GB1569386A - 1-lower alkyl-4,5-dihydro-5-phenyl-2-lower alkoxy carbonylaminoimidazoles and substituted phenyl derivatives - Google Patents
1-lower alkyl-4,5-dihydro-5-phenyl-2-lower alkoxy carbonylaminoimidazoles and substituted phenyl derivatives Download PDFInfo
- Publication number
- GB1569386A GB1569386A GB30729/77A GB3072977A GB1569386A GB 1569386 A GB1569386 A GB 1569386A GB 30729/77 A GB30729/77 A GB 30729/77A GB 3072977 A GB3072977 A GB 3072977A GB 1569386 A GB1569386 A GB 1569386A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- dihydro
- methyl
- carbon atoms
- total number
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 alkoxy carbonylaminoimidazoles Chemical class 0.000 title claims description 457
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 248
- 238000000034 method Methods 0.000 claims description 115
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 115
- 150000003839 salts Chemical class 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- IUEBEACSGQRJBB-UHFFFAOYSA-N methyl n-(1h-imidazol-2-yl)carbamate Chemical compound COC(=O)NC1=NC=CN1 IUEBEACSGQRJBB-UHFFFAOYSA-N 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 28
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 claims description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- BEPSSQAKMVCCFV-UHFFFAOYSA-N 2-isocyanato-1h-imidazole Chemical compound O=C=NC1=NC=CN1 BEPSSQAKMVCCFV-UHFFFAOYSA-N 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 206010010904 Convulsion Diseases 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000000950 dibromo group Chemical group Br* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 10
- 210000003169 central nervous system Anatomy 0.000 claims description 9
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 8
- 125000002346 iodo group Chemical group I* 0.000 claims description 8
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- SAYAMCOWJNUODI-UHFFFAOYSA-N methyl n-(1-methyl-5-phenyl-4,5-dihydroimidazol-2-yl)carbamate Chemical compound CN1C(NC(=O)OC)=NCC1C1=CC=CC=C1 SAYAMCOWJNUODI-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000002936 tranquilizing effect Effects 0.000 claims description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 208000023178 Musculoskeletal disease Diseases 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- WZDFPZZNDBLYPR-UHFFFAOYSA-N methyl n-(1-ethyl-5-phenyl-4,5-dihydroimidazol-2-yl)carbamate Chemical compound C1N=C(NC(=O)OC)N(CC)C1C1=CC=CC=C1 WZDFPZZNDBLYPR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005910 alkyl carbonate group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 230000001624 sedative effect Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 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 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 230000000694 effects Effects 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- 239000007858 starting material Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- 239000000935 antidepressant agent Substances 0.000 description 16
- 229940005513 antidepressants Drugs 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- 239000012458 free base Substances 0.000 description 15
- KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 14
- 230000001430 anti-depressive effect Effects 0.000 description 14
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000006309 butyl amino group Chemical group 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 229960003147 reserpine Drugs 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 10
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 9
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 9
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 9
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000001961 anticonvulsive agent Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 9
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000001773 anti-convulsant effect Effects 0.000 description 8
- 229960003965 antiepileptics Drugs 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 150000007530 organic bases Chemical class 0.000 description 7
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000003158 myorelaxant agent Substances 0.000 description 6
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 210000002027 skeletal muscle Anatomy 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 5
- PFJOTFSIBVZGPK-UHFFFAOYSA-N 1-ethyl-2-methylhydrazine Chemical compound CCNNC PFJOTFSIBVZGPK-UHFFFAOYSA-N 0.000 description 5
- 230000001078 anti-cholinergic effect Effects 0.000 description 5
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical group CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000000994 depressogenic effect Effects 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 150000003947 ethylamines Chemical class 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- SIJNLDDSNHLXGQ-UHFFFAOYSA-N methyl n-(5-methyl-4-phenyl-4,5-dihydro-1h-imidazol-2-yl)carbamate Chemical compound CC1NC(NC(=O)OC)=NC1C1=CC=CC=C1 SIJNLDDSNHLXGQ-UHFFFAOYSA-N 0.000 description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- WJBMRZAHTUFBGE-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC(CCN)=C1 WJBMRZAHTUFBGE-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
- 230000036461 convulsion Effects 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000006635 hexyloxycarbonylamino group Chemical group 0.000 description 4
- 230000002631 hypothermal effect Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- IILPUHXLVPEPAV-UHFFFAOYSA-N n-ethyl-2,3-dimethylaniline Chemical compound CCNC1=CC=CC(C)=C1C IILPUHXLVPEPAV-UHFFFAOYSA-N 0.000 description 4
- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 4
- WWONUZXEGYMTKR-UHFFFAOYSA-N n-ethyl-3,4-difluoroaniline Chemical compound CCNC1=CC=C(F)C(F)=C1 WWONUZXEGYMTKR-UHFFFAOYSA-N 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- PPNCOQHHSGMKGI-UHFFFAOYSA-N 1-cyclononyldiazonane Chemical compound C1CCCCCCCC1N1NCCCCCCC1 PPNCOQHHSGMKGI-UHFFFAOYSA-N 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 3
- OVZILCZVNWFHKZ-UHFFFAOYSA-N 2-phenylethanamine;dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=CC=C1 OVZILCZVNWFHKZ-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003874 central nervous system depressant Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- NMHBKSHIKGHTFR-UHFFFAOYSA-N ethyl n-(1h-imidazol-2-yl)carbamate Chemical compound CCOC(=O)NC1=NC=CN1 NMHBKSHIKGHTFR-UHFFFAOYSA-N 0.000 description 3
- 125000006631 isobutoxycarbonylamino group Chemical group 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- QCGFQSVVAJTHOD-UHFFFAOYSA-N n-ethyl-3,5-dimethoxyaniline Chemical compound CCNC1=CC(OC)=CC(OC)=C1 QCGFQSVVAJTHOD-UHFFFAOYSA-N 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 230000028527 righting reflex Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000001256 tonic effect Effects 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- MQPUAVYKVIHUJP-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C(Cl)=C1 MQPUAVYKVIHUJP-UHFFFAOYSA-N 0.000 description 2
