JPH0346466B2 - - Google Patents

Info

Publication number: JPH0346466B2
Authority: JP; Japan
Prior art keywords: group; formula; following general; general formula; pyrrolidinyl
Prior art date: 1979-06-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP61061971A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61280470A (ja

Inventor

Betsuingu Hansu

Biideruman Yurugen

Materune Karushuten

Noizeru Horuken

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Daiichi Pharmaceutical Co Ltd

Original Assignee

Daiichi Pharmaceutical Co Ltd

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.)

1979-06-13

Filing date

1986-03-19

Publication date

1991-07-16

1986-03-19 Application filed by Daiichi Pharmaceutical Co Ltd filed Critical Daiichi Pharmaceutical Co Ltd

1986-12-11 Publication of JPS61280470A publication Critical patent/JPS61280470A/ja

1991-07-16 Publication of JPH0346466B2 publication Critical patent/JPH0346466B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 37
-1 aminoethoxycarbonyl groups Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 9
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
210000004556 brain Anatomy 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
201000010099 disease Diseases 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000004083 survival effect Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000002381 Brain Hypoxia Diseases 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
238000010171 animal model Methods 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
230000002490 cerebral effect Effects 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
230000002503 metabolic effect Effects 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000009101 premedication Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
JGPIWNNFLKDTSR-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)acetic acid Chemical compound OC(=O)CN1CCCC1=O JGPIWNNFLKDTSR-UHFFFAOYSA-N 0.000 description 2
SDWWBSPLLLYOJH-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)propanoic acid Chemical compound OC(=O)C(C)N1CCCC1=O SDWWBSPLLLYOJH-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
208000000044 Amnesia Diseases 0.000 description 2
208000031091 Amnestic disease Diseases 0.000 description 2
206010008096 Cerebral atrophy Diseases 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
230000006986 amnesia Effects 0.000 description 2
208000007502 anemia Diseases 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
230000004087 circulation Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000002981 neuropathic effect Effects 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
229960004526 piracetam Drugs 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
239000007929 subcutaneous injection Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
230000002227 vasoactive effect Effects 0.000 description 2
RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
IKEJVRZKDFTLKH-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)-n-pyridin-3-ylpropanamide Chemical compound C=1C=CN=CC=1NC(=O)C(C)N1CCCC1=O IKEJVRZKDFTLKH-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LARPKBYKCBGIEF-UHFFFAOYSA-N 4-propan-2-ylsulfanylaniline Chemical compound CC(C)SC1=CC=C(N)C=C1 LARPKBYKCBGIEF-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
240000002470 Amphicarpaea bracteata Species 0.000 description 1
206010003694 Atrophy Diseases 0.000 description 1
208000024806 Brain atrophy Diseases 0.000 description 1
208000014644 Brain disease Diseases 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 1
SLCRCNCPOKHKNY-UHFFFAOYSA-N C1=CC(SC(C)CC)=CC=C1NC(=O)C(C)N1C(=O)CCC1 Chemical compound C1=CC(SC(C)CC)=CC=C1NC(=O)C(C)N1C(=O)CCC1 SLCRCNCPOKHKNY-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
XZTYGFHCIAKPGJ-UHFFFAOYSA-N Meclofenoxate Chemical compound CN(C)CCOC(=O)COC1=CC=C(Cl)C=C1 XZTYGFHCIAKPGJ-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
ZKPHYUDUHAIMCK-UHFFFAOYSA-N ambtos828244 Chemical compound C12=CC=CC(=O)N2CC2CN(CC(=O)OC)CC1C2 ZKPHYUDUHAIMCK-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000036770 blood supply Effects 0.000 description 1
239000010951 brass Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
229960000876 cinnarizine Drugs 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000006837 decompression Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
AOHCBEAZXHZMOR-ZDUSSCGKSA-N hypaphorine Chemical compound C1=CC=C2C(C[C@H]([N+](C)(C)C)C([O-])=O)=CNC2=C1 AOHCBEAZXHZMOR-ZDUSSCGKSA-N 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229960003442 meclofenoxate Drugs 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000011707 mineral Substances 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002664 nootropic agent Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
SIXLXDIJGIWWFU-UHFFFAOYSA-N pyritinol Chemical compound OCC1=C(O)C(C)=NC=C1CSSCC1=CN=C(C)C(O)=C1CO SIXLXDIJGIWWFU-UHFFFAOYSA-N 0.000 description 1
229960004986 pyritinol Drugs 0.000 description 1
230000004044 response Effects 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
230000035939 shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms

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Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP61061971A 1979-06-13 1986-03-19 ピロリジニルアルキルカルボン酸アミド誘導体およびその製造方法 Granted JPS61280470A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19792923975 DE2923975A1 (de)	1979-06-13	1979-06-13	Pyrrolidinone, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE2924011.7		1979-06-13
DE2923975.6		1979-06-13

Publications (2)

Publication Number	Publication Date
JPS61280470A JPS61280470A (ja)	1986-12-11
JPH0346466B2 true JPH0346466B2 (de)	1991-07-16

Family

ID=6073167

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP7846680A Granted JPS562960A (en)	1979-06-13	1980-06-12	Pyrrolidinylalkylcarboxylic acid amide derivative* its manufacture and medicinal composition
JP61061971A Granted JPS61280470A (ja)	1979-06-13	1986-03-19	ピロリジニルアルキルカルボン酸アミド誘導体およびその製造方法

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
JP7846680A Granted JPS562960A (en)	1979-06-13	1980-06-12	Pyrrolidinylalkylcarboxylic acid amide derivative* its manufacture and medicinal composition

Country Status (2)

Country	Link
JP (2)	JPS562960A (de)
DE (1)	DE2923975A1 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH647234A5 (en) *	1981-07-24	1985-01-15	Hoffmann La Roche	Pyrrolidine derivatives
FR2515179A1 (fr) *	1981-07-24	1983-04-29	Hoffmann La Roche	Derives de pyrrolidine, leur procede de preparation, les intermediaires pour leur synthese et leur application therapeutique
DE3326724A1 (de) *	1983-07-25	1985-02-07	Boehringer Ingelheim KG, 6507 Ingelheim	In 1-stellung substituierte 4-hydroxymethyl-pyrrolidinone, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen und zwischenprodukte
DE3336024A1 (de) *	1983-10-04	1985-04-18	Boehringer Ingelheim KG, 6507 Ingelheim	4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel
DE3813416A1 (de) *	1988-04-21	1989-11-02	Hoechst Ag	3,4-dihydroxypyrrolidin-2-on-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte
CH680293A5 (de) *	1990-06-26	1992-07-31	Lonza Ag
WO1996029308A1 (fr) *	1995-03-23	1996-09-26	Daiichi Pharmaceutical Co., Ltd.	Cristaux anhydres
WO1998014213A1 (fr)	1996-10-01	1998-04-09	Daiichi Pharmaceutical Co., Ltd.	Stabilisateur de la membrane mitochondriale
ATE266401T1 (de) *	1997-07-15	2004-05-15	Daiichi Seiyaku Co	Nefiracetam zur prophylaxe und behandlung von propofol verursachtem gedächtnisschwund
US6423739B1 (en)	2000-02-23	2002-07-23	Daiichi Pharmaceutical Co., Ltd.	Method for aiding cerebral recovery following neurodegeneration
JPWO2002053153A1 (ja)	2000-12-28	2004-04-30	第一製薬株式会社	神経因性疼痛治療及び予防薬

1979
- 1979-06-13 DE DE19792923975 patent/DE2923975A1/de active Granted
1980
- 1980-06-12 JP JP7846680A patent/JPS562960A/ja active Granted
1986
- 1986-03-19 JP JP61061971A patent/JPS61280470A/ja active Granted

Also Published As

Publication number	Publication date
DE2923975C2 (de)	1988-07-21
DE2923975A1 (de)	1980-12-18
JPS562960A (en)	1981-01-13
JPS61280470A (ja)	1986-12-11
JPS625404B2 (de)	1987-02-04

Publication	Publication Date	Title
US4341790A (en)	1982-07-27	Pyrrolidinylalkylcarboxylic acid amide derivatives, their preparation and pharmaceutical compositions containing them
USRE33024E (en)	1989-08-15	Bronchodilating 8-hydroxy-5-(1R)-1-hydroxy-2-(N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)-amino)ethyl) carbostyril and intermediates thereof
SU984407A3 (ru)	1982-12-23	Способ получени производных пирролидина
US6479488B1 (en)	2002-11-12	Tetrahydroquinoline derivatives as EAA antagonists
HU223945B1 (hu)	2005-03-29	1,2,3,4-Tetrahidro-kinoxalin-dion-származékok és ezeket tartalmazó gyógyszerkészítmények
FR2487829A2 (fr)	1982-02-05	Nouveaux imino acides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme
KR20060009900A (ko)	2006-02-01	피페리디닐- 및 피페라지닐-알킬 카르바메이트 유도체,그의 제조 방법 및 그의 치료 용도
IE920943A1 (en)	1992-10-07	New heterocycle-substituted alkylamides, process for¹preparing them and pharmaceutical compositions containing¹them
JPH0346466B2 (de)	1991-07-16
KR840001836B1 (ko)	1984-10-22	9-아미노알킬플루오렌의 제조방법
EP0326106B1 (de)	1994-07-27	Alkylen-diamine
PL175707B1 (pl)	1999-01-29	Nowe estry 1-aryloksy-3-alkiloamino-2-propanolu
US4912135A (en)	1990-03-27	Amide compounds
DE3719699A1 (de)	1987-12-17	Indolderivate
DE69910787T2 (de)	2004-07-08	Neuartige, pharmazeutisch aktive verbindung
DE3940074A1 (de)	1990-08-09	Kondensierte 3-oxo-propannitrilderivate und verfahren zu ihrer herstellung
KR100191386B1 (ko)	1999-06-15	3-(1,2-벤즈이속사졸-3-일)-4-피리딘아민 및 유도체,이를 함유하는 약제학적 조성물 및 이의 제조방법
KR850001880B1 (ko)	1985-12-28	트란스-4-[n-(3', 4'-메틸렌디옥시벤질리덴)아미노메틸] 사이클로헥산-1-카복실산 및 이의 유도체의 제조방법
US4034100A (en)	1977-07-05	Antihypertensive agents
US5036086A (en)	1991-07-30	Novel benzothiazole derivatives
US4673676A (en)	1987-06-16	Pyrimidoisoquinoline derivatives useful for treating allergies
EP0816359B1 (de)	2004-11-03	4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
US6858744B2 (en)	2005-02-22	Dihydoxyhexanoic acid derivatives, their intermediates, and methods of making
US6028068A (en)	2000-02-22	Substituted 6H-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetising, cardiovascular and hypometabolic agents, and a pharmaceutical composition containing them
US6117867A (en)	2000-09-12	Substituted 6-R-1,3,4-thiadiazine-2-amines, the use thereof as anaesthetizing, cardiovascular and hypometabolic agents, and a pharmaceutical composition containing them