DD259866A5 - Verfahren zur herstellung von neuen thiozdiolin-4(s)-carbonsaeure-derivaten - Google Patents

Verfahren zur herstellung von neuen thiozdiolin-4(s)-carbonsaeure-derivaten Download PDF

Info

Publication number: DD259866A5
Authority: DD; German Democratic Republic
Prior art keywords: carboxylic acid; thiazolidine; dimethyl; hydrogen; optionally substituted
Prior art date: 1985-06-18

Application number

DD86291335A

Other languages

German (de)

English (en)

Inventor

Zoltan Gyoergydeak

Istvan Kovacs

Rezsoe Bognar

Geza Horvath

Terezia Mile

Nee Ham Judit Krusper

Ferenc Pusztai

Nee Huszka Mariann Fekete

Sandor Jancso

Janos Balint

Nee Borbely Ildiko Mihok

Attila Jakab

Andras Jenei

Bela Szende

Karoly Lapis

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.)

1985-06-18

Filing date

1986-06-16

Publication date

1988-09-07

1986-06-16 Application filed by ��@��k�� filed Critical ��@��k��

1988-09-07 Publication of DD259866A5 publication Critical patent/DD259866A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 73
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
-1 pyrryl Chemical group 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 11
125000002252 acyl group Chemical group 0.000 claims abstract description 10
229910052784 alkaline earth metal Chemical group 0.000 claims abstract description 7
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
150000001340 alkali metals Chemical group 0.000 claims abstract description 4
150000001342 alkaline earth metals Chemical group 0.000 claims abstract description 4
125000002541 furyl group Chemical group 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
125000001544 thienyl group Chemical group 0.000 claims abstract description 4
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 123
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
150000001299 aldehydes Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
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229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 2
239000003513 alkali Substances 0.000 claims 2
230000002378 acidificating effect Effects 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
125000001624 naphthyl group Chemical group 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
DZLNHFMRPBPULJ-GSVOUGTGSA-N D-thioproline Chemical class OC(=O)[C@H]1CSCN1 DZLNHFMRPBPULJ-GSVOUGTGSA-N 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 10
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
238000000921 elemental analysis Methods 0.000 description 31
239000000047 product Substances 0.000 description 28
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238000005160 1H NMR spectroscopy Methods 0.000 description 26
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000002244 precipitate Substances 0.000 description 19
239000000155 melt Substances 0.000 description 16
238000009835 boiling Methods 0.000 description 11
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XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000012043 crude product Substances 0.000 description 8
210000004185 liver Anatomy 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 5
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 5
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210000002966 serum Anatomy 0.000 description 5
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DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical class OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 5
DHVYVJWDRANRAT-RGURZIINSA-N (4s)-2-(4-fluorophenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=C(F)C=C1 DHVYVJWDRANRAT-RGURZIINSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 3
HRLVWWHWYVOSPG-RGURZIINSA-N (4s)-2-(2-hydroxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=CC=C1O HRLVWWHWYVOSPG-RGURZIINSA-N 0.000 description 3
FFAYNBRPBLHUJI-RGURZIINSA-N (4s)-2-(4-hydroxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=C(O)C=C1 FFAYNBRPBLHUJI-RGURZIINSA-N 0.000 description 3
206010067125 Liver injury Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
102000003929 Transaminases Human genes 0.000 description 3
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231100000234 hepatic damage Toxicity 0.000 description 3
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QVESCBQLLIMLIA-ROUUACIJSA-N (2s,4s)-3-[2-(4-chlorophenoxy)-2-methylpropanoyl]-5,5-dimethyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1([C@H](C(C)(C)S[C@H]1C=1C=CC=CC=1)C(O)=O)C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 QVESCBQLLIMLIA-ROUUACIJSA-N 0.000 description 2
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ABAPBQKHTSNFEE-RGURZIINSA-N (4s)-2-(2-carboxyphenyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=CC=C1C(O)=O ABAPBQKHTSNFEE-RGURZIINSA-N 0.000 description 2