- OMQUELHMHMORKS-UHFFFAOYSA-N 2-chloro-n-ethylaniline Chemical compound CCNC1=CC=CC=C1Cl OMQUELHMHMORKS-UHFFFAOYSA-N 0.000 description 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- 208000008238 Muscle Spasticity Diseases 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000005325 alkali earth metal hydroxides Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- SZABQYKYIILDEG-UHFFFAOYSA-N butyl N-(1H-imidazol-2-yl)carbamate Chemical compound C(CCC)OC(=O)NC=1NC=CN1 SZABQYKYIILDEG-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- FPKGTVXPIULTIP-UHFFFAOYSA-N n-ethyl-1,3-benzodioxol-5-amine Chemical compound CCNC1=CC=C2OCOC2=C1 FPKGTVXPIULTIP-UHFFFAOYSA-N 0.000 description 2
- QNSZDXLOSMUCPQ-UHFFFAOYSA-N n-ethyl-2-fluoroaniline Chemical compound CCNC1=CC=CC=C1F QNSZDXLOSMUCPQ-UHFFFAOYSA-N 0.000 description 2
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000004089 psychotropic agent Substances 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000006748 scratching Methods 0.000 description 2
- 230000002393 scratching effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JWDYCNIAQWPBHD-UHFFFAOYSA-N 1-(2-methylphenyl)glycerol Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 1
- WOLLYMTVSRHDIV-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-ethyl-2-methylhydrazine Chemical compound CNN(CC)C1=CC(=CC=C1)Cl WOLLYMTVSRHDIV-UHFFFAOYSA-N 0.000 description 1
- SFOKYOTZCINXKA-UHFFFAOYSA-N 1-ethyl-2-(2-phenylethyl)hydrazine Chemical compound C(C)NNCCC1=CC=CC=C1 SFOKYOTZCINXKA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- AEUDKTNSAHIGJY-UHFFFAOYSA-N 1-methyl-2-(2-phenylethyl)hydrazine;dihydrochloride Chemical compound Cl.Cl.CNNCCC1=CC=CC=C1 AEUDKTNSAHIGJY-UHFFFAOYSA-N 0.000 description 1
- UPOFVKWXGKWLGU-UHFFFAOYSA-N 1-methyl-4-phenyl-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.N1=C(N)N(C)CC1C1=CC=CC=C1 UPOFVKWXGKWLGU-UHFFFAOYSA-N 0.000 description 1
- NSVHJGXHRJORRF-UHFFFAOYSA-N 1-methyl-5-phenyl-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.C1N=C(N)N(C)C1C1=CC=CC=C1 NSVHJGXHRJORRF-UHFFFAOYSA-N 0.000 description 1
- BJHDRDSESRROKS-UHFFFAOYSA-N 2,3-dichloro-n-ethylaniline Chemical compound CCNC1=CC=CC(Cl)=C1Cl BJHDRDSESRROKS-UHFFFAOYSA-N 0.000 description 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- WNCUVUUEJZEATP-UHFFFAOYSA-N 2,5-Dimethoxy-phenethylamine Chemical compound COC1=CC=C(OC)C(CCN)=C1 WNCUVUUEJZEATP-UHFFFAOYSA-N 0.000 description 1
- FMIYOUUEDNUNBC-UHFFFAOYSA-N 2,6-dichloro-n-ethylaniline Chemical compound CCNC1=C(Cl)C=CC=C1Cl FMIYOUUEDNUNBC-UHFFFAOYSA-N 0.000 description 1
- KSKAHYBZLQUACF-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)ethanamine Chemical compound NCCC1=CC(Cl)=CC=C1Cl KSKAHYBZLQUACF-UHFFFAOYSA-N 0.000 description 1
- RNEFNTMBBIKOFO-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)ethanamine Chemical compound CC1=CC=C(C)C(CCN)=C1 RNEFNTMBBIKOFO-UHFFFAOYSA-N 0.000 description 1
- WLPSCBCFPTVLLY-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-(methylamino)acetonitrile Chemical compound CNC(C#N)C1=CC=CC=C1Cl WLPSCBCFPTVLLY-UHFFFAOYSA-N 0.000 description 1
- PWVUXRBUUYZMKM-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCO PWVUXRBUUYZMKM-UHFFFAOYSA-N 0.000 description 1
- VCLVMXMXPDLKQW-UHFFFAOYSA-N 2-(ethylamino)-2-phenylacetonitrile Chemical compound CCNC(C#N)C1=CC=CC=C1 VCLVMXMXPDLKQW-UHFFFAOYSA-N 0.000 description 1
- BCESCHGDVIYYPC-UHFFFAOYSA-N 2-(ethylamino)phenol Chemical compound CCNC1=CC=CC=C1O BCESCHGDVIYYPC-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- JXPQMHIXNPWEEK-UHFFFAOYSA-N 2-[3,4-bis(phenylmethoxy)phenyl]ethanamine Chemical compound C=1C=CC=CC=1COC1=CC(CCN)=CC=C1OCC1=CC=CC=C1 JXPQMHIXNPWEEK-UHFFFAOYSA-N 0.000 description 1
- FLRJSHVTNSVDDI-UHFFFAOYSA-N 2-bromo-n-ethylaniline Chemical compound CCNC1=CC=CC=C1Br FLRJSHVTNSVDDI-UHFFFAOYSA-N 0.000 description 1
- MLYZUSIOIGXXTO-UHFFFAOYSA-N 2-ethoxy-n-ethylaniline Chemical compound CCNC1=CC=CC=C1OCC MLYZUSIOIGXXTO-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- TVKZDKSHNITMRZ-UHFFFAOYSA-N 3-(ethylamino)phenol Chemical compound CCNC1=CC=CC(O)=C1 TVKZDKSHNITMRZ-UHFFFAOYSA-N 0.000 description 1
- LUNFYXBUYWMPBY-UHFFFAOYSA-N 3-chloro-n-ethylaniline Chemical compound CCNC1=CC=CC(Cl)=C1 LUNFYXBUYWMPBY-UHFFFAOYSA-N 0.000 description 1
- PERUGIXDQKVIKY-UHFFFAOYSA-N 3-ethoxy-n-ethylaniline Chemical compound CCNC1=CC=CC(OCC)=C1 PERUGIXDQKVIKY-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- JSWYQVNSFHUBAC-UHFFFAOYSA-N 4-(ethylamino)benzene-1,3-diol Chemical compound CCNC1=CC=C(O)C=C1O JSWYQVNSFHUBAC-UHFFFAOYSA-N 0.000 description 1
- VYSQUDVPQJEULO-UHFFFAOYSA-N 4-bromo-n-ethylaniline Chemical compound CCNC1=CC=C(Br)C=C1 VYSQUDVPQJEULO-UHFFFAOYSA-N 0.000 description 1
- KLWDPIXDUVYHMS-UHFFFAOYSA-N 4-chloro-n-ethylaniline Chemical compound CCNC1=CC=C(Cl)C=C1 KLWDPIXDUVYHMS-UHFFFAOYSA-N 0.000 description 1
- LCIDBIBUGVRZAC-UHFFFAOYSA-N 4-ethoxy-n-ethylaniline Chemical compound CCNC1=CC=C(OCC)C=C1 LCIDBIBUGVRZAC-UHFFFAOYSA-N 0.000 description 1
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- PHDQQFSMMXZRTI-UHFFFAOYSA-N N-ethyl-3-pentoxyaniline Chemical compound C(CCCC)OC=1C=C(C=CC1)NCC PHDQQFSMMXZRTI-UHFFFAOYSA-N 0.000 description 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 240000002114 Satureja hortensis Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940031768 diglycol stearate Drugs 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 201000003104 endogenous depression Diseases 0.000 description 1
- MBMJDELICBDLEE-UHFFFAOYSA-N ethanamine;dihydrochloride Chemical compound Cl.Cl.CCN MBMJDELICBDLEE-UHFFFAOYSA-N 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229940047127 fiore Drugs 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000001153 interneuron Anatomy 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006629 isopropoxycarbonylamino group Chemical group 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- QRYFGTULTGLGHU-NBERXCRTSA-N iturelix Chemical compound C([C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CCCCNC(=O)C=1C=NC=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)CCCNC(=O)C1=CC=CN=C1 QRYFGTULTGLGHU-NBERXCRTSA-N 0.000 description 1
- 108010083551 iturelix Proteins 0.000 description 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- FKWSMBAMOQCVPV-UHFFFAOYSA-N magnesium dicyanide Chemical compound [Mg+2].N#[C-].N#[C-] FKWSMBAMOQCVPV-UHFFFAOYSA-N 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229960003861 mephenesin Drugs 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- KWCFYMXHJICOBP-UHFFFAOYSA-N methyl n-(1h-imidazol-5-yl)carbamate Chemical compound COC(=O)NC1=CN=CN1 KWCFYMXHJICOBP-UHFFFAOYSA-N 0.000 description 1
- SBUKTYMKOFPXBT-UHFFFAOYSA-N methyl n-(5-phenyl-4,5-dihydro-1h-imidazol-2-yl)carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1 SBUKTYMKOFPXBT-UHFFFAOYSA-N 0.000 description 1
- DIWUZBRQWBJZQD-UHFFFAOYSA-N methyl n-[5-(2,3-dimethylphenyl)-1-methyl-4,5-dihydroimidazol-2-yl]carbamate Chemical compound CN1C(NC(=O)OC)=NCC1C1=CC=CC(C)=C1C DIWUZBRQWBJZQD-UHFFFAOYSA-N 0.000 description 1
- LJTJBIYLDAEOHC-UHFFFAOYSA-N methyl n-[5-(2,6-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound N1C(NC(=O)OC)=NCC1C1=C(Cl)C=CC=C1Cl LJTJBIYLDAEOHC-UHFFFAOYSA-N 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- RRIRDPSOCUCGBV-UHFFFAOYSA-N methylenedioxyphenethylamine Chemical compound NCCC1=CC=C2OCOC2=C1 RRIRDPSOCUCGBV-UHFFFAOYSA-N 0.000 description 1
- 239000002637 mydriatic agent Substances 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- LHTGBZMVHWJBQB-UHFFFAOYSA-N n,2-diethylaniline Chemical compound CCNC1=CC=CC=C1CC LHTGBZMVHWJBQB-UHFFFAOYSA-N 0.000 description 1
- HIPBGESCMZUXNS-UHFFFAOYSA-N n,3-diethylaniline Chemical compound CCNC1=CC=CC(CC)=C1 HIPBGESCMZUXNS-UHFFFAOYSA-N 0.000 description 1
- FULYIGBEGXLDLX-UHFFFAOYSA-N n,4-diethylaniline Chemical compound CCNC1=CC=C(CC)C=C1 FULYIGBEGXLDLX-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- OYRMOFUGINVIIP-UHFFFAOYSA-N n-ethyl-2,3-difluoroaniline Chemical compound CCNC1=CC=CC(F)=C1F OYRMOFUGINVIIP-UHFFFAOYSA-N 0.000 description 1
- SXXLALYAVYIVGB-UHFFFAOYSA-N n-ethyl-2,4-difluoroaniline Chemical compound CCNC1=CC=C(F)C=C1F SXXLALYAVYIVGB-UHFFFAOYSA-N 0.000 description 1
- VGFWTVZRANPVQZ-UHFFFAOYSA-N n-ethyl-2,4-dimethylaniline Chemical compound CCNC1=CC=C(C)C=C1C VGFWTVZRANPVQZ-UHFFFAOYSA-N 0.000 description 1
- OMDDWSDIFNYMAY-UHFFFAOYSA-N n-ethyl-2,5-difluoroaniline Chemical compound CCNC1=CC(F)=CC=C1F OMDDWSDIFNYMAY-UHFFFAOYSA-N 0.000 description 1
- AGBOLUHHTNPORL-UHFFFAOYSA-N n-ethyl-2,6-difluoroaniline Chemical compound CCNC1=C(F)C=CC=C1F AGBOLUHHTNPORL-UHFFFAOYSA-N 0.000 description 1
- HKLYFRBMZTWRTJ-UHFFFAOYSA-N n-ethyl-2,6-dimethoxyaniline Chemical compound CCNC1=C(OC)C=CC=C1OC HKLYFRBMZTWRTJ-UHFFFAOYSA-N 0.000 description 1
- OAPVPGPVBZRARK-UHFFFAOYSA-N n-ethyl-2,6-dimethylaniline Chemical compound CCNC1=C(C)C=CC=C1C OAPVPGPVBZRARK-UHFFFAOYSA-N 0.000 description 1
- DVDNUGFZTXJCKK-UHFFFAOYSA-N n-ethyl-2-(trifluoromethyl)aniline Chemical compound CCNC1=CC=CC=C1C(F)(F)F DVDNUGFZTXJCKK-UHFFFAOYSA-N 0.000 description 1
- RUSPWDWPGXKTFO-UHFFFAOYSA-N n-ethyl-2-methoxyaniline Chemical compound CCNC1=CC=CC=C1OC RUSPWDWPGXKTFO-UHFFFAOYSA-N 0.000 description 1
- BNBCNJSNRMAIGH-UHFFFAOYSA-N n-ethyl-3,5-difluoroaniline Chemical compound CCNC1=CC(F)=CC(F)=C1 BNBCNJSNRMAIGH-UHFFFAOYSA-N 0.000 description 1
- NKVRBCWUWUEDLT-UHFFFAOYSA-N n-ethyl-3-(trifluoromethyl)aniline Chemical compound CCNC1=CC=CC(C(F)(F)F)=C1 NKVRBCWUWUEDLT-UHFFFAOYSA-N 0.000 description 1
- SBNPVCZGSKLRSJ-UHFFFAOYSA-N n-ethyl-3-fluoroaniline Chemical compound CCNC1=CC=CC(F)=C1 SBNPVCZGSKLRSJ-UHFFFAOYSA-N 0.000 description 1
- ZMJIPFKIUFDIOV-UHFFFAOYSA-N n-ethyl-3-hexylaniline Chemical compound CCCCCCC1=CC=CC(NCC)=C1 ZMJIPFKIUFDIOV-UHFFFAOYSA-N 0.000 description 1
- WCYOGLOQLHPTRU-UHFFFAOYSA-N n-ethyl-3-iodoaniline Chemical compound CCNC1=CC=CC(I)=C1 WCYOGLOQLHPTRU-UHFFFAOYSA-N 0.000 description 1
- ZFVSSAGTWMDGJX-UHFFFAOYSA-N n-ethyl-4-(trifluoromethyl)aniline Chemical compound CCNC1=CC=C(C(F)(F)F)C=C1 ZFVSSAGTWMDGJX-UHFFFAOYSA-N 0.000 description 1
- ZXENOWJVIYGKAZ-UHFFFAOYSA-N n-ethyl-4-hexylaniline Chemical compound CCCCCCC1=CC=C(NCC)C=C1 ZXENOWJVIYGKAZ-UHFFFAOYSA-N 0.000 description 1
- PXNMEMVYTRYCNH-UHFFFAOYSA-N n-ethyl-4-iodoaniline Chemical compound CCNC1=CC=C(I)C=C1 PXNMEMVYTRYCNH-UHFFFAOYSA-N 0.000 description 1
- MCPNIYHJPMRCQU-UHFFFAOYSA-N n-ethyl-4-methoxyaniline Chemical compound CCNC1=CC=C(OC)C=C1 MCPNIYHJPMRCQU-UHFFFAOYSA-N 0.000 description 1
- AASABFUMCBTXRL-UHFFFAOYSA-N n-ethyl-4-methylaniline Chemical compound CCNC1=CC=C(C)C=C1 AASABFUMCBTXRL-UHFFFAOYSA-N 0.000 description 1
