NO750557L - - Google Patents
Info
- Publication number
- NO750557L NO750557L NO750557A NO750557A NO750557L NO 750557 L NO750557 L NO 750557L NO 750557 A NO750557 A NO 750557A NO 750557 A NO750557 A NO 750557A NO 750557 L NO750557 L NO 750557L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- guanidine
- hydrazone
- bis
- chlorobenzylideneamino
- Prior art date
Links
- -1 cyan Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 150000007857 hydrazones Chemical class 0.000 claims description 10
- JGGFDEJXWLAQKR-UHFFFAOYSA-N 1,2-diaminoguanidine Chemical class NNC(N)=NN JGGFDEJXWLAQKR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- FQQQSNAVVZSYMB-UHFFFAOYSA-N 1,1-diaminoguanidine Chemical class NN(N)C(N)=N FQQQSNAVVZSYMB-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- MJTWYBXJJBDJCG-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=CC=C1 MJTWYBXJJBDJCG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- KMNMZRDABHCHSD-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 KMNMZRDABHCHSD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- YURDSJGWWXAEBA-UHFFFAOYSA-N (4-chlorophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=C(Cl)C=C1 YURDSJGWWXAEBA-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OHWFZCUCQSPPSJ-UHFFFAOYSA-N benzoyl isocyanide Chemical compound [C-]#[N+]C(=O)C1=CC=CC=C1 OHWFZCUCQSPPSJ-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 4
- 208000003495 Coccidiosis Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010023076 Isosporiasis Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BAJBVTWTYVBTIL-UHFFFAOYSA-N (4-bromophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=C(Br)C=C1 BAJBVTWTYVBTIL-UHFFFAOYSA-N 0.000 description 2
- DTWXQPNQLDOYHA-UHFFFAOYSA-N (4-fluorophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=C(F)C=C1 DTWXQPNQLDOYHA-UHFFFAOYSA-N 0.000 description 2
- AIWPXJBZZDHCAG-UHFFFAOYSA-N (4-iodophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=C(I)C=C1 AIWPXJBZZDHCAG-UHFFFAOYSA-N 0.000 description 2
- IGMHTADUHJUTSD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethylidenehydrazine Chemical compound NN=C(C)C1=CC=C(Cl)C=C1 IGMHTADUHJUTSD-UHFFFAOYSA-N 0.000 description 2
- KJTVYMFBLBFDNN-UHFFFAOYSA-N 4-methanehydrazonoylbenzonitrile Chemical compound NN=CC1=CC=C(C#N)C=C1 KJTVYMFBLBFDNN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PGAHUJGUYJGSDA-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methylidenehydrazine Chemical compound NN=CC1=CC=C(C(F)(F)F)C=C1 PGAHUJGUYJGSDA-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- YDEPPZLNWKEDJL-UHFFFAOYSA-N n-[(4-chlorophenyl)methylideneamino]methanamine Chemical compound CNN=CC1=CC=C(Cl)C=C1 YDEPPZLNWKEDJL-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SBHIPXJVXKKBGK-UHFFFAOYSA-N (2,4-dichlorophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=C(Cl)C=C1Cl SBHIPXJVXKKBGK-UHFFFAOYSA-N 0.000 description 1
- IZKCWJUTZCUYDW-UHFFFAOYSA-N (2-chlorophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=CC=C1Cl IZKCWJUTZCUYDW-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YQLRALIFVMSFSX-UHFFFAOYSA-N (3,4-dichlorophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=C(Cl)C(Cl)=C1 YQLRALIFVMSFSX-UHFFFAOYSA-N 0.000 description 1
- UWOUMSRAKRIWOA-UHFFFAOYSA-N (3-chlorophenyl)methylidenehydrazine Chemical compound NN=CC1=CC=CC(Cl)=C1 UWOUMSRAKRIWOA-UHFFFAOYSA-N 0.000 description 1
- OMQISHOVJFXWIE-UHFFFAOYSA-N 1,2-bis(propan-2-ylideneamino)guanidine Chemical compound CC(C)=NNC(=N)NN=C(C)C OMQISHOVJFXWIE-UHFFFAOYSA-N 0.000 description 1
- HKXKTTNQHHTCBV-UHFFFAOYSA-N 1,3-bis[(4-chlorophenyl)methylideneamino]-2-[(2,4-dimethylphenyl)methyl]guanidine Chemical compound CC1=CC(C)=CC=C1CN=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 HKXKTTNQHHTCBV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SEDQCXNPRHNRAI-UHFFFAOYSA-N 2,6-dichlorobenzoyl isocyanide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)[N+]#[C-] SEDQCXNPRHNRAI-UHFFFAOYSA-N 0.000 description 1
- AUQKWAUBDKHPJD-UHFFFAOYSA-N 2-methylbenzoyl isocyanide Chemical compound C=1(C(=CC=CC=1)C(=O)[N+]#[C-])C AUQKWAUBDKHPJD-UHFFFAOYSA-N 0.000 description 1
- KETSXKGCGOYEJC-UHFFFAOYSA-N 3-nitrobenzoyl isocyanide Chemical compound [N+](=O)([O-])C=1C=C(C(=O)[N+]#[C-])C=CC=1 KETSXKGCGOYEJC-UHFFFAOYSA-N 0.000 description 1
- JHAWWJQGHKGXHA-UHFFFAOYSA-N 6-tert-butylquinoline Chemical compound N1=CC=CC2=CC(C(C)(C)C)=CC=C21 JHAWWJQGHKGXHA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000007575 Calluna vulgaris Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical group COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DUOIRRBIUOAKPD-UHFFFAOYSA-N n-[(4-chlorophenyl)methylideneamino]butan-1-amine Chemical compound CCCCNN=CC1=CC=C(Cl)C=C1 DUOIRRBIUOAKPD-UHFFFAOYSA-N 0.000 description 1
- UPMREZPSRCZZEC-UHFFFAOYSA-N n-[(4-chlorophenyl)methylideneamino]ethanamine Chemical compound CCNN=CC1=CC=C(Cl)C=C1 UPMREZPSRCZZEC-UHFFFAOYSA-N 0.000 description 1
- VMECRIIAXMFRDT-UHFFFAOYSA-N n-[[2-[(4-bromophenyl)methylidene]hydrazinyl]-[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Br)=CC=1)=NC(=O)C1=CC=CC=C1 VMECRIIAXMFRDT-UHFFFAOYSA-N 0.000 description 1
- RXCAZNPNPIRHTE-UHFFFAOYSA-N n-[[2-[(4-chlorophenyl)methylidene]hydrazinyl]-[2-[(4-fluorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(F)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=CC=C1 RXCAZNPNPIRHTE-UHFFFAOYSA-N 0.000 description 1
- WXYDSEDHIBSNBA-UHFFFAOYSA-N n-[[2-[(4-chlorophenyl)methylidene]hydrazinyl]-[2-[(4-iodophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(I)=CC=1)=NC(=O)C1=CC=CC=C1 WXYDSEDHIBSNBA-UHFFFAOYSA-N 0.000 description 1
- QIQWGIAUKVAWJM-UHFFFAOYSA-N n-[[2-[(4-chlorophenyl)methylidene]hydrazinyl]-[2-[[4-(trifluoromethyl)phenyl]methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=CC=C1 QIQWGIAUKVAWJM-UHFFFAOYSA-N 0.000 description 1
- LKONRFAAFUICGE-UHFFFAOYSA-N n-[[[(4-chlorophenyl)methylideneamino]-methylamino]-[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C=1C=C(Cl)C=CC=1C=NNC(=NC(=O)C=1C=CC=CC=1)N(C)N=CC1=CC=C(Cl)C=C1 LKONRFAAFUICGE-UHFFFAOYSA-N 0.000 description 1
- XUNLQTZSRKOPIX-UHFFFAOYSA-N n-[bis(2-benzylidenehydrazinyl)methylidene]benzamide Chemical compound C=1C=CC=CC=1C(=O)N=C(NN=CC=1C=CC=CC=1)NN=CC1=CC=CC=C1 XUNLQTZSRKOPIX-UHFFFAOYSA-N 0.000 description 1
- BNEIUJKKVQFVPA-UHFFFAOYSA-N n-[bis[2-[(2,4-dichlorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound ClC1=CC(Cl)=CC=C1C=NNC(NN=CC=1C(=CC(Cl)=CC=1)Cl)=NC(=O)C1=CC=CC=C1 BNEIUJKKVQFVPA-UHFFFAOYSA-N 0.000 description 1
- BVLQXZCKQXKVGS-UHFFFAOYSA-N n-[bis[2-[(2-chlorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound ClC1=CC=CC=C1C=NNC(NN=CC=1C(=CC=CC=1)Cl)=NC(=O)C1=CC=CC=C1 BVLQXZCKQXKVGS-UHFFFAOYSA-N 0.000 description 1
- JSAWEFFBLFUMEF-UHFFFAOYSA-N n-[bis[2-[(3-chlorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound ClC1=CC=CC(C=NNC(NN=CC=2C=C(Cl)C=CC=2)=NC(=O)C=2C=CC=CC=2)=C1 JSAWEFFBLFUMEF-UHFFFAOYSA-N 0.000 description 1
- LPURMSMOHVTVIB-UHFFFAOYSA-N n-[bis[2-[(4-bromophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(Br)=CC=C1C=NNC(NN=CC=1C=CC(Br)=CC=1)=NC(=O)C1=CC=CC=C1 LPURMSMOHVTVIB-UHFFFAOYSA-N 0.000 description 1
- BKFUWLYJLPJHQU-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,3-dimethylbenzamide Chemical compound CC1=CC=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1C BKFUWLYJLPJHQU-UHFFFAOYSA-N 0.000 description 1
- XRSDHBMLVVHKIU-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,4,5-trimethylbenzamide Chemical compound C1=C(C)C(C)=CC(C)=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 XRSDHBMLVVHKIU-UHFFFAOYSA-N 0.000 description 1
- NVFFTZJUGIXFTQ-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,4,6-trimethylbenzamide Chemical compound CC1=CC(C)=CC(C)=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 NVFFTZJUGIXFTQ-UHFFFAOYSA-N 0.000 description 1
- DCEAGDRGYCXREJ-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,4-dichlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=C(Cl)C=C1Cl DCEAGDRGYCXREJ-UHFFFAOYSA-N 0.000 description 1
- HOZYRNAJZNZCMW-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,5-dichlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC(Cl)=CC=C1Cl HOZYRNAJZNZCMW-UHFFFAOYSA-N 0.000 description 1
- XTTWFSHYHCYIAC-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,5-dimethylbenzamide Chemical compound CC1=CC=C(C)C(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 XTTWFSHYHCYIAC-UHFFFAOYSA-N 0.000 description 1
- ZABGGFMETLIJNE-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2,6-dichlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=C(Cl)C=CC=C1Cl ZABGGFMETLIJNE-UHFFFAOYSA-N 0.000 description 1
- GOHQGBZJWZEELU-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=CC=C1Cl GOHQGBZJWZEELU-UHFFFAOYSA-N 0.000 description 1
- IIHSBRLFPPRAMB-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 IIHSBRLFPPRAMB-UHFFFAOYSA-N 0.000 description 1
- VQXNSJOJTWGBTA-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2-methyl-4-nitrobenzamide Chemical compound CC1=CC([N+]([O-])=O)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 VQXNSJOJTWGBTA-UHFFFAOYSA-N 0.000 description 1
- DJEQPVMKFJORFS-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 DJEQPVMKFJORFS-UHFFFAOYSA-N 0.000 description 1
- TUOUITGYOBZFIZ-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 TUOUITGYOBZFIZ-UHFFFAOYSA-N 0.000 description 1
- XYANPKPXCHWCOP-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3,4-dimethylbenzamide Chemical compound C1=C(C)C(C)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 XYANPKPXCHWCOP-UHFFFAOYSA-N 0.000 description 1
- JVXDCGLHZVTYDS-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3,5-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 JVXDCGLHZVTYDS-UHFFFAOYSA-N 0.000 description 1
- SWHXMUNRAGUXFE-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3,5-dimethylbenzamide Chemical compound CC1=CC(C)=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 SWHXMUNRAGUXFE-UHFFFAOYSA-N 0.000 description 1
- OEUXCQQLLXBYQK-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 OEUXCQQLLXBYQK-UHFFFAOYSA-N 0.000 description 1
- UWLJYXYMFOMBRT-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-bromo-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=C(Cl)C(Br)=C1 UWLJYXYMFOMBRT-UHFFFAOYSA-N 0.000 description 1
- WWFKLDNTHCWXFJ-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-chloro-4-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 WWFKLDNTHCWXFJ-UHFFFAOYSA-N 0.000 description 1
- UZLSVOJRSWYXRV-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-chloro-4-methylbenzamide Chemical compound C1=C(Cl)C(C)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 UZLSVOJRSWYXRV-UHFFFAOYSA-N 0.000 description 1
- DJMFGOFCMLYPFX-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=CC(Cl)=C1 DJMFGOFCMLYPFX-UHFFFAOYSA-N 0.000 description 1
- RGMZKKBRSFEZJH-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 RGMZKKBRSFEZJH-UHFFFAOYSA-N 0.000 description 1
- PBYFTIXNMXYDML-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 PBYFTIXNMXYDML-UHFFFAOYSA-N 0.000 description 1
- YLVBSPPHLAJQFU-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-bromobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=C(Br)C=C1 YLVBSPPHLAJQFU-UHFFFAOYSA-N 0.000 description 1
- HCPKIEXVGOSLQN-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-chloro-3-nitrobenzamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)N=C(NN=CC=2C=CC(Cl)=CC=2)NN=CC=2C=CC(Cl)=CC=2)=C1 HCPKIEXVGOSLQN-UHFFFAOYSA-N 0.000 description 1
- JYKGUXRUQUHFQH-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=C(Cl)C=C1 JYKGUXRUQUHFQH-UHFFFAOYSA-N 0.000 description 1
- SIISAQVDYFLBFD-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-cyanobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=C(C#N)C=C1 SIISAQVDYFLBFD-UHFFFAOYSA-N 0.000 description 1
- FNPNGYLMIHRVFE-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-ethoxybenzamide Chemical compound C1=CC(OCC)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 FNPNGYLMIHRVFE-UHFFFAOYSA-N 0.000 description 1
- BZFBFONZJYOWBS-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 BZFBFONZJYOWBS-UHFFFAOYSA-N 0.000 description 1
- QQWOCXKGECKJHC-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 QQWOCXKGECKJHC-UHFFFAOYSA-N 0.000 description 1
- JRKFABJUEVTLID-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-hexylbenzamide Chemical compound C1=CC(CCCCCC)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 JRKFABJUEVTLID-UHFFFAOYSA-N 0.000 description 1
- HJPDHHARHAVFHN-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-iodobenzamide Chemical compound C1=CC(Cl)=CC=C1C=NNC(NN=CC=1C=CC(Cl)=CC=1)=NC(=O)C1=CC=C(I)C=C1 HJPDHHARHAVFHN-UHFFFAOYSA-N 0.000 description 1
- HMOKIBKPHRWIRC-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-4-methyl-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 HMOKIBKPHRWIRC-UHFFFAOYSA-N 0.000 description 1
- UWWDZVQKWBPTCC-UHFFFAOYSA-N n-[bis[2-[(4-chlorophenyl)methylidene]hydrazinyl]methylidene]-5-chloro-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(=O)N=C(NN=CC=1C=CC(Cl)=CC=1)NN=CC1=CC=C(Cl)C=C1 UWWDZVQKWBPTCC-UHFFFAOYSA-N 0.000 description 1
- ILEXNAJFLSGMKB-UHFFFAOYSA-N n-[bis[2-[(4-cyanophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C=1C=CC=CC=1C(=O)N=C(NN=CC=1C=CC(=CC=1)C#N)NN=CC1=CC=C(C#N)C=C1 ILEXNAJFLSGMKB-UHFFFAOYSA-N 0.000 description 1
- UOIUUHRQOXAUHV-UHFFFAOYSA-N n-[bis[2-[(4-fluorophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(F)=CC=C1C=NNC(NN=CC=1C=CC(F)=CC=1)=NC(=O)C1=CC=CC=C1 UOIUUHRQOXAUHV-UHFFFAOYSA-N 0.000 description 1
- VALHIHVNCVZRPJ-UHFFFAOYSA-N n-[bis[2-[(4-iodophenyl)methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(I)=CC=C1C=NNC(NN=CC=1C=CC(I)=CC=1)=NC(=O)C1=CC=CC=C1 VALHIHVNCVZRPJ-UHFFFAOYSA-N 0.000 description 1
- LVMYNDSGZBZQKB-UHFFFAOYSA-N n-[bis[2-[[4-(trifluoromethyl)phenyl]methylidene]hydrazinyl]methylidene]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C=NNC(NN=CC=1C=CC(=CC=1)C(F)(F)F)=NC(=O)C1=CC=CC=C1 LVMYNDSGZBZQKB-UHFFFAOYSA-N 0.000 description 1
- YPINULDRAIKEEW-UHFFFAOYSA-N n-[bis[[(4-chlorophenyl)methylideneamino]-ethylamino]methylidene]benzamide Chemical compound C=1C=CC=CC=1C(=O)N=C(N(CC)N=CC=1C=CC(Cl)=CC=1)N(CC)N=CC1=CC=C(Cl)C=C1 YPINULDRAIKEEW-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- MOOFYEJFXBSZGE-UHFFFAOYSA-N robenidine Chemical compound C=1C=C(Cl)C=CC=1C=NN=C(N)NN=CC1=CC=C(Cl)C=C1 MOOFYEJFXBSZGE-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742408289 DE2408289A1 (de) | 1974-02-21 | 1974-02-21 | Substituierte diaminoguanidine und ihre herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO750557L true NO750557L (de) | 1975-08-22 |
Family
ID=5908038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO750557A NO750557L (de) | 1974-02-21 | 1975-02-19 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3950539A (de) |
| JP (1) | JPS50117740A (de) |
| AU (1) | AU7835575A (de) |
| BE (1) | BE825805A (de) |
| DD (1) | DD117874A5 (de) |
| DE (1) | DE2408289A1 (de) |
| DK (1) | DK63875A (de) |
| ES (3) | ES434772A1 (de) |
| FI (1) | FI750462A (de) |
| FR (1) | FR2261759A1 (de) |
| IL (1) | IL46648A0 (de) |
| IT (1) | IT1037155B (de) |
| LU (1) | LU71885A1 (de) |
| NL (1) | NL7501756A (de) |
| NO (1) | NO750557L (de) |
| SE (1) | SE7501972L (de) |
| ZA (1) | ZA751074B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4369883A (en) * | 1981-04-27 | 1983-01-25 | Stravitz David M | Tape cassette storage and carrying case |
| US5749636A (en) * | 1995-06-28 | 1998-05-12 | Boury; Nabil | Storage rack for compact discs or the like |
| EP1305347B1 (de) * | 2000-07-25 | 2005-09-14 | Membrana GmbH | Modifizierter polymerer formkörper, verfahren zu seiner herstellung und seine verwendung |
| JP5954504B1 (ja) * | 2014-09-12 | 2016-07-20 | 三菱瓦斯化学株式会社 | 変性ゴム及びその製造方法、ゴム組成物、並びにタイヤ |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206478A (en) * | 1961-10-05 | 1965-09-14 | Ciba Geigy Corp | Aminoarylalkanone |
| CH479559A (de) * | 1967-09-26 | 1969-10-15 | Wander Ag Dr A | Verfahren zur Herstellung von Acylguanidinen |
| US3621056A (en) * | 1968-08-16 | 1971-11-16 | Sandoz Ag | Substituted benzylideneamino guanidines |
| GB1298112A (en) * | 1969-02-20 | 1972-11-29 | Wander Ag Dr A | Phenyl acetyl guanidine derivatives |
| US3769432A (en) * | 1970-12-02 | 1973-10-30 | American Cyanamid Co | Compositions and method of use of substituted guanidines |
| US3856975A (en) * | 1971-11-19 | 1974-12-24 | Merck & Co Inc | Anticoccidial composition containing guanidine derivatives |
| BE791536A (fr) * | 1971-11-19 | 1973-05-17 | Merck & Co Inc | Nouvelles 1,3-diamino guanidines substituees |
| US3795692A (en) * | 1972-03-24 | 1974-03-05 | Merck & Co Inc | Compounds and processes |
| US3901944A (en) * | 1972-05-08 | 1975-08-26 | American Cyanamid Co | 1,3-bis(substituted benzylideneamino)guanidines |
-
1974
- 1974-02-21 DE DE19742408289 patent/DE2408289A1/de active Pending
-
1975
- 1975-02-14 NL NL7501756A patent/NL7501756A/xx unknown
- 1975-02-15 ES ES434772A patent/ES434772A1/es not_active Expired
- 1975-02-17 IL IL46648A patent/IL46648A0/xx unknown
- 1975-02-19 US US05/550,917 patent/US3950539A/en not_active Expired - Lifetime
- 1975-02-19 DD DD184296A patent/DD117874A5/xx unknown
- 1975-02-19 IT IT20451/75A patent/IT1037155B/it active
- 1975-02-19 NO NO750557A patent/NO750557L/no unknown
- 1975-02-19 FI FI750462A patent/FI750462A/fi not_active Application Discontinuation
- 1975-02-19 AU AU78355/75A patent/AU7835575A/en not_active Expired
- 1975-02-19 LU LU71885A patent/LU71885A1/xx unknown
- 1975-02-19 FR FR7505138A patent/FR2261759A1/fr not_active Withdrawn
- 1975-02-20 DK DK63875*#A patent/DK63875A/da unknown
- 1975-02-20 ZA ZA00751074A patent/ZA751074B/xx unknown
- 1975-02-21 BE BE153581A patent/BE825805A/xx unknown
- 1975-02-21 SE SE7501972A patent/SE7501972L/ unknown
- 1975-02-21 JP JP50021088A patent/JPS50117740A/ja active Pending
-
1976
- 1976-02-25 ES ES445529A patent/ES445529A1/es not_active Expired
- 1976-02-25 ES ES445528A patent/ES445528A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD117874A5 (de) | 1976-02-05 |
| IT1037155B (it) | 1979-11-10 |
| DE2408289A1 (de) | 1975-09-11 |
| NL7501756A (nl) | 1975-08-25 |
| FI750462A (de) | 1975-08-22 |
| ES445528A1 (es) | 1977-06-16 |
| AU7835575A (en) | 1976-08-19 |
| BE825805A (fr) | 1975-08-21 |
| LU71885A1 (de) | 1977-01-05 |
| ZA751074B (en) | 1976-01-28 |
| IL46648A0 (en) | 1975-04-25 |
| SE7501972L (de) | 1975-08-22 |
| JPS50117740A (de) | 1975-09-16 |
| US3950539A (en) | 1976-04-13 |
| FR2261759A1 (de) | 1975-09-19 |
| ES445529A1 (es) | 1977-06-16 |
| ES434772A1 (es) | 1977-02-01 |
| DK63875A (de) | 1975-10-20 |
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