IUDYPSDWEFGLQG-AKGZTFGVSA-N (4s)-2-(hydroxymethyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC1(C)SC(CO)N[C@H]1C(O)=O IUDYPSDWEFGLQG-AKGZTFGVSA-N 0.000 description 2
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XDUYZVGWRAFEKL-RGURZIINSA-N (4s)-5,5-dimethyl-2-(3-nitrophenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=CC([N+]([O-])=O)=C1 XDUYZVGWRAFEKL-RGURZIINSA-N 0.000 description 2
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LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
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231100000403 acute toxicity Toxicity 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
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DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
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OMRPJKRBLSMJKT-VUWPPUDQSA-N (4s)-5,5-dimethyl-2-(4-methylsulfanylphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound C1=CC(SC)=CC=C1C1SC(C)(C)[C@H](C(O)=O)N1 OMRPJKRBLSMJKT-VUWPPUDQSA-N 0.000 description 1
XUHPOBAOEPCZKK-JAMMHHFISA-N (4s)-5,5-dimethyl-2-(5-nitrofuran-2-yl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=C([N+]([O-])=O)O1 XUHPOBAOEPCZKK-JAMMHHFISA-N 0.000 description 1
CULRMXDEHPITBT-IENPIDJESA-N (4s)-5,5-dimethyl-2-pyridin-4-yl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)SC1C1=CC=NC=C1 CULRMXDEHPITBT-IENPIDJESA-N 0.000 description 1
YNGGRNROMJXLCP-UHFFFAOYSA-N 2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound O=CC1=CC=C2CCCC2=C1 YNGGRNROMJXLCP-UHFFFAOYSA-N 0.000 description 1
YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
RJJRNNMWUUYKJM-UHFFFAOYSA-N 2-(2-phenoxyacetyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound N1C(C(=O)O)CSC1C(=O)COC1=CC=CC=C1 RJJRNNMWUUYKJM-UHFFFAOYSA-N 0.000 description 1
KHBBQMHTRDEPCR-UHFFFAOYSA-N 2-(3-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(C=O)=C1 KHBBQMHTRDEPCR-UHFFFAOYSA-N 0.000 description 1
RNPHHSNQUNHCEW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RNPHHSNQUNHCEW-UHFFFAOYSA-N 0.000 description 1
ADDZHRRCUWNSCS-UHFFFAOYSA-N 2-Benzofurancarboxaldehyde Chemical compound C1=CC=C2OC(C=O)=CC2=C1 ADDZHRRCUWNSCS-UHFFFAOYSA-N 0.000 description 1
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
GEJJIOSHWKHWMK-UHFFFAOYSA-N 2-imino-3-methyl-5-[(5-nitrofuran-2-yl)methylidene]-1,3-thiazolidin-4-one Chemical class O=C1N(C)C(=N)SC1=CC1=CC=C([N+]([O-])=O)O1 GEJJIOSHWKHWMK-UHFFFAOYSA-N 0.000 description 1
JCAKCGQZNBEITC-UHFFFAOYSA-N 2-methyl-1,3-thiazolidine-2,4-dicarboxylic acid Chemical compound OC(=O)C1(C)NC(C(O)=O)CS1 JCAKCGQZNBEITC-UHFFFAOYSA-N 0.000 description 1
JUEZYTFQWZACEL-UHFFFAOYSA-N 2-nitrosoacetamide Chemical compound NC(=O)CN=O JUEZYTFQWZACEL-UHFFFAOYSA-N 0.000 description 1
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
HVXXOIGTXJOVON-UHFFFAOYSA-N 6-formyl-2,3-dimethoxybenzoic acid Chemical compound COC1=CC=C(C=O)C(C(O)=O)=C1OC HVXXOIGTXJOVON-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004201 L-cysteine Substances 0.000 description 1
235000013878 L-cysteine Nutrition 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
DZLNHFMRPBPULJ-VKHMYHEASA-N L-thioproline Chemical class OC(=O)[C@@H]1CSCN1 DZLNHFMRPBPULJ-VKHMYHEASA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
229920006222 acrylic ester polymer Polymers 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000000421 anti-necrotic effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
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239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
229960001305 cysteine hydrochloride Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003412 degenerative effect Effects 0.000 description 1
KPUNOVLMCQQCSK-UHFFFAOYSA-N diazomethane;ethoxyethane Chemical compound C=[N+]=[N-].CCOCC KPUNOVLMCQQCSK-UHFFFAOYSA-N 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
125000002228 disulfide group Chemical group 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000005228 liver tissue Anatomy 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
JTBUPXSNDNYBCX-IUCAKERBSA-N methyl (2s,4s)-5,5-dimethyl-2-(5-nitrofuran-2-yl)-1,3-thiazolidine-4-carboxylate Chemical compound S1C(C)(C)[C@H](C(=O)OC)N[C@@H]1C1=CC=C([N+]([O-])=O)O1 JTBUPXSNDNYBCX-IUCAKERBSA-N 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
FCHXJFJNDJXENQ-UHFFFAOYSA-N pyridoxal hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(C=O)=C1O FCHXJFJNDJXENQ-UHFFFAOYSA-N 0.000 description 1
RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
DAXBISKSIDBYEU-UHFFFAOYSA-N tidiacic Chemical compound OC(=O)C1CSC(C(O)=O)N1 DAXBISKSIDBYEU-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Gastroenterology & Hepatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

