GB1473819A - Derivatives of imidazo 1,2-a pyridine - Google Patents
Derivatives of imidazo 1,2-a pyridineInfo
- Publication number
- GB1473819A GB1473819A GB337176A GB337176A GB1473819A GB 1473819 A GB1473819 A GB 1473819A GB 337176 A GB337176 A GB 337176A GB 337176 A GB337176 A GB 337176A GB 1473819 A GB1473819 A GB 1473819A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- alkyl
- pyridine
- compounds
- haloketone
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 antiulcer Substances 0.000 abstract 2
- 150000003930 2-aminopyridines Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000001631 hypertensive effect Effects 0.000 abstract 1
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000004968 inflammatory condition Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000003033 spasmogenic effect Effects 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1473819 Imidazo[1,2-a]pyridine derivatives ANTONIO GALLARDO SA 28 Jan 1976 03371/76 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R is H or C 1-6 alkyl; R<SP>1</SP> is H, halogen, amino, nitro, or C 1-6 alkyl, alkoxy or alkylsulphonyl; and R<SP>2</SP> is C 1-6 alkyl (optionally substituted by 1 or more C 1-6 alkoxy radicals). The compounds are prepared by reacting (1) an R-substituted 2-aminopyridine with the alpha-haloketone or (2) an R-substituted pyridine with the said alpha-haloketone to give a substituted 1:phenacylpyridinium halide, of which the oxime is formed and cyclized in situ. Therapeutic compositions having antiinflammatory, analgesic, antipyretic, antiulcer, anticonvulsant, spasmogenic, spasmolytic and hypertensive activity, and said to be especially useful for treating inflammatory conditions of the gastro-intestinal tract, comprise compounds of the above formula. They may be administered orally, parenterally, rectally or topically.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB337176A GB1473819A (en) | 1976-01-28 | 1976-01-28 | Derivatives of imidazo 1,2-a pyridine |
| ES454823A ES454823A1 (en) | 1976-01-28 | 1977-01-05 | Derivatives of imidazo 1,2-a pyridine |
| ES454824A ES454824A1 (en) | 1976-01-28 | 1977-01-05 | Derivatives of imidazo 1,2-a pyridine |
| DE19772702790 DE2702790A1 (en) | 1976-01-28 | 1977-01-24 | NEW THERAPEUTICS BASED ON IMIDAZO (1,2-A) PYRIDINE |
| FR7702785A FR2339612A1 (en) | 1976-01-28 | 1977-01-25 | NEW DERIVATIVES OF IMIDAZO 1,2-A PYRIDINE |
| JP861277A JPS52116494A (en) | 1976-01-28 | 1977-01-28 | Imidazo*1*22a*pyridine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB337176A GB1473819A (en) | 1976-01-28 | 1976-01-28 | Derivatives of imidazo 1,2-a pyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1473819A true GB1473819A (en) | 1977-05-18 |
Family
ID=9757057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB337176A Expired GB1473819A (en) | 1976-01-28 | 1976-01-28 | Derivatives of imidazo 1,2-a pyridine |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS52116494A (en) |
| DE (1) | DE2702790A1 (en) |
| ES (2) | ES454823A1 (en) |
| FR (1) | FR2339612A1 (en) |
| GB (1) | GB1473819A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052016A1 (en) * | 1980-11-11 | 1982-05-19 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds, compositions containing same and processes for preparing same |
| EP0261912A3 (en) * | 1986-09-22 | 1989-09-20 | Ortho Pharmaceutical Corporation | 2- or 3- Aryl substituted imidazo [1,2-a] pyridines |
| EP2083009A1 (en) * | 2008-01-22 | 2009-07-29 | Grünenthal GmbH | Substituted tetrahydroimidazopyridine compounds and their use in medicine |
| US20100249418A1 (en) * | 2007-10-24 | 2010-09-30 | Nihon Medi-Physics Co., Ltd. | Novel compound having affinity for amyloid |
| US8569504B2 (en) | 2009-06-17 | 2013-10-29 | Ono Pharmaceutical Co., Ltd. | Imidazopyridine compound |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154835A (en) * | 1977-10-12 | 1979-05-15 | Merck & Co., Inc. | Anthelmintic imidazo [1,2-a] pyridines |
| DE10247271A1 (en) * | 2002-10-10 | 2004-08-26 | Grünenthal GmbH | Use of new and known 7-(methyl or trifluoromethyl)-imidazo-(1,2-a)-pyridines as nitrogen monoxide synthase inhibitors useful e.g. for treating migraine, neurodegenerative diseases, inflammatory pain, diabetes or cancer |
-
1976
- 1976-01-28 GB GB337176A patent/GB1473819A/en not_active Expired
-
1977
- 1977-01-05 ES ES454823A patent/ES454823A1/en not_active Expired
- 1977-01-05 ES ES454824A patent/ES454824A1/en not_active Expired
- 1977-01-24 DE DE19772702790 patent/DE2702790A1/en not_active Ceased
- 1977-01-25 FR FR7702785A patent/FR2339612A1/en active Pending
- 1977-01-28 JP JP861277A patent/JPS52116494A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052016A1 (en) * | 1980-11-11 | 1982-05-19 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds, compositions containing same and processes for preparing same |
| EP0261912A3 (en) * | 1986-09-22 | 1989-09-20 | Ortho Pharmaceutical Corporation | 2- or 3- Aryl substituted imidazo [1,2-a] pyridines |
| US20100249418A1 (en) * | 2007-10-24 | 2010-09-30 | Nihon Medi-Physics Co., Ltd. | Novel compound having affinity for amyloid |
| EP2083009A1 (en) * | 2008-01-22 | 2009-07-29 | Grünenthal GmbH | Substituted tetrahydroimidazopyridine compounds and their use in medicine |
| WO2009092565A1 (en) * | 2008-01-22 | 2009-07-30 | Grünenthal GmbH | Substituted tetrahydroimidazopyridine compounds and the use thereof in pharmaceuticals |
| US8288424B2 (en) | 2008-01-22 | 2012-10-16 | Gruenenthal Gmbh | Substituted tetrahydroimidazopyridine compounds and the use thereof in the treatment of pain and other conditions |
| US8569504B2 (en) | 2009-06-17 | 2013-10-29 | Ono Pharmaceutical Co., Ltd. | Imidazopyridine compound |
Also Published As
| Publication number | Publication date |
|---|---|
| ES454823A1 (en) | 1978-01-01 |
| ES454824A1 (en) | 1978-01-01 |
| JPS52116494A (en) | 1977-09-29 |
| DE2702790A1 (en) | 1977-08-04 |
| FR2339612A1 (en) | 1977-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |