HU218950B - Kondenzált imidazo-piridin-származékok, az ezeket tartalmazó gyógyszerkészítmények és eljárás előállításukra - Google Patents
Kondenzált imidazo-piridin-származékok, az ezeket tartalmazó gyógyszerkészítmények és eljárás előállításukra Download PDFInfo
- Publication number
- HU218950B HU218950B HU9300376A HU9300376A HU218950B HU 218950 B HU218950 B HU 218950B HU 9300376 A HU9300376 A HU 9300376A HU 9300376 A HU9300376 A HU 9300376A HU 218950 B HU218950 B HU 218950B
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- formula
- ring
- pyridine
- optionally substituted
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 146
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 239000002249 anxiolytic agent Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000012190 activator Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 69
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
- 239000005557 antagonist Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 230000003444 anaesthetic effect Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- ITPFSYAYHHPKRT-UHFFFAOYSA-N 4-(1,2-oxazol-3-yl)-12-oxa-3,5,8-triazatricyclo[7.4.0.02,6]trideca-1,3,6,8-tetraene Chemical compound N1C2=C3COCCC3=NC=C2N=C1C=1C=CON=1 ITPFSYAYHHPKRT-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 230000003925 brain function Effects 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000000506 psychotropic effect Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000004089 psychotropic agent Substances 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 206010002091 Anaesthesia Diseases 0.000 abstract 1
- 230000037005 anaesthesia Effects 0.000 abstract 1
- 238000001949 anaesthesia Methods 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000002490 cerebral effect Effects 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
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- 239000000243 solution Substances 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
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- 229940049706 benzodiazepine Drugs 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
- 239000000556 agonist Substances 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 10
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- 230000000694 effects Effects 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 229940125425 inverse agonist Drugs 0.000 description 7
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- 238000002474 experimental method Methods 0.000 description 6
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- QHFOJENASUVKQL-UHFFFAOYSA-N 4-chloro-5,6,7,8-tetrahydroquinolin-3-amine Chemical compound C1CCCC2=C(Cl)C(N)=CN=C21 QHFOJENASUVKQL-UHFFFAOYSA-N 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- XZWMTTHOJMWSQN-UHFFFAOYSA-N n-(4-oxo-5,6,7,8-tetrahydro-1h-quinolin-3-yl)benzamide Chemical compound C=1NC=2CCCCC=2C(=O)C=1NC(=O)C1=CC=CC=C1 XZWMTTHOJMWSQN-UHFFFAOYSA-N 0.000 description 1
- KDIVHZJZRUIRKN-UHFFFAOYSA-N n-(7,8-dihydro-5h-pyrano[4,3-b]pyridin-3-yl)-2,2,2-trifluoroacetamide Chemical compound C1COCC2=CC(NC(=O)C(F)(F)F)=CN=C21 KDIVHZJZRUIRKN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000005229 pyrazolopyridines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KKHJTSPUUIRIOP-UHFFFAOYSA-J tetrachlorostannane;hydrate Chemical compound O.Cl[Sn](Cl)(Cl)Cl KKHJTSPUUIRIOP-UHFFFAOYSA-J 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 208000028500 tonic seizure Diseases 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5934792 | 1992-02-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9300376D0 HU9300376D0 (en) | 1993-04-28 |
| HUT70035A HUT70035A (en) | 1995-09-28 |
| HU218950B true HU218950B (hu) | 2001-01-29 |
Family
