DD246994A5 - Verfahren zur herstellung neuer bi-2h-pyrroli(di)ndione - Google Patents

Verfahren zur herstellung neuer bi-2h-pyrroli(di)ndione Download PDF

Info

Publication number: DD246994A5
Authority: DD; German Democratic Republic
Prior art keywords: lower alkyl; alkyl; hydroxy; pyrrole; carbamyl
Prior art date: 1985-02-22

Application number

DD86287241A

Other languages

German (de)

English (en)

Inventor

Romeo Paioni

Original Assignee

��`��@��k��

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.)

1985-02-22

Filing date

1986-02-21

Publication date

1987-06-24

1986-02-21 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1987-06-24 Publication of DD246994A5 publication Critical patent/DD246994A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 133
150000003839 salts Chemical class 0.000 claims abstract description 112
238000000034 method Methods 0.000 claims abstract description 95
238000002360 preparation method Methods 0.000 claims abstract description 32
239000000203 mixture Substances 0.000 claims abstract description 19
GGZYWOFYDFFJBR-UHFFFAOYSA-N 3-(2H-pyrrol-4-yl)-2H-pyrrole Chemical compound N=1CC(=CC=1)C1=CCN=C1 GGZYWOFYDFFJBR-UHFFFAOYSA-N 0.000 claims abstract 4
125000000217 alkyl group Chemical group 0.000 claims description 259
-1 hydroxy- Chemical class 0.000 claims description 140
229910052757 nitrogen Inorganic materials 0.000 claims description 69
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 48
HKTQRFISOFMLRJ-UHFFFAOYSA-N 3-hydroxy-4-(5-oxo-1,2-dihydropyrrol-3-yl)-1,2-dihydropyrrol-5-one Chemical compound O=C1NCC(O)=C1C1=CC(=O)NC1 HKTQRFISOFMLRJ-UHFFFAOYSA-N 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
125000003545 alkoxy group Chemical group 0.000 claims description 30
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000011734 sodium Substances 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
229910052708 sodium Inorganic materials 0.000 claims description 21
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 20
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
241000534944 Thia Species 0.000 claims description 14
125000003282 alkyl amino group Chemical group 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 11
XKXFKLBJKBIKAH-UHFFFAOYSA-N 2-[3-[1-(2-amino-2-oxoethyl)-3-hydroxy-5-oxo-2h-pyrrol-4-yl]-5-oxo-2h-pyrrol-1-yl]acetamide Chemical class O=C1N(CC(=O)N)CC(C=2C(N(CC(N)=O)CC=2O)=O)=C1 XKXFKLBJKBIKAH-UHFFFAOYSA-N 0.000 claims description 8
CVCPEFUZYNZWQI-UHFFFAOYSA-N 2-[3-[1-(carboxymethyl)-3-hydroxy-5-oxo-2h-pyrrol-4-yl]-5-oxo-2h-pyrrol-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)CC(C=2C(N(CC(O)=O)CC=2O)=O)=C1 CVCPEFUZYNZWQI-UHFFFAOYSA-N 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
150000003863 ammonium salts Chemical class 0.000 claims description 8
125000001589 carboacyl group Chemical group 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
159000000000 sodium salts Chemical class 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical class OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 claims description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
125000004450 alkenylene group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000000477 aza group Chemical group 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 2
HWTWNWAWBPFZMH-UHFFFAOYSA-N 4-(5-oxo-1,2-dihydropyrrol-3-yl)-1,2-dihydropyrrol-5-one Chemical class O=C1NCC(C=2C(NCC=2)=O)=C1 HWTWNWAWBPFZMH-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
230000001777 nootropic effect Effects 0.000 abstract description 6
239000008186 active pharmaceutical agent Substances 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
239000002585 base Substances 0.000 description 36
239000000243 solution Substances 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000002253 acid Substances 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 24
150000001412 amines Chemical class 0.000 description 22
239000013078 crystal Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 15
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
229920002472 Starch Polymers 0.000 description 13
239000004480 active ingredient Substances 0.000 description 13
239000007858 starting material Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000003826 tablet Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
235000019698 starch Nutrition 0.000 description 10
239000000725 suspension Substances 0.000 description 10
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
239000013081 microcrystal Substances 0.000 description 9
239000000454 talc Substances 0.000 description 9
229910052623 talc Inorganic materials 0.000 description 9
235000012222 talc Nutrition 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
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 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
229910000102 alkali metal hydride Inorganic materials 0.000 description 8
150000008046 alkali metal hydrides Chemical class 0.000 description 8
150000001340 alkali metals Chemical class 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000008101 lactose Substances 0.000 description 8
235000019359 magnesium stearate Nutrition 0.000 description 8
229920001223 polyethylene glycol Polymers 0.000 description 8
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
239000008107 starch Substances 0.000 description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
239000011230 binding agent Substances 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 5
229910000272 alkali metal oxide Inorganic materials 0.000 description 5
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 5
150000003973 alkyl amines Chemical class 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
238000010306 acid treatment Methods 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
238000010533 azeotropic distillation Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000008298 dragée Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
229940100445 wheat starch Drugs 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
229910001863 barium hydroxide Inorganic materials 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001718 carbodiimides Chemical class 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
230000002490 cerebral effect Effects 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229940014259 gelatin Drugs 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
UIEBVKAYSUDNAW-UHFFFAOYSA-N methyl 2-[3-[3-hydroxy-1-(2-methoxy-2-oxoethyl)-5-oxo-2h-pyrrol-4-yl]-5-oxo-2h-pyrrol-1-yl]acetate Chemical compound O=C1N(CC(=O)OC)CC(C=2C(N(CC(=O)OC)CC=2O)=O)=C1 UIEBVKAYSUDNAW-UHFFFAOYSA-N 0.000 description 3
CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
229940093429 polyethylene glycol 6000 Drugs 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 2
JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 2
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125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
238000012792 lyophilization process Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 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
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000011302 passive avoidance test Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003864 primary ammonium salts Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
238000009738 saturating Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Semiconductor Lasers (AREA)
Pyrrole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Luminescent Compositions (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Electroluminescent Light Sources (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

DD86287241A 1985-02-22 1986-02-21 Verfahren zur herstellung neuer bi-2h-pyrroli(di)ndione DD246994A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH82885		1985-02-22

Publications (1)

Publication Number	Publication Date
DD246994A5 true DD246994A5 (de)	1987-06-24

Family

ID=4196139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86287241A DD246994A5 (de)	1985-02-22	1986-02-21	Verfahren zur herstellung neuer bi-2h-pyrroli(di)ndione

Country Status (20)

Country	Link
US (2)	US4789674A (da)
EP (1)	EP0192255B1 (da)
JP (1)	JPH0610192B2 (da)
KR (1)	KR900000737B1 (da)
AT (1)	ATE55377T1 (da)
AU (1)	AU589945B2 (da)
CA (1)	CA1331756C (da)
DD (1)	DD246994A5 (da)
DE (1)	DE3673186D1 (da)
DK (1)	DK81686A (da)
ES (3)	ES8802492A1 (da)
FI (1)	FI83510C (da)
GR (1)	GR860487B (da)
HU (1)	HU194824B (da)
IE (1)	IE58274B1 (da)
NO (1)	NO168888C (da)
NZ (1)	NZ215255A (da)
PH (1)	PH25925A (da)
PT (1)	PT82060B (da)
ZA (1)	ZA861302B (da)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH666483A5 (de) *	1985-01-16	1988-07-29	Lonza Ag	Verfahren zur herstellung von thiotetronsaeure.
IL80071A0 (en) *	1985-09-24	1986-12-31	Lonza Ag	Pyrrolidine acetamide derivatives
HU195773B (en) *	1985-09-24	1988-07-28	Lonza Ag	Process for preparing alkyl esters of 4-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid
CH668423A5 (de) *	1986-06-19	1988-12-30	Lonza Ag	Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-onen.
CH668424A5 (de) *	1986-06-26	1988-12-30	Lonza Ag	4-benzyloxy-3-pyrrolin-2-on-l-yl-acetamid, dessen herstellung und verwendung.
CH668422A5 (de) *	1986-06-26	1988-12-30	Lonza Ag	4-benzyloxy-3-pyrrolin-2-on, dessen herstellung und verwendung zur synthese von tetramsaeure.
CH667655A5 (de) *	1986-09-24	1988-10-31	Lonza Ag	Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen.
CH670644A5 (da) *	1986-12-18	1989-06-30	Lonza Ag
DE58909320D1 (de) *	1988-09-06	1995-08-03	Lonza Ag	Verfahren zur Herstellung von 5-Alkyltetramsäuren.
FI95034C (fi) *	1989-03-15	1995-12-11	Lonza Ag	Menetelmä 1,3-substituoidun tetrahydro-1H-tieno/3,4-d/-imidatsol-2(3H)-on-4-ylideenipentaanihappoesterin valmistamiseksi
US7419911B2 (en) *	2003-11-10	2008-09-02	Ekc Technology, Inc.	Compositions and methods for rapidly removing overfilled substrates

