CA1043339A - 4-oxo-2-imidazolidinylidene ureas - Google Patents

4-oxo-2-imidazolidinylidene ureas

Info

Publication number: CA1043339A
Authority: CA; Canada
Prior art keywords: oxo; methyl; urea; imidazolidinylidene; hydrogen
Prior art date: 1973-10-19
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

Application number

CA211,775A

Other languages

English (en)

French (fr)

Other versions

CA211775S (en

Inventor

Chris R. Rasmussen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceuticals Inc

Original Assignee

McNeil Laboratories Inc

Priority date (The priority date 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 date listed.)

1973-10-19

Filing date

1974-10-18

Publication date

1978-11-28

1974-10-18 Application filed by McNeil Laboratories Inc filed Critical McNeil Laboratories Inc

1978-11-28 Application granted granted Critical

1978-11-28 Publication of CA1043339A publication Critical patent/CA1043339A/en

Status Expired legal-status Critical Current

Links

-1 4-oxo-2-imidazolidinylidene ureas Chemical class 0.000 title claims abstract description 12
235000013877 carbamide Nutrition 0.000 title abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
239000001257 hydrogen Substances 0.000 claims abstract description 28
125000003118 aryl group Chemical group 0.000 claims abstract description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims description 38
238000000034 method Methods 0.000 claims description 30
239000004202 carbamide Substances 0.000 claims description 23
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 22
229940109239 creatinine Drugs 0.000 claims description 19
YQLRKXVEALTVCZ-UHFFFAOYSA-N 2-isocyanato-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1N=C=O YQLRKXVEALTVCZ-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000012948 isocyanate Substances 0.000 claims description 5
HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 claims description 4
GUCKTQWFKFEVTN-UHFFFAOYSA-N 1-(3-bromophenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC(Br)=C1 GUCKTQWFKFEVTN-UHFFFAOYSA-N 0.000 claims description 3
FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 claims description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 11
239000000126 substance Substances 0.000 claims 11
DWPQODZAOSWNHB-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(3-methyl-5-oxo-4H-imidazol-2-yl)urea Chemical compound CN1CC(=O)N=C1NC(=O)NC1=CC=CC(Cl)=C1 DWPQODZAOSWNHB-UHFFFAOYSA-N 0.000 claims 2
VVSYKPWWZACODP-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound COC1=CC=CC(NC(=O)N=C2N(CC(=O)N2)C)=C1 VVSYKPWWZACODP-UHFFFAOYSA-N 0.000 claims 2
FKVLPIOPJSASLK-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(3-methylphenyl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC(C)=C1 FKVLPIOPJSASLK-UHFFFAOYSA-N 0.000 claims 2
UGAKYEVNTSKJHX-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(4-methylphenyl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=C(C)C=C1 UGAKYEVNTSKJHX-UHFFFAOYSA-N 0.000 claims 2
BSJGRAZXJZXELO-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-phenylurea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC=C1 BSJGRAZXJZXELO-UHFFFAOYSA-N 0.000 claims 2
RLMQUNASFASQQF-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=C(Cl)C=C1 RLMQUNASFASQQF-UHFFFAOYSA-N 0.000 claims 2
HBCKYXDOCVRYBP-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)N=C1N(C)CC(=O)N1 HBCKYXDOCVRYBP-UHFFFAOYSA-N 0.000 claims 2
QTPPSTCTONVWRD-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=C(C)C=CC=C1C QTPPSTCTONVWRD-UHFFFAOYSA-N 0.000 claims 1
VQVBCZQTXSHJGF-UHFFFAOYSA-N 1-bromo-3-isocyanatobenzene Chemical compound BrC1=CC=CC(N=C=O)=C1 VQVBCZQTXSHJGF-UHFFFAOYSA-N 0.000 claims 1
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 claims 1
NPOVTGVGOBJZPY-UHFFFAOYSA-N 1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1 NPOVTGVGOBJZPY-UHFFFAOYSA-N 0.000 claims 1
MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 8
239000003874 central nervous system depressant Substances 0.000 abstract description 4
239000002731 stomach secretion inhibitor Substances 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
239000000047 product Substances 0.000 description 25
241000700159 Rattus Species 0.000 description 20
229910001868 water Inorganic materials 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 13
230000000694 effects Effects 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 10
239000000243 solution Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000004044 response Effects 0.000 description 6
239000000725 suspension Substances 0.000 description 6
TYKJILJOXAHUFO-UHFFFAOYSA-N 2-amino-1,4-dihydroimidazol-5-one Chemical compound NC1=NC(=O)CN1 TYKJILJOXAHUFO-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
230000000049 anti-anxiety effect Effects 0.000 description 5
239000002249 anxiolytic agent Substances 0.000 description 5
230000037396 body weight Effects 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
239000008267 milk Substances 0.000 description 5
210000004080 milk Anatomy 0.000 description 5
235000013336 milk Nutrition 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000003556 assay Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000035939 shock Effects 0.000 description 4
239000007787 solid 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
NQLHETVWDMRIPV-UHFFFAOYSA-N 2-imino-1,3-dimethylimidazolidin-4-one Chemical compound CN1CC(=O)N(C)C1=N NQLHETVWDMRIPV-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000019901 Anxiety disease Diseases 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000001262 anti-secretory effect Effects 0.000 description 3
230000036506 anxiety Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
QSACPWSIIRFHHR-UHFFFAOYSA-N dimethylphenyl isocyanide Natural products CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
230000002787 reinforcement Effects 0.000 description 3
229960005453 strychnine Drugs 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241000699670 Mus sp. Species 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 2
239000003158 myorelaxant agent Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000013049 sediment Substances 0.000 description 2
210000002027 skeletal muscle Anatomy 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QJEFFCBCSNNXRH-UHFFFAOYSA-N 1-(1,3-dimethyl-4-oxoimidazolidin-2-ylidene)-3-(2,6-dimethylphenyl)urea Chemical compound CN1CC(=O)N(C)C1=NC(=O)NC1=C(C)C=CC=C1C QJEFFCBCSNNXRH-UHFFFAOYSA-N 0.000 description 1
XZGXSOBANCPPEP-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=C(Cl)C=CC=C1Cl XZGXSOBANCPPEP-UHFFFAOYSA-N 0.000 description 1
BHRPFIUBFPHGMF-UHFFFAOYSA-N 1-(3-chloro-2,6-dimethylphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=C(C)C=CC(Cl)=C1C BHRPFIUBFPHGMF-UHFFFAOYSA-N 0.000 description 1
RUEJBUCHAUGKRS-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(3-octyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CCCCCCCCN1CC(=O)NC1=NC(=O)NC1=CC=CC(Cl)=C1 RUEJBUCHAUGKRS-UHFFFAOYSA-N 0.000 description 1
UVMJRAGOQOABOE-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(5-oxo-1,4-dihydroimidazol-2-yl)urea Chemical compound ClC1=CC=CC(NC(=O)N=C2NC(=O)CN2)=C1 UVMJRAGOQOABOE-UHFFFAOYSA-N 0.000 description 1
SIQXOHSXPPLXBG-UHFFFAOYSA-N 1-chloro-3-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(Cl)C(C)=C1N=C=O SIQXOHSXPPLXBG-UHFFFAOYSA-N 0.000 description 1
GFFGYTMCNVMFAJ-UHFFFAOYSA-N 1-isocyanato-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(N=C=O)=C1 GFFGYTMCNVMFAJ-UHFFFAOYSA-N 0.000 description 1
KMAGLUVYQQBXIR-UHFFFAOYSA-N 2-amino-4,4-diphenyl-1h-imidazol-5-one Chemical compound O=C1NC(N)=NC1(C=1C=CC=CC=1)C1=CC=CC=C1 KMAGLUVYQQBXIR-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical group C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
206010065713 Gastric Fistula Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
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241000699666 Mus <mouse, genus> Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
208000000112 Myalgia Diseases 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
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210000001015 abdomen Anatomy 0.000 description 1
210000003815 abdominal wall Anatomy 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
GANYMSDHMBJFIL-UHFFFAOYSA-N acetonitrile;ethoxyethane Chemical compound CC#N.CCOCC GANYMSDHMBJFIL-UHFFFAOYSA-N 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
DNKYMRIVXIQCFO-UHFFFAOYSA-N benzene pentane Chemical compound CCCCC.CCCCC.C1=CC=CC=C1 DNKYMRIVXIQCFO-UHFFFAOYSA-N 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
238000007664 blowing Methods 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
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
230000002550 fecal effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000005065 mining Methods 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
230000003387 muscular Effects 0.000 description 1
WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000000902 placebo Substances 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000036642 wellbeing Effects 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/88—Nitrogen atoms, e.g. allantoin

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA211,775A 1973-10-19 1974-10-18 4-oxo-2-imidazolidinylidene ureas Expired CA1043339A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US40802273A	1973-10-19	1973-10-19
US50879574A	1974-09-23	1974-09-23

Publications (1)

Publication Number	Publication Date
CA1043339A true CA1043339A (en)	1978-11-28

Family

ID=27020109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA211,775A Expired CA1043339A (en)	1973-10-19	1974-10-18	4-oxo-2-imidazolidinylidene ureas

Country Status (22)

Country	Link
JP (1)	JPS5077367A (de)
AR (1)	AR210320A1 (de)
AT (1)	AT348536B (de)
BE (1)	BE821099A (de)
CA (1)	CA1043339A (de)
CH (1)	CH614198A5 (de)
DD (1)	DD114079A5 (de)
DE (1)	DE2448869A1 (de)
DK (1)	DK548874A (de)
ES (1)	ES431153A1 (de)
FI (1)	FI59993C (de)
FR (1)	FR2248042B1 (de)
GB (1)	GB1479909A (de)
HU (1)	HU170857B (de)
IE (1)	IE40067B1 (de)
IL (1)	IL45865A (de)
IN (1)	IN139447B (de)
NL (1)	NL7413718A (de)
NO (1)	NO141162C (de)
RO (1)	RO64926A (de)
SE (1)	SE414173B (de)
YU (1)	YU36932B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI800559A7 (fi) *	1979-03-14	1981-01-01	F Hoffmann La Roche & Co	Virtsa-ainejohdannaiset.
US4265900A (en) *	1979-10-29	1981-05-05	Mcneilab, Inc.	N-Aryl-N'-imidazol-2-ylureas
EP2335701B1 (de) *	2003-12-15	2012-07-11	Schering Corporation	Heterocyclische Aspartyl-Protease Inhibitoren
CA2899938C (en)	2013-02-12	2021-10-19	Buck Institute For Research On Aging	Hydantoins that modulate bace-mediated app processing

1974
- 1974-10-14 DE DE19742448869 patent/DE2448869A1/de not_active Withdrawn
- 1974-10-15 SE SE7412959A patent/SE414173B/xx unknown
- 1974-10-15 BE BE149558A patent/BE821099A/xx unknown
- 1974-10-16 AR AR256117A patent/AR210320A1/es active
- 1974-10-17 RO RO197480253A patent/RO64926A/ro unknown
- 1974-10-17 IL IL45865A patent/IL45865A/xx unknown
- 1974-10-17 CH CH1395174A patent/CH614198A5/xx not_active IP Right Cessation
- 1974-10-18 YU YU2797/74A patent/YU36932B/xx unknown
- 1974-10-18 DK DK548874A patent/DK548874A/da not_active Application Discontinuation
- 1974-10-18 FI FI3065/74A patent/FI59993C/fi active
- 1974-10-18 IE IE2146/74A patent/IE40067B1/xx unknown
- 1974-10-18 JP JP49119494A patent/JPS5077367A/ja active Pending
- 1974-10-18 NO NO743771A patent/NO141162C/no unknown
- 1974-10-18 AT AT840974A patent/AT348536B/de not_active IP Right Cessation
- 1974-10-18 ES ES431153A patent/ES431153A1/es not_active Expired
- 1974-10-18 GB GB45246/74A patent/GB1479909A/en not_active Expired
- 1974-10-18 HU HU74ME00001786A patent/HU170857B/hu unknown
- 1974-10-18 CA CA211,775A patent/CA1043339A/en not_active Expired
- 1974-10-18 FR FR7435155A patent/FR2248042B1/fr not_active Expired
- 1974-10-18 NL NL7413718A patent/NL7413718A/xx not_active Application Discontinuation
- 1974-10-21 DD DD181808A patent/DD114079A5/xx unknown
- 1974-11-07 IN IN2451/CAL/74A patent/IN139447B/en unknown

Also Published As

Publication number	Publication date
GB1479909A (en)	1977-07-13
YU279774A (en)	1982-06-18
DK548874A (de)	1975-07-07
FR2248042A1 (de)	1975-05-16
AU7443874A (en)	1976-04-29
FI59993B (fi)	1981-07-31
SE414173B (sv)	1980-07-14
DE2448869A1 (de)	1975-09-04
IL45865A (en)	1978-01-31
DD114079A5 (de)	1975-07-12
ES431153A1 (es)	1977-02-01
IN139447B (de)	1976-06-19
IL45865A0 (en)	1975-02-10
NL7413718A (nl)	1975-04-22
SE7412959L (de)	1975-04-21
FI306574A7 (de)	1975-04-20
NO141162B (no)	1979-10-15
FI59993C (fi)	1981-11-10
JPS5077367A (de)	1975-06-24
NO743771L (de)	1975-05-20
YU36932B (en)	1984-08-31
HU170857B (hu)	1977-09-28
IE40067L (en)	1975-04-19
IE40067B1 (en)	1979-02-28
RO64926A (fr)	1980-01-15
AR210320A1 (es)	1977-07-29
CH614198A5 (en)	1979-11-15
FR2248042B1 (de)	1978-07-21
ATA840974A (de)	1978-07-15
NO141162C (no)	1980-01-23
BE821099A (fr)	1975-04-15
AT348536B (de)	1979-02-26

Publication	Publication Date	Title
CY1446A (en)	1989-03-10	Chemical compounds derived from cyclobutene
EP0124476B1 (de)	1988-06-22	Carboxamide, Verfahren zur Herstellung und pharmazeutische Präparate, die diese enthalten
JPS5946221B2 (ja)	1984-11-10	複素環化合物の製法
DE2821410A1 (de)	1978-11-30	Aminoalkylbenzolderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen
US4265900A (en)	1981-05-05	N-Aryl-N'-imidazol-2-ylureas
US3983135A (en)	1976-09-28	4-Oxo-2-imidazolidinylidene ureas
CA1043339A (en)	1978-11-28	4-oxo-2-imidazolidinylidene ureas
US4025517A (en)	1977-05-24	4-Oxo-2-hexahydropyrimidinylidene ureas
US4665083A (en)	1987-05-12	Iminothiazolidine derivatives
US4046909A (en)	1977-09-06	Pyrrolidylidene, piperidylidene and hexahydroazepinylidene ureas as CNS depressants
KR880002706B1 (ko)	1988-12-26	설포닐 우레아의 제조방법
DE2723464A1 (de)	1977-12-08	Aryltrifluoraethylamine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
US3449357A (en)	1969-06-10	2-((2,6-substituted)phenoxymethyl)-2-imidazolines
US4649150A (en)	1987-03-10	Antiulcerogenic amidine derivatives of 2-substituted 4-phenylimidazole
US4072675A (en)	1978-02-07	N-phenyl amidines
DD258812A1 (de)	1988-08-03	Verfahren zur herstellung neuer ixoxazolderivate
US5087640A (en)	1992-02-11	Novel cyanoguanidine derivatives
US4001425A (en)	1977-01-04	Methods of treating hypertension and pharmaceutical compositions comprising 1-tertiary-alkyl-3-(substituted furyl)ureas as antihypertensive agents
US5021429A (en)	1991-06-04	Pharmacologically active aminoalkylphenyl compounds and their use
DE2313256A1 (de)	1973-09-20	1,2-benzisoxazolderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3021107A1 (de)	1981-12-17	Carbamoyloxyamino-1,4-benzodiazepine, verfahren zu irer herstellung und diese enthaltende arzneimittel
KR800000039B1 (ko)	1980-01-28	4-옥소-2-이미다조리디닐리덴 우레아의 제조방법
EP0004904B1 (de)	1981-07-29	2-Amino-3a,4,5,6-tetrahydro-perimidin-Derivate, diese enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DD210266A5 (de)	1984-06-06	Verfahren zur herstellung von 3-(ureidocyclohexylamino)-propan-1,2-diolderivaten
US3998958A (en)	1976-12-21	Pyrrolidylidene, piperidylidene and hexahydroazepinylidene ureas as CNS depressants