DD86291335A 1985-06-18 1986-06-16 Verfahren zur herstellung von neuen thiozdiolin-4(s)-carbonsaeure-derivaten DD259866A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU852388A HU200177B (en)	1985-06-18	1985-06-18	Process for producing thiazolidinecarboxylic acids and pharmaceutical compositions comprising such compounds

Publications (1)

Publication Number	Publication Date
DD259866A5 true DD259866A5 (de)	1988-09-07

Family

ID=10959103

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86291335A DD259866A5 (de)	1985-06-18	1986-06-16	Verfahren zur herstellung von neuen thiozdiolin-4(s)-carbonsaeure-derivaten

Country Status (21)

Country	Link
US (1)	US4775675A (da)
EP (1)	EP0206197A1 (da)
JP (1)	JPS6248672A (da)
KR (1)	KR870000312A (da)
CN (1)	CN86104085A (da)
AR (1)	AR241532A1 (da)
BG (1)	BG46457A3 (da)
DD (1)	DD259866A5 (da)
DK (1)	DK259386A (da)
ES (1)	ES8800919A1 (da)
FI (1)	FI862608A7 (da)
GB (1)	GB2177089B (da)
GR (1)	GR861517B (da)
HU (1)	HU200177B (da)
IL (1)	IL78942A0 (da)
IN (1)	IN165646B (da)
NO (1)	NO862408L (da)
PH (1)	PH22790A (da)
PL (2)	PL149453B1 (da)
PT (1)	PT82769B (da)
SU (2)	SU1443800A3 (da)

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CN1030415A (zh) *	1987-02-20	1989-01-18	山之内制药株式会社	饱和的杂环碳酰胺衍生物和它的制备方法
IT1223565B (it) *	1987-12-21	1990-09-19	Zambon Spa	Derivati dell'acido tiazolidin 4 carbossilico ad attivita' farmaceutica
JP2726999B2 (ja) *	1988-06-22	1998-03-11	日研化学株式会社	イミダゾ［２，１−ｂ］ベンゾチアゾール誘導体及び該化合物を有効成分とする抗潰瘍剤
GB9026114D0 (en) *	1990-11-30	1991-01-16	Norsk Hydro As	New compounds
ES2092539T3 (es) *	1991-01-10	1996-12-01	Transcend Therapeutics Inc	Uso de derivados de la tiazolidina-4-carboxilato para el tratamiento de enfermedades pulmonares.
US5747459A (en) *	1991-02-04	1998-05-05	Nestec, Ltd.	Method for insuring adequate intracellular glutathione in tissue
US5849686A (en) *	1991-03-11	1998-12-15	Creative Biomolecules, Inc.	Morphogen-induced liver regeneration
US5214062A (en) *	1992-04-08	1993-05-25	Clintec Nutrition Co.	Method and composition for treating immune disorders, inflammation and chronic infections
US5430045A (en) *	1992-04-23	1995-07-04	Free Radical Sciences, Inc.	Method of reducing or preventing bone marrow hypoplasia
US5447712A (en) *	1993-12-09	1995-09-05	Free Radical Sciences	Method of reducing cyclophosphamide induced hemorrhagic cystitis
US6083966A (en) *	1998-08-31	2000-07-04	University Of Florida	Thiazoline acid derivatives
EP1143951A3 (en) *	1998-09-21	2002-02-06	University Of Florida Research Foundation, Inc.	Antimalarial agents
AU5319700A (en)	1999-06-02	2000-12-18	S. Mbua Ngale Efange	Nicotine receptor ligands
CA2419845A1 (en)	1999-08-17	2002-02-22	Phyllis G. Paterson	Improved treatment for acute physical insult to the central nervous system
WO2005034949A1 (en) *	2003-09-09	2005-04-21	University Of Florida	Desferrithiocin derivatives and their use as iron chelators
DE102004021658A1 (de) *	2004-05-03	2005-12-01	Rudy Dr. Susilo	Kombinationspräparate enthaltend 2-Methylthiazolidin-2,4-dicarbonsäure
PL1866296T3 (pl)	2005-04-04	2017-05-31	University Of Florida Research Foundation, Inc.	Polieterowe analogi desferritiocyny
US8324397B2 (en)	2007-03-15	2012-12-04	University Of Florida Research Foundation, Inc.	Desferrithiocin polyether analogues
US20140343110A1 (en)	2011-12-16	2014-11-20	University Of Florida Research Foundation, Inc.	Uses of 4'-desferrithiocin analogs
PL2968346T3 (pl) *	2013-03-15	2024-11-04	Cancer Research Technologies Llc	Sposoby i kompozycje do modulacji cyklu gamma-glutamylowego
AU2014352780A1 (en)	2013-11-22	2016-06-09	University Of Florida Research Foundation, Inc.	Desferrithiocin analogs and uses thereof
WO2016176343A1 (en)	2015-04-27	2016-11-03	University Of Florida Research Foundation, Incorporated	Metabolically programmed metal chelators and uses thereof

