DD291996A5 - Verfahren zur herstellung von ausgangsverbindungen zur synthese von perhydroazacycloaka(1,2-a)imidazol-derivaten - Google Patents

Verfahren zur herstellung von ausgangsverbindungen zur synthese von perhydroazacycloaka(1,2-a)imidazol-derivaten Download PDF

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Publication number: DD291996A5
Authority: DD; German Democratic Republic
Prior art keywords: compounds; hydrogen; isobutyl; title compound; compound
Prior art date: 1988-02-08

Application number

DD89337916A

Other languages

German (de)

English (en)

Inventor

Mario Pinza

Carlo Farina

Alberto Cerri

Maria T Riccaboni

Original Assignee

�K�K�K@�K�K�Kk��

Priority date (The priority date 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 date listed.)

1988-02-08

Filing date

1989-02-06

Publication date

1991-07-18

1989-02-06 Application filed by �K�K�K@�K�K�Kk�� filed Critical �K�K�K@�K�K�Kk��

1991-07-18 Publication of DD291996A5 publication Critical patent/DD291996A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 105
238000004519 manufacturing process Methods 0.000 title abstract description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 37
238000003786 synthesis reaction Methods 0.000 title description 7
230000015572 biosynthetic process Effects 0.000 title description 6
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 33
238000002360 preparation method Methods 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims abstract description 5
239000007858 starting material Substances 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 4
230000001777 nootropic effect Effects 0.000 abstract description 4
229940079593 drug Drugs 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 description 54
239000001257 hydrogen Substances 0.000 description 50
239000000243 solution Substances 0.000 description 34
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
150000002431 hydrogen Chemical class 0.000 description 21
239000000203 mixture Substances 0.000 description 20
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 18
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 17
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 17
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 17
125000000217 alkyl group Chemical group 0.000 description 17
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 17
229960002646 scopolamine Drugs 0.000 description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
239000002904 solvent Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
101150065749 Churc1 gene Proteins 0.000 description 10
102100038239 Protein Churchill Human genes 0.000 description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 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
-1 alkali metal alkoxide Chemical class 0.000 description 8
239000003054 catalyst Substances 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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000000354 decomposition reaction Methods 0.000 description 7
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-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
239000000706 filtrate Substances 0.000 description 6
229960001227 oxiracetam Drugs 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 4
208000024827 Alzheimer disease Diseases 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229940024606 amino acid Drugs 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
229960004132 diethyl ether Drugs 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000009472 formulation Methods 0.000 description 4
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
238000007363 ring formation reaction Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XBYQWDDMVAKFOF-ONEGZZNKSA-N 2-methylpropyl (e)-4-oxobut-2-enoate Chemical compound CC(C)COC(=O)\C=C\C=O XBYQWDDMVAKFOF-ONEGZZNKSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
101000929663 Homo sapiens Phospholipid-transporting ATPase ABCA7 Proteins 0.000 description 3
STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
102100036620 Phospholipid-transporting ATPase ABCA7 Human genes 0.000 description 3
241000700159 Rattus Species 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000007822 coupling agent Substances 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000005897 peptide coupling reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
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
MEAVLRNBGURMFI-UHFFFAOYSA-N 2-imidazol-1-ylacetamide Chemical compound NC(=O)CN1C=CN=C1 MEAVLRNBGURMFI-UHFFFAOYSA-N 0.000 description 2
KLQCEQLRGRMLBI-UHFFFAOYSA-N 2-methylpropyl 2-(oxiran-2-yl)acetate Chemical compound CC(C)COC(=O)CC1CO1 KLQCEQLRGRMLBI-UHFFFAOYSA-N 0.000 description 2
MWOOKDULMBMMPN-UHFFFAOYSA-N 3-(2-ethyl-1,2-oxazol-2-ium-5-yl)benzenesulfonate Chemical compound O1[N+](CC)=CC=C1C1=CC=CC(S([O-])(=O)=O)=C1 MWOOKDULMBMMPN-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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206010039966 Senile dementia Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
229960004373 acetylcholine Drugs 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012267 brine Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
230000003920 cognitive function Effects 0.000 description 2
230000006735 deficit Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
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239000003480 eluent Substances 0.000 description 2
HELHKLNWSVLNDP-UHFFFAOYSA-N ethyl acetate;methanol;propan-2-one Chemical compound OC.CC(C)=O.CCOC(C)=O HELHKLNWSVLNDP-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
QAFBDRSXXHEXGB-UHFFFAOYSA-N imidazol-1-ylacetic acid Chemical compound OC(=O)CN1C=CN=C1 QAFBDRSXXHEXGB-UHFFFAOYSA-N 0.000 description 2
LBDHGGGMUHKPJG-UHFFFAOYSA-N methyl 5-(4-oxoimidazolidin-2-yl)pentanoate Chemical compound COC(=O)CCCCC1NCC(=O)N1 LBDHGGGMUHKPJG-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
STMOVTSFWYRCOB-DKWTVANSSA-N (2s)-2-amino-3-hydroxypropanoic acid;hydrochloride Chemical compound Cl.OC[C@H](N)C(O)=O STMOVTSFWYRCOB-DKWTVANSSA-N 0.000 description 1
KLHLGTPNBQXSJT-QRPNPIFTSA-N (2s)-2-amino-3-phenylpropanamide;hydrochloride Chemical compound Cl.NC(=O)[C@@H](N)CC1=CC=CC=C1 KLHLGTPNBQXSJT-QRPNPIFTSA-N 0.000 description 1
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125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
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VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
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229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
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239000004089 psychotropic agent Substances 0.000 description 1
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UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
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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)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Biochemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Proteomics, Peptides & Aminoacids (AREA)
General Chemical & Material Sciences (AREA)
Biophysics (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)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

