DD283393A5 - Verfahren zur herstellung von perhydroazacycloalka (1,2-a)-imidazol-derivaten - Google Patents
Verfahren zur herstellung von perhydroazacycloalka (1,2-a)-imidazol-derivaten Download PDFInfo
- Publication number
- DD283393A5 DD283393A5 DD89325551A DD32555189A DD283393A5 DD 283393 A5 DD283393 A5 DD 283393A5 DD 89325551 A DD89325551 A DD 89325551A DD 32555189 A DD32555189 A DD 32555189A DD 283393 A5 DD283393 A5 DD 283393A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- imidazole
- hydrogen
- pyrrole
- compound
- alkyl
- Prior art date
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 52
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 5
- 150000001413 amino acids Chemical class 0.000 claims abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
- MEAVLRNBGURMFI-UHFFFAOYSA-N 2-imidazol-1-ylacetamide Chemical compound NC(=O)CN1C=CN=C1 MEAVLRNBGURMFI-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 4
- 239000002664 nootropic agent Substances 0.000 abstract description 4
- 230000001777 nootropic effect Effects 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
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- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 16
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- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 16
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 16
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- 238000001816 cooling Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 10
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 239000003054 catalyst Substances 0.000 description 9
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- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 229960001227 oxiracetam Drugs 0.000 description 8
- AAFMVGHJBLBRHQ-UHFFFAOYSA-N 2-methylpropyl 4-oxobutanoate Chemical compound CC(C)COC(=O)CCC=O AAFMVGHJBLBRHQ-UHFFFAOYSA-N 0.000 description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- -1 alkali metal alkoxide Chemical class 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- 101000929663 Homo sapiens Phospholipid-transporting ATPase ABCA7 Proteins 0.000 description 3
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- FIAINKIUSZGVGX-UHFFFAOYSA-N (1-amino-1-oxopropan-2-yl)azanium;chloride Chemical compound Cl.CC(N)C(N)=O FIAINKIUSZGVGX-UHFFFAOYSA-N 0.000 description 2
- MYZCBJRJVXAQIV-UHFFFAOYSA-N 2-amino-n-benzylacetamide Chemical compound NCC(=O)NCC1=CC=CC=C1 MYZCBJRJVXAQIV-UHFFFAOYSA-N 0.000 description 2
- YBOGXFQRMBJMOU-ONEGZZNKSA-N 2-methylpropyl (e)-4-hydroxybut-2-enoate Chemical compound CC(C)COC(=O)\C=C\CO YBOGXFQRMBJMOU-ONEGZZNKSA-N 0.000 description 2
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- WNVIKKJVLZAFBY-UHFFFAOYSA-N 2-methylpropyl 3-(4-oxoimidazolidin-2-yl)propanoate Chemical compound CC(C)COC(=O)CCC1NCC(=O)N1 WNVIKKJVLZAFBY-UHFFFAOYSA-N 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
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- 238000010420 art technique Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HQYMUNCIMNFLDT-UHFFFAOYSA-N benzyl n-(2-amino-2-oxoethyl)carbamate Chemical compound NC(=O)CNC(=O)OCC1=CC=CC=C1 HQYMUNCIMNFLDT-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
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- 239000012230 colorless oil Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- TXIJJFIRKLJUBY-UHFFFAOYSA-N ethyl 3-(1-benzyl-4-oxoimidazolidin-2-yl)propanoate Chemical compound CCOC(=O)CCC1NC(=O)CN1CC1=CC=CC=C1 TXIJJFIRKLJUBY-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- HELHKLNWSVLNDP-UHFFFAOYSA-N ethyl acetate;methanol;propan-2-one Chemical compound OC.CC(C)=O.CCOC(C)=O HELHKLNWSVLNDP-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- QAFBDRSXXHEXGB-UHFFFAOYSA-N imidazol-1-ylacetic acid Chemical compound OC(=O)CN1C=CN=C1 QAFBDRSXXHEXGB-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000863 loss of memory Toxicity 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940066974 medicated patch Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- LBDHGGGMUHKPJG-UHFFFAOYSA-N methyl 5-(4-oxoimidazolidin-2-yl)pentanoate Chemical compound COC(=O)CCCCC1NCC(=O)N1 LBDHGGGMUHKPJG-UHFFFAOYSA-N 0.000 description 1