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FR923562A (fr) *	1946-02-01	1947-07-10		Tube électronique
CH540234A (de) *	1968-09-06	1973-08-15	Degussa	Verfahren zur Herstellung von Penicillamin
ES381037A1 (es) *	1969-06-05	1973-07-01	Ferlux	Acido tiazolidin dicarboxilico-2,4 y sus derivados y proce-dimiento para su obtencion.
DE2116629A1 (en) *	1971-04-05	1972-10-19	Institutul de Biochimie, Bukarest	4-thiazolidinecarboxylic acid derivs - with in vivo thiol liberating activity
CA962269A (en) *	1971-05-05	1975-02-04	Uniroyal Ltd.	Thiazoles, and their use as insecticides
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DE2446100C3 (de) *	1974-09-26	1982-01-14	Ludwig Merckle Kg Chem. Pharm. Fabrik, 7902 Blaubeuren	Phenoxyalkancarbonsäureamide von Thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und Arzneimittel
GB1473752A (en) *	1975-04-09	1977-05-18	Rexolin Chem Ab	Composition of nitrofurans and its use in controlling formation of slime
FR2356423A1 (fr) *	1976-07-01	1978-01-27	Oeriu Simion	Derives de l'acide thiazolidinecarboxylique, leur preparation et leur application comme medicaments
DE3170401D1 (en) *	1980-07-28	1985-06-13	Ciba Geigy Ag	Triazoline derivatives and processes for their preparation

1985
- 1985-06-18 HU HU852388A patent/HU200177B/hu not_active IP Right Cessation
1986
- 1986-05-27 IL IL78942A patent/IL78942A0/xx unknown
- 1986-06-02 DK DK259386A patent/DK259386A/da not_active Application Discontinuation
- 1986-06-04 IN IN416/CAL/86A patent/IN165646B/en unknown
- 1986-06-05 PH PH33857A patent/PH22790A/en unknown
- 1986-06-11 GR GR861517A patent/GR861517B/el unknown
- 1986-06-13 US US06/874,111 patent/US4775675A/en not_active Expired - Fee Related
- 1986-06-16 PL PL1986273754A patent/PL149453B1/pl unknown
- 1986-06-16 PT PT82769A patent/PT82769B/pt not_active IP Right Cessation
- 1986-06-16 PL PL1986260106A patent/PL148541B1/pl unknown
- 1986-06-16 DD DD86291335A patent/DD259866A5/de not_active IP Right Cessation
- 1986-06-16 GB GB8614616A patent/GB2177089B/en not_active Expired
- 1986-06-17 JP JP61139386A patent/JPS6248672A/ja active Pending
- 1986-06-17 ES ES556135A patent/ES8800919A1/es not_active Expired
- 1986-06-17 NO NO862408A patent/NO862408L/no unknown
- 1986-06-18 AR AR86304306A patent/AR241532A1/es active
- 1986-06-18 CN CN198686104085A patent/CN86104085A/zh active Pending
- 1986-06-18 FI FI862608A patent/FI862608A7/fi not_active Application Discontinuation
- 1986-06-18 SU SU864027696A patent/SU1443800A3/ru active
- 1986-06-18 KR KR1019860004835A patent/KR870000312A/ko not_active Abandoned
- 1986-06-18 BG BG075405A patent/BG46457A3/xx unknown
- 1986-06-18 EP EP86108186A patent/EP0206197A1/de active Pending
- 1986-11-19 SU SU864028509A patent/SU1475905A1/ru active

Also Published As

Publication number	Publication date
SU1443800A3 (ru)	1988-12-07
DK259386D0 (da)	1986-06-02
US4775675A (en)	1988-10-04
GB2177089B (en)	1989-07-19
JPS6248672A (ja)	1987-03-03
FI862608A7 (fi)	1986-12-19
DK259386A (da)	1986-12-19
PT82769A (en)	1986-07-01
IN165646B (da)	1989-12-02
FI862608A0 (fi)	1986-06-18
ES8800919A1 (es)	1987-12-01
IL78942A0 (en)	1986-09-30
CN86104085A (zh)	1987-04-22
SU1475905A1 (ru)	1989-04-30
PL148541B1 (en)	1989-10-31
ES556135A0 (es)	1987-12-01
GB2177089A (en)	1987-01-14
GB8614616D0 (en)	1986-07-23
AR241532A1 (es)	1992-08-31
EP0206197A1 (de)	1986-12-30
BG46457A3 (bg)	1989-12-15
NO862408L (no)	1986-12-19
KR870000312A (ko)	1987-02-17
HUT41774A (en)	1987-05-28
HU200177B (en)	1990-04-28
PL149453B1 (en)	1990-02-28
NO862408D0 (no)	1986-06-17
GR861517B (en)	1986-10-10
PT82769B (pt)	1988-04-21
PH22790A (en)	1988-12-12

Legal Events

Date	Code	Title	Description
1997-01-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
US4775675A (en)	1988-10-04	Thiazolidinecarboxylic acid derivatives and treatment of liver diseases therewith
US4267174A (en)	1981-05-12	Immune-stimulating and cancerostatic 1-acyl-2-cyanoaziridines
CH621800A5 (da)	1981-02-27
DE2537070C2 (da)	1987-06-25
EP0041215A2 (de)	1981-12-09	Imidazoazolalkensäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
DD233847A5 (de)	1986-03-12	Verfahren zur herstellung von methylendiphosphon-derivaten mit antireuhmatischen eigenschaften
DE69018847T2 (de)	1995-08-24	Maleimidverbindungen und diese enthaltende Fungizide.
DE3739882A1 (de)	1989-06-08	Substituierte hydroxylamine
DE2201478A1 (de)	1972-08-17	Alpha-Acylamino-acrylsaeurealkylester,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Insektizide
DE2828578C2 (de)	1983-12-15	Thiazolidine, ihre Herstellung sowie Verwendung
DD291551A5 (de)	1991-07-04	Verfahren zur herstellung von substituierten hydroxamsaeurederivaten
EP0021207A1 (de)	1981-01-07	Alphacarbamoyl-pyrrolpropionitrile, Verfahren zu ihrer Herstellung, sowie pharmazeutische Präparate die diese Verbindungen enthalten
DE69402004T2 (de)	1997-06-19	Beta-mercapto-propanamidderivate verwendbar zur Behandlung kardiovaskularer Krankheiten oder Erkrankungen
CH621780A5 (da)	1981-02-27
CH633773A5 (en)	1982-12-31	N(2)-Arylsulphonyl-L-arginamides, process for their preparation and medicaments containing them
DE69623656T2 (de)	2003-05-22	Trans apovincaminsäure-esterderivate als arzneimittel
EP0371342B1 (de)	1994-12-14	2-Halogensubstituierte N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
FR2472563A1 (fr)	1981-07-03	3-acylamino-5 (pyridinyl)-2 (1 h)-pyridinones, leur preparation et leur utilisation comme agents cardiotoniques
DE3586150T2 (de)	1993-01-14	Amidderivate der 2-(p-aminobenzyl)-buttersaeure und ihrer ester mit blutfettgehaltsenkender wirkung.
DE2045098C3 (de)	1973-09-27	N-substituierte N-Thioformylhydroxylamine, Verfahren zu ihrer Herstellung und ihre Verwendung als antibacterielles oder fungicides Mittel
DE2038919A1 (de)	1971-02-18	Neue 3-Amino-delta?-pyrazolinderivate und Verfahren zur Herstellung derselben
DE2424740B2 (de)	1980-06-12	ThJophenderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0064026B1 (de)	1985-07-03	Neue dioxaheterocyclische Verbindungen, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
AT363085B (de)	1981-07-10	Verfahren zur herstellung von neuen substituierten thiazolidin-, thiazan- und verwandten carbonsaeuren und von deren salzen und isomeren
AT362353B (de)	1981-05-11	Verfahren zur herstellung von neuen in 4- -stellung substituierten 3-sulfamoyl-5-pyrrolyl - oder -5-pyrrolylalkylbenzoesaeuren und ihren salzen