DE3042392A1 - Imidazo (1,2-a) pyridin mit antigeschwueraktivitaet - Google Patents
Imidazo (1,2-a) pyridin mit antigeschwueraktivitaetInfo
- Publication number
- DE3042392A1 DE3042392A1 DE19803042392 DE3042392A DE3042392A1 DE 3042392 A1 DE3042392 A1 DE 3042392A1 DE 19803042392 DE19803042392 DE 19803042392 DE 3042392 A DE3042392 A DE 3042392A DE 3042392 A1 DE3042392 A1 DE 3042392A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- imidazo
- ethyl
- pyridin
- cyano
- 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.)
- Withdrawn
Links
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title claims description 3
- 230000000694 effects Effects 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 230000002496 gastric effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- -1 imidazo [1,2-a] pyridin-3-yl Chemical group 0.000 claims description 2
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 10
- 208000025865 Ulcer Diseases 0.000 description 10
- 231100000397 ulcer Toxicity 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000767 anti-ulcer Effects 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- 206010002091 Anaesthesia Diseases 0.000 description 5
- 230000037005 anaesthesia Effects 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 241000700157 Rattus norvegicus Species 0.000 description 4
- 230000001262 anti-secretory effect Effects 0.000 description 4
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 4
- 229960001380 cimetidine Drugs 0.000 description 4
- 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 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 3
- 210000003041 ligament Anatomy 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT27292/79A IT1127228B (it) | 1979-11-14 | 1979-11-14 | Imidazo 1,2-a piridine ad azione antiulcera |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3042392A1 true DE3042392A1 (de) | 1981-05-21 |
Family
ID=11221362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803042392 Withdrawn DE3042392A1 (de) | 1979-11-14 | 1980-11-10 | Imidazo (1,2-a) pyridin mit antigeschwueraktivitaet |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4311702A (OSRAM) |
| JP (1) | JPS5686183A (OSRAM) |
| DE (1) | DE3042392A1 (OSRAM) |
| ES (1) | ES8200365A1 (OSRAM) |
| FR (1) | FR2469414A1 (OSRAM) |
| GB (1) | GB2064521B (OSRAM) |
| IT (1) | IT1127228B (OSRAM) |
-
1979
- 1979-11-14 IT IT27292/79A patent/IT1127228B/it active
-
1980
- 1980-10-30 US US06/202,055 patent/US4311702A/en not_active Expired - Lifetime
- 1980-11-10 DE DE19803042392 patent/DE3042392A1/de not_active Withdrawn
- 1980-11-10 GB GB8036075A patent/GB2064521B/en not_active Expired
- 1980-11-13 ES ES496792A patent/ES8200365A1/es not_active Expired
- 1980-11-13 FR FR8024154A patent/FR2469414A1/fr active Granted
- 1980-11-14 JP JP16067280A patent/JPS5686183A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5686183A (en) | 1981-07-13 |
| IT1127228B (it) | 1986-05-21 |
| FR2469414A1 (fr) | 1981-05-22 |
| US4311702A (en) | 1982-01-19 |
| GB2064521A (en) | 1981-06-17 |
| IT7927292A0 (it) | 1979-11-14 |
| ES496792A0 (es) | 1981-11-01 |
| ES8200365A1 (es) | 1981-11-01 |
| FR2469414B1 (OSRAM) | 1984-12-14 |
| GB2064521B (en) | 1983-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |