SU1287752A3 - Способ получени имидазо /1,2- @ / пиримидинов или их аддитивных солей с кислотами - Google Patents
Способ получени имидазо /1,2- @ / пиримидинов или их аддитивных солей с кислотами Download PDFInfo
- Publication number
- SU1287752A3 SU1287752A3 SU833643057A SU3643057A SU1287752A3 SU 1287752 A3 SU1287752 A3 SU 1287752A3 SU 833643057 A SU833643057 A SU 833643057A SU 3643057 A SU3643057 A SU 3643057A SU 1287752 A3 SU1287752 A3 SU 1287752A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- radical
- linear
- alkyl
- lower alkyl
- compound
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- 239000002253 acid Substances 0.000 title claims abstract 7
- 238000000034 method Methods 0.000 title claims description 7
- 150000007513 acids Chemical class 0.000 title abstract 2
- 239000000654 additive Substances 0.000 title abstract 2
- 230000000996 additive effect Effects 0.000 title abstract 2
- 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 230000000694 effects Effects 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
- 208000019901 Anxiety disease Diseases 0.000 claims abstract 2
- 230000036506 anxiety Effects 0.000 claims abstract 2
- 239000012528 membrane Substances 0.000 claims abstract 2
- 230000000144 pharmacologic effect Effects 0.000 claims abstract 2
- 210000004129 prosencephalon Anatomy 0.000 claims abstract 2
- 230000001624 sedative effect Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Chemical group 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229960002200 flunitrazepam Drugs 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 102220044643 rs587781450 Human genes 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940049706 benzodiazepine Drugs 0.000 abstract 1
- 150000001557 benzodiazepines Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229940125904 compound 1 Drugs 0.000 abstract 1
- 230000014155 detection of activity Effects 0.000 abstract 1
- 229940000406 drug candidate Drugs 0.000 abstract 1
- 150000005237 imidazopyrimidines Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 230000009870 specific binding Effects 0.000 abstract 1
- -1 4-methoxy-1- (3-phenyl -2,3-dioxopropyl) -5,6,7,8-tetrahydro-2-quinazolinimine Chemical compound 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- VWPIUVPYXFOGMA-UHFFFAOYSA-N (4-fluorophenyl)-pyrimidin-2-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=NC=CC=N1 VWPIUVPYXFOGMA-UHFFFAOYSA-N 0.000 description 1
- QZYKNQASNNLMQJ-UHFFFAOYSA-N 1-pyrimidin-2-ylpropan-2-one Chemical compound CC(=O)CC1=NC=CC=N1 QZYKNQASNNLMQJ-UHFFFAOYSA-N 0.000 description 1
- XNHDJBJSICAZMR-UHFFFAOYSA-N 3-bromo-1-phenylpropane-1,2-dione Chemical compound BrCC(=O)C(=O)C1=CC=CC=C1 XNHDJBJSICAZMR-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- BPMMMGDHKQIAKZ-UHFFFAOYSA-N 5-ethyl-4-methoxy-6-methylpyrimidin-2-amine Chemical compound CCC1=C(C)N=C(N)N=C1OC BPMMMGDHKQIAKZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101150006573 PAN1 gene Proteins 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- XZLNAWWMGIFOKV-UHFFFAOYSA-N [Cl-].[NH4+].N1=CN=CC=C1 Chemical compound [Cl-].