CA1157470A - Imidazo[1,2,a]pyridine derivatives useful in therapy and their preparations - Google Patents
Imidazo[1,2,a]pyridine derivatives useful in therapy and their preparationsInfo
- Publication number
- CA1157470A CA1157470A CA000388385A CA388385A CA1157470A CA 1157470 A CA1157470 A CA 1157470A CA 000388385 A CA000388385 A CA 000388385A CA 388385 A CA388385 A CA 388385A CA 1157470 A CA1157470 A CA 1157470A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- hydrogen
- formula
- compound
- alkyl
- 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
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003222 pyridines Chemical class 0.000 title abstract 2
- 238000002560 therapeutic procedure Methods 0.000 title description 3
- -1 C1-4 alkyl radical Chemical class 0.000 claims abstract description 30
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 150000003254 radicals Chemical class 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 16
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003140 primary amides Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000007958 sleep Effects 0.000 abstract description 4
- 230000001773 anti-convulsant effect Effects 0.000 abstract description 3
- 230000000949 anxiolytic effect Effects 0.000 abstract description 3
- 230000000147 hypnotic effect Effects 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 230000000496 anti-anoxic effect Effects 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 230000001939 inductive effect Effects 0.000 abstract description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 54
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 4
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- YDHIMEXEGOCNHU-UHFFFAOYSA-N 2-pyridin-3-ylacetamide Chemical compound NC(=O)CC1=CC=CN=C1 YDHIMEXEGOCNHU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical class C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 230000000803 paradoxical effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004622 sleep time Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- OIPHWUPMXHQWLR-UHFFFAOYSA-N 2-pyridin-3-ylacetonitrile Chemical compound N#CCC1=CC=CN=C1 OIPHWUPMXHQWLR-UHFFFAOYSA-N 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000012886 Vertigo Diseases 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000003970 cerebral vascular damage Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 230000037322 slow-wave sleep Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 231100000889 vertigo Toxicity 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
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8022537 | 1980-10-22 | ||
| FR8022537A FR2492382A1 (fr) | 1980-10-22 | 1980-10-22 | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1157470A true CA1157470A (en) | 1983-11-22 |
Family
ID=9247171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000388385A Expired CA1157470A (en) | 1980-10-22 | 1981-10-21 | Imidazo[1,2,a]pyridine derivatives useful in therapy and their preparations |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4382938A (enExample) |
| EP (1) | EP0050563B1 (enExample) |
| JP (1) | JPS5798283A (enExample) |
| AT (1) | ATE7393T1 (enExample) |
| AU (1) | AU544345B2 (enExample) |
| CA (1) | CA1157470A (enExample) |
| DE (1) | DE3163524D1 (enExample) |
| DK (1) | DK154429C (enExample) |
| ES (1) | ES8207537A1 (enExample) |
| FI (1) | FI71143C (enExample) |
| FR (1) | FR2492382A1 (enExample) |
| GR (1) | GR74701B (enExample) |
| IE (1) | IE51686B1 (enExample) |
| IL (1) | IL64091A (enExample) |
| LU (1) | LU88228I2 (enExample) |
| MX (1) | MX6463E (enExample) |
| NL (1) | NL930044I2 (enExample) |
| NO (1) | NO155664C (enExample) |
| NZ (1) | NZ198722A (enExample) |
| OA (1) | OA07076A (enExample) |
| PT (1) | PT73863B (enExample) |
| ZA (1) | ZA817297B (enExample) |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2525601A1 (fr) * | 1982-04-21 | 1983-10-28 | Synthelabo | Derives d'imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| FR2525602A1 (fr) * | 1982-04-21 | 1983-10-28 | Synthelabo | Imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| FR2568879B1 (fr) * | 1984-08-07 | 1986-12-12 | Synthelabo | Imidazo(1,2-a)quinolines, leur preparation et leur application en therapeutique |
| FR2581646B1 (fr) * | 1985-05-07 | 1987-09-18 | Synthelabo | Derives d'imidazopyridine, leur preparation et leur application en therapeutique |
| FR2593179B1 (fr) * | 1986-01-22 | 1988-04-01 | Synthelabo | Derives d'imidazo(1,2-a)quinoleines, leur preparation et leur application en therapeutique |
| ES2032455T3 (es) * | 1986-01-22 | 1993-02-16 | Synthelabo | Procedimiento para preparar derivados de 3-acilaminometil-imidazo (-1,2-a)piridinas. |
| FR2593817B1 (fr) * | 1986-01-31 | 1988-04-15 | Synthelabo | Derives de tetrahydro-5,6,7,8 imidazo(1,2-a)pyridine, leur preparation et leur application en therapeutique |
| FR2599368B1 (fr) * | 1986-06-02 | 1988-08-05 | Synthelabo | Derives hydroxyles d'imidazopyridines, leur preparation et leur application en therapeutique |
| FR2600650B1 (fr) * | 1986-06-27 | 1988-09-09 | Synthelabo | Procede de preparation d'imidazopyridines et composes intermediaires |
| FR2606409B1 (fr) * | 1986-11-07 | 1989-05-05 | Synthelabo | Derives d'imidazopyridine, leur preparation et leur application en therapeutique |
| FR2606411B1 (fr) * | 1986-11-07 | 1989-04-07 | Synthelabo | Imidazopyridine-acetamides, leur preparation et leur application en therapeutique |
| FR2606410B1 (fr) * | 1986-11-07 | 1989-02-24 | Synthelabo | Imidazopyridines, leur preparation et leur application en therapeutique |
| EP0289371B1 (fr) * | 1987-03-27 | 1991-09-25 | Synthelabo | Dérivés d'imidazopyridines, leur préparation et leur application en thérapeutique |
| FR2612928B1 (fr) * | 1987-03-27 | 1989-06-16 | Synthelabo | Derives hydroxyles d'imidazopyridines, leur preparation et leur application en therapeutique |
| FR2612927B1 (fr) * | 1987-03-27 | 1989-06-09 | Synthelabo | Derives d'imidazopyridines, leur preparation et leur application en therapeutique |
| US5032595A (en) * | 1989-11-24 | 1991-07-16 | Fidia-Georgetown Institute For The Neurosciences | Method of stimulating steroidogenesis with alpidem |
| US5912246A (en) * | 1995-02-15 | 1999-06-15 | Pharmacia & Upjohn Company | Imidazo 1,2-a!pyridines for the treatment of CNS and cardiac diseases |
| IT1276522B1 (it) * | 1995-04-07 | 1997-10-31 | Elena Benincasa | Uso dello zolpidem per il trattamento terapeudico di sindromi neuropsichiatriche associate a disfunsione e di circuiti neurali dei |
| US6013654A (en) * | 1997-08-14 | 2000-01-11 | Pharmacia & Upjohn Company | Imidazo[1,2-A]pyridines for the treatment of CNS and cardiac diseases |
| AUPP278498A0 (en) | 1998-04-03 | 1998-04-30 | Australian Nuclear Science & Technology Organisation | Peripheral benzodiazepine receptor binding agents |
| EP1005863A1 (en) * | 1998-12-04 | 2000-06-07 | Synthelabo | Controlled-release dosage forms comprising a short acting hypnotic or a salt thereof |
| EP1038875B1 (en) * | 1999-03-25 | 2003-06-04 | Synthon B.V. | Imidazopyridine derivatives and process for making them |
| ATE297924T1 (de) * | 1999-03-25 | 2005-07-15 | Synthon Bv | Zolpidem salze |
| US6333345B1 (en) | 1999-05-14 | 2001-12-25 | Sepracor, Inc. | Methods of using and compositions comprising N-desmethylzolpidem |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336194A (en) * | 1963-04-30 | 1967-08-15 | Merck & Co Inc | Indolyl acid amides |
| GB1076089A (en) * | 1965-11-09 | 1967-07-19 | Selvi & C Lab Bioterapico | New derivatives of imidazo [1,2-a]-pyridine and a process for the manufacture thereof |
-
1980
- 1980-10-22 FR FR8022537A patent/FR2492382A1/fr active Granted
-
1981
- 1981-10-15 AT AT81401606T patent/ATE7393T1/de active
- 1981-10-15 DE DE8181401606T patent/DE3163524D1/de not_active Expired
- 1981-10-15 EP EP81401606A patent/EP0050563B1/fr not_active Expired
- 1981-10-15 LU LU88228C patent/LU88228I2/xx unknown
- 1981-10-19 MX MX81101627U patent/MX6463E/es unknown
- 1981-10-21 IE IE2470/81A patent/IE51686B1/en not_active IP Right Cessation
- 1981-10-21 GR GR66315A patent/GR74701B/el unknown
- 1981-10-21 DK DK465181A patent/DK154429C/da not_active IP Right Cessation
- 1981-10-21 NZ NZ198722A patent/NZ198722A/xx unknown
- 1981-10-21 US US06/313,601 patent/US4382938A/en not_active Expired - Lifetime
- 1981-10-21 NO NO813551A patent/NO155664C/no not_active IP Right Cessation
- 1981-10-21 AU AU76687/81A patent/AU544345B2/en not_active Expired
- 1981-10-21 JP JP56169392A patent/JPS5798283A/ja active Granted
- 1981-10-21 FI FI813288A patent/FI71143C/fi not_active IP Right Cessation
- 1981-10-21 CA CA000388385A patent/CA1157470A/en not_active Expired
- 1981-10-21 ZA ZA817297A patent/ZA817297B/xx unknown
- 1981-10-21 ES ES506412A patent/ES8207537A1/es not_active Expired
- 1981-10-21 IL IL64091A patent/IL64091A/xx not_active IP Right Cessation
- 1981-10-21 PT PT73863A patent/PT73863B/pt unknown
-
1982
- 1982-04-21 OA OA57664A patent/OA07076A/xx unknown
-
1983
- 1983-02-10 US US06/465,605 patent/US4460592A/en not_active Expired - Lifetime
-
1993
- 1993-05-28 NL NL930044C patent/NL930044I2/nl unknown
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