ID=13110672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9300376A HU218950B (hu) | 1992-02-12 | 1993-02-12 | Kondenzált imidazo-piridin-származékok, az ezeket tartalmazó gyógyszerkészítmények és eljárás előállításukra |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US5378848A (Sortimente) |
| EP (1) | EP0556008B1 (Sortimente) |
| JP (1) | JP2863396B2 (Sortimente) |
| KR (1) | KR100242398B1 (Sortimente) |
| AT (1) | ATE153023T1 (Sortimente) |
| CA (1) | CA2088798C (Sortimente) |
| DE (1) | DE69310563T2 (Sortimente) |
| DK (1) | DK0556008T3 (Sortimente) |
| ES (1) | ES2105099T3 (Sortimente) |
| GR (1) | GR3023498T3 (Sortimente) |
| HU (1) | HU218950B (Sortimente) |
| TW (1) | TW221435B (Sortimente) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6780873B2 (en) | 1999-06-10 | 2004-08-24 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6784188B2 (en) | 1999-06-10 | 2004-08-31 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6888000B2 (en) | 2001-12-21 | 2005-05-03 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US10071156B2 (en) | 2005-02-04 | 2018-09-11 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9711257D0 (en) * | 1997-05-30 | 1997-07-30 | Smithkline Beecham Plc | Novel compounds |
| GB9720052D0 (en) * | 1997-09-19 | 1997-11-19 | Smithkline Beecham Plc | Novel compounds |
| TW550080B (en) * | 1998-11-17 | 2003-09-01 | Shionogi & Co | Transdermic preparation comprising cerebral function activating agent |
| CZ20023276A3 (cs) | 2000-03-30 | 2003-02-12 | Shionogi & Co., Ltd. | Nové syntetické způsoby přípravy a krystalická forma kondenzovaných imidazopyridinových derivátů |
| WO2003008421A1 (en) * | 2001-07-16 | 2003-01-30 | Shionogi & Co., Ltd. | Process for preparation of amidine derivatives |
| EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| WO2003028723A1 (fr) * | 2001-09-27 | 2003-04-10 | Saitama Daiichi Pharmaceutical Co., Ltd. | Compositions pharmaceutiques destinee a l'absorption par voie percutanee contenant des derives d'imidazopyridine fondus |
| WO2004078173A1 (ja) * | 2003-02-05 | 2004-09-16 | Shionogi & Co., Ltd. | 溶出性の改善された錠剤 |
| US20040214851A1 (en) * | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| CA2535120A1 (en) * | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| US7897597B2 (en) * | 2003-08-27 | 2011-03-01 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| US20050054665A1 (en) * | 2003-09-05 | 2005-03-10 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| EP1673087B1 (en) * | 2003-10-03 | 2015-05-13 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| JP2007511527A (ja) | 2003-11-14 | 2007-05-10 | スリーエム イノベイティブ プロパティズ カンパニー | オキシム置換イミダゾ環化合物 |
| AU2004291122A1 (en) * | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| AR046781A1 (es) * | 2003-11-25 | 2005-12-21 | 3M Innovative Properties Co | Derivados de imidazoquinolinas. composiciones farmaceuticas. |
| US8802853B2 (en) * | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| AU2004312508A1 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| AU2005228150A1 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) * | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US20070259881A1 (en) * | 2004-06-18 | 2007-11-08 | Dellaria Joseph F Jr | Substituted Imidazo Ring Systems and Methods |
| WO2006065280A2 (en) * | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
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| WO2006009826A1 (en) * | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US20090270443A1 (en) * | 2004-09-02 | 2009-10-29 | Doris Stoermer | 1-amino imidazo-containing compounds and methods |
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| US8034938B2 (en) | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| JP2008530113A (ja) | 2005-02-11 | 2008-08-07 | コーリー ファーマシューティカル グループ，インコーポレイテッド | オキシムおよびヒドロキシラミン置換イミダゾ［４，５−ｃ］環化合物および方法 |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
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| CN102379684B (zh) | 2005-04-28 | 2014-11-19 | 普罗透斯数字保健公司 | 药物信息系统 |
| JP4551962B2 (ja) * | 2005-09-23 | 2010-09-29 | コーリー ファーマシューティカル グループ，インコーポレイテッド | １Ｈ−イミダゾ［４，５−ｃ］ピリジンおよびその類似体のための方法 |
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| TWI321503B (en) | 2007-06-15 | 2010-03-11 | Univ Nat Taiwan Science Tech | The analytical method of the effective polishing frequency and number of times towards the polishing pads having different grooves and profiles |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| CN110075069A (zh) | 2009-05-06 | 2019-08-02 | 实验室护肤股份有限公司 | 包含活性剂-磷酸钙颗粒复合物的皮肤递送组合物及其应用 |
| US8461328B2 (en) * | 2010-01-12 | 2013-06-11 | Genentech, Inc. | Tricyclic heterocyclic compounds, compositions and methods of use thereof |
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Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1263651A (en) * | 1984-07-09 | 1989-12-05 | Ciba-Geigy Ag | Certain ring-fused pyrazolo ¬3,4-d|-pyridin-3-one derivatives |
| CA1306260C (en) * | 1985-10-18 | 1992-08-11 | Shionogi & Co., Ltd. | Condensed imidazopyridine derivatives |
-
1993
- 1993-02-02 US US08/012,424 patent/US5378848A/en not_active Expired - Lifetime
- 1993-02-04 TW TW082100759A patent/TW221435B/zh active
- 1993-02-04 CA CA002088798A patent/CA2088798C/en not_active Expired - Fee Related
- 1993-02-08 DK DK93300901.1T patent/DK0556008T3/da active
- 1993-02-08 DE DE69310563T patent/DE69310563T2/de not_active Expired - Fee Related
- 1993-02-08 EP EP93300901A patent/EP0556008B1/en not_active Expired - Lifetime
- 1993-02-08 ES ES93300901T patent/ES2105099T3/es not_active Expired - Lifetime
- 1993-02-08 AT AT93300901T patent/ATE153023T1/de not_active IP Right Cessation
- 1993-02-10 JP JP5022444A patent/JP2863396B2/ja not_active Expired - Fee Related
- 1993-02-11 KR KR1019930001859A patent/KR100242398B1/ko not_active Expired - Fee Related
- 1993-02-12 HU HU9300376A patent/HU218950B/hu not_active IP Right Cessation
-
1994
- 1994-08-30 US US08/297,885 patent/US5461062A/en not_active Expired - Lifetime
-
1997
- 1997-05-20 GR GR970401147T patent/GR3023498T3/el unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6780873B2 (en) | 1999-06-10 | 2004-08-24 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6784188B2 (en) | 1999-06-10 | 2004-08-31 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6897221B2 (en) | 1999-06-10 | 2005-05-24 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US7157453B2 (en) | 1999-06-10 | 2007-01-02 | 3M Innovation Properties Company | Urea substituted imidazoquinolines |
| US7393859B2 (en) | 1999-06-10 | 2008-07-01 | Coley Pharmaceutical Group, Inc. | Amide substituted imidazoquinolines |
| US6888000B2 (en) | 2001-12-21 | 2005-05-03 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6924293B2 (en) | 2001-12-21 | 2005-08-02 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US7199131B2 (en) | 2001-12-21 | 2007-04-03 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US10071156B2 (en) | 2005-02-04 | 2018-09-11 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2088798C (en) | 2003-08-05 |
| US5378848A (en) | 1995-01-03 |
| DE69310563T2 (de) | 1997-11-13 |
| HUT70035A (en) | 1995-09-28 |
| EP0556008B1 (en) | 1997-05-14 |
| US5461062A (en) | 1995-10-24 |
| JP2863396B2 (ja) | 1999-03-03 |
| GR3023498T3 (en) | 1997-08-29 |
| EP0556008A1 (en) | 1993-08-18 |
| KR100242398B1 (ko) | 2000-03-02 |
| TW221435B (Sortimente) | 1994-03-01 |
| ES2105099T3 (es) | 1997-10-16 |
| KR930017904A (ko) | 1993-09-20 |
| HU9300376D0 (en) | 1993-04-28 |
| ATE153023T1 (de) | 1997-05-15 |
| JPH05286973A (ja) | 1993-11-02 |
| DK0556008T3 (da) | 1997-06-09 |
| DE69310563D1 (de) | 1997-06-19 |
| CA2088798A1 (en) | 1993-08-23 |
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