US US06/174,495 patent/US4338448A/en not_active Expired - Lifetime
- 1980-08-01 US US06/174,493 patent/US4338447A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2962500D1 (en) | 1982-05-27 |
| EP0006286A1 (en) | 1980-01-09 |
| JPS54160377A (en) | 1979-12-19 |
| ATE852T1 (de) | 1982-04-15 |
| JPS6330903B2 (en, 2012) | 1988-06-21 |
| US4338448A (en) | 1982-07-06 |
| EP0006286B1 (en) | 1982-04-14 |
| US4338447A (en) | 1982-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |