NO751618L - - Google Patents
Info
- Publication number
- NO751618L NO751618L NO75751618A NO751618A NO751618L NO 751618 L NO751618 L NO 751618L NO 75751618 A NO75751618 A NO 75751618A NO 751618 A NO751618 A NO 751618A NO 751618 L NO751618 L NO 751618L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- guanidine
- methoxycarbonyl
- phenyl
- phenoxy
- Prior art date
Links
- -1 amino-phenyl group Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical class NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 229940124339 anthelmintic agent Drugs 0.000 claims description 3
- 239000000921 anthelmintic agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002541 isothioureas Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000006968 Helminthiasis Diseases 0.000 claims 1
- 102000004316 Oxidoreductases Human genes 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 1
- 229960001413 acetanilide Drugs 0.000 description 206
- 238000002844 melting Methods 0.000 description 71
- 230000008018 melting Effects 0.000 description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 239000013543 active substance Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000004202 carbamide Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- MMZDUHCTUSJDHW-UHFFFAOYSA-N methyl n-[amino-(methoxycarbonylamino)methylidene]carbamate Chemical compound COC(=O)NC(=N)NC(=O)OC MMZDUHCTUSJDHW-UHFFFAOYSA-N 0.000 description 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- KWCPQPFOPUCWPH-UHFFFAOYSA-N 1-(oxomethylidene)guanidine Chemical compound NC(=N)N=C=O KWCPQPFOPUCWPH-UHFFFAOYSA-N 0.000 description 7
- 230000000507 anthelmentic effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000007903 gelatin capsule 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
- PAVDBWFMFPEZIE-UHFFFAOYSA-N methyl n-(diaminomethylidene)carbamate Chemical compound COC(=O)NC(N)=N PAVDBWFMFPEZIE-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- YACRZPZDVSEDGI-UHFFFAOYSA-N 2-amino-5-phenoxy-n-phenylbenzamide Chemical compound C1=C(C(=O)NC=2C=CC=CC=2)C(N)=CC=C1OC1=CC=CC=C1 YACRZPZDVSEDGI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000760148 Aspiculuris tetraptera Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001464384 Hymenolepis nana Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 241001126260 Nippostrongylus Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- GAYRVKNOXPSDIN-UHFFFAOYSA-N methyl n-(methoxycarbonylcarbamothioyl)carbamate Chemical compound COC(=O)NC(S)=NC(=O)OC GAYRVKNOXPSDIN-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- MHKWLKXZLMBCNW-UHFFFAOYSA-N n-(diaminomethylidene)propanamide Chemical compound CCC(=O)NC(N)=N MHKWLKXZLMBCNW-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- TWOSZEKTJKDQFU-UHFFFAOYSA-N 2-amino-4-(3-methylphenyl)sulfanyl-n-phenylbutanamide Chemical compound CC1=CC=CC(SCCC(N)C(=O)NC=2C=CC=CC=2)=C1 TWOSZEKTJKDQFU-UHFFFAOYSA-N 0.000 description 2
- VAVQSGUOABLSPJ-UHFFFAOYSA-N 2-amino-4-(4-methylphenyl)sulfanyl-n-phenylbutanamide Chemical compound C1=CC(C)=CC=C1SCCC(N)C(=O)NC1=CC=CC=C1 VAVQSGUOABLSPJ-UHFFFAOYSA-N 0.000 description 2
- BDBZOYHQIPSPGH-UHFFFAOYSA-N 2-amino-n,4-diphenylbutanethioamide Chemical compound C=1C=CC=CC=1NC(=S)C(N)CCC1=CC=CC=C1 BDBZOYHQIPSPGH-UHFFFAOYSA-N 0.000 description 2
- 241001465677 Ancylostomatoidea Species 0.000 description 2
- 241000244188 Ascaris suum Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 2
- 241000243974 Haemonchus contortus Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000243796 Trichostrongylus colubriformis Species 0.000 description 2
- 241000571980 Uncinaria stenocephala Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- AADPFSUWWWZNEP-UHFFFAOYSA-N methyl (ne)-n-[(2-benzamido-4-phenoxyanilino)-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(NC(NC(=O)OC)=NC(=O)OC)=CC=C1OC1=CC=CC=C1 AADPFSUWWWZNEP-UHFFFAOYSA-N 0.000 description 2
- NMFKBAYGDYCTSY-UHFFFAOYSA-N methyl (ne)-n-[[4-phenoxy-2-(propanoylamino)anilino]-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(=O)CC)C(NC(NC(=O)CC)=NC(=O)OC)=CC=C1OC1=CC=CC=C1 NMFKBAYGDYCTSY-UHFFFAOYSA-N 0.000 description 2
- KCISOGPFZLHQAK-UHFFFAOYSA-N methyl N-(N-propanoylcarbamimidoyl)carbamate Chemical compound COC(=O)NC(N)=NC(CC)=O KCISOGPFZLHQAK-UHFFFAOYSA-N 0.000 description 2
- ZEPJDKGDXJGZFB-UHFFFAOYSA-N methyl n-[(2-acetamido-4-phenoxyanilino)-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC)=NC(=O)OC)=CC=C1OC1=CC=CC=C1 ZEPJDKGDXJGZFB-UHFFFAOYSA-N 0.000 description 2
- DZUBGXXPPAMZOX-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-[5-phenoxy-2-(propanoylamino)anilino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CC)=CC=C1OC1=CC=CC=C1 DZUBGXXPPAMZOX-UHFFFAOYSA-N 0.000 description 2
- KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 description 2
- QPDZCCPAGVOHFD-UHFFFAOYSA-N methyl n-[[2-(butanoylamino)-4-phenoxyanilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCC)=CC(OC=2C=CC=CC=2)=C1 QPDZCCPAGVOHFD-UHFFFAOYSA-N 0.000 description 2
- YTSSLAJKHSPYMV-UHFFFAOYSA-N methyl n-[[2-(butanoylamino)-4-phenylsulfanylanilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCC)=CC(SC=2C=CC=CC=2)=C1 YTSSLAJKHSPYMV-UHFFFAOYSA-N 0.000 description 2
- SJRIXBPIMNYGAG-UHFFFAOYSA-N methyl n-[[4-(benzenesulfonyl)-2-(butanoylamino)anilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 SJRIXBPIMNYGAG-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- SDFATCIQJDMAOB-UHFFFAOYSA-N 1-(2-amino-4-phenoxyphenyl)-3-butylurea Chemical compound C1=C(N)C(NC(=O)NCCCC)=CC=C1OC1=CC=CC=C1 SDFATCIQJDMAOB-UHFFFAOYSA-N 0.000 description 1
- ZDVJRUVIHKJINQ-UHFFFAOYSA-N 1-(2-amino-4-phenoxyphenyl)-3-ethylurea Chemical compound C1=C(N)C(NC(=O)NCC)=CC=C1OC1=CC=CC=C1 ZDVJRUVIHKJINQ-UHFFFAOYSA-N 0.000 description 1
- NYWNWTMSDNJBCY-UHFFFAOYSA-N 1-(2-amino-4-phenoxyphenyl)-3-phenylurea Chemical compound C=1C=C(NC(=O)NC=2C=CC=CC=2)C(N)=CC=1OC1=CC=CC=C1 NYWNWTMSDNJBCY-UHFFFAOYSA-N 0.000 description 1
- UQLCCPOODHDZII-UHFFFAOYSA-N 1-(2-amino-4-phenylsulfanylphenyl)-3-butylurea Chemical compound C1=C(N)C(NC(=O)NCCCC)=CC=C1SC1=CC=CC=C1 UQLCCPOODHDZII-UHFFFAOYSA-N 0.000 description 1
- BCYWJGYDBVLVCP-UHFFFAOYSA-N 1-(2-amino-4-phenylsulfanylphenyl)-3-methylurea Chemical compound C1=C(N)C(NC(=O)NC)=CC=C1SC1=CC=CC=C1 BCYWJGYDBVLVCP-UHFFFAOYSA-N 0.000 description 1
- JIMPJIAIVRHPBO-UHFFFAOYSA-N 1-(2-amino-4-phenylsulfanylphenyl)-3-phenylurea Chemical compound C=1C=C(NC(=O)NC=2C=CC=CC=2)C(N)=CC=1SC1=CC=CC=C1 JIMPJIAIVRHPBO-UHFFFAOYSA-N 0.000 description 1
- VZULZRKJRKQRNC-UHFFFAOYSA-N 1-(2-amino-5-phenoxyphenyl)-3-benzylurea Chemical compound C1=C(NC(=O)NCC=2C=CC=CC=2)C(N)=CC=C1OC1=CC=CC=C1 VZULZRKJRKQRNC-UHFFFAOYSA-N 0.000 description 1
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- LUZLTMFBWXZGTH-UHFFFAOYSA-N methyl (ne)-n-[[4-(benzenesulfonyl)-2-[(2-methoxyacetyl)amino]anilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(N\C(NC(=O)OC)=N/C(=O)OC)C(NC(=O)COC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 LUZLTMFBWXZGTH-UHFFFAOYSA-N 0.000 description 1
- GQBUHHAWTRFYLM-UHFFFAOYSA-N methyl (ne)-n-[[4-(benzenesulfonyl)-2-[(2-phenoxyacetyl)amino]anilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound COC(=O)NC(=NC(=O)OC)NC1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1NC(=O)COC1=CC=CC=C1 GQBUHHAWTRFYLM-UHFFFAOYSA-N 0.000 description 1
- SDAVMKBXVZANDG-UHFFFAOYSA-N methyl (ne)-n-[[5-(benzenesulfinyl)-2-(butanoylamino)anilino]-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)CC)=NC(=O)OC)C(NC(=O)CCC)=CC=C1S(=O)C1=CC=CC=C1 SDAVMKBXVZANDG-UHFFFAOYSA-N 0.000 description 1
- MEMCSMLVKQCMJI-UHFFFAOYSA-N methyl (ne)-n-[[5-phenoxy-2-(propanoylamino)anilino]-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(=O)CC)C(NC(NC(=O)CC)=NC(=O)OC)=CC(OC=2C=CC=CC=2)=C1 MEMCSMLVKQCMJI-UHFFFAOYSA-N 0.000 description 1
- QRKSUNCJYQOLTR-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-4-phenoxyanilino)-(butanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CCC)=NC(=O)OC)=CC=C1OC1=CC=CC=C1 QRKSUNCJYQOLTR-UHFFFAOYSA-N 0.000 description 1
- CHZSPIGTALDQFI-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-4-phenoxyanilino)-(cyclohexanecarbonylamino)methylidene]carbamate Chemical compound C=1C=C(OC=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1CCCCC1 CHZSPIGTALDQFI-UHFFFAOYSA-N 0.000 description 1
- SWYLFFMHSFZFGH-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-4-phenoxyanilino)-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC)=CC=C1OC1=CC=CC=C1 SWYLFFMHSFZFGH-UHFFFAOYSA-N 0.000 description 1
- LNBGEGLLIPTHFK-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-4-phenoxyanilino)-[(2-phenoxyacetyl)amino]methylidene]carbamate Chemical compound C=1C=C(OC=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)COC1=CC=CC=C1 LNBGEGLLIPTHFK-UHFFFAOYSA-N 0.000 description 1
- DZSDMQIFDJUCRK-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-4-phenylsulfanylanilino)-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC)=CC=C1SC1=CC=CC=C1 DZSDMQIFDJUCRK-UHFFFAOYSA-N 0.000 description 1
- XGXBPPAIWMZJJC-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenoxyanilino)-(cyclohexanecarbonylamino)methylidene]carbamate Chemical compound C=1C(OC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1CCCCC1 XGXBPPAIWMZJJC-UHFFFAOYSA-N 0.000 description 1
- ZLANZJMUAAYDRB-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenoxyanilino)-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC)=CC(OC=2C=CC=CC=2)=C1 ZLANZJMUAAYDRB-UHFFFAOYSA-N 0.000 description 1
- LQKFCYZGHFMQOU-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenoxyanilino)-[(2-phenoxyacetyl)amino]methylidene]carbamate Chemical compound C=1C(OC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)COC1=CC=CC=C1 LQKFCYZGHFMQOU-UHFFFAOYSA-N 0.000 description 1
- YPXFKSHYSCWZBX-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenoxyanilino)-benzamidomethylidene]carbamate Chemical compound C=1C(OC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1=CC=CC=C1 YPXFKSHYSCWZBX-UHFFFAOYSA-N 0.000 description 1
- DGKPSSSQABHBEF-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenylsulfanylanilino)-(butanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CCC)=NC(=O)OC)=CC(SC=2C=CC=CC=2)=C1 DGKPSSSQABHBEF-UHFFFAOYSA-N 0.000 description 1
- RGQJHTJFAAECAC-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenylsulfanylanilino)-(cyclohexanecarbonylamino)methylidene]carbamate Chemical compound C=1C(SC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1CCCCC1 RGQJHTJFAAECAC-UHFFFAOYSA-N 0.000 description 1
- IBXOOQJNVBDIIZ-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenylsulfanylanilino)-[(2-phenoxyacetyl)amino]methylidene]carbamate Chemical compound C=1C(SC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)COC1=CC=CC=C1 IBXOOQJNVBDIIZ-UHFFFAOYSA-N 0.000 description 1
- WIXXADDIGZAUKJ-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenylsulfanylanilino)-[(2-phenylacetyl)amino]methylidene]carbamate Chemical compound C=1C(SC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)CC1=CC=CC=C1 WIXXADDIGZAUKJ-UHFFFAOYSA-N 0.000 description 1
- HLPBSLBTIGJZOZ-UHFFFAOYSA-N methyl (nz)-n-[(2-acetamido-5-phenylsulfanylanilino)-benzamidomethylidene]carbamate Chemical compound C=1C(SC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1=CC=CC=C1 HLPBSLBTIGJZOZ-UHFFFAOYSA-N 0.000 description 1
- QHBUZJWUZQGGQG-UHFFFAOYSA-N methyl (nz)-n-[[2-acetamido-4-(benzenesulfinyl)anilino]-[(2-phenylacetyl)amino]methylidene]carbamate Chemical compound C=1C=C(S(=O)C=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)CC1=CC=CC=C1 QHBUZJWUZQGGQG-UHFFFAOYSA-N 0.000 description 1
- BYSDIMATNSPSSX-UHFFFAOYSA-N methyl (nz)-n-[[2-acetamido-4-(benzenesulfonyl)anilino]-[(2-phenylacetyl)amino]methylidene]carbamate Chemical compound C=1C=C(S(=O)(=O)C=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)CC1=CC=CC=C1 BYSDIMATNSPSSX-UHFFFAOYSA-N 0.000 description 1
- KIINNSBQOFXCLR-UHFFFAOYSA-N methyl (nz)-n-[[2-acetamido-5-(benzenesulfinyl)anilino]-[(2-phenoxyacetyl)amino]methylidene]carbamate Chemical compound C=1C(S(=O)C=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)COC1=CC=CC=C1 KIINNSBQOFXCLR-UHFFFAOYSA-N 0.000 description 1
- RMBUZAYYYLSPKM-UHFFFAOYSA-N methyl (nz)-n-[[2-acetamido-5-(benzenesulfinyl)anilino]-[(2-phenylacetyl)amino]methylidene]carbamate Chemical compound C=1C(S(=O)C=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)CC1=CC=CC=C1 RMBUZAYYYLSPKM-UHFFFAOYSA-N 0.000 description 1
- PWEBVWIQDVUNPL-UHFFFAOYSA-N methyl (nz)-n-[[4-(benzenesulfinyl)-2-[(2-methoxyacetyl)amino]anilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(N\C(NC(=O)OC)=N/C(=O)OC)C(NC(=O)COC)=CC(S(=O)C=2C=CC=CC=2)=C1 PWEBVWIQDVUNPL-UHFFFAOYSA-N 0.000 description 1
- ONGWPKZZMBSZRK-UHFFFAOYSA-N methyl (nz)-n-[acetamido-(2-acetamido-4-phenoxyanilino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(C)=O)=NC(=O)OC)=CC=C1OC1=CC=CC=C1 ONGWPKZZMBSZRK-UHFFFAOYSA-N 0.000 description 1
- WSVMJXSKDHMEQS-UHFFFAOYSA-N methyl (nz)-n-[acetamido-(2-acetamido-4-phenylsulfanylanilino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(C)=O)=NC(=O)OC)=CC=C1SC1=CC=CC=C1 WSVMJXSKDHMEQS-UHFFFAOYSA-N 0.000 description 1
- QNOUGPQIJVTGNE-UHFFFAOYSA-N methyl (nz)-n-[acetamido-(2-acetamido-5-phenoxyanilino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(C)=O)=NC(=O)OC)=CC(OC=2C=CC=CC=2)=C1 QNOUGPQIJVTGNE-UHFFFAOYSA-N 0.000 description 1
- YVEGEORZIMDEIC-UHFFFAOYSA-N methyl (nz)-n-[acetamido-(2-acetamido-5-phenylsulfanylanilino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(C)=O)=NC(=O)OC)=CC(SC=2C=CC=CC=2)=C1 YVEGEORZIMDEIC-UHFFFAOYSA-N 0.000 description 1
- SVSYMMQRQHPSBN-UHFFFAOYSA-N methyl (nz)-n-[acetamido-[2-acetamido-4-(benzenesulfinyl)anilino]methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(C)=O)=NC(=O)OC)=CC=C1S(=O)C1=CC=CC=C1 SVSYMMQRQHPSBN-UHFFFAOYSA-N 0.000 description 1
- UGQFXTHAKDVZGX-UHFFFAOYSA-N methyl 4-(3-amino-4-anilino-4-oxobutoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCC(N)C(=O)NC1=CC=CC=C1 UGQFXTHAKDVZGX-UHFFFAOYSA-N 0.000 description 1
- BXPLDVWKTWUEJY-UHFFFAOYSA-N methyl 4-(3-amino-4-anilino-4-oxobutyl)sulfanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1SCCC(N)C(=O)NC1=CC=CC=C1 BXPLDVWKTWUEJY-UHFFFAOYSA-N 0.000 description 1
- SUCGTXUDGKOHHI-UHFFFAOYSA-N methyl 4-(3-amino-4-anilino-4-oxobutyl)sulfinylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1S(=O)CCC(N)C(=O)NC1=CC=CC=C1 SUCGTXUDGKOHHI-UHFFFAOYSA-N 0.000 description 1
- FGNZNPUBTDSTOS-UHFFFAOYSA-N methyl 4-(3-amino-4-anilino-4-oxobutyl)sulfonylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1S(=O)(=O)CCC(N)C(=O)NC1=CC=CC=C1 FGNZNPUBTDSTOS-UHFFFAOYSA-N 0.000 description 1
- WHHOQKDGIGVZRY-UHFFFAOYSA-N methyl N-[N'-(2-acetamido-4-phenoxyphenyl)-N-(2-phenylacetyl)carbamimidoyl]carbamate Chemical compound C=1C=C(OC=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)CC1=CC=CC=C1 WHHOQKDGIGVZRY-UHFFFAOYSA-N 0.000 description 1
- BHTXYDQMYDUDQA-UHFFFAOYSA-N methyl N-[N'-(2-acetamido-5-phenoxyphenyl)-N-(2-phenylacetyl)carbamimidoyl]carbamate Chemical compound C=1C(OC=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)CC1=CC=CC=C1 BHTXYDQMYDUDQA-UHFFFAOYSA-N 0.000 description 1
- RJJGUGQUUXDXNC-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-4-(benzenesulfinyl)phenyl]-N-methoxycarbonylcarbamimidoyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC)=NC(=O)OC)=CC=C1S(=O)C1=CC=CC=C1 RJJGUGQUUXDXNC-UHFFFAOYSA-N 0.000 description 1
- BHQRSVSCMXLQLL-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-4-(benzenesulfonyl)phenyl]-N-(2-phenoxyacetyl)carbamimidoyl]carbamate Chemical compound C=1C=C(S(=O)(=O)C=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)COC1=CC=CC=C1 BHQRSVSCMXLQLL-UHFFFAOYSA-N 0.000 description 1
- IANYYHVCMYRNNT-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-4-(benzenesulfonyl)phenyl]-N-(cyclohexanecarbonyl)carbamimidoyl]carbamate Chemical compound C=1C=C(S(=O)(=O)C=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1CCCCC1 IANYYHVCMYRNNT-UHFFFAOYSA-N 0.000 description 1
- OUKRDBUJPSOIMP-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-4-(benzenesulfonyl)phenyl]-N-benzoylcarbamimidoyl]carbamate Chemical compound C=1C=C(S(=O)(=O)C=2C=CC=CC=2)C=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1=CC=CC=C1 OUKRDBUJPSOIMP-UHFFFAOYSA-N 0.000 description 1
- ZIMXXLDCKJJZFS-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-4-(benzenesulfonyl)phenyl]-N-propanoylcarbamimidoyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC)=CC=C1S(=O)(=O)C1=CC=CC=C1 ZIMXXLDCKJJZFS-UHFFFAOYSA-N 0.000 description 1
- ZBCTVCVDZDQKPU-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-5-(benzenesulfinyl)phenyl]-N-benzoylcarbamimidoyl]carbamate Chemical compound C=1C(S(=O)C=2C=CC=CC=2)=CC=C(NC(C)=O)C=1NC(=NC(=O)OC)NC(=O)C1=CC=CC=C1 ZBCTVCVDZDQKPU-UHFFFAOYSA-N 0.000 description 1
- ZGEMYWZXAUTDKA-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-5-(benzenesulfinyl)phenyl]-N-butanoylcarbamimidoyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CCC)=NC(=O)OC)=CC(S(=O)C=2C=CC=CC=2)=C1 ZGEMYWZXAUTDKA-UHFFFAOYSA-N 0.000 description 1
- BIXQALWAYBWUKY-UHFFFAOYSA-N methyl N-[N'-[2-acetamido-5-(benzenesulfonyl)phenyl]-N-acetylcarbamimidoyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(C)=O)=NC(=O)OC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 BIXQALWAYBWUKY-UHFFFAOYSA-N 0.000 description 1
- PBDKIOQUVGOHIH-UHFFFAOYSA-N methyl N-[N'-[2-benzamido-5-(benzenesulfonyl)phenyl]-N-propanoylcarbamimidoyl]carbamate Chemical compound CCC(=O)NC(=NC(=O)OC)NC1=CC(S(=O)(=O)C=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1 PBDKIOQUVGOHIH-UHFFFAOYSA-N 0.000 description 1
- KZZALAJYICLRFH-UHFFFAOYSA-N methyl N-[N'-[4-(benzenesulfonyl)-2-[(2-phenylacetyl)amino]phenyl]-N-methoxycarbonylcarbamimidoyl]carbamate Chemical compound COC(=O)NC(=NC(=O)OC)NC1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1NC(=O)CC1=CC=CC=C1 KZZALAJYICLRFH-UHFFFAOYSA-N 0.000 description 1
- DBTGWGCIGBXSPR-UHFFFAOYSA-N methyl N-[N'-[4-phenylsulfanyl-2-(propanoylamino)phenyl]-N-propanoylcarbamimidoyl]carbamate Chemical compound C1=C(NC(=O)CC)C(NC(NC(=O)CC)=NC(=O)OC)=CC=C1SC1=CC=CC=C1 DBTGWGCIGBXSPR-UHFFFAOYSA-N 0.000 description 1
- IHSVBHRRJJJNBA-UHFFFAOYSA-N methyl N-[N'-[5-(benzenesulfinyl)-2-(pentanoylamino)phenyl]-N-methoxycarbonylcarbamimidoyl]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCCC)=CC=C1S(=O)C1=CC=CC=C1 IHSVBHRRJJJNBA-UHFFFAOYSA-N 0.000 description 1
- FSSDUBONZTUEQD-UHFFFAOYSA-N methyl N-[N'-[5-(benzenesulfonyl)-2-(hexanoylamino)phenyl]-N-methoxycarbonylcarbamimidoyl]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCCCC)=CC=C1S(=O)(=O)C1=CC=CC=C1 FSSDUBONZTUEQD-UHFFFAOYSA-N 0.000 description 1
- CUOIQZAKPJAUJH-UHFFFAOYSA-N methyl N-[N'-[5-(benzenesulfonyl)-2-(propanoylamino)phenyl]-N-methoxycarbonylcarbamimidoyl]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CC)=CC=C1S(=O)(=O)C1=CC=CC=C1 CUOIQZAKPJAUJH-UHFFFAOYSA-N 0.000 description 1
- VZBQHGKUJDJXPC-UHFFFAOYSA-N methyl N-[N'-[5-phenylsulfanyl-2-(propanoylamino)phenyl]-N-propanoylcarbamimidoyl]carbamate Chemical compound C1=C(NC(=O)CC)C(NC(NC(=O)CC)=NC(=O)OC)=CC(SC=2C=CC=CC=2)=C1 VZBQHGKUJDJXPC-UHFFFAOYSA-N 0.000 description 1
- MTQNTAKSEURDBT-UHFFFAOYSA-N methyl N-[N-methoxycarbonyl-N'-[2-[(2-phenylacetyl)amino]-4-phenylsulfanylphenyl]carbamimidoyl]carbamate Chemical compound C1=C(NC(=O)CC=2C=CC=CC=2)C(NC(NC(=O)OC)=NC(=O)OC)=CC=C1SC1=CC=CC=C1 MTQNTAKSEURDBT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- MMBXQPGOPHKATO-UHFFFAOYSA-N methyl n-[(ethoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound CCOC(=O)NC(SC)=NC(=O)OC MMBXQPGOPHKATO-UHFFFAOYSA-N 0.000 description 1
- DJJYXCILDJTCRG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-[2-(pentanoylamino)-4-phenoxyanilino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCCC)=CC(OC=2C=CC=CC=2)=C1 DJJYXCILDJTCRG-UHFFFAOYSA-N 0.000 description 1
- RHNLKIHXNRFZPC-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-[2-(pentanoylamino)-5-phenoxyanilino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCCC)=CC=C1OC1=CC=CC=C1 RHNLKIHXNRFZPC-UHFFFAOYSA-N 0.000 description 1
- XBVLHOZYRXOTQT-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-[4-phenylsulfanyl-2-(propanoylamino)anilino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CC)=CC(SC=2C=CC=CC=2)=C1 XBVLHOZYRXOTQT-UHFFFAOYSA-N 0.000 description 1
- XHUISROJZTTZKF-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-[5-phenylsulfanyl-2-(propanoylamino)anilino]methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CC)=CC=C1SC1=CC=CC=C1 XHUISROJZTTZKF-UHFFFAOYSA-N 0.000 description 1
- XUOSGEGGDXGPIG-UHFFFAOYSA-N methyl n-[4-(3-amino-4-anilino-4-oxobutoxy)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1OCCC(N)C(=O)NC1=CC=CC=C1 XUOSGEGGDXGPIG-UHFFFAOYSA-N 0.000 description 1
- PUSBKEIFGQISKY-UHFFFAOYSA-N methyl n-[4-(3-amino-4-anilino-4-oxobutyl)sulfonylphenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1S(=O)(=O)CCC(N)C(=O)NC1=CC=CC=C1 PUSBKEIFGQISKY-UHFFFAOYSA-N 0.000 description 1
- YBLJYPXSWNYNFY-UHFFFAOYSA-N methyl n-[4-(benzenesulfinyl)-2-(butanoylamino)phenyl]-n-[(e)-n'-methoxycarbonylcarbamimidoyl]carbamate Chemical compound C1=C(N(C(=N)NC(=O)OC)C(=O)OC)C(NC(=O)CCC)=CC(S(=O)C=2C=CC=CC=2)=C1 YBLJYPXSWNYNFY-UHFFFAOYSA-N 0.000 description 1
- NRLLBCIDUBUQTE-UHFFFAOYSA-N methyl n-[[(2-ethoxyacetyl)amino]-methylsulfanylmethylidene]carbamate Chemical compound CCOCC(=O)N=C(SC)NC(=O)OC NRLLBCIDUBUQTE-UHFFFAOYSA-N 0.000 description 1
- COVVCYQCAKAGLA-UHFFFAOYSA-N methyl n-[[2-(butanoylamino)-5-phenylsulfanylanilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCC)=CC=C1SC1=CC=CC=C1 COVVCYQCAKAGLA-UHFFFAOYSA-N 0.000 description 1
- MOSADQUHMXIIBE-UHFFFAOYSA-N methyl n-[[2-(hexanoylamino)-4-phenylsulfanylanilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCCCC)=CC(SC=2C=CC=CC=2)=C1 MOSADQUHMXIIBE-UHFFFAOYSA-N 0.000 description 1
- KDKNYHMQAQLFHF-UHFFFAOYSA-N methyl n-[[5-(benzenesulfinyl)-2-(butanoylamino)anilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CCC)=CC=C1S(=O)C1=CC=CC=C1 KDKNYHMQAQLFHF-UHFFFAOYSA-N 0.000 description 1
- VAJIYEKUMMTJIM-UHFFFAOYSA-N methyl n-[[5-(benzenesulfinyl)-2-(propanoylamino)anilino]-(methoxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC)=NC(=O)OC)C(NC(=O)CC)=CC=C1S(=O)C1=CC=CC=C1 VAJIYEKUMMTJIM-UHFFFAOYSA-N 0.000 description 1
- XQLWPOXMLSCQLM-UHFFFAOYSA-N methyl n-[methylsulfanyl-(propanoylamino)methylidene]carbamate Chemical compound CCC(=O)N=C(SC)NC(=O)OC XQLWPOXMLSCQLM-UHFFFAOYSA-N 0.000 description 1
- BMIDSMRAJCMLNC-UHFFFAOYSA-N methyl n-carbamothioyl-n-methoxycarbonylcarbamate Chemical compound COC(=O)N(C(S)=N)C(=O)OC BMIDSMRAJCMLNC-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 description 1
- OZRCULZKJLSCQW-UHFFFAOYSA-N n-(diaminomethylidene)butanamide Chemical compound CCCC(=O)N=C(N)N OZRCULZKJLSCQW-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- XAUGWFWQVYXATQ-UHFFFAOYSA-N n-phenylbenzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=CC=CC=C1 XAUGWFWQVYXATQ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YXPIYBHVIOGILV-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-4-phenoxyanilino)-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)=CC=C1OC1=CC=CC=C1 YXPIYBHVIOGILV-UHFFFAOYSA-N 0.000 description 1
- OCLQWUYQEDVCAC-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-4-phenoxyanilino)-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC(C)C)=CC=C1OC1=CC=CC=C1 OCLQWUYQEDVCAC-UHFFFAOYSA-N 0.000 description 1
- HAGWFWGCMCLBDK-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-4-phenylsulfanylanilino)-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)=CC=C1SC1=CC=CC=C1 HAGWFWGCMCLBDK-UHFFFAOYSA-N 0.000 description 1
- NMHZKFKQMTYYRC-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-4-phenylsulfanylanilino)-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC(C)C)=CC=C1SC1=CC=CC=C1 NMHZKFKQMTYYRC-UHFFFAOYSA-N 0.000 description 1
- DXKOOXUXMWVLNE-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-5-phenoxyanilino)-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)=CC(OC=2C=CC=CC=2)=C1 DXKOOXUXMWVLNE-UHFFFAOYSA-N 0.000 description 1
- MKHFENCBQAKSGX-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-5-phenoxyanilino)-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC(C)C)=CC(OC=2C=CC=CC=2)=C1 MKHFENCBQAKSGX-UHFFFAOYSA-N 0.000 description 1
- OFEZYHROZYTSAV-UHFFFAOYSA-N propan-2-yl (ne)-n-[(2-acetamido-5-phenylsulfanylanilino)-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)=CC(SC=2C=CC=CC=2)=C1 OFEZYHROZYTSAV-UHFFFAOYSA-N 0.000 description 1
- MKTODDOSYGLZCF-UHFFFAOYSA-N propan-2-yl (ne)-n-[[2-acetamido-4-(benzenesulfinyl)anilino]-(propanoylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)CC)=NC(=O)OC(C)C)=CC=C1S(=O)C1=CC=CC=C1 MKTODDOSYGLZCF-UHFFFAOYSA-N 0.000 description 1
- RJRJCRDKZQMVEF-UHFFFAOYSA-N propan-2-yl (ne)-n-[[2-acetamido-5-(benzenesulfinyl)anilino]-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)=CC(S(=O)C=2C=CC=CC=2)=C1 RJRJCRDKZQMVEF-UHFFFAOYSA-N 0.000 description 1
- MCYQKEHFMFKRRC-UHFFFAOYSA-N propan-2-yl (ne)-n-[[2-acetamido-5-(benzenesulfonyl)anilino]-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 MCYQKEHFMFKRRC-UHFFFAOYSA-N 0.000 description 1
- XKBSKWWBLQEEJJ-UHFFFAOYSA-N propan-2-yl (ne)-n-[[4-phenoxy-2-(propanoylamino)anilino]-(propan-2-yloxycarbonylamino)methylidene]carbamate Chemical compound C1=C(NC(NC(=O)OC(C)C)=NC(=O)OC(C)C)C(NC(=O)CC)=CC(OC=2C=CC=CC=2)=C1 XKBSKWWBLQEEJJ-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D45/00—Separating dispersed particles from gases or vapours by gravity, inertia, or centrifugal forces
- B01D45/04—Separating dispersed particles from gases or vapours by gravity, inertia, or centrifugal forces by utilising inertia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D47/00—Separating dispersed particles from gases, air or vapours by liquid as separating agent
- B01D47/06—Spray cleaning
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742423679 DE2423679C3 (de) | 1974-05-15 | Substituierte Phenylguanidine, ein Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751618L true NO751618L (fr) | 1975-11-18 |
Family
ID=5915671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO75751618A NO751618L (fr) | 1974-05-15 | 1975-05-06 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3993682A (fr) |
| JP (3) | JPS5833842B2 (fr) |
| AR (2) | AR208696A1 (fr) |
| AT (2) | AT348540B (fr) |
| BE (1) | BE829052A (fr) |
| BR (1) | BR7503008A (fr) |
| CA (1) | CA1071649A (fr) |
| CH (1) | CH612925A5 (fr) |
| DD (1) | DD119224A5 (fr) |
| DK (1) | DK134282C (fr) |
| EG (1) | EG11983A (fr) |
| ES (1) | ES437692A1 (fr) |
| FI (1) | FI63020C (fr) |
| FR (1) | FR2270861B1 (fr) |
| GB (1) | GB1466839A (fr) |
| HK (1) | HK1680A (fr) |
| HU (1) | HU174257B (fr) |
| IE (1) | IE41058B1 (fr) |
| IL (1) | IL47269A (fr) |
| IN (1) | IN142490B (fr) |
| IT (1) | IT1047751B (fr) |
| KE (1) | KE2773A (fr) |
| LU (1) | LU72462A1 (fr) |
| MY (1) | MY8000187A (fr) |
| NL (1) | NL186811C (fr) |
| NO (1) | NO751618L (fr) |
| PH (1) | PH17307A (fr) |
| PL (2) | PL99857B1 (fr) |
| SE (1) | SE430887B (fr) |
| SU (1) | SU662006A3 (fr) |
| ZA (1) | ZA753122B (fr) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2609994A1 (de) * | 1976-03-10 | 1977-09-15 | Bayer Ag | 2-formylamino-phenylguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2651467A1 (de) * | 1976-11-11 | 1978-05-18 | Bayer Ag | Substituierte o-phenylendiaminderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2653766A1 (de) * | 1976-11-26 | 1978-06-01 | Bayer Ag | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4293569A (en) * | 1978-05-12 | 1981-10-06 | E. R. Squibb & Sons, Inc. | Substituted phenylguanindines and method |
| DE2841882A1 (de) * | 1978-09-26 | 1980-04-03 | Bayer Ag | Endoparasitizide pasten fuer pferde |
| US4217358A (en) * | 1979-04-18 | 1980-08-12 | E. R. Squibb & Sons, Inc. | Substituted phenylguanidines and method |
| US4328241A (en) * | 1981-07-20 | 1982-05-04 | E. R. Squibb & Sons, Inc. | Substituted phenylguanidines and method |
| JPS5987303A (ja) * | 1982-11-10 | 1984-05-19 | Toyo Seikan Kaisha Ltd | フランジ曲り部の検出装置 |
| JPH0538773Y2 (fr) * | 1985-05-22 | 1993-09-30 | ||
| DE3705227A1 (de) * | 1987-02-19 | 1988-09-01 | Bayer Ag | Anthelminthische wirkstoffkombinationen |
| EP0333863A4 (en) * | 1987-08-22 | 1991-07-31 | Shusuke Yano | Far infrared ray generator |
| US6593466B1 (en) | 1999-07-07 | 2003-07-15 | Isis Pharmaceuticals, Inc. | Guanidinium functionalized nucleotides and precursors thereof |
| US20060205681A1 (en) * | 2002-06-21 | 2006-09-14 | Maryam Moaddeb | Homogenous paste formulations |
| US7001889B2 (en) * | 2002-06-21 | 2006-02-21 | Merial Limited | Anthelmintic oral homogeneous veterinary pastes |
| US7396819B2 (en) | 2003-08-08 | 2008-07-08 | Virbac Corporation | Anthelmintic formulations |
| WO2005094210A2 (fr) * | 2004-03-12 | 2005-10-13 | The Hartz Mountain Corporation | Formulations anthelmintiques a actions multiples |
| PT1913009E (pt) * | 2005-07-28 | 2010-06-25 | Intervet Int Bv | Novos (tio)carbamatos de benzimidazole com actividade antiparasitária e sua síntese |
| US20080027011A1 (en) * | 2005-12-20 | 2008-01-31 | Hassan Nached | Homogeneous paste and gel formulations |
| AU2007345301A1 (en) * | 2006-06-12 | 2008-07-31 | Smith And Nephew Inc | Systems, methods and devices for tibial resection |
| KR101403135B1 (ko) | 2006-06-14 | 2014-06-19 | 인터벳 인터내셔널 비.브이. | 벤지미다졸 카르바메이트 및 폴리솔베이트를 포함하는 현탁물 |
| CN113773221B (zh) * | 2021-10-08 | 2023-09-29 | 湖北工业大学 | 一种对苯醌类化合物及其制备方法 |
| CN117466786A (zh) * | 2023-12-25 | 2024-01-30 | 湖南一格制药有限公司 | 盐酸戊乙奎醚杂质及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758608A (fr) * | 1969-11-06 | 1971-05-06 | Bayer Ag | Nouvelles ureidophenylguanidines leur procede de preparation etleur application comme fongicides |
-
1975
- 1975-04-16 IN IN765/CAL/75A patent/IN142490B/en unknown
- 1975-04-28 US US05/572,224 patent/US3993682A/en not_active Expired - Lifetime
- 1975-05-06 NO NO75751618A patent/NO751618L/no unknown
- 1975-05-06 PH PH17141A patent/PH17307A/en unknown
- 1975-05-07 CA CA226,458A patent/CA1071649A/fr not_active Expired
- 1975-05-10 EG EG279/75A patent/EG11983A/xx active
- 1975-05-11 SU SU752132095A patent/SU662006A3/ru active
- 1975-05-12 IL IL7547269A patent/IL47269A/xx unknown
- 1975-05-13 IT IT49558/75A patent/IT1047751B/it active Protection Beyond IP Right Term
- 1975-05-13 AT AT365475A patent/AT348540B/de not_active IP Right Cessation
- 1975-05-13 PL PL1975180339A patent/PL99857B1/pl unknown
- 1975-05-13 FI FI751399A patent/FI63020C/fi not_active IP Right Cessation
- 1975-05-13 JP JP50055545A patent/JPS5833842B2/ja not_active Expired
- 1975-05-13 PL PL1975193602A patent/PL98595B1/pl unknown
- 1975-05-13 DD DD185999A patent/DD119224A5/xx unknown
- 1975-05-13 CH CH615375A patent/CH612925A5/xx not_active IP Right Cessation
- 1975-05-13 LU LU72462A patent/LU72462A1/xx unknown
- 1975-05-13 NL NLAANVRAGE7505603,A patent/NL186811C/xx not_active IP Right Cessation
- 1975-05-13 JP JP50055544A patent/JPS5915904B2/ja not_active Expired
- 1975-05-14 ZA ZA00753122A patent/ZA753122B/xx unknown
- 1975-05-14 SE SE7505527A patent/SE430887B/xx not_active IP Right Cessation
- 1975-05-14 DK DK211775A patent/DK134282C/da active
- 1975-05-14 BE BE156330A patent/BE829052A/fr not_active IP Right Cessation
- 1975-05-14 GB GB2036275A patent/GB1466839A/en not_active Expired
- 1975-05-14 IE IE1078/75A patent/IE41058B1/xx unknown
- 1975-05-14 ES ES437692A patent/ES437692A1/es not_active Expired
- 1975-05-15 AR AR258791A patent/AR208696A1/es active
- 1975-05-15 HU HUBA003268 patent/HU174257B/hu unknown
- 1975-05-15 FR FR7515272A patent/FR2270861B1/fr not_active Expired
- 1975-05-15 BR BR3831/75A patent/BR7503008A/pt unknown
-
1976
- 1976-04-06 AR AR262796A patent/AR210116A1/es active
-
1977
- 1977-06-29 AT AT0462777A patent/AT365475B/de active
- 1977-09-08 KE KE2773A patent/KE2773A/xx unknown
-
1980
- 1980-01-10 HK HK16/80A patent/HK1680A/xx unknown
- 1980-12-31 MY MY1980187A patent/MY8000187A/xx unknown
-
1983
- 1983-01-07 JP JP58000561A patent/JPS5945672B2/ja not_active Expired
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