IL37323A - Thiazolidine derivatives,process for their preparation and compositions containing the same - Google Patents

Thiazolidine derivatives,process for their preparation and compositions containing the same

Info

Publication number: IL37323A
Authority: IL; Israel
Prior art keywords: general formula; thiazolidine; radical; thiazolidin; derivatives
Prior art date: 1970-07-17

Application number

IL37323A

Other languages

English (en)

Other versions

IL37323A0 (en

Original Assignee

Rhone Poulenc 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.)

1970-07-17

Filing date

1971-07-16

Publication date

1973-10-25

1970-07-17 Priority claimed from FR7026473A external-priority patent/FR2097674A5/fr

1970-10-09 Priority claimed from FR7036617A external-priority patent/FR2108834A1/fr

1970-10-09 Priority claimed from FR7036618A external-priority patent/FR2109285A6/fr

1971-04-16 Priority claimed from FR7113534A external-priority patent/FR2135703A6/fr

1971-04-16 Priority claimed from FR7113535A external-priority patent/FR2133523A2/fr

1971-07-16 Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa

1971-10-20 Publication of IL37323A0 publication Critical patent/IL37323A0/xx

1973-10-25 Publication of IL37323A publication Critical patent/IL37323A/en

Links

150000003548 thiazolidines Chemical class 0.000 title claims description 39
239000000203 mixture Substances 0.000 title claims description 37
238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 11
-1 alkyl radical Chemical class 0.000 claims description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
239000003085 diluting agent Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
241001465754 Metazoa Species 0.000 claims description 9
230000000855 fungicidal effect Effects 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
239000003995 emulsifying agent Substances 0.000 claims description 6
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
150000001448 anilines Chemical class 0.000 claims description 4
241001494479 Pecora Species 0.000 claims description 3
239000002270 dispersing agent Substances 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
238000009736 wetting Methods 0.000 claims description 3
239000000080 wetting agent Substances 0.000 claims description 3
HBUDLYUIONCYJJ-UHFFFAOYSA-N 3-(2-nitrophenyl)-1,3-thiazolidine Chemical compound [O-][N+](=O)C1=CC=CC=C1N1CSCC1 HBUDLYUIONCYJJ-UHFFFAOYSA-N 0.000 claims description 2
241000283690 Bos taurus Species 0.000 claims description 2
241000283707 Capra Species 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
230000037396 body weight Effects 0.000 claims description 2
239000011248 coating agent Substances 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
241000947840 Alteromonadales Species 0.000 claims 1
208000006968 Helminthiasis Diseases 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
244000000013 helminth Species 0.000 claims 1
150000008040 ionic compounds Chemical class 0.000 claims 1
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000000243 solution Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
239000002244 precipitate Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
238000001035 drying Methods 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
230000000507 anthelmentic effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000417 fungicide Substances 0.000 description 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
238000005303 weighing Methods 0.000 description 3
QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical compound NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229940124339 anthelmintic agent Drugs 0.000 description 2
239000000921 anthelmintic agent Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000227 grinding Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
NGMFILCLOWBSCB-UHFFFAOYSA-N methyl n-[(2-acetamidophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(C)=O NGMFILCLOWBSCB-UHFFFAOYSA-N 0.000 description 2
BETSSSXVDWPLFQ-UHFFFAOYSA-N methyl n-[3-(2-aminophenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamate Chemical compound COC(=O)N=C1SCC(=O)N1C1=CC=CC=C1N BETSSSXVDWPLFQ-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
229940116357 potassium thiocyanate Drugs 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
241001120669 Colletotrichum lindemuthianum Species 0.000 description 1
206010013786 Dry skin Diseases 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
241000243974 Haemonchus contortus Species 0.000 description 1
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 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
241001337928 Podosphaera leucotricha Species 0.000 description 1
241000221300 Puccinia Species 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
241000122945 Trichostrongylus axei Species 0.000 description 1
241000243796 Trichostrongylus colubriformis Species 0.000 description 1
241000209140 Triticum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
240000000359 Triticum dicoccon Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000007799 cork Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
206010014881 enterobiasis Diseases 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
229920000940 maneb Polymers 0.000 description 1
LKSLIUUNCPSGAZ-UHFFFAOYSA-N methyl N-[3-(2-acetamidophenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamate Chemical compound COC(=O)N=C1SCC(N1C1=C(C=CC=C1)NC(C)=O)=O LKSLIUUNCPSGAZ-UHFFFAOYSA-N 0.000 description 1
JBPRIUQDAGQXFY-UHFFFAOYSA-N methyl N-[3-(2-formamidophenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamate Chemical compound COC(=O)N=C1SCC(N1C1=C(C=CC=C1)NC=O)=O JBPRIUQDAGQXFY-UHFFFAOYSA-N 0.000 description 1
LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
MPXAYYWSDIKNTP-UHFFFAOYSA-N n-(2-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1N MPXAYYWSDIKNTP-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
244000045947 parasite Species 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 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
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

IL37323A 1970-07-17 1971-07-16 Thiazolidine derivatives,process for their preparation and compositions containing the same IL37323A (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
FR7026473A FR2097674A5 (en)	1970-07-17	1970-07-17	Alkoxycarbonylimino-thiazolidines - with anthelmintic and antifungal activity
FR7036617A FR2108834A1 (en)	1970-10-09	1970-10-09	Alkoxycarbonylimino-thiazolidines - with anthelmintic and antifungal activity
FR7036618A FR2109285A6 (en)	1970-10-09	1970-10-09	Alkoxycarbonylimino-thiazolidines - with anthelmintic and antifungal activity
FR7113534A FR2135703A6 (en)	1971-04-16	1971-04-16	Alkoxycarbonylimino-thiazolidines - with anthelmintic and antifungal activity
FR7113535A FR2133523A2 (en)	1971-04-16	1971-04-16	Alkoxycarbonylimino-thiazolidines - with anthelmintic and antifungal activity

Publications (2)

Publication Number	Publication Date
IL37323A0 IL37323A0 (en)	1971-10-20
IL37323A true IL37323A (en)	1973-10-25

Family

ID=27515353

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL37323A IL37323A (en)	1970-07-17	1971-07-16	Thiazolidine derivatives,process for their preparation and compositions containing the same

Country Status (7)

Country	Link
AU (1)	AU451128B2 (fr)
BE (1)	BE770148A (fr)
DE (1)	DE2135736A1 (fr)
DK (1)	DK126332B (fr)
IL (1)	IL37323A (fr)
NL (1)	NL7109536A (fr)
SE (1)	SE365519B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20020064736A1 (en)	2000-09-27	2002-05-30	Fuji Photo Film Co., Ltd.	Dye-forming coupler, silver halide photographic light-sensitive material, and method for producing an azomethine dye

1971
- 1971-07-09 NL NL7109536A patent/NL7109536A/xx not_active Application Discontinuation
- 1971-07-16 BE BE770148A patent/BE770148A/fr unknown
- 1971-07-16 IL IL37323A patent/IL37323A/en unknown
- 1971-07-16 DK DK352671AA patent/DK126332B/da unknown
- 1971-07-16 DE DE19712135736 patent/DE2135736A1/de active Pending
- 1971-07-16 AU AU31338/71A patent/AU451128B2/en not_active Expired
- 1971-07-16 SE SE09263/71A patent/SE365519B/xx unknown

Also Published As

Publication number	Publication date
AU451128B2 (en)	1974-07-25
DE2135736A1 (de)	1972-01-20
SE365519B (fr)	1974-03-25
NL7109536A (fr)	1972-01-19
BE770148A (fr)	1972-01-17
AU3133871A (en)	1973-01-18
IL37323A0 (en)	1971-10-20
DK126332B (da)	1973-07-02

Publication	Publication Date	Title
DE69021502T2 (de)	1996-01-11	Benzimidazolderivate, Verfahren zu deren Herstellung und Anwendung.
US4022901A (en)	1977-05-10	3-Pyridinyl-5-isothiocyanophenyl oxadiazoles
FI56531C (fi)	1980-02-11	Foerfarande foer framstaellning av isotiocyanobenstiazoler med anthelmintisk och mikrobicid verkan
EP0138464A2 (fr)	1985-04-24	Dérivés de 2-amino-5-hydroxy-4-méthylpyrimidine
FI75821B (fi)	1988-04-29	Foerfarande foer framstaellning av terapeutiskt aktiva 2-guanidino-4-heteroaryltiazoler.
JPS6210990B2 (fr)	1987-03-10
DE2110396A1 (de)	1971-09-23	Substituierte Benzimidazole
US3759938A (en)	1973-09-18	Thiazolidine derivatives
US3686110A (en)	1972-08-22	1-oxybenzimidazoles
US5214053A (en)	1993-05-25	Thiourea derivatives and antimicrobial agent and antiulcer agent containing the same
US4076824A (en)	1978-02-28	Anthelmintic oxadiazolinone derivatives
DE68924221T2 (de)	1996-02-15	Imidazolderivate.
JPH0260671B2 (fr)	1990-12-17
SE444314B (sv)	1986-04-07	Forfarande for framstellning av bensimidazolderivat
IL37323A (en)	1973-10-25	Thiazolidine derivatives,process for their preparation and compositions containing the same
PL128998B1 (en)	1984-03-31	Process for preparing novel 2-amino-3-benzoylphenylacetamides and their derivatives
US4666932A (en)	1987-05-19	Formamidine derivatives and pharmaceutical use
DE69107874T2 (de)	1995-07-13	Imidazolderivate und diese Imidazolderivate als Wirkstoffe enthaltende Antiepileptika.
US3705174A (en)	1972-12-05	Polyhaloalkyl benzimidazoles
US3985782A (en)	1976-10-12	Phenylthiourea derivatives
NZ201696A (en)	1984-11-09	2-arylazo and 2-arylhydrazino-2-thiazoline derivatives and ecto-and endo-parasiticidal compositions
CS197255B2 (en)	1980-04-30	Method of producing basicly substituted 2-alkoxycarbonyl-amino-benzimidazol-5/6/-ylphenyl esters and ketones
US3980796A (en)	1976-09-14	Substituted 2-alkoxycarbonylamine-5-(6)-phenylmercapto-benzimidazoles
US3865948A (en)	1975-02-11	Treatment of helminth infections with substituted phenyl-thioureas
IE42443B1 (en)	1980-08-13	1-substituted-5-(substituted phenyl)-3-methyl-1,3,5-triazapenta-1,4-dienes and acaricidal and insecticidal compositions containing them