JPS587619B2 - ピロリジリデン尿素、ピペリジデン尿素およびヘキサヒドロアゼピニリデン尿素の製造方法 - Google Patents
ピロリジリデン尿素、ピペリジデン尿素およびヘキサヒドロアゼピニリデン尿素の製造方法Info
- Publication number
- JPS587619B2 JPS587619B2 JP48031342A JP3134273A JPS587619B2 JP S587619 B2 JPS587619 B2 JP S587619B2 JP 48031342 A JP48031342 A JP 48031342A JP 3134273 A JP3134273 A JP 3134273A JP S587619 B2 JPS587619 B2 JP S587619B2
- Authority
- JP
- Japan
- Prior art keywords
- urea
- methyl
- pyrrolidylidene
- benzene
- mol
- 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
- COXWIKJGOHZKIO-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-ylurea Chemical compound NC(=O)NC1=NCCC1 COXWIKJGOHZKIO-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- ITDOBWWRWYKLQJ-UHFFFAOYSA-N 2,3,4,5-tetrahydropyridin-6-ylurea Chemical compound NC(=O)NC1=NCCCC1 ITDOBWWRWYKLQJ-UHFFFAOYSA-N 0.000 title description 2
- GBGPFEUIUBKMBG-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2h-azepin-7-ylurea Chemical compound NC(=O)NC1=NCCCCC1 GBGPFEUIUBKMBG-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 30
- -1 methylthiophenyl Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 176
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 114
- 235000013877 carbamide Nutrition 0.000 description 63
- 239000004202 carbamide Substances 0.000 description 57
- 239000000243 solution Substances 0.000 description 46
- 238000002844 melting Methods 0.000 description 40
- 230000008018 melting Effects 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 239000000047 product Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000012458 free base Substances 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 6
- KGVDKNYFTLFECV-UHFFFAOYSA-N 1-methylpyrrolidin-2-imine Chemical compound CN1CCCC1=N KGVDKNYFTLFECV-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000008267 milk Substances 0.000 description 6
- 210000004080 milk Anatomy 0.000 description 6
- 235000013336 milk Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- YQLRKXVEALTVCZ-UHFFFAOYSA-N 2-isocyanato-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1N=C=O YQLRKXVEALTVCZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 210000003169 central nervous system Anatomy 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
- 229940127204 compound 29 Drugs 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- QSACPWSIIRFHHR-UHFFFAOYSA-N dimethylphenyl isocyanide Natural products CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- VAODBZOYKXWEQR-UHFFFAOYSA-N 1-(1-methylpyrrolidin-2-ylidene)-3-(4-nitrophenyl)urea Chemical compound CN1CCCC1=NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 VAODBZOYKXWEQR-UHFFFAOYSA-N 0.000 description 2
- KJMVNLKAOWEYRF-UHFFFAOYSA-N 1-(1-methylpyrrolidin-2-ylidene)-3-phenylurea Chemical compound CN1CCCC1=NC(=O)NC1=CC=CC=C1 KJMVNLKAOWEYRF-UHFFFAOYSA-N 0.000 description 2
- PAXRPWSXCPTPCA-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(1-methylpyrrolidin-2-ylidene)urea Chemical compound CN1CCCC1=NC(=O)NC1=C(C)C=CC=C1C PAXRPWSXCPTPCA-UHFFFAOYSA-N 0.000 description 2
- BKJABLMNBSVKCV-UHFFFAOYSA-N 1-isocyanato-3-methylsulfanylbenzene Chemical compound CSC1=CC=CC(N=C=O)=C1 BKJABLMNBSVKCV-UHFFFAOYSA-N 0.000 description 2
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 2
- DHGUMNJVFYRSIG-UHFFFAOYSA-N 2,3,4,5-tetrahydropyridin-6-amine Chemical compound NC1=NCCCC1 DHGUMNJVFYRSIG-UHFFFAOYSA-N 0.000 description 2
- GTLJSJNKRLFVSJ-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2h-azepin-7-amine Chemical compound N=C1CCCCCN1 GTLJSJNKRLFVSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229910004039 HBF4 Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001279009 Strychnos toxifera Species 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
- 241000906446 Theraps Species 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- LXXTVGKSGJADFU-UHFFFAOYSA-N (4-nitrophenyl)urea Chemical compound NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 LXXTVGKSGJADFU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ASEPHGOCQCYMTN-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-imine Chemical compound CC1CCC(=N)N1C ASEPHGOCQCYMTN-UHFFFAOYSA-N 0.000 description 1
- UUVOERGIZPSCTE-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)N=C1N(CC=2C=CC=CC=2)CCC1 UUVOERGIZPSCTE-UHFFFAOYSA-N 0.000 description 1
- NRDOKZRJTSMHLS-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-(3-chloro-4-fluorophenyl)urea Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)N=C1N(CC=2C=CC=CC=2)CCC1 NRDOKZRJTSMHLS-UHFFFAOYSA-N 0.000 description 1
- IRECNTZCOKMDSS-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-(3-chlorophenyl)urea Chemical compound ClC1=CC=CC(NC(=O)N=C2N(CCC2)CC=2C=CC=CC=2)=C1 IRECNTZCOKMDSS-UHFFFAOYSA-N 0.000 description 1
- JZJGALBPEFDZFD-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-(4-fluoro-3-nitrophenyl)urea Chemical compound C1=C(F)C([N+](=O)[O-])=CC(NC(=O)N=C2N(CCC2)CC=2C=CC=CC=2)=C1 JZJGALBPEFDZFD-UHFFFAOYSA-N 0.000 description 1
- MAMMJYHQNQQJIV-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)N=C1N(CC=2C=CC=CC=2)CCC1 MAMMJYHQNQQJIV-UHFFFAOYSA-N 0.000 description 1
- YHMKXDFGWNKURT-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)N=C1N(CC=2C=CC=CC=2)CCC1 YHMKXDFGWNKURT-UHFFFAOYSA-N 0.000 description 1
- DMGYISBTKKRKOT-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-[3-(trifluoromethyl)phenyl]urea;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(NC(=O)N=C2N(CCC2)CC=2C=CC=CC=2)=C1 DMGYISBTKKRKOT-UHFFFAOYSA-N 0.000 description 1
- REAFHDJMSKPOQX-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)N=C2N(CCC2)CC=2C=CC=CC=2)=C1 REAFHDJMSKPOQX-UHFFFAOYSA-N 0.000 description 1
- CEDWPQRAOSMZKS-UHFFFAOYSA-N 1-(1-benzylpyrrolidin-2-ylidene)-3-phenylurea Chemical compound C1CCN(CC=2C=CC=CC=2)C1=NC(=O)NC1=CC=CC=C1 CEDWPQRAOSMZKS-UHFFFAOYSA-N 0.000 description 1
