FR2492382A1 - Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique - Google Patents
Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2492382A1 FR2492382A1 FR8022537A FR8022537A FR2492382A1 FR 2492382 A1 FR2492382 A1 FR 2492382A1 FR 8022537 A FR8022537 A FR 8022537A FR 8022537 A FR8022537 A FR 8022537A FR 2492382 A1 FR2492382 A1 FR 2492382A1
- Authority
- FR
- France
- Prior art keywords
- radical
- alkyl
- atom
- derivatives according
- hydrogen
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- -1 C1-4 alkyl radical Chemical class 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 150000003140 primary amides Chemical class 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000003545 alkoxy 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
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 claims description 2
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000147 hypnotic effect Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 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
- 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
- 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 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 3
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 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
- BXHJPAVYXUNXMP-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-1h-imidazole Chemical compound ClC1=CC(Cl)=CC=C1C1=CNC=N1 BXHJPAVYXUNXMP-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- ZPHLXYYPDRCBMG-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid Chemical compound N1=C2C=CC=CN2C(CC(=O)O)=C1C1=CC=C(Cl)C=C1 ZPHLXYYPDRCBMG-UHFFFAOYSA-N 0.000 description 1
- PJWDPOBWIWWXCP-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-3-ylacetonitrile Chemical compound C1=CC=CN2C(CC#N)=CN=C21 PJWDPOBWIWWXCP-UHFFFAOYSA-N 0.000 description 1
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8022537A FR2492382A1 (fr) | 1980-10-22 | 1980-10-22 | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
| AT81401606T ATE7393T1 (de) | 1980-10-22 | 1981-10-15 | Imidazo(1,2-a)pyridinderivate, verfahren zu ihrer herstellung und ihre therapeutische anwendung. |
| LU88228C LU88228I2 (enExample) | 1980-10-22 | 1981-10-15 | |
| EP81401606A EP0050563B1 (fr) | 1980-10-22 | 1981-10-15 | Dérivés d'imidazo(1,2-a)pyridine, leur préparation et leur application en thérapeutique |
| DE8181401606T DE3163524D1 (en) | 1980-10-22 | 1981-10-15 | Imidazo(1,2-a)pyridine derivatives, process for their preparation and their therapeutical use |
| MX81101627U MX6463E (es) | 1980-10-22 | 1981-10-19 | Procedimiento para preparar derivados de imidazo(1,2-a)-piridina |
| ES506412A ES8207537A1 (es) | 1980-10-22 | 1981-10-21 | Procedimiento de preparacion de imidazo (1,2-a)piridinas |
| DK465181A DK154429C (da) | 1980-10-22 | 1981-10-21 | Analogifremgangsmaade til fremstilling af imidazooe1,2-aaapyridinderivater eller syreadditionssalte heraf |
| GR66315A GR74701B (enExample) | 1980-10-22 | 1981-10-21 | |
| IE2470/81A IE51686B1 (en) | 1980-10-22 | 1981-10-21 | Imidazo(1,2-a)pyridine derivatives useful in therapy and their preparation |
| NZ198722A NZ198722A (en) | 1980-10-22 | 1981-10-21 | N-substituted-2-(phenyl or naphthyl)imidazo(1,2-a)-pyrid-3-ylacetamides |
| ZA817297A ZA817297B (en) | 1980-10-22 | 1981-10-21 | Imidazo(1,2-a)pyridine derivatives useful in therapy and their preparation |
| PT73863A PT73863B (fr) | 1980-10-22 | 1981-10-21 | Procede de preparation de derives d'imidazo^1,2-a[pyridine applicables en therapeutique |
| FI813288A FI71143C (fi) | 1980-10-22 | 1981-10-21 | Foerfarande foer framstaellning av terapeutiskt anvaendbara imdazo/1,2-a/pyridiner |
| IL64091A IL64091A (en) | 1980-10-22 | 1981-10-21 | Arylimidazo(1,2-a)pyridine acetamide derivatives,their preparation and pharmaceutical compositions containing them |
| CA000388385A CA1157470A (en) | 1980-10-22 | 1981-10-21 | Imidazo[1,2,a]pyridine derivatives useful in therapy and their preparations |
| JP56169392A JPS5798283A (en) | 1980-10-22 | 1981-10-21 | Imidazopyridine derivative |
| AU76687/81A AU544345B2 (en) | 1980-10-22 | 1981-10-21 | Imidazo(1,2-a)pyridine derivatives |
| NO813551A NO155664C (no) | 1980-10-22 | 1981-10-21 | Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazo(1,2-a)-pyridiner. |
| US06/313,601 US4382938A (en) | 1980-10-22 | 1981-10-21 | Imidazo[1,2-a] pyridine derivatives and their application as pharmaceuticals |
| OA57664A OA07076A (fr) | 1980-10-22 | 1982-04-21 | Dérivés d'imidazo [1,2-a] pyridine et leur application en thérapeutique. |
| US06/465,605 US4460592A (en) | 1980-10-22 | 1983-02-10 | 6-Methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylacetamide |
| NL930044C NL930044I2 (nl) | 1980-10-22 | 1993-05-28 | ImidazoÄ1,2-aÜ pyridinederivaten, de bereiding hiervan en de therapeutische toepassing. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8022537A FR2492382A1 (fr) | 1980-10-22 | 1980-10-22 | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2492382A1 true FR2492382A1 (fr) | 1982-04-23 |
| FR2492382B1 FR2492382B1 (enExample) | 1983-07-29 |
Family
ID=9247171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8022537A Granted FR2492382A1 (fr) | 1980-10-22 | 1980-10-22 | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
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 |
|---|---|---|---|---|
| FR2525602A1 (fr) * | 1982-04-21 | 1983-10-28 | Synthelabo | Imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| FR2525601A1 (fr) * | 1982-04-21 | 1983-10-28 | Synthelabo | Derives d'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 |
| EP0234970B1 (fr) * | 1986-01-22 | 1991-04-17 | Synthelabo | Dérivés d'acylaminométhyl-3 imidazo[1,2-a]pyridines, leur préparation et leur application en thérapeutique |
| 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 |
| FR2606410B1 (fr) * | 1986-11-07 | 1989-02-24 | Synthelabo | Imidazopyridines, leur preparation et leur application en therapeutique |
| 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 |
| ES2026666T3 (es) * | 1987-03-27 | 1992-05-01 | Synthelabo | Procedimiento para preparar derivados de imidazopiridinas. |
| FR2612927B1 (fr) * | 1987-03-27 | 1989-06-09 | Synthelabo | Derives d'imidazopyridines, leur preparation et leur application en therapeutique |
| FR2612928B1 (fr) * | 1987-03-27 | 1989-06-16 | Synthelabo | Derives hydroxyles 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 |
| WO1996025414A1 (en) * | 1995-02-15 | 1996-08-22 | 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 |
| AU3464200A (en) * | 1999-03-25 | 2000-10-16 | Synthon B.V. | Zolpidem salts |
| SI1038875T1 (en) * | 1999-03-25 | 2003-12-31 | Synthon B.V. | Imidazopyridine derivatives and process for making them |
| US6333345B1 (en) | 1999-05-14 | 2001-12-25 | Sepracor, Inc. | Methods of using and compositions comprising N-desmethylzolpidem |
| US6399621B1 (en) | 1999-08-10 | 2002-06-04 | American Cyanamid Company | N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1, 5-α]-pyrimidin-7-yl}phenyl)acetamide and compositions and methods related thereto |
| US20030091632A1 (en) * | 1999-08-26 | 2003-05-15 | Neurocrine Biosciences, Inc. | Controlled-release sedative-hypnotic compositions and methods related thereto |
| US6485746B1 (en) | 2000-08-25 | 2002-11-26 | Neurocrine Biosciences, Inc. | Controlled-release sedative-hypnotic compositions and methods related thereto |
| US6384221B1 (en) | 1999-09-02 | 2002-05-07 | Neurocrine Biosciences, Inc. | Polymorphs of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide and compositions and methods related thereto |
| WO2001078725A2 (en) * | 2000-04-13 | 2001-10-25 | Synthon B.V. | Modified release formulations containing a hypnotic agent |
| EP1600159A1 (en) | 2000-04-24 | 2005-11-30 | Teva Pharmaceutical Industries Ltd | A method for synthesizing different Zolpidem hemitartrate derivatives |
| ES2277301T3 (es) * | 2000-04-24 | 2007-07-01 | Teva Pharmaceutical Industries Ltd. | Solvato de hemitartrato de zolpidem. |
| WO2001092257A1 (en) * | 2000-05-26 | 2001-12-06 | Neurogen Corporation | Oxo-imidazopyrimidine-carboxamides and their use as gaba brain receptor ligands |
| WO2002002557A2 (en) * | 2000-06-30 | 2002-01-10 | Neurogen Corporation | 2-phenylimidazo[1,2-a]pyridine derivatives: a new class of gaba brain receptor ligands |
| IT1318624B1 (it) * | 2000-07-14 | 2003-08-27 | Dinamite Dipharma S P A In For | Processo per la preparazione di 2-fenil-imidazo (1,2-a)piridin-3-acetammidi. |
| US6514969B2 (en) * | 2000-08-16 | 2003-02-04 | Boehringer Ingelheim Pharma Kg | β-amyloid inhibitors, processes for preparing them, and their use in pharmaceutical compositions |
| DE10040016A1 (de) * | 2000-08-16 | 2002-02-28 | Boehringer Ingelheim Pharma | Neue beta-Amyloid Inhibitoren, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| WO2002014306A1 (en) * | 2000-08-17 | 2002-02-21 | Cilag Ag | Process for the preparation of imidazopyridines |
| AU2001284322A1 (en) * | 2000-08-29 | 2002-03-13 | Ranbaxy Laboratories Limited | Synthesis of n,n-dimethyl-3-(4-methyl) benzoyl propionamide, a key intermediate of zolpidem |
| US6596731B2 (en) | 2001-03-27 | 2003-07-22 | Hoffmann-La Roche Inc. | Substituted imidazo[1,2-A] pyridine derivatives |
| DE10117183A1 (de) * | 2001-04-05 | 2002-10-10 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]-pyridinverbindungen als Arzneimittel |
| KR100433502B1 (ko) * | 2001-10-10 | 2004-06-07 | 철 양 | 확장부가 형성된 종이컵 |
| DE10247271A1 (de) * | 2002-10-10 | 2004-08-26 | Grünenthal GmbH | Substituierte C-Imidazo[1,2-a]pyridin-3-yle |
| US7385056B2 (en) * | 2002-12-18 | 2008-06-10 | Mallinckrodt Inc. | Synthesis of heteroaryl acetamides |
| US20040204443A1 (en) * | 2003-01-27 | 2004-10-14 | Arthur Zaks | Method for inducing pain relief using imidazo[1,2-a]pyridine derivatives |
| US20040241100A1 (en) * | 2003-03-17 | 2004-12-02 | Fabre Kramer Pharmaceutical, Inc. | Nasally administrable compositions of zolpidem and methods of use |