- KFNUASICPPNYSX-UHFFFAOYSA-N n-ethyl-4-propan-2-yloxyaniline Chemical compound CCNC1=CC=C(OC(C)C)C=C1 KFNUASICPPNYSX-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229960002511 phenobarbital sodium Drugs 0.000 description 1
- WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- KJIFDYWXFOVFGM-UHFFFAOYSA-N propan-2-yl N-[4-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1H-imidazol-2-yl]carbamate Chemical compound CC1N=C(NC1C1=C(C=CC=C1)O)NC(=O)OC(C)C KJIFDYWXFOVFGM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- OPILPBBMPUERGU-UHFFFAOYSA-N propyl N-(1H-imidazol-2-yl)carbamate Chemical compound C(CC)OC(=O)NC=1NC=CN=1 OPILPBBMPUERGU-UHFFFAOYSA-N 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/708,651 US4088771A (en) | 1976-07-26 | 1976-07-26 | 1-Lower alkyl-4,5-dihydro-5-phenyl-2-lower alkoxy carbonylaminoimidazoles and substituted phenyl derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1569386A true GB1569386A (en) | 1980-06-11 |
Family
ID=24846651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30729/77A Expired GB1569386A (en) | 1976-07-26 | 1977-07-21 | 1-lower alkyl-4,5-dihydro-5-phenyl-2-lower alkoxy carbonylaminoimidazoles and substituted phenyl derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4088771A (enExample) |
| JP (1) | JPS5315376A (enExample) |
| AU (1) | AU2734977A (enExample) |
| BE (1) | BE857112R (enExample) |
| DE (1) | DE2733698A1 (enExample) |
| DK (1) | DK21177A (enExample) |
| ES (2) | ES461036A2 (enExample) |
| FI (1) | FI770159A7 (enExample) |
| FR (1) | FR2359828A1 (enExample) |
| GB (1) | GB1569386A (enExample) |
| NL (1) | NL7708084A (enExample) |
| NZ (1) | NZ184714A (enExample) |
| SE (1) | SE7700705L (enExample) |
| ZA (1) | ZA774527B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4172204A (en) * | 1977-10-07 | 1979-10-23 | Syntex (U.S.A.) Inc. | Method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and intermediates thereof |
| US4198422A (en) * | 1979-05-17 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Substituted 2,3-naphthimidazole carbamates and method |
| US4294844A (en) * | 1979-06-04 | 1981-10-13 | Syntex (U.S.A.) Inc. | Use of 4,5-dihydro-2-lower alkoxycarbonylamino-4-phenyl imidazoles and substituted phenyl derivatives thereof as anti-hypertensive agents |
| US4322421A (en) * | 1979-08-31 | 1982-03-30 | Syntex (U.S.A.) Inc. | 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydro-pyrimidine derivatives |
| YU204680A (en) * | 1979-08-31 | 1983-10-31 | Syntex Inc | Process for obtaining 4-phenyl-and 5-phenyl-1,4,5,6-tetrahydro pyrimidine derivatives |
| US4261995A (en) * | 1979-08-31 | 1981-04-14 | Syntex (U.S.A.) Inc. | 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives |
| US7063532B1 (en) | 1997-06-20 | 2006-06-20 | Align Technology, Inc. | Subdividing a digital dentition model |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080335A (en) * | 1975-07-28 | 1978-03-21 | Beecham Group Limited | Anorexic chromans |
-
1976
- 1976-07-26 US US05/708,651 patent/US4088771A/en not_active Expired - Lifetime
-
1977
- 1977-01-19 FI FI770159A patent/FI770159A7/fi not_active Application Discontinuation
- 1977-01-20 DK DK21177A patent/DK21177A/da unknown
- 1977-01-24 SE SE7700705A patent/SE7700705L/xx unknown
- 1977-07-20 NL NL7708084A patent/NL7708084A/xx not_active Application Discontinuation
- 1977-07-21 GB GB30729/77A patent/GB1569386A/en not_active Expired
- 1977-07-22 NZ NZ184714A patent/NZ184714A/xx unknown
- 1977-07-25 FR FR7722797A patent/FR2359828A1/fr active Granted
- 1977-07-25 BE BE179599A patent/BE857112R/xx active
- 1977-07-25 JP JP8914677A patent/JPS5315376A/ja active Pending