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1061755A (fr) *	1951-02-28	1954-04-15		Procédé pour l'obtention de corps à forme lactame
GB1039113A (en) *	1964-08-06	1966-08-17	Ucb Sa	New n-substituted lactams
US4144246A (en) *	1976-11-15	1979-03-13	Parke, Davis & Company	Pyrrolidineacetic acid esters
JPS567765A (en) *	1979-06-29	1981-01-27	Yasumitsu Tamura	4,4'-methylenebis-(1-substituted-3-phenylamino-5-oxo-3,4-dehydropiperidine) derivative

1986
- 1986-02-17 FI FI860709A patent/FI83510C/fi not_active IP Right Cessation
- 1986-02-18 PH PH33427A patent/PH25925A/en unknown
- 1986-02-19 EP EP86102155A patent/EP0192255B1/de not_active Expired - Lifetime
- 1986-02-19 DE DE8686102155T patent/DE3673186D1/de not_active Expired - Lifetime
- 1986-02-19 AT AT86102155T patent/ATE55377T1/de not_active IP Right Cessation
- 1986-02-20 GR GR860487A patent/GR860487B/el unknown
- 1986-02-20 ES ES552229A patent/ES8802492A1/es not_active Expired
- 1986-02-20 PT PT82060A patent/PT82060B/pt not_active IP Right Cessation
- 1986-02-21 DD DD86287241A patent/DD246994A5/de not_active IP Right Cessation
- 1986-02-21 JP JP61035368A patent/JPH0610192B2/ja not_active Expired - Lifetime
- 1986-02-21 NZ NZ215255A patent/NZ215255A/xx unknown
- 1986-02-21 CA CA000502393A patent/CA1331756C/en not_active Expired - Fee Related
- 1986-02-21 HU HU86743A patent/HU194824B/hu not_active IP Right Cessation
- 1986-02-21 ZA ZA861302A patent/ZA861302B/xx unknown
- 1986-02-21 AU AU53880/86A patent/AU589945B2/en not_active Ceased
- 1986-02-21 DK DK81686A patent/DK81686A/da not_active Application Discontinuation
- 1986-02-21 KR KR1019860001227A patent/KR900000737B1/ko not_active Expired
- 1986-02-21 NO NO860655A patent/NO168888C/no unknown
- 1986-02-24 IE IE47886A patent/IE58274B1/en not_active IP Right Cessation
1987
- 1987-06-16 ES ES557605A patent/ES8802609A1/es not_active Expired
- 1987-06-16 ES ES557604A patent/ES8801916A1/es not_active Expired
- 1987-06-24 US US07/065,800 patent/US4789674A/en not_active Expired - Fee Related
- 1987-06-25 US US07/068,783 patent/US4758575A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FI860709A7 (fi)	1986-08-23
ATE55377T1 (de)	1990-08-15
AU5388086A (en)	1986-08-28
AU589945B2 (en)	1989-10-26
ES8802492A1 (es)	1988-06-16
HUT40409A (en)	1986-12-28
PT82060B (pt)	1988-07-01
ES552229A0 (es)	1988-06-16
NO168888C (no)	1992-04-15
ZA861302B (en)	1986-12-30
PH25925A (en)	1991-12-19
KR900000737B1 (ko)	1990-02-10
NZ215255A (en)	1989-06-28
CA1331756C (en)	1994-08-30
HU194824B (en)	1988-03-28
ES557605A0 (es)	1988-09-01
US4758575A (en)	1988-07-19
EP0192255A3 (en)	1987-08-26
GR860487B (en)	1986-06-18
JPS61194067A (ja)	1986-08-28
ES557604A0 (es)	1988-03-01
IE58274B1 (en)	1993-08-25
ES8801916A1 (es)	1988-03-01
FI860709A0 (fi)	1986-02-17
DE3673186D1 (de)	1990-09-13
EP0192255A2 (de)	1986-08-27
IE860478L (en)	1986-08-22
JPH0610192B2 (ja)	1994-02-09
NO860655L (no)	1986-08-25
ES8802609A1 (es)	1988-09-01
FI83510B (fi)	1991-04-15
FI83510C (fi)	1991-07-25
KR860006457A (ko)	1986-09-11
DK81686D0 (da)	1986-02-21
US4789674A (en)	1988-12-06
PT82060A (de)	1986-03-01
DK81686A (da)	1986-08-23
NO168888B (no)	1992-01-06
EP0192255B1 (de)	1990-08-08