| WO2005010002A1 (en) * | 2003-07-31 | 2005-02-03 | Ranbaxy Laboratories Limited | Process for the synthesis of zolpidem |
| WO2005044818A2 (en) * | 2003-10-28 | 2005-05-19 | Sepracor, Inc. | Imidazo[1,2-a]pyridine anxiolytics |
| PL1691811T3 (pl) | 2003-12-11 | 2014-12-31 | Sunovion Pharmaceuticals Inc | Skojarzenie leku uspokajającego i modulatora neuroprzekaźnikowego oraz sposoby poprawy jakości snu i leczenia depresji |
| US7658945B2 (en) * | 2004-02-17 | 2010-02-09 | Transcept Pharmaceuticals, Inc. | Compositions for delivering hypnotic agents across the oral mucosa and methods of use thereof |
| CA2556870C (en) | 2004-02-18 | 2014-01-28 | Timothy J. Barberich | Dopamine-agonist combination therapy for improving sleep quality |
| WO2006008636A2 (en) * | 2004-07-16 | 2006-01-26 | Ranbaxy Laboratories Limited | Processes for the preparation of zolpidem and its hemitartrate |
| US20060084806A1 (en) * | 2004-07-21 | 2006-04-20 | Ramasubramanian Sridharan | Processes for the preparation of imidazo[1,2-a] pyridine derivatives |
| FR2874611B1 (fr) * | 2004-08-31 | 2006-11-17 | Servier Lab | Nouveaux derives d'imidazopyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US20070287740A1 (en) * | 2005-05-25 | 2007-12-13 | Transcept Pharmaceuticals, Inc. | Compositions and methods of treating middle-of-the night insomnia |
| NZ563979A (en) * | 2005-05-25 | 2011-02-25 | Transcept Pharmaceuticals Inc | Solid compositions and methods for treating middle-of-the night insomnia |
| US20070225322A1 (en) * | 2005-05-25 | 2007-09-27 | Transoral Pharmaceuticals, Inc. | Compositions and methods for treating middle-of-the night insomnia |
| US20070020333A1 (en) * | 2005-07-20 | 2007-01-25 | Chin-Chih Chiang | Controlled release of hypnotic agents |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP2377530A3 (en) | 2005-10-21 | 2012-06-20 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| DE602006008339D1 (en) | 2005-11-18 | 2009-09-17 | Synhton B V | Zolpidemtabletten |
| EP1803722A1 (en) * | 2006-01-03 | 2007-07-04 | Ferrer Internacional, S.A. | Imidazo[1,2-a]pyridin-3-yl-acetic acid hydrazides, processes for their preparation and pharmaceutical uses thereof |
| US8309104B2 (en) * | 2006-03-02 | 2012-11-13 | Watson Pharmaceuticals, Inc. | Oral controlled release formulation for sedative and hypnotic agents |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP1845098A1 (en) * | 2006-03-29 | 2007-10-17 | Ferrer Internacional, S.A. | Imidazo[1,2-b]pyridazines, their processes of preparation and their use as GABA receptor ligands |
| WO2007134136A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| US7772248B2 (en) * | 2006-06-05 | 2010-08-10 | Auspex Pharmaceuticals, Inc. | Preparation and utility of substituted imidazopyridine compounds with hypnotic effects |
| US20100209345A1 (en) * | 2006-08-24 | 2010-08-19 | Australian Nuclear Science & Technology Organisation | Fluorinated Ligands for Targeting Peripheral Benzodiazepine Receptors |
| AU2007292848A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US20080145425A1 (en) * | 2006-12-15 | 2008-06-19 | Pliva Research & Development Limited | Pharmaceutical composition of zolpidem |
| US20090076066A1 (en) * | 2007-09-19 | 2009-03-19 | Protia, Llc | Deuterium-enriched zolpidem |