[NH4+].N1=CN=CC=C1 XZLNAWWMGIFOKV-UHFFFAOYSA-N 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LIVQKHTVWSQZOY-UHFFFAOYSA-N cyclohexylmethanone Chemical compound O=[C+]C1CCCCC1 LIVQKHTVWSQZOY-UHFFFAOYSA-N 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- RBWRWAUAVRMBAC-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=[C-]C=C1 RBWRWAUAVRMBAC-UHFFFAOYSA-M 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- CCOXWRVWKFVFDG-UHFFFAOYSA-N pyrimidine-2-carbaldehyde Chemical compound O=CC1=NC=CC=N1 CCOXWRVWKFVFDG-UHFFFAOYSA-N 0.000 description 1
- LSYJHRREPKXURZ-UHFFFAOYSA-N pyrimidine;hydrate Chemical compound O.C1=CN=CN=C1 LSYJHRREPKXURZ-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8224606 | 1982-08-27 | ||
| GB838303612A GB8303612D0 (en) | 1983-02-09 | 1983-02-09 | Imidazo 1,2-a pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1287752A3 true SU1287752A3 (ru) | 1987-01-30 |
Family
ID=26283682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833643057A SU1287752A3 (ru) | 1982-08-27 | 1983-08-26 | Способ получени имидазо /1,2- @ / пиримидинов или их аддитивных солей с кислотами |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4532243A (OSRAM) |
| EP (1) | EP0104104B1 (OSRAM) |
| KR (1) | KR890003000B1 (OSRAM) |
| AR (1) | AR241020A1 (OSRAM) |
| AU (1) | AU559419B2 (OSRAM) |
| CA (1) | CA1228589A (OSRAM) |
| DD (1) | DD215550A5 (OSRAM) |
| DE (1) | DE3366467D1 (OSRAM) |
| DK (1) | DK390583A (OSRAM) |
| ES (1) | ES8506314A1 (OSRAM) |
| FI (1) | FI74010C (OSRAM) |
| GB (1) | GB2128989B (OSRAM) |
| GR (1) | GR79375B (OSRAM) |
| IE (1) | IE55900B1 (OSRAM) |
| IL (1) | IL69417A (OSRAM) |
| NZ (1) | NZ205387A (OSRAM) |
| PH (1) | PH20037A (OSRAM) |
| PT (1) | PT77258B (OSRAM) |
| SU (1) | SU1287752A3 (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL69417A (en) * | 1982-08-27 | 1987-12-20 | Roussel Uclaf | 2-acyl imidazo(1,2-a)pyrimidines,their preparation and pharmaceutical compositions containing them |
| GB8334210D0 (en) * | 1983-12-22 | 1984-02-01 | Roussel Lab Ltd | Imidazo(1 2-c)pyrimidines |
| GB8432073D0 (en) * | 1984-12-19 | 1985-01-30 | Roussel Lab Ltd | Chemical compounds |
| GB8613591D0 (en) * | 1986-06-04 | 1986-07-09 | Roussel Lab Ltd | Chemical compounds |
| GB8620060D0 (en) * | 1986-08-18 | 1986-10-01 | Roussel Lab Ltd | Chemical compounds |
| US4731446A (en) * | 1987-05-01 | 1988-03-15 | The Dow Chemical Company | Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides |
| GB8712466D0 (en) * | 1987-05-27 | 1987-07-01 | Roussel Lab Ltd | Chemical compounds |
| GB8719368D0 (en) * | 1987-08-15 | 1987-09-23 | Wellcome Found | Heterocyclic compounds |
| US5302586A (en) * | 1991-12-19 | 1994-04-12 | G. D. Searle & Co. | Phosphonomethyl-imidazo[1,2-a]pyrimidine-2-carboxylic acid compounds for treatment of neurotoxic injury |
| HRP20030675A2 (en) * | 2001-01-26 | 2004-08-31 | Bristol Myers Squibb Co | Imidazolyl derivatives as corticotropin relasing factor inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3594379A (en) * | 1968-09-16 | 1971-07-20 | Sandoz Ag | 2,3-dihydroimidazo(1,2-c)quinazolines |
| US4223031A (en) * | 1978-05-05 | 1980-09-16 | Mead Johnson & Company | Azolopyrimidinones |
| US4236005A (en) * | 1979-07-02 | 1980-11-25 | American Cyanamid Company | Imidazo[1,5-a]pyrimidines |
| FR2502622A1 (fr) * | 1981-03-25 | 1982-10-01 | Synthelabo | Derives d'imidazo (1,2-a) pyrimidines, leur preparation et leur application en therapeutique |
| US4374988A (en) * | 1981-11-05 | 1983-02-22 | American Cyanamid Company | 4-Heteroarylimidazo-[1,5-A]pyrimidines |
| IL69417A (en) * | 1982-08-27 | 1987-12-20 | Roussel Uclaf | 2-acyl imidazo(1,2-a)pyrimidines,their preparation and pharmaceutical compositions containing them |
-
1983
- 1983-08-03 IL IL69417A patent/IL69417A/xx unknown
- 1983-08-23 EP EP83401696A patent/EP0104104B1/fr not_active Expired
- 1983-08-23 DE DE8383401696T patent/DE3366467D1/de not_active Expired
- 1983-08-24 US US06/526,046 patent/US4532243A/en not_active Expired - Fee Related
- 1983-08-24 PH PH29567A patent/PH20037A/en unknown
- 1983-08-25 AR AR294010A patent/AR241020A1/es active
- 1983-08-25 GR GR72300A patent/GR79375B/el unknown
- 1983-08-25 KR KR1019830003982A patent/KR890003000B1/ko not_active Expired
- 1983-08-26 CA CA000435419A patent/CA1228589A/en not_active Expired
- 1983-08-26 GB GB08322993A patent/GB2128989B/en not_active Expired
- 1983-08-26 SU SU833643057A patent/SU1287752A3/ru active
- 1983-08-26 NZ NZ205387A patent/NZ205387A/en unknown
- 1983-08-26 IE IE2001/83A patent/IE55900B1/en not_active IP Right Cessation
- 1983-08-26 FI FI833055A patent/FI74010C/fi not_active IP Right Cessation
- 1983-08-26 DK DK390583A patent/DK390583A/da not_active Application Discontinuation
- 1983-08-26 DD DD83254274A patent/DD215550A5/de not_active IP Right Cessation
- 1983-08-26 ES ES525186A patent/ES8506314A1/es not_active Expired
- 1983-08-26 AU AU18461/83A patent/AU559419B2/en not_active Ceased
- 1983-08-26 PT PT77258A patent/PT77258B/pt not_active IP Right Cessation
-
1985
- 1985-05-15 US US06/734,590 patent/US4588720A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Эльдерфильд Р. Гетероциклические соединени . Т. 5, Изд-во И.Л.. М., с. 223. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US4588720A (en) | 1986-05-13 |
| IL69417A0 (en) | 1983-11-30 |
| AU1846183A (en) | 1984-03-01 |
| DK390583D0 (da) | 1983-08-26 |
| IE832001L (en) | 1984-02-27 |
| FI833055L (fi) | 1984-02-28 |
| AR241020A2 (es) | 1991-04-30 |
| KR890003000B1 (ko) | 1989-08-18 |
| PH20037A (en) | 1986-09-04 |
| DD215550A5 (de) | 1984-11-14 |
| FI74010C (fi) | 1987-12-10 |
| ES525186A0 (es) | 1985-07-01 |
| EP0104104B1 (fr) | 1986-09-24 |
| US4532243A (en) | 1985-07-30 |
| GR79375B (OSRAM) | 1984-10-22 |
| KR840005812A (ko) | 1984-11-19 |
| GB8322993D0 (en) | 1983-09-28 |
| IE55900B1 (en) | 1991-02-14 |
| PT77258B (en) | 1986-03-21 |
| FI74010B (fi) | 1987-08-31 |
| AU559419B2 (en) | 1987-03-12 |
| IL69417A (en) | 1987-12-20 |
| AR241020A1 (es) | 1991-04-30 |
| PT77258A (en) | 1983-09-01 |
| FI833055A0 (fi) | 1983-08-26 |
| DE3366467D1 (en) | 1986-10-30 |
| EP0104104A1 (fr) | 1984-03-28 |
| ES8506314A1 (es) | 1985-07-01 |
| GB2128989B (en) | 1986-03-19 |
| NZ205387A (en) | 1986-06-11 |
| DK390583A (da) | 1984-02-28 |
| GB2128989A (en) | 1984-05-10 |
| CA1228589A (en) | 1987-10-27 |
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