DD89337916A 1988-02-08 1989-02-06 Verfahren zur herstellung von ausgangsverbindungen zur synthese von perhydroazacycloaka(1,2-a)imidazol-derivaten DD291996A5 (de)

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
DD291996A5 true DD291996A5 (de)	1991-07-18

Family

ID=11156852

Family Applications (2)

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
DD89325551A DD283393A5 (de)	1988-02-08	1989-02-06	Verfahren zur herstellung von perhydroazacycloalka (1,2-a)-imidazol-derivaten

Family Applications After (1)

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

Country Status (21)

Country	Link
US (2)	US5053422A (xx)
EP (1)	EP0335483A3 (xx)
JP (1)	JPH01246281A (xx)
KR (1)	KR890013013A (xx)
CN (1)	CN1036204A (xx)
AU (2)	AU616240B2 (xx)
BR (1)	BR8900541A (xx)
CA (1)	CA1324378C (xx)
DD (2)	DD291996A5 (xx)
DK (1)	DK55089A (xx)
FI (1)	FI890438A (xx)
HU (2)	HU204794B (xx)
IT (1)	IT1233860B (xx)
NO (1)	NO168424C (xx)
NZ (1)	NZ227833A (xx)
PL (1)	PL158198B1 (xx)
PT (1)	PT89657B (xx)
RO (4)	RO104070B1 (xx)
RU (1)	RU1799383C (xx)
ZA (1)	ZA89894B (xx)
ZW (1)	ZW1489A1 (xx)

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GB9123641D0 (en) *	1991-11-07	1992-01-02	Isf Spa	Process
TW304167B (xx) *	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
ZA964008B (en) *	1995-06-02	1997-07-11	Akzo Nobel Nv	Imidazo[1,5a]pyridine derived serine protease inhibitors
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
PT2598504E (pt) *	2010-07-26	2014-07-14	Neurotune Ag	Novo processo de fabrico de dimiracetam
CN104968750B (zh)	2013-02-11	2017-04-19	道康宁公司	簇合官能化聚有机硅氧烷、形成所述簇合官能化聚有机硅氧烷的工艺及其使用方法
US10370574B2 (en)	2013-02-11	2019-08-06	Dow Silicones Corporation	Method for forming thermally conductive thermal radical cure silicone compositions
WO2014124388A1 (en)	2013-02-11	2014-08-14	Dow Corning Corporation	Alkoxy-functional organopolysiloxane resin and polymer and related methods for forming same
JP6426629B2 (ja)	2013-02-11	2018-11-21	ダウシリコーンズコーポレーション	アルコキシ官能性シロキサン反応性樹脂を含む湿気硬化性ホットメルトシリコーン接着剤組成物
KR102192489B1 (ko)	2013-02-11	2020-12-17	다우 실리콘즈 코포레이션	열 전도성 열 라디칼 경화 실리콘 조성물을 형성하는 원 위치 방법
CN104968749B (zh)	2013-02-11	2017-03-29	道康宁公司	稳定性热自由基可固化有机硅粘合剂组合物
WO2014124378A1 (en)	2013-02-11	2014-08-14	Dow Corning Corporation	Curable silicone compositions comprising clustured functional polyorganosiloxanes and silicone reactive diluents
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