| JPWO2009054496A1 (ja) * | 2007-10-24 | 2011-03-10 | 日本メジフィジックス株式会社 | 新規アミロイド親和性化合物 |
| WO2009085310A1 (en) * | 2007-12-26 | 2009-07-09 | Teva Pharmaceutical Industries Ltd. | Extended-release pharmaceutical compositions containing zolpidem |
| AU2009284695A1 (en) * | 2008-08-19 | 2010-02-25 | The University Of Sydney | Novel compounds and their uses in diagnosis |
| US10478438B2 (en) | 2008-10-16 | 2019-11-19 | David Reed Helton | Treatment of organophosphate exposure with ocinaplon |
| US8555875B2 (en) | 2008-12-23 | 2013-10-15 | Map Pharmaceuticals, Inc. | Inhalation devices and related methods for administration of sedative hypnotic compounds |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| WO2010122576A1 (en) | 2009-04-20 | 2010-10-28 | Matrix Laboratories Ltd | Improved process for the preparation of 6-methyl-2-[4-methyl phenyl] imidazo [1, 2-a] pyridine-3-n, n-dimethyl acetamide. |
| JP5433508B2 (ja) * | 2009-06-25 | 2014-03-05 | 高田製薬株式会社 | ゾルピデム酒石酸塩含有内用液剤 |
| CN102234275B (zh) * | 2010-04-27 | 2015-12-16 | 溧阳合誉药物科技有限公司 | 治疗失眠的氘代咪唑并[1,2-a]吡啶衍生物、制备方法及其应用 |
| US8741888B2 (en) | 2010-11-09 | 2014-06-03 | Carl A. Forest | Sleep aid composition and method |
| IN2013MU02428A (enExample) * | 2013-07-22 | 2015-06-19 | 3A Chemie Private Ltd | |
| US10202376B2 (en) | 2014-12-24 | 2019-02-12 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP3468545A4 (en) | 2016-06-08 | 2020-07-22 | President and Fellows of Harvard College | METHODS AND COMPOSITIONS FOR REDUCING TACTILE DYSFUNCTION AND ANXIETY ASSOCIATED WITH AUTISM SPECTRUM DISORDER, RETT SYNDROME AND FRAGILE X SYNDROME |
| JP7279067B2 (ja) * | 2018-03-28 | 2023-05-22 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
| EP3797097A4 (en) | 2018-05-22 | 2022-03-09 | President and Fellows of Harvard College | Compositions and methods for reducing tactile dysfunction, anxiety, and social impairment |
| US11434244B2 (en) | 2018-05-29 | 2022-09-06 | President And Fellows Of Harvard College | Compositions and methods for reducing tactile dysfunction, anxiety, and social impairment |
| EP3946390A4 (en) | 2019-03-25 | 2022-12-21 | President and Fellows of Harvard College | COMPOSITIONS AND METHODS TO REDUCE TACTILE DYSFUNCTION, ANXIETY AND SOCIAL DISABILITIES |
| JP2021050161A (ja) | 2019-09-25 | 2021-04-01 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336194A (en) * | 1963-04-30 | 1967-08-15 | Merck & Co Inc | Indolyl acid amides |
-
1980
- 1980-10-22 FR FR8022537A patent/FR2492382A1/fr active Granted
-
1981
- 1981-10-15 DE DE8181401606T patent/DE3163524D1/de not_active Expired
- 1981-10-15 LU LU88228C patent/LU88228I2/xx unknown
- 1981-10-15 AT AT81401606T patent/ATE7393T1/de active
- 1981-10-15 EP EP81401606A patent/EP0050563B1/fr not_active Expired
- 1981-10-19 MX MX81101627U patent/MX6463E/es unknown
- 1981-10-21 CA CA000388385A patent/CA1157470A/en not_active Expired
- 1981-10-21 ZA ZA817297A patent/ZA817297B/xx unknown
- 1981-10-21 DK DK465181A patent/DK154429C/da not_active IP Right Cessation
- 1981-10-21 FI FI813288A patent/FI71143C/fi not_active IP Right Cessation
- 1981-10-21 US US06/313,601 patent/US4382938A/en not_active Expired - Lifetime
- 1981-10-21 NZ NZ198722A patent/NZ198722A/xx unknown
- 1981-10-21 JP JP56169392A patent/JPS5798283A/ja active Granted
- 1981-10-21 AU AU76687/81A patent/AU544345B2/en not_active Expired
- 1981-10-21 IL IL64091A patent/IL64091A/xx not_active IP Right Cessation
- 1981-10-21 IE IE2470/81A patent/IE51686B1/en not_active IP Right Cessation
- 1981-10-21 PT PT73863A patent/PT73863B/pt unknown
- 1981-10-21 NO NO813551A patent/NO155664C/no not_active IP Right Cessation
- 1981-10-21 ES ES506412A patent/ES8207537A1/es not_active Expired
- 1981-10-21 GR GR66315A patent/GR74701B/el 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/69 * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2492382A1 (fr) | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique | |
| US6635647B2 (en) | Decahydro-isoquinolines | |
| CZ244793A3 (en) | Novel perhydroisoindole derivatives, process of their preparation and pharmaceutical preparations in which they are comprised | |
| EP0172096A1 (fr) | Dérivés d'acylaminométhyl-3 imidazo[1,2-a]pyridines, leur préparation et leur application en thérapeutique | |
| EP0092459B1 (fr) | Imidazo(1,2-a)pyridines, leur préparation et leur application en thérapeutique | |
| EP0302788A1 (fr) | Dérivés de [(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 9H-pyrido[3,4-b]indole, leur préparation et leur application en thérapeutique | |
| EP0092458A2 (fr) | Dérives d'imidazo(1,2-a)pyridine, leur préparation et leur application en thérapeutique | |
| FR2630328A1 (fr) | Derive de l'histamine, sa preparation et son application en therapeutique | |
| FR2644456A1 (fr) | Nouveaux derives du 1h, 3h-pyrrolo(1,2-c)thiazolecarboxamide-7, leur preparation et les compositions pharmaceutiques qui les contiennent | |
| FR2631625A1 (fr) | Derives de phenyl-6 piperazinylalkyl-3 1h,3h-pyrimidinedione-2,4, leur preparation et leur application en therapeutique | |
| DD255344A5 (de) | Heteroaryl-oxy-beta-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel | |
| EP0076199B1 (fr) | Nouvelles triazoloquinazolones et leurs sels, procédé et intermédiaires de préparation, leur application comme médicaments et les compositions les renfermant | |
| EP0115979B1 (fr) | Nouveaux dérivés du 1H,3H-pyrrolo (1,2-c) thiazole leur préparation et les médicaments qui les contiennent | |
| US4358451A (en) | Pyrimido- and imidazo-pyridoindole derivatives | |
| KR100191386B1 (ko) | 3-(1,2-벤즈이속사졸-3-일)-4-피리딘아민 및 유도체,이를 함유하는 약제학적 조성물 및 이의 제조방법 | |
| JPH04244083A (ja) | 三環状ピリドン誘導体 | |
| US4530843A (en) | Isoindole amidoxime derivatives | |
| FI102898B (fi) | Menetelmä pyrido£1,2-a|pyratsiinivälituotteiden valmistamiseksi | |
| EP0233800A1 (fr) | Dérivés d'imidazo[1,2-a]quinoléines, leur préparation et leur application en thérapeutique | |
| CA1207768A (fr) | Carboxamidoguanidines, leur procede d'obtention et les compositions pharmaceutiques en renfermant | |
| EP0351283A1 (fr) | Dérivés de [(pipéridinyl-4) méthyl]-2 dihydro-2,3 1H-isoindole et tétrahydro-2,3,4,5 1H-benzazépines, leur préparation et leur application en thérapeutique | |
| EP0234971A1 (fr) | Nouveaux amides substitues, leur preparation et les compositions pharmaceutiques qui les contiennent | |
| EP0015786B1 (fr) | Imidazo et pyrimido-pyrido-indoles, leur préparation et médicaments les contenant | |
| KR20070107119A (ko) | 일반적으로 세포독성, 특히 아폽토시스와 관련된 유해상태의 예방 및 치료용 글루타티온-ｓ-트랜스퍼라제 및ｎａｄｐｈ 퀴논 옥시도-리덕타제의 유도인자인[1,2,4]-디티아졸린 및 -디티아졸리딘 유도체 | |
| EP0145304B1 (en) | Tetrahydro-beta-carboline derivatives and process for the preparation thereof |