- YBTZROCKNUIONO-UHFFFAOYSA-N methyl 5-oxopentanoate Chemical compound COC(=O)CCCC=O YBTZROCKNUIONO-UHFFFAOYSA-N 0.000 description 1
- FDNFXHCDOASWAY-UHFFFAOYSA-N methyl 6-oxohexanoate Chemical compound COC(=O)CCCCC=O FDNFXHCDOASWAY-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000001722 neurochemical effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000012178 vegetable wax Substances 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8819336A IT1233860B (it) | 1988-02-08 | 1988-02-08 | Derivati del peridroazacicloalca (1,2-a) imidazolo ad attivita' nootropa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD283393A5 true DD283393A5 (de) | 1990-10-10 |
Family
ID=11156852
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89325551A DD283393A5 (de) | 1988-02-08 | 1989-02-06 | Verfahren zur herstellung von perhydroazacycloalka (1,2-a)-imidazol-derivaten |
| DD89337916A DD291996A5 (de) | 1988-02-08 | 1989-02-06 | Verfahren zur herstellung von ausgangsverbindungen zur synthese von perhydroazacycloaka(1,2-a)imidazol-derivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89337916A DD291996A5 (de) | 1988-02-08 | 1989-02-06 | Verfahren zur herstellung von ausgangsverbindungen zur synthese von perhydroazacycloaka(1,2-a)imidazol-derivaten |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5053422A (pt) |
| EP (1) | EP0335483A3 (pt) |
| JP (1) | JPH01246281A (pt) |
| KR (1) | KR890013013A (pt) |
| CN (1) | CN1036204A (pt) |
| AU (2) | AU616240B2 (pt) |
| BR (1) | BR8900541A (pt) |
| CA (1) | CA1324378C (pt) |
| DD (2) | DD283393A5 (pt) |
| DK (1) | DK55089A (pt) |
| FI (1) | FI890438A (pt) |
| HU (2) | HU203104B (pt) |
| IT (1) | IT1233860B (pt) |
| NO (1) | NO168424C (pt) |
| NZ (1) | NZ227833A (pt) |
| PL (1) | PL158198B1 (pt) |
| PT (1) | PT89657B (pt) |
| RO (4) | RO105964B1 (pt) |
| RU (1) | RU1799383C (pt) |
| ZA (1) | ZA89894B (pt) |
| ZW (1) | ZW1489A1 (pt) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9123641D0 (en) * | 1991-11-07 | 1992-01-02 | Isf Spa | Process |
| TW304167B (pt) * | 1995-01-30 | 1997-05-01 | Lilly Co Eli | |
| PE17897A1 (es) * | 1995-02-17 | 1997-06-12 | Lilly Co Eli | Formulacion transdermica en parche del 3-(4-butiltio)-1,2,5-tiadiazol-3-il)-1-azabiciclo (2,2,2) octano |
| IL118323A (en) * | 1995-06-02 | 1999-11-30 | Akzo Nobel Nv | 3,8-Diamino-8- hydroxyimidazo (1,5-a) pyridine -1(5H)-one derived serine protease inhibitors and pharmaceutical compositions containing them |
| JP3905409B2 (ja) | 2002-04-10 | 2007-04-18 | タレックス光学工業株式会社 | 光学レンズ成型用ポリウレタン樹脂組成物および耐衝撃性合成樹脂レンズ |
| ITMI20030573A1 (it) * | 2003-03-24 | 2004-09-25 | Nikem Research Srl | Composti ad azione nootropica, loro preparazione, |
| ITMI20070770A1 (it) | 2007-04-16 | 2008-10-17 | Brane Discovery S R L | Impiego di dimiracetam nel trattamento del dolore cronico |
| US9593209B2 (en) | 2009-10-22 | 2017-03-14 | Dow Corning Corporation | Process for preparing clustered functional polyorganosiloxanes, and methods for their use |
| CN103052638B (zh) * | 2010-07-26 | 2015-09-30 | 神经协调股份公司 | 制备地来西坦的方法 |
| EP3004275B1 (en) | 2013-02-11 | 2020-10-21 | Dow Silicones Corporation | In situ method for forming thermally conductive thermal radical cure silicone composition |
| KR102206708B1 (ko) | 2013-02-11 | 2021-01-25 | 다우 실리콘즈 코포레이션 | 안정한 열 라디칼 경화성 실리콘 접착제 조성물 |
| JP6370812B2 (ja) | 2013-02-11 | 2018-08-08 | ダウ シリコーンズ コーポレーション | クラスタ化官能性ポリオルガノシロキサン、これを生成するプロセス、及びこれを使用する方法 |
| CN105189685B (zh) | 2013-02-11 | 2017-08-08 | 道康宁公司 | 用于形成导热热自由基固化有机硅组合物的方法 |
| JP6426628B2 (ja) | 2013-02-11 | 2018-11-21 | ダウ シリコーンズ コーポレーション | 官能基密集型ポリオルガノシロキサン及びシリコーン反応性希釈剤を含む硬化性シリコーン組成物 |
| US10370572B2 (en) | 2013-02-11 | 2019-08-06 | Dow Silicones Corporation | Moisture-curable hot melt silicone adhesive compositions including an alkoxy-functional siloxane reactive resin |
| WO2014124388A1 (en) | 2013-02-11 | 2014-08-14 | Dow Corning Corporation | Alkoxy-functional organopolysiloxane resin and polymer and related methods for forming same |
| EP3196229B1 (en) | 2015-11-05 | 2018-09-26 | Dow Silicones Corporation | Branched polyorganosiloxanes and related curable compositions, methods, uses and devices |
| JOP20190251A1 (ar) | 2017-05-31 | 2019-10-21 | Metys Pharmaceuticals AG | تركيبات تآزرية تشتمل على (r)-ديميراسيتام (1) و(s)-ديميراسيتام (2) بنسبة غير راسيمية |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3334099A (en) * | 1965-03-31 | 1967-08-01 | Sandoz Ag | Novel pyrrolo-diazepines, pyrrolo-imidazolidines, and pyrrolo-pyrimidines |
| FR2358891A1 (fr) * | 1976-07-22 | 1978-02-17 | Yamanouchi Pharma Co Ltd | Composes heterocycliques contenant un azote, utilise comme agents analgesiques et anti-inflammatoires |
| US4372966A (en) * | 1980-09-15 | 1983-02-08 | Warner-Lambert Company | Use of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione as a cognition activator |
| US4582838A (en) * | 1984-08-24 | 1986-04-15 | Warner-Lambert Company | Derivatives of dihydro-1H-pyrrolo[1,2-c]imidazol-3,5-dione as cognition activators |
| US4677098A (en) * | 1985-11-22 | 1987-06-30 | Warner-Lambert Company | Substituted dihydro-1H-pyrolizine-3,5(2H,6H)-diones |
| JPS62289581A (ja) * | 1986-06-09 | 1987-12-16 | Idemitsu Kosan Co Ltd | イミダゾピロリンジオン誘導体，その製造方法およびそれを有効成分とする除草剤 |
| JPS62292783A (ja) * | 1986-06-12 | 1987-12-19 | Idemitsu Kosan Co Ltd | イミダゾピロリンジオン誘導体，その製造方法およびそれを有効成分として含有する除草剤 |
-
1988
- 1988-02-08 IT IT8819336A patent/IT1233860B/it active
-
1989
- 1989-01-30 FI FI890438A patent/FI890438A/fi not_active Application Discontinuation
- 1989-02-02 NZ NZ227833A patent/NZ227833A/xx unknown
- 1989-02-03 BR BR898900541A patent/BR8900541A/pt unknown
- 1989-02-03 ZW ZW14/89A patent/ZW1489A1/xx unknown
- 1989-02-04 CN CN89101740A patent/CN1036204A/zh active Pending
- 1989-02-06 DD DD89325551A patent/DD283393A5/de not_active IP Right Cessation
- 1989-02-06 DD DD89337916A patent/DD291996A5/de not_active IP Right Cessation
- 1989-02-06 EP EP19890301123 patent/EP0335483A3/en not_active Ceased
- 1989-02-06 CA CA000590213A patent/CA1324378C/en not_active Expired - Lifetime
- 1989-02-06 ZA ZA89894A patent/ZA89894B/xx unknown
- 1989-02-06 US US07/307,012 patent/US5053422A/en not_active Expired - Lifetime
- 1989-02-07 HU HU89574A patent/HU203104B/hu not_active IP Right Cessation
- 1989-02-07 AU AU29692/89A patent/AU616240B2/en not_active Ceased
- 1989-02-07 PL PL1989277610A patent/PL158198B1/pl unknown
- 1989-02-07 DK DK055089A patent/DK55089A/da not_active Application Discontinuation
- 1989-02-07 NO NO890515A patent/NO168424C/no unknown
- 1989-02-07 RU SU894613489A patent/RU1799383C/ru active
- 1989-02-07 HU HU904864A patent/HU204794B/hu not_active IP Right Cessation
- 1989-02-08 KR KR1019890001446A patent/KR890013013A/ko not_active Application Discontinuation
- 1989-02-08 RO RO145764A patent/RO105964B1/ro unknown
- 1989-02-08 PT PT89657A patent/PT89657B/pt active IP Right Grant
- 1989-02-08 RO RO138146A patent/RO104070B1/ro unknown
- 1989-02-08 RO RO145763A patent/RO105963B1/ro unknown
- 1989-02-08 JP JP1029571A patent/JPH01246281A/ja active Pending
- 1989-02-08 RO RO145765A patent/RO105965B1/ro unknown
-
1991
- 1991-03-15 US US07/669,806 patent/US5130319A/en not_active Expired - Lifetime
- 1991-07-01 AU AU79479/91A patent/AU7947991A/en not_active Abandoned
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