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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 DD89337916A patent/DD291996A5/de not_active IP Right Cessation
- 1989-02-06 EP EP19890301123 patent/EP0335483A3/en not_active Ceased
- 1989-02-06 DD DD89325551A patent/DD283393A5/de not_active IP Right Cessation
- 1989-02-06 ZA ZA89894A patent/ZA89894B/xx unknown
- 1989-02-06 US US07/307,012 patent/US5053422A/en not_active Expired - Lifetime
- 1989-02-06 CA CA000590213A patent/CA1324378C/en not_active Expired - Lifetime
- 1989-02-07 HU HU904864A patent/HU204794B/hu not_active IP Right Cessation
- 1989-02-07 AU AU29692/89A patent/AU616240B2/en not_active Ceased
- 1989-02-07 RU SU894613489A patent/RU1799383C/ru active
- 1989-02-07 DK DK055089A patent/DK55089A/da not_active Application Discontinuation
- 1989-02-07 NO NO890515A patent/NO168424C/no unknown
- 1989-02-07 HU HU89574A patent/HU203104B/hu not_active IP Right Cessation
- 1989-02-07 PL PL1989277610A patent/PL158198B1/pl 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 KR KR1019890001446A patent/KR890013013A/ko not_active Application Discontinuation
- 1989-02-08 JP JP1029571A patent/JPH01246281A/ja active Pending
- 1989-02-08 RO RO145764A patent/RO105964B1/ro unknown
- 1989-02-08 RO RO145765A patent/RO105965B1/ro unknown
- 1989-02-08 RO RO145763A patent/RO105963B1/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

Also Published As

Publication number	Publication date
DK55089D0 (da)	1989-02-07
AU2969289A (en)	1989-08-10
NZ227833A (en)	1991-09-25
NO168424B (no)	1991-11-11
ZW1489A1 (en)	1989-08-02
US5053422A (en)	1991-10-01
AU616240B2 (en)	1991-10-24
HU203104B (en)	1991-05-28
IT8819336A0 (it)	1988-02-08
NO890515D0 (no)	1989-02-07
RU1799383C (ru)	1993-02-28
RO105963B1 (ro)	1993-01-30
RO105964B1 (ro)	1993-01-30
DD283393A5 (de)	1990-10-10
HUT53363A (en)	1990-10-28
HU204794B (en)	1992-02-28
DK55089A (da)	1989-08-09
FI890438A0 (fi)	1989-01-30
FI890438A (fi)	1989-08-09
PT89657A (pt)	1989-10-04
CN1036204A (zh)	1989-10-11
RO105965B1 (ro)	1993-01-30
EP0335483A2 (en)	1989-10-04
NO890515L (no)	1989-08-09
PL158198B1 (pl)	1992-08-31
CA1324378C (en)	1993-11-16
BR8900541A (pt)	1989-10-03
JPH01246281A (ja)	1989-10-02
HU904864D0 (en)	1991-01-28
US5130319A (en)	1992-07-14
PT89657B (pt)	1994-02-28
AU7947991A (en)	1991-09-12
KR890013013A (ko)	1989-09-20
EP0335483A3 (en)	1991-12-18
RO104070B1 (en)	1993-07-20
NO168424C (no)	1992-02-19
IT1233860B (it)	1992-04-21
ZA89894B (en)	1991-10-30

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