- DHXXNASEMJOAIX-UHFFFAOYSA-N 1-(1-butylpyrrolidin-2-ylidene)-3-(2,6-dimethylphenyl)urea Chemical compound CCCCN1CCCC1=NC(=O)NC1=C(C)C=CC=C1C DHXXNASEMJOAIX-UHFFFAOYSA-N 0.000 description 1
- PSQJVEVKDLZJQK-UHFFFAOYSA-N 1-(1-butylpyrrolidin-2-ylidene)-3-(3-chloro-2-methylphenyl)urea;hydrate;hydrochloride Chemical compound O.Cl.CCCCN1CCCC1=NC(=O)NC1=CC=CC(Cl)=C1C PSQJVEVKDLZJQK-UHFFFAOYSA-N 0.000 description 1
- ZFVGJPJHQLLUCF-UHFFFAOYSA-N 1-(1-butylpyrrolidin-2-ylidene)-3-(3-chlorophenyl)urea Chemical compound CCCCN1CCCC1=NC(=O)NC1=CC=CC(Cl)=C1 ZFVGJPJHQLLUCF-UHFFFAOYSA-N 0.000 description 1
- GAAMPAAKCYOPFV-UHFFFAOYSA-N 1-(1-methylazepan-2-ylidene)-3-naphthalen-1-ylurea Chemical compound CN1CCCCCC1=NC(=O)NC1=CC=CC2=CC=CC=C12 GAAMPAAKCYOPFV-UHFFFAOYSA-N 0.000 description 1
- CCUGBEXWPJBQNQ-UHFFFAOYSA-N 1-(1-methylpiperidin-2-ylidene)-3-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)N=C2N(CCCC2)C)=C1 CCUGBEXWPJBQNQ-UHFFFAOYSA-N 0.000 description 1
- DNRIKUKZNYFONM-UHFFFAOYSA-N 1-(1-methylpiperidin-2-ylidene)-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)N=C1N(C)CCCC1 DNRIKUKZNYFONM-UHFFFAOYSA-N 0.000 description 1
- MMNUVEJHPQKMEN-UHFFFAOYSA-N 1-(1-methylpiperidin-2-ylidene)-3-phenylurea Chemical compound CN1CCCCC1=NC(=O)NC1=CC=CC=C1 MMNUVEJHPQKMEN-UHFFFAOYSA-N 0.000 description 1
- AXMGITIIUSOPCY-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-1-methyl-3-(1-methylpiperidin-2-ylidene)urea Chemical compound COC1=CC=C(OC)C(N(C)C(=O)N=C2N(CCCC2)C)=C1 AXMGITIIUSOPCY-UHFFFAOYSA-N 0.000 description 1
- CKGAIEIRVSZDRU-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-1-methyl-3-(1-methylpyrrolidin-2-ylidene)urea Chemical compound COC1=CC=C(OC)C(N(C)C(=O)N=C2N(CCC2)C)=C1 CKGAIEIRVSZDRU-UHFFFAOYSA-N 0.000 description 1
- NHCCTBWOAODARV-UHFFFAOYSA-N 1-(2,6-dimethoxyphenyl)-3-(1-methylpiperidin-2-ylidene)urea Chemical compound COC1=CC=CC(OC)=C1NC(=O)N=C1N(C)CCCC1 NHCCTBWOAODARV-UHFFFAOYSA-N 0.000 description 1
- ZMRXHCWGDDGDRQ-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(1,5-dimethylpyrrolidin-2-ylidene)urea Chemical compound CN1C(C)CCC1=NC(=O)NC1=C(C)C=CC=C1C ZMRXHCWGDDGDRQ-UHFFFAOYSA-N 0.000 description 1
- PVNGOCNXOPJFAM-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(1-ethylpyrrolidin-2-ylidene)urea Chemical compound CCN1CCCC1=NC(=O)NC1=C(C)C=CC=C1C PVNGOCNXOPJFAM-UHFFFAOYSA-N 0.000 description 1
- VTGSBSWQVDDPLJ-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(1-methylpiperidin-2-ylidene)urea Chemical compound CN1CCCCC1=NC(=O)NC1=C(C)C=CC=C1C VTGSBSWQVDDPLJ-UHFFFAOYSA-N 0.000 description 1
- KIEKZKLQIRABBK-UHFFFAOYSA-N 1-(2-isocyanatophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1N=C=O KIEKZKLQIRABBK-UHFFFAOYSA-N 0.000 description 1
- TXRCFVVZNXALKB-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-(1-methylpyrrolidin-2-ylidene)urea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)N=C1N(C)CCC1 TXRCFVVZNXALKB-UHFFFAOYSA-N 0.000 description 1
- XIBORKBMOQNCTL-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-(1-methylpyrrolidin-2-ylidene)urea Chemical compound CN1CCCC1=NC(=O)NC1=CC=CC(C(C)=O)=C1 XIBORKBMOQNCTL-UHFFFAOYSA-N 0.000 description 1
- FGRVKUUZWATAPG-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(1,5-dimethylpyrrolidin-2-ylidene)urea Chemical compound CN1C(C)CCC1=NC(=O)NC1=CC=CC(Cl)=C1 FGRVKUUZWATAPG-UHFFFAOYSA-N 0.000 description 1
- HHLZNCAJWUTDFB-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(1-ethylpyrrolidin-2-ylidene)urea Chemical compound CCN1CCCC1=NC(=O)NC1=CC=CC(Cl)=C1 HHLZNCAJWUTDFB-UHFFFAOYSA-N 0.000 description 1
- SINSISHOQIDCEP-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(1-methylpyrrolidin-2-ylidene)urea Chemical compound CN1CCCC1=NC(=O)NC1=CC=CC(Cl)=C1 SINSISHOQIDCEP-UHFFFAOYSA-N 0.000 description 1
- JASTZOAHAWBRLM-UHFFFAOYSA-N 1-(3-isocyanatophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N=C=O)=C1 JASTZOAHAWBRLM-UHFFFAOYSA-N 0.000 description 1
- BPCSJNVZNFSKBN-UHFFFAOYSA-N 1-(4-fluoro-3-nitrophenyl)-3-(1-methylpiperidin-3-ylidene)urea Chemical compound C1N(C)CCCC1=NC(=O)NC1=CC=C(F)C([N+]([O-])=O)=C1 BPCSJNVZNFSKBN-UHFFFAOYSA-N 0.000 description 1
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- OISVAZWPUJOXEH-UHFFFAOYSA-N 1-butyl-1-(2-chlorophenyl)-3-(1-methylpyrrolidin-2-ylidene)urea Chemical compound C=1C=CC=C(Cl)C=1N(CCCC)C(=O)N=C1CCCN1C OISVAZWPUJOXEH-UHFFFAOYSA-N 0.000 description 1
- WEPYOPYMWSHRIW-UHFFFAOYSA-N 1-chloro-2-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(N=C=O)=C1 WEPYOPYMWSHRIW-UHFFFAOYSA-N 0.000 description 1
- NGQMCUWZGVMILT-UHFFFAOYSA-N 1-chloro-3-isocyanato-2-methylbenzene Chemical compound CC1=C(Cl)C=CC=C1N=C=O NGQMCUWZGVMILT-UHFFFAOYSA-N 0.000 description 1
- ZPQNQBQLWPXWAW-UHFFFAOYSA-N 1-ethyl-3-(1-methylpyrrolidin-2-ylidene)-1-phenylurea Chemical compound C=1C=CC=CC=1N(CC)C(=O)N=C1CCCN1C ZPQNQBQLWPXWAW-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- SAMNTACLZJOQNJ-UHFFFAOYSA-N 1-methyl-3-(1-methylpiperidin-2-ylidene)-1-[2-(trifluoromethyl)phenyl]urea Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C(=O)N=C1CCCCN1C SAMNTACLZJOQNJ-UHFFFAOYSA-N 0.000 description 1
- ONDCCQVACTUWJH-UHFFFAOYSA-N 1-methyl-3-(1-methylpiperidin-2-ylidene)-1-phenylurea Chemical compound C=1C=CC=CC=1N(C)C(=O)N=C1CCCCN1C ONDCCQVACTUWJH-UHFFFAOYSA-N 0.000 description 1
- QCHYFRPQMBYVGC-UHFFFAOYSA-N 1-methylazepan-2-imine Chemical compound CN1CCCCCC1=N QCHYFRPQMBYVGC-UHFFFAOYSA-N 0.000 description 1
- XMNODJDCVGLMPH-UHFFFAOYSA-N 1-methylpiperidin-2-imine;hydrochloride Chemical compound Cl.CN1CCCCC1=N XMNODJDCVGLMPH-UHFFFAOYSA-N 0.000 description 1
- KPPNLSKVTKSSTG-UHFFFAOYSA-N 2-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1Cl KPPNLSKVTKSSTG-UHFFFAOYSA-N 0.000 description 1
- CKQHAYFOPRIUOM-UHFFFAOYSA-N 3'-Aminoacetophenone Chemical compound CC(=O)C1=CC=CC(N)=C1 CKQHAYFOPRIUOM-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- KCHLDNLIJVSRPK-UHFFFAOYSA-N 3-methylsulfanylaniline Chemical compound CSC1=CC=CC(N)=C1 KCHLDNLIJVSRPK-UHFFFAOYSA-N 0.000 description 1
- WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
- NYTBFFZQIRSGLL-UHFFFAOYSA-N 4-isocyanato-1,2-dimethoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1OC NYTBFFZQIRSGLL-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000009227 behaviour therapy Methods 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960002944 cyclofenil Drugs 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical group [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 229960005337 lysine hydrochloride Drugs 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- USRHDGLFPXTWQK-UHFFFAOYSA-N n-ethyl-n-(2-ethylphenyl)carbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=CC=C1CC USRHDGLFPXTWQK-UHFFFAOYSA-N 0.000 description 1
- CDGCUPPKLDOYGV-UHFFFAOYSA-N n-ethyl-n-phenylcarbamoyl chloride Chemical compound CCN(C(Cl)=O)C1=CC=CC=C1 CDGCUPPKLDOYGV-UHFFFAOYSA-N 0.000 description 1
- CPGWSLFYXMRNDV-UHFFFAOYSA-N n-methyl-n-phenylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1=CC=CC=C1 CPGWSLFYXMRNDV-UHFFFAOYSA-N 0.000 description 1
- YSBUANSGDLZTKV-UHFFFAOYSA-N n-phenylcarbamoyl chloride Chemical compound ClC(=O)NC1=CC=CC=C1 YSBUANSGDLZTKV-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002746 orthostatic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 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
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4458—Non condensed piperidines, e.g. piperocaine only substituted in position 2, e.g. methylphenidate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23581672A | 1972-03-17 | 1972-03-17 | |
| US235816 | 1972-03-17 | ||
| US335845 | 1973-02-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS4911872A JPS4911872A (enrdf_load_stackoverflow) | 1974-02-01 |
| JPS587619B2 true JPS587619B2 (ja) | 1983-02-10 |
Family
ID=22887026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48031342A Expired JPS587619B2 (ja) | 1972-03-17 | 1973-03-17 | ピロリジリデン尿素、ピペリジデン尿素およびヘキサヒドロアゼピニリデン尿素の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS587619B2 (enrdf_load_stackoverflow) |
| HU (1) | HU164938B (enrdf_load_stackoverflow) |
| SE (1) | SE390964B (enrdf_load_stackoverflow) |
| YU (1) | YU36293B (enrdf_load_stackoverflow) |
| ZA (1) | ZA731860B (enrdf_load_stackoverflow) |
-
1973
- 1973-03-15 SE SE7303623A patent/SE390964B/xx unknown
- 1973-03-16 HU HUMA2462A patent/HU164938B/hu unknown
- 1973-03-16 YU YU706/73A patent/YU36293B/xx unknown
- 1973-03-16 ZA ZA731860A patent/ZA731860B/xx unknown
- 1973-03-17 JP JP48031342A patent/JPS587619B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE390964B (sv) | 1977-01-31 |
| AU5346073A (en) | 1974-09-19 |
| YU36293B (en) | 1982-06-18 |
| ZA731860B (en) | 1974-11-27 |
| JPS4911872A (enrdf_load_stackoverflow) | 1974-02-01 |
| YU70673A (en) | 1981-08-31 |
| HU164938B (enrdf_load_stackoverflow) | 1974-05-28 |
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