CA1093078A - Derives de l'hydroxy-4 thiazolidinethione-2, leur preparation et les compositions qui les contiennent - Google Patents

Derives de l'hydroxy-4 thiazolidinethione-2, leur preparation et les compositions qui les contiennent

Info

Publication number: CA1093078A
Authority: CA; Canada
Prior art keywords: radical; alkyl; carbon atoms; phenyl; hydrogen atom
Prior art date: 1977-05-17
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

Application number

CA303,554A

Other languages

English (en)

French (fr)

Inventor

Jean-Dominique Bourzat

Andre Leger

Daniel Farge

Gerard Ponsinet

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.)

Rhone Poulenc Industries SA

Original Assignee

Rhone Poulenc Industries SA

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.)

1977-05-17

Filing date

1978-05-17

Publication date

1981-01-06

1977-05-17 Priority claimed from FR7715072A external-priority patent/FR2391212A1/fr

1978-04-25 Priority claimed from FR7812185A external-priority patent/FR2424269A2/fr

1978-05-17 Application filed by Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA

1981-01-06 Application granted granted Critical

1981-01-06 Publication of CA1093078A publication Critical patent/CA1093078A/fr

Status Expired legal-status Critical Current

Links

-1 alkylthio radical Chemical class 0.000 claims abstract description 175
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 64
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 53
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
125000005843 halogen group Chemical group 0.000 claims abstract description 26
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
AYLIEDQYYJIGDP-UHFFFAOYSA-N [C]1=CC=CS1 Chemical compound [C]1=CC=CS1 AYLIEDQYYJIGDP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 109
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000004429 atom Chemical group 0.000 claims description 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 20
239000012990 dithiocarbamate Substances 0.000 claims description 20
150000003254 radicals Chemical class 0.000 claims description 20
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 18
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 17
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 7
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
229910052751 metal Chemical class 0.000 claims description 2
239000002184 metal Chemical class 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
241000352333 Amegilla alpha Species 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
230000000507 anthelmentic effect Effects 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
229940124339 anthelmintic agent Drugs 0.000 abstract 1
239000000921 anthelmintic agent Substances 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 177
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 118
239000000047 product Substances 0.000 description 94
238000006243 chemical reaction Methods 0.000 description 71
238000001953 recrystallisation Methods 0.000 description 58
238000002844 melting Methods 0.000 description 52
230000008018 melting Effects 0.000 description 52
239000000243 solution Substances 0.000 description 51
239000000203 mixture Substances 0.000 description 47
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
TYYNJHRLNPGVET-UHFFFAOYSA-M C(N)([S-])=S.N1=C(C=CC=C1)[N+](CC)(CC)CC Chemical compound C(N)([S-])=S.N1=C(C=CC=C1)[N+](CC)(CC)CC TYYNJHRLNPGVET-UHFFFAOYSA-M 0.000 description 34
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 26
229910052753 mercury Inorganic materials 0.000 description 26
235000019271 petrolatum Nutrition 0.000 description 25
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 24
229960001701 chloroform Drugs 0.000 description 22
239000012153 distilled water Substances 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
238000001914 filtration Methods 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 11
239000013078 crystal Substances 0.000 description 11
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
239000000725 suspension Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
IHJWFFDXQRAIJG-UHFFFAOYSA-N pyridin-2-yl carbamodithioate Chemical compound C(N)(SC1=NC=CC=C1)=S IHJWFFDXQRAIJG-UHFFFAOYSA-N 0.000 description 7
WZQDRRLBAPWQMS-UHFFFAOYSA-N pyridin-2-ylcarbamodithioic acid Chemical compound SC(=S)NC1=CC=CC=N1 WZQDRRLBAPWQMS-UHFFFAOYSA-N 0.000 description 7
238000011282 treatment Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
101100029145 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) PE25 gene Proteins 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 5
IEMUUZKOMRJGHD-UHFFFAOYSA-N (5-chloropyridin-2-yl)carbamodithioic acid Chemical compound SC(=S)NC1=CC=C(Cl)C=N1 IEMUUZKOMRJGHD-UHFFFAOYSA-N 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000004061 bleaching Methods 0.000 description 4
QPHMMPRFMVERHL-UHFFFAOYSA-N carbamodithioic acid;n,n-diethylethanamine Chemical compound NC([S-])=S.CC[NH+](CC)CC QPHMMPRFMVERHL-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
ZERJVEQLQZTTQS-UHFFFAOYSA-N n,n-diethylethanamine;pyridin-2-ylcarbamodithioic acid Chemical compound CCN(CC)CC.SC(=S)NC1=CC=CC=N1 ZERJVEQLQZTTQS-UHFFFAOYSA-N 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
201000006353 Filariasis Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
ALHZEIINTQJLOT-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) acetate Chemical compound ClC(=O)C(C)OC(C)=O ALHZEIINTQJLOT-UHFFFAOYSA-N 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-UHFFFAOYSA-N 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000243780 Heligmosomoides polygyrus Species 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
241000243994 Litomosoides carinii Species 0.000 description 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
206010029148 Nephrolithiasis Diseases 0.000 description 2
241000144290 Sigmodon hispidus Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
239000008119 colloidal silica Substances 0.000 description 2
238000010908 decantation Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229940017219 methyl propionate Drugs 0.000 description 2
WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 2
239000012264 purified product Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
229940100445 wheat starch Drugs 0.000 description 2
DREUDSSRCCTWOW-UHFFFAOYSA-N (3,3-dimethyl-2-oxobutyl) carbamate Chemical compound CC(C)(C)C(=O)COC(N)=O DREUDSSRCCTWOW-UHFFFAOYSA-N 0.000 description 1
RCYPBSKFQORSRJ-UHFFFAOYSA-N (3-chloro-3-oxopropyl) acetate Chemical compound CC(=O)OCCC(Cl)=O RCYPBSKFQORSRJ-UHFFFAOYSA-N 0.000 description 1
WDNUUFGBCDAYFZ-UHFFFAOYSA-N (3-methoxyphenyl) carbamate Chemical compound COC1=CC=CC(OC(N)=O)=C1 WDNUUFGBCDAYFZ-UHFFFAOYSA-N 0.000 description 1
KHQRHTUBTJVFQE-UHFFFAOYSA-N (4-chloro-3-oxobutyl) acetate Chemical compound CC(=O)OCCC(=O)CCl KHQRHTUBTJVFQE-UHFFFAOYSA-N 0.000 description 1
FPNOQCDEHOMKJO-UHFFFAOYSA-N (4-methoxyphenyl) carbamodithioate Chemical compound C(N)(SC1=CC=C(C=C1)OC)=S FPNOQCDEHOMKJO-UHFFFAOYSA-N 0.000 description 1
OLHRHZHIACZQNE-UHFFFAOYSA-N 1-(2-chlorocyclopropyl)ethanone Chemical compound CC(=O)C1CC1Cl OLHRHZHIACZQNE-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
HKGZGKXNOQKDLD-UHFFFAOYSA-N 1-chloro-1-methylsulfanylpropan-2-one Chemical compound CSC(Cl)C(C)=O HKGZGKXNOQKDLD-UHFFFAOYSA-N 0.000 description 1
ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 1
KLTWFFAVGWWIKL-UHFFFAOYSA-N 2-bromo-2-methylpropanal Chemical compound CC(C)(Br)C=O KLTWFFAVGWWIKL-UHFFFAOYSA-N 0.000 description 1
QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 description 1
XHCWDDGZFBAXRT-UHFFFAOYSA-N 3-bromo-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)Br XHCWDDGZFBAXRT-UHFFFAOYSA-N 0.000 description 1
UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 1
XTIKIVWSYBVJJK-UHFFFAOYSA-N 5-bromo-4-oxopentanoic acid Chemical compound OC(=O)CCC(=O)CBr XTIKIVWSYBVJJK-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
241001465677 Ancylostomatoidea Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
BEGGKYJGVPGIES-UHFFFAOYSA-N C(N)(SC1=NC=CC=C1)=S.C(C)N(CC)CC Chemical compound C(N)(SC1=NC=CC=C1)=S.C(C)N(CC)CC BEGGKYJGVPGIES-UHFFFAOYSA-N 0.000 description 1
TWTCVSXJIJDGCZ-UHFFFAOYSA-M C(N)([O-])=O.N1=C(C=CC=C1)SS[N+](CC)(CC)CC Chemical compound C(N)([O-])=O.N1=C(C=CC=C1)SS[N+](CC)(CC)CC TWTCVSXJIJDGCZ-UHFFFAOYSA-M 0.000 description 1
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000283073 Equus caballus Species 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
206010016675 Filariasis lymphatic Diseases 0.000 description 1
241000581652 Hagenia abyssinica Species 0.000 description 1
208000006968 Helminthiasis Diseases 0.000 description 1
101000635799 Homo sapiens Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-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
208000037263 Lymphatic filariasis Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
101100136064 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) PE13 gene Proteins 0.000 description 1
241000243985 Onchocerca volvulus Species 0.000 description 1
102100032341 PCNA-interacting partner Human genes 0.000 description 1
101710196737 PCNA-interacting partner Proteins 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
241001494479 Pecora Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 1
IOEJYZSZYUROLN-UHFFFAOYSA-M Sodium diethyldithiocarbamate Chemical compound [Na+].CCN(CC)C([S-])=S IOEJYZSZYUROLN-UHFFFAOYSA-M 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
229930006000 Sucrose Natural products 0.000 description 1
241000534944 Thia Species 0.000 description 1
241000607143 Toxascaris leonina Species 0.000 description 1
241000244030 Toxocara canis Species 0.000 description 1
241000571986 Uncinaria Species 0.000 description 1
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
201000000751 autosomal recessive congenital ichthyosis Diseases 0.000 description 1
230000000721 bacterilogical effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
208000008576 dracunculiasis Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
208000005239 filarial elephantiasis Diseases 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
208000002042 onchocerciasis Diseases 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
MQDROCHXJOXBET-UHFFFAOYSA-N phenacyl carbamodithioate Chemical compound C(N)(SCC(=O)C1=CC=CC=C1)=S MQDROCHXJOXBET-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 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
230000002265 prevention Effects 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)

CA303,554A 1977-05-17 1978-05-17 Derives de l'hydroxy-4 thiazolidinethione-2, leur preparation et les compositions qui les contiennent Expired CA1093078A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR7715072		1977-05-17
FR7715072A FR2391212A1 (fr)	1977-05-17	1977-05-17	Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent
FR7812185A FR2424269A2 (fr)	1978-04-25	1978-04-25	Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent
FR7812185		1978-04-25

Publications (1)

Publication Number	Publication Date
CA1093078A true CA1093078A (fr)	1981-01-06

Family

ID=26220024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA303,554A Expired CA1093078A (fr)	1977-05-17	1978-05-17	Derives de l'hydroxy-4 thiazolidinethione-2, leur preparation et les compositions qui les contiennent

Country Status (17)

Country	Link
AT (1)	ATA356778A (de)
AU (1)	AU3613778A (de)
BE (1)	BE867128A (de)
CA (1)	CA1093078A (de)
DE (1)	DE2821555A1 (de)
DK (1)	DK214078A (de)
ES (1)	ES469883A1 (de)
GB (1)	GB1586917A (de)
IE (1)	IE46829B1 (de)
IL (1)	IL54735A0 (de)
IT (1)	IT1096219B (de)
LU (1)	LU79663A1 (de)
NZ (1)	NZ187290A (de)
OA (1)	OA05950A (de)
PT (1)	PT68047B (de)
SE (1)	SE7805589L (de)
SU (1)	SU852171A3 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2464954A2 (fr) *	1979-09-12	1981-03-20	Rhone Poulenc Ind	Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent

1978
- 1978-04-27 OA OA56480BISA patent/OA05950A/xx unknown
- 1978-05-16 IL IL54735A patent/IL54735A0/xx unknown
- 1978-05-16 DK DK214078A patent/DK214078A/da unknown
- 1978-05-16 AU AU36137/78A patent/AU3613778A/en active Pending
- 1978-05-16 SE SE7805589A patent/SE7805589L/xx unknown
- 1978-05-16 GB GB19926/78A patent/GB1586917A/en not_active Expired
- 1978-05-16 LU LU79663A patent/LU79663A1/xx unknown
- 1978-05-16 PT PT197868047A patent/PT68047B/pt unknown
- 1978-05-16 ES ES469883A patent/ES469883A1/es not_active Expired
- 1978-05-16 BE BE187744A patent/BE867128A/xx unknown
- 1978-05-16 IE IE983/78A patent/IE46829B1/en unknown
- 1978-05-16 IT IT23473/78A patent/IT1096219B/it active
- 1978-05-16 NZ NZ187290A patent/NZ187290A/xx unknown
- 1978-05-17 DE DE19782821555 patent/DE2821555A1/de not_active Withdrawn
- 1978-05-17 SU SU782615706A patent/SU852171A3/ru active
- 1978-05-17 CA CA303,554A patent/CA1093078A/fr not_active Expired
- 1978-05-17 AT AT356778A patent/ATA356778A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT68047B (fr)	1979-09-28
SU852171A3 (ru)	1981-07-30
OA05950A (fr)	1981-06-30
PT68047A (fr)	1978-06-01
IT1096219B (it)	1985-08-26
ES469883A1 (es)	1979-09-16
IE780983L (en)	1978-11-17
LU79663A1 (fr)	1979-02-02
ATA356778A (de)	1981-01-15
SE7805589L (sv)	1978-11-18
DE2821555A1 (de)	1978-11-30
GB1586917A (en)	1981-03-25
NZ187290A (en)	1981-04-24
IE46829B1 (en)	1983-10-05
IT7823473A0 (it)	1978-05-16
BE867128A (fr)	1978-11-16
IL54735A0 (en)	1978-07-31
AU3613778A (en)	1979-11-22
DK214078A (da)	1978-11-18

Legal Events

Date	Code	Title	Description
1998-01-06	MKEX	Expiry

Publication	Publication Date	Title
EP0228447A1 (de)	1987-07-15	Pestizide polyhaloalkenabkömmlinge
HUP0000449A2 (hu)	2001-02-28	N-szubsztituált dioxo-tiazolidil-benzamid-származékok és eljárás a vegyületek előállítására
KR0176243B1 (ko)	1999-03-20	염증성 장 질환 치료용 화합물
MC1389A1 (fr)	1982-04-27	Derives d'imidazole et procede pour leur preparation
CH655114A5 (fr)	1986-03-27	Derives de l'imidazotetrazinone, leur preparation et compositions pharmaceutiques les contenant.
FR2663332A1 (fr)	1991-12-20	Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus.
JPH09503792A (ja)	1997-04-15	新規なチアゾリジン−４−オン誘導体
AU2014348451A1 (en)	2016-06-16	Antiparasitic compounds
CA1093078A (fr)	1981-01-06	Derives de l'hydroxy-4 thiazolidinethione-2, leur preparation et les compositions qui les contiennent
EP0533827B1 (de)	1994-08-24	Oxazolederivate, ihre herstellung und diese enthaltende pharmazeutischen zubereitungen
HU203548B (en)	1991-08-28	Process for producing benzoxazine derivatives and pharmaceutical compositions containing them
CA1092120A (fr)	1980-12-23	Derives de l'hydroxy-4 thiazolidine thione-2, leur preparation et les compositions qui les contiennent
CH639388A5 (fr)	1983-11-15	Cephalosporines derivees de l'acide 7-/2-(2-amino 4-thiazolyl) 2-(carboxymethoxyimino) acetamido/ 3-substitue cephalosporanique, leurs procedes de preparation et medicaments les renfermant.
FR2583417A1 (fr)	1986-12-19	Acides 3-acylamino-2-oxo-1-azetidinesulfoniques a action therapeutique.
LU83713A1 (fr)	1982-05-07	Derives de la pyrimidine,leur procede de preparation et les compositions pharmaceutiques les contenant
CH633010A5 (fr)	1982-11-15	Derives de l'isoquinoleine, leur preparation et medicament qui les contient.
FR2576900A1 (fr)	1986-08-08	Derives de cyclohepto-imidazole 2-substitue, agents anti-ulcereux et procede pour leur preparation
CH642648A5 (fr)	1984-04-30	Derives de l'acide 2-(aminothiazolyl) 2-hydroxyimino acetique.
FR2612188A1 (fr)	1988-09-16	3-(2-haloalkyl)-1,4-oxathiines et 2-(2-haloalkyl)-1,4-dithiines, compositions pharmaceutiques les contenant et procede pour le traitement de la leucemie et des tumeurs les utilisant
FR2528844A1 (fr)	1983-12-23	Nouvelles thiazolyl-2 hydrazones, leur procede de preparation et leur application en therapeutique
DD297803A5 (de)	1992-01-23	Substituierte biphenyle
LU81892A1 (fr)	1980-06-05	Nouveaux dithiocarbamates, leur preparation et les medicaments qui les contiennent
LU84375A1 (fr)	1983-06-07	Nouveaux derives de n"-cyano n-oxydo-1 pyridinio-4 guanidine n'-substituee utiles comme medicaments antihypertenseurs et procede de leur preparation
CH643267A5 (fr)	1984-05-30	Oximes de l'acide 7-amino thiazolyl acetamido cephalosporanique, leurs procedes de preparation et les medicaments les renfermant.
LU81843A1 (fr)	1980-05-07	Nouveaux derives de l'hydroxy-4 thiazolidinethione-2 et les compositions pharmaceutiques qui les contiennent