- 1977-07-26 AU AU27349/77A patent/AU2734977A/en active Pending
- 1977-07-26 ES ES461036A patent/ES461036A2/es not_active Expired
- 1977-07-26 ZA ZA00774527A patent/ZA774527B/xx unknown
- 1977-07-26 DE DE19772733698 patent/DE2733698A1/de active Pending
- 1977-10-11 ES ES463139A patent/ES463139A2/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2359828A1 (fr) | 1978-02-24 |
| FI770159A7 (enExample) | 1978-01-27 |
| NZ184714A (en) | 1979-10-25 |
| DK21177A (da) | 1978-01-27 |
| ES463139A2 (es) | 1978-10-16 |
| ES461036A2 (es) | 1978-06-01 |
| AU2734977A (en) | 1979-02-01 |
| FR2359828B1 (enExample) | 1979-07-20 |
| JPS5315376A (en) | 1978-02-13 |
| DE2733698A1 (de) | 1978-02-02 |
| NL7708084A (nl) | 1978-01-30 |
| SE7700705L (sv) | 1978-01-27 |
| US4088771A (en) | 1978-05-09 |
| ZA774527B (en) | 1979-02-28 |
| BE857112R (fr) | 1978-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3325361A (en) | Anticonvulsant agents | |
| CA1120928A (en) | Acetohydroxamic acids | |
| KR100467760B1 (ko) | 할로겐기가치환된2-페닐-1,2-에탄디올카바메이트화합물 | |
| US4146647A (en) | Substituted phenyl-amidines | |
| EP0007206B1 (en) | Phenethanolamines, their formulations, preparation and use | |
| CA1070697A (en) | 4,5 dihydro-2-lower-alkoxycarbonyl-amino-4-phenylimidazoles and substituted phenyl derivatives thereof | |
| US5646303A (en) | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein | |
| US5334720A (en) | Diphenyl-1-(aminoalkyl)-2-piperidinone and -2-pyrrolidinone derivatives having anticonvulsant properties | |
| US4628056A (en) | Novel oxopyrimidine derivatives, pharmaceutical compositions containing them and their use as anticonvulsant, antianxiety and muscle relaxant agents | |
| US6689808B2 (en) | Substituted phthalides, a process for their preparations and pharmaceutical compositions containing them | |
| GB1569386A (en) | 1-lower alkyl-4,5-dihydro-5-phenyl-2-lower alkoxy carbonylaminoimidazoles and substituted phenyl derivatives | |
| EP0039780A1 (fr) | Xanthines di- ou trisubstituées ayant des propriétés neuroleptiques, procédés de préparation et médicament les contenant | |
| US4004029A (en) | Compositions and method for treating epilepsy and convulsions | |
| HU193530B (en) | Process for preparing 9-/3-0-monosubstituted or 1,3-di-0-substituted propoxymethyl/-guanine derivatives and pharmaceutical compositions comprising such active substances | |
| DE2131034A1 (de) | Acylharnstoffe und verfahren zu ihrer herstellung | |
| SU1375132A3 (ru) | Способ получени производных иминотиазолидина или их гидрохлоридов | |
| EP0004529B1 (de) | Tantomere Arylaminoimidazolinderivate, deren Herstellung und sie enthaltende Arzneimittel zur Bekämpfung von Schmerzzuständen | |
| US4110463A (en) | Imidazole-2-carbamates | |
| US3915984A (en) | N-phenyl-carbamic acid-{8 imidazolyl-(1)-methyl{9 {0 esters | |
| US3242209A (en) | Iminomethyleneureas | |
| EP0024776B1 (en) | 4-phenyl and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives, pharmaceutical compositions containing said derivatives, and process for preparing said derivatives | |
| EP0054839A2 (de) | 2-Acylaminomethyl-1,4-benzodiazepine und deren Salze sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2337414C3 (de) | 1 (m-Chlorphenyl)-3- [2-(33-dimethylazetidin-1 -yl)ethyl] -2-imidazolidinon und dessen pharmazeutisch akzeptablen Salze sowie Verfahren zu deren Herstellung | |
| US4056525A (en) | 2,3-dialkoxy-3h-1,4-benzodiazepines | |
| DE1420954C (de) | Halogensubstituierte 5-Phenyl-2-aminooxazolon-(4)-derivate und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |