PL59248B1

PL59248B1 -

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Publication number: PL59248B1
Authority: PL; Poland
Prior art keywords: formula; compound; thiadiazole; chloro; group
Prior art date: 1966-09-27

Application number

PL116637A

Other languages

English (en)

Polish (pl)

Original Assignee

Merck And Co

Filing date

1966-09-27

Publication date

1969-12-29

1966-09-27 Application filed by Merck And Co filed Critical Merck And Co

1969-12-29 Publication of PL59248B1 publication Critical patent/PL59248B1/pl

Links

150000001875 compounds Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
229910052783 alkali metal Chemical group 0.000 claims 2
150000001340 alkali metals Chemical group 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
239000002585 base Substances 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
230000020477 pH reduction Effects 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
-1 (N4-benzoylsulfanilamide) -1,2,5-thiadiazole Chemical compound 0.000 description 9
241000287828 Gallus gallus Species 0.000 description 7
235000013330 chicken meat Nutrition 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002699 waste material Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
239000003224 coccidiostatic agent Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
229940088594 vitamin Drugs 0.000 description 3
239000011782 vitamin Substances 0.000 description 3
235000013343 vitamin Nutrition 0.000 description 3
229930003231 vitamin Natural products 0.000 description 3
241000271566 Aves Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
208000003495 Coccidiosis Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
206010023076 Isosporiasis Diseases 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000005133 alkynyloxy group Chemical group 0.000 description 2
LCTXBFGHZLGBNU-UHFFFAOYSA-M amprolium Chemical compound [Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C LCTXBFGHZLGBNU-UHFFFAOYSA-M 0.000 description 2
229960003683 amprolium Drugs 0.000 description 2
YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 description 2
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229940124530 sulfonamide Drugs 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
DDQHLKLRCTUFRW-UHFFFAOYSA-N 3-but-2-ynoxy-4-chloro-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1OCC#CC DDQHLKLRCTUFRW-UHFFFAOYSA-N 0.000 description 1
LWJPYRFOSYZGKP-UHFFFAOYSA-N 3-chloro-4-prop-2-ynoxy-1,2,5-thiadiazole Chemical class ClC1=NSN=C1OCC#C LWJPYRFOSYZGKP-UHFFFAOYSA-N 0.000 description 1
WWCLVQQGRCZLLD-UHFFFAOYSA-N 4-amino-3-but-2-ynoxy-N-(1,2,5-thiadiazol-3-yl)benzenesulfonamide Chemical compound C(C#CC)OC=1C=C(S(=O)(=O)NC2=NSN=C2)C=CC1N WWCLVQQGRCZLLD-UHFFFAOYSA-N 0.000 description 1
FFZQQPOZDHKNAT-UHFFFAOYSA-N 4-amino-3-prop-2-ynoxy-N-(1,2,5-thiadiazol-3-yl)benzenesulfonamide Chemical compound C(C#C)OC=1C=C(S(=O)(=O)NC2=NSN=C2)C=CC1N FFZQQPOZDHKNAT-UHFFFAOYSA-N 0.000 description 1
XLYOGWXIKVUXCL-UHFFFAOYSA-N 4-bromobut-1-yne Chemical compound BrCCC#C XLYOGWXIKVUXCL-UHFFFAOYSA-N 0.000 description 1
BHBZGQBBRQJXCY-UHFFFAOYSA-N 4-chloro-1,2,5-thiadiazol-3-one Chemical compound OC1=NSN=C1Cl BHBZGQBBRQJXCY-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000019743 Choline chloride Nutrition 0.000 description 1
239000004470 DL Methionine Substances 0.000 description 1
241000499566 Eimeria brunetti Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
XIILFRYLHKYCPV-UHFFFAOYSA-N N-[4-[(4-but-2-ynoxy-1,2,5-thiadiazol-3-yl)sulfamoyl]phenyl]acetamide Chemical compound C(C#CC)OC1=NSN=C1NS(=O)(C1=CC=C(C=C1)NC(C)=O)=O XIILFRYLHKYCPV-UHFFFAOYSA-N 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000005905 alkynylation reaction Methods 0.000 description 1
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229960002079 calcium pantothenate Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
229960003178 choline chloride Drugs 0.000 description 1
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
230000002192 coccidiostatic effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
210000003736 gastrointestinal content Anatomy 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
235000006109 methionine Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
VGYAUYNBRQPION-UHFFFAOYSA-N n-(4-sulfamoylphenyl)benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)C1=CC=CC=C1 VGYAUYNBRQPION-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
210000003250 oocyst Anatomy 0.000 description 1
210000000287 oocyte Anatomy 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
235000015099 wheat brans Nutrition 0.000 description 1

PL116637A 1966-09-27 PL59248B1 (cs)