Legal Events

Date	Code	Title	Description
1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0084164B1 (de)	1987-01-28	Neue Derivate bicyclischer Aminosäuren, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung sowie neue bicyclische Aminosäuren als Zwischenstufen und Verfahren zu deren Herstellung
EP0136658A2 (de)	1985-04-10	1-Benzyl-aminoalkyl-pyrrolidinone und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel
DE69417235T2 (de)	1999-07-08	IMIDAZO[1,2-a]PYRAZIN-4-ON-DERIVATE ANTAGONISTEN DER AMPA UND NMDA REZEPTOREN
DD246994A5 (de)	1987-06-24	Verfahren zur herstellung neuer bi-2h-pyrroli(di)ndione
DE3002367A1 (de)	1980-07-24	2-substituierte trans-5-aryl-2,3,4,4a,5, 9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
DE2851028A1 (de)	1979-05-31	Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung
DD235256A5 (de)	1986-04-30	Verfahren zur herstellung neuer substituierter pyrrolidinone
CH641757A5 (en)	1984-03-15	O-Alkylated hydroxylamines and process for the preparation thereof
DE69527786T2 (de)	2003-04-10	Diaminomethyliden-derivate
WO1988001268A1 (fr)	1988-02-25	Derives d'imidazole
DE2747369C2 (da)	1987-11-12
DE19945594A1 (de)	2001-03-29	Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
DD151408A5 (de)	1981-10-21	Verfahren zur herstellung neuer pharmazeutisch aktiver phenylpiperazinderivate
DE3027106A1 (de)	1981-02-19	1-(4-aminobenzyl)-2,3-dioxopiperazin- derivate, saeureadditionssalze derselben und verfahren zur herstellung derselben
EP0266308B1 (de)	1991-07-24	Indolo-pyrazino-benzodiazepin-Derivate
EP0248414B1 (de)	1992-09-23	Aralkylimidazolderivate
EP0472166A1 (de)	1992-02-26	Tricyclische Pyridonderivate
EP0236263B1 (de)	1992-12-30	Substituierte Pyrrolidinone
EP0187619A2 (de)	1986-07-16	1,3-disubstituierte Tetrahydropyridine
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