CA1070697A - 4,5 dihydro-2-lower-alkoxycarbonyl-amino-4-phenylimidazoles and substituted phenyl derivatives thereof - Google Patents
4,5 dihydro-2-lower-alkoxycarbonyl-amino-4-phenylimidazoles and substituted phenyl derivatives thereofInfo
- Publication number
- CA1070697A CA1070697A CA257,631A CA257631A CA1070697A CA 1070697 A CA1070697 A CA 1070697A CA 257631 A CA257631 A CA 257631A CA 1070697 A CA1070697 A CA 1070697A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- dihydro
- beta
- prepared
- methoxycarbonylaminoimidazole
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 274
- 238000000034 method Methods 0.000 claims abstract description 208
- 150000003839 salts Chemical class 0.000 claims abstract description 127
- -1 chloro, bromo, iodo Chemical group 0.000 claims abstract description 119
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 91
- 239000001257 hydrogen Substances 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 16
- 230000008569 process Effects 0.000 claims description 136
- 239000000203 mixture Substances 0.000 claims description 90
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 34
- KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 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 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 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 claims description 16
- 239000012458 free base Substances 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- SCENJXMYGONCSK-UHFFFAOYSA-N methyl n-[5-(2-methylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1C SCENJXMYGONCSK-UHFFFAOYSA-N 0.000 claims description 9
- NACPWUMSPVYYFT-UHFFFAOYSA-N methyl n-[5-(3-fluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound N1C(NC(=O)OC)=NCC1C1=CC=CC(F)=C1 NACPWUMSPVYYFT-UHFFFAOYSA-N 0.000 claims description 8
- OLLVZDTWVNJNSN-UHFFFAOYSA-N methyl n-[5-(3-methylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(C)=C1 OLLVZDTWVNJNSN-UHFFFAOYSA-N 0.000 claims description 8
- AUNRPCRRCFPQJS-UHFFFAOYSA-N methyl n-[5-(2-ethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCOC1=CC=CC=C1C1N=C(NC(=O)OC)NC1 AUNRPCRRCFPQJS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- COJIWGFZGMBLRV-UHFFFAOYSA-N methyl n-[5-(3-methoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(OC)=C1 COJIWGFZGMBLRV-UHFFFAOYSA-N 0.000 claims description 6
- KPLTVMAZMSYGGH-UHFFFAOYSA-N methyl n-[5-(4-chlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(Cl)C=C1 KPLTVMAZMSYGGH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 5
- UIPVWSZQCRYQKY-UHFFFAOYSA-N methyl n-[5-(4-methylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(C)C=C1 UIPVWSZQCRYQKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- WKFHCBPNWQSRAN-UHFFFAOYSA-N methyl n-[5-(2-bromophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1Br WKFHCBPNWQSRAN-UHFFFAOYSA-N 0.000 claims description 4
- PXAFVMSGRCJTBU-UHFFFAOYSA-N methyl n-[5-(2-chlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1Cl PXAFVMSGRCJTBU-UHFFFAOYSA-N 0.000 claims description 4
- LKQNTDMZVXADOZ-UHFFFAOYSA-N methyl n-[5-(2-fluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound N1C(NC(=O)OC)=NCC1C1=CC=CC=C1F LKQNTDMZVXADOZ-UHFFFAOYSA-N 0.000 claims description 4
- LRXOSVQHYWVZRI-UHFFFAOYSA-N methyl n-[5-(2-iodophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1I LRXOSVQHYWVZRI-UHFFFAOYSA-N 0.000 claims description 4
- CXMLQTOTIFQLJW-UHFFFAOYSA-N methyl n-[5-(4-fluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(F)C=C1 CXMLQTOTIFQLJW-UHFFFAOYSA-N 0.000 claims description 4
- CCCMYBZGMWPGAX-UHFFFAOYSA-N methyl n-[5-(4-hydroxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(O)C=C1 CCCMYBZGMWPGAX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- RDXKDYIMJXATGU-UHFFFAOYSA-N methyl n-[5-(2,4-diethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCOC1=CC(OCC)=CC=C1C1N=C(NC(=O)OC)NC1 RDXKDYIMJXATGU-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- UEAZHXZPNBDPJP-UHFFFAOYSA-N methyl n-[5-(2-methoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1OC UEAZHXZPNBDPJP-UHFFFAOYSA-N 0.000 claims description 3
- GNIZQSUJWQKUDE-UHFFFAOYSA-N methyl n-[5-(3,5-difluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(F)=CC(F)=C1 GNIZQSUJWQKUDE-UHFFFAOYSA-N 0.000 claims description 3
- LUPZGMPBLXFXEZ-UHFFFAOYSA-N methyl n-[5-(3-chlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(Cl)=C1 LUPZGMPBLXFXEZ-UHFFFAOYSA-N 0.000 claims description 3
- QXXCSFQQXIZWFF-UHFFFAOYSA-N methyl n-[5-(4-ethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1=CC(OCC)=CC=C1C1N=C(NC(=O)OC)NC1 QXXCSFQQXIZWFF-UHFFFAOYSA-N 0.000 claims description 3
- ZLDOJTHEEJPHCD-UHFFFAOYSA-N methyl n-[5-(4-ethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1=CC(CC)=CC=C1C1N=C(NC(=O)OC)NC1 ZLDOJTHEEJPHCD-UHFFFAOYSA-N 0.000 claims description 3
- UEXSJZQANZASTC-UHFFFAOYSA-N methyl n-[5-(4-hexylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1=CC(CCCCCC)=CC=C1C1N=C(NC(=O)OC)NC1 UEXSJZQANZASTC-UHFFFAOYSA-N 0.000 claims description 3
- WDBCIKBJISOGJW-UHFFFAOYSA-N methyl n-[5-(2,5-difluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(F)=CC=C1F WDBCIKBJISOGJW-UHFFFAOYSA-N 0.000 claims description 2
- XIINOCXUFYAACI-UHFFFAOYSA-N methyl n-[5-(2,5-dimethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(C)=CC=C1C XIINOCXUFYAACI-UHFFFAOYSA-N 0.000 claims description 2
- FOEBGTBETWQAQU-UHFFFAOYSA-N methyl n-[5-(2,6-dibromophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=C(Br)C=CC=C1Br FOEBGTBETWQAQU-UHFFFAOYSA-N 0.000 claims description 2
- OYCGJUPVHCQMLQ-UHFFFAOYSA-N methyl n-[5-(3,4-difluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(F)C(F)=C1 OYCGJUPVHCQMLQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical group [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- USZJSWGRYCQBMT-UHFFFAOYSA-N methyl n-[2-(1,3-benzodioxol-5-yl)imidazolidin-2-yl]carbamate Chemical compound C=1C=C2OCOC2=CC=1C1(NC(=O)OC)NCCN1 USZJSWGRYCQBMT-UHFFFAOYSA-N 0.000 claims 2
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- ZPESCLUTTFJXPZ-UHFFFAOYSA-N methyl n-[5-(2,3-difluorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(F)=C1F ZPESCLUTTFJXPZ-UHFFFAOYSA-N 0.000 claims 1
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- 230000002159 abnormal effect Effects 0.000 abstract description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
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- 239000000047 product Substances 0.000 description 26
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 23
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- 235000011167 hydrochloric acid Nutrition 0.000 description 17
- 229960000443 hydrochloric acid Drugs 0.000 description 17
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 229960001701 chloroform Drugs 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
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- UYCJLHOFBCOWPW-UHFFFAOYSA-N methyl n-(7,7a-dihydroimidazo[1,5-b][1,4,2]dioxazol-5-yl)carbamate Chemical compound O1CON2C(NC(=O)OC)=NCC21 UYCJLHOFBCOWPW-UHFFFAOYSA-N 0.000 description 1
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- QGLHWLHLKXWMBJ-UHFFFAOYSA-N methyl n-[5-(2,3-diethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCC1=CC=CC(C2N=C(NC(=O)OC)NC2)=C1CC QGLHWLHLKXWMBJ-UHFFFAOYSA-N 0.000 description 1
- CTOXMVCDUSVTLJ-UHFFFAOYSA-N methyl n-[5-(2,3-dihydroxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(O)=C1O CTOXMVCDUSVTLJ-UHFFFAOYSA-N 0.000 description 1
- XSEFPDQVUQIKKY-UHFFFAOYSA-N methyl n-[5-(2,3-dimethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(OC)=C1OC XSEFPDQVUQIKKY-UHFFFAOYSA-N 0.000 description 1
- YTRMMDLFEDZUMJ-UHFFFAOYSA-N methyl n-[5-(2,3-dimethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC(C)=C1C YTRMMDLFEDZUMJ-UHFFFAOYSA-N 0.000 description 1
- PCPZBOKNBSFYEY-UHFFFAOYSA-N methyl n-[5-(2,4-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(Cl)C=C1Cl PCPZBOKNBSFYEY-UHFFFAOYSA-N 0.000 description 1
- SIFTYLPDKGHPHN-UHFFFAOYSA-N methyl n-[5-(2,4-diethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCC1=CC(CC)=CC=C1C1N=C(NC(=O)OC)NC1 SIFTYLPDKGHPHN-UHFFFAOYSA-N 0.000 description 1
- DNDIVVXVULHIME-UHFFFAOYSA-N methyl n-[5-(2,4-dihydroxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(O)C=C1O DNDIVVXVULHIME-UHFFFAOYSA-N 0.000 description 1
- XTQQSBAHNOAASS-UHFFFAOYSA-N methyl n-[5-(2,4-diiodophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(I)C=C1I XTQQSBAHNOAASS-UHFFFAOYSA-N 0.000 description 1
- PKBMWEGQPFCCHA-UHFFFAOYSA-N methyl n-[5-(2,4-dimethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(C)C=C1C PKBMWEGQPFCCHA-UHFFFAOYSA-N 0.000 description 1
- IQLWPTYYUBLTOM-UHFFFAOYSA-N methyl n-[5-(2,5-diethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCOC1=CC=C(OCC)C(C2N=C(NC(=O)OC)NC2)=C1 IQLWPTYYUBLTOM-UHFFFAOYSA-N 0.000 description 1
- LDXREGQSDVZIIZ-UHFFFAOYSA-N methyl n-[5-(2,5-diethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCC1=CC=C(CC)C(C2N=C(NC(=O)OC)NC2)=C1 LDXREGQSDVZIIZ-UHFFFAOYSA-N 0.000 description 1
- WFJWKPRYIYDTEI-UHFFFAOYSA-N methyl n-[5-(2,5-dihydroxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(O)=CC=C1O WFJWKPRYIYDTEI-UHFFFAOYSA-N 0.000 description 1
- GXJDFSBDCDXQKG-UHFFFAOYSA-N methyl n-[5-(2,5-dimethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(OC)=CC=C1OC GXJDFSBDCDXQKG-UHFFFAOYSA-N 0.000 description 1
- RVRJSSDYLIROOU-UHFFFAOYSA-N methyl n-[5-(2,6-diethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCC1=CC=CC(CC)=C1C1N=C(NC(=O)OC)NC1 RVRJSSDYLIROOU-UHFFFAOYSA-N 0.000 description 1
- USOQWKPXJDDCDB-UHFFFAOYSA-N methyl n-[5-(2,6-dihydroxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=C(O)C=CC=C1O USOQWKPXJDDCDB-UHFFFAOYSA-N 0.000 description 1
- VYWPLXYYADKISQ-UHFFFAOYSA-N methyl n-[5-(2,6-dipropylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCCC1=CC=CC(CCC)=C1C1N=C(NC(=O)OC)NC1 VYWPLXYYADKISQ-UHFFFAOYSA-N 0.000 description 1
- KKAGJZBREFIUNM-UHFFFAOYSA-N methyl n-[5-(2-hexylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound CCCCCCC1=CC=CC=C1C1N=C(NC(=O)OC)NC1 KKAGJZBREFIUNM-UHFFFAOYSA-N 0.000 description 1
- RGIDCVHTNAYXBC-UHFFFAOYSA-N methyl n-[5-(2-propan-2-ylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=CC=C1C(C)C RGIDCVHTNAYXBC-UHFFFAOYSA-N 0.000 description 1
- FRKGYMQJUJBMPT-UHFFFAOYSA-N methyl n-[5-(3,4-dibromophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(Br)C(Br)=C1 FRKGYMQJUJBMPT-UHFFFAOYSA-N 0.000 description 1
- KVEVRJKQMABTRJ-UHFFFAOYSA-N methyl n-[5-(3,4-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(Cl)C(Cl)=C1 KVEVRJKQMABTRJ-UHFFFAOYSA-N 0.000 description 1
- HTDZFHYECYNVCG-UHFFFAOYSA-N methyl n-[5-(3,4-dimethylphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC=C(C)C(C)=C1 HTDZFHYECYNVCG-UHFFFAOYSA-N 0.000 description 1
- LLEIQWZCUAAAGA-UHFFFAOYSA-N methyl n-[5-(3,5-dibromophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(Br)=CC(Br)=C1 LLEIQWZCUAAAGA-UHFFFAOYSA-N 0.000 description 1
- BYAPBUKIAFIJQG-UHFFFAOYSA-N methyl n-[5-(3,5-dichlorophenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(Cl)=CC(Cl)=C1 BYAPBUKIAFIJQG-UHFFFAOYSA-N 0.000 description 1
- LZGYYMGZHLWMIH-UHFFFAOYSA-N methyl n-[5-(3,5-dihydroxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(O)=CC(O)=C1 LZGYYMGZHLWMIH-UHFFFAOYSA-N 0.000 description 1
- HAAZHULWKKXGNT-UHFFFAOYSA-N methyl n-[5-(3,5-dimethoxyphenyl)-4,5-dihydro-1h-imidazol-2-yl]carbamate Chemical compound C1NC(NC(=O)OC)=NC1C1=CC(OC)=CC(OC)=C1 HAAZHULWKKXGNT-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59969475A | 1975-07-28 | 1975-07-28 | |
| US59955175A | 1975-07-28 | 1975-07-28 | |
| US68268276A | 1976-05-03 | 1976-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070697A true CA1070697A (en) | 1980-01-29 |
Family
ID=27416783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA257,631A Expired CA1070697A (en) | 1975-07-28 | 1976-07-23 | 4,5 dihydro-2-lower-alkoxycarbonyl-amino-4-phenylimidazoles and substituted phenyl derivatives thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4080335A (enExample) |
| AT (1) | AT353263B (enExample) |
| AU (1) | AU504595B2 (enExample) |
| BE (1) | BE844515A (enExample) |
| CA (1) | CA1070697A (enExample) |
| DE (1) | DE2633679A1 (enExample) |
| FR (1) | FR2319349A1 (enExample) |
| GB (1) | GB1519689A (enExample) |
| NL (1) | NL7608383A (enExample) |
| SE (1) | SE7608479L (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088771A (en) * | 1976-07-26 | 1978-05-09 | Syntex (U.S.A.) Inc. | 1-Lower alkyl-4,5-dihydro-5-phenyl-2-lower alkoxy carbonylaminoimidazoles and substituted phenyl derivatives thereof |
| US4110463A (en) * | 1977-06-03 | 1978-08-29 | Syntex (U.S.A.) Inc. | Imidazole-2-carbamates |
| 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 |
| 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 |
| 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 |
| US4261995A (en) * | 1979-08-31 | 1981-04-14 | Syntex (U.S.A.) Inc. | 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives |
| US4329459A (en) * | 1980-05-05 | 1982-05-11 | The Upjohn Company | Tetrahydrobenzopyran derivatives |
| US4999356A (en) * | 1987-08-07 | 1991-03-12 | Hoechst-Roussel Pharmaceuticals, Inc. | 1-phenyl-3-(1-piperazinyl)-1H-indazoles |
| FR2639227A1 (fr) * | 1988-11-23 | 1990-05-25 | Sanofi Sa | Utilisation de derives du chromane pour le traitement des etats depressifs |
| EP2343145A1 (en) * | 2003-03-05 | 2011-07-13 | Mitsubishi Materials Corporation | Throw-away tipped drill, throw-away tip, and drill main body |
| AU2007208127A1 (en) * | 2006-01-25 | 2007-08-02 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| US9196844B2 (en) * | 2012-06-01 | 2015-11-24 | Semiconductor Energy Laboratory Co., Ltd. | Method of synthesizing pyrazine derivative, and light-emitting element, light-emitting device, electronic device, and lighting device |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1357633A (en) * | 1971-03-02 | 1974-06-26 | Beecham Group Ltd | Chromanone basic ether derivatives |
-
1976
- 1976-01-26 US US05/652,041 patent/US4080335A/en not_active Expired - Lifetime
- 1976-07-23 CA CA257,631A patent/CA1070697A/en not_active Expired
- 1976-07-26 AU AU16221/76A patent/AU504595B2/en not_active Expired
- 1976-07-26 BE BE169237A patent/BE844515A/xx unknown
- 1976-07-26 FR FR7622762A patent/FR2319349A1/fr active Granted
- 1976-07-27 DE DE19762633679 patent/DE2633679A1/de active Pending
- 1976-07-27 SE SE7608479A patent/SE7608479L/xx unknown
- 1976-07-28 NL NL7608383A patent/NL7608383A/xx not_active Application Discontinuation
- 1976-07-28 AT AT554876A patent/AT353263B/de not_active IP Right Cessation
- 1976-07-28 GB GB30915/76A patent/GB1519689A/en not_active Expired
-
1977
- 1977-10-17 US US05/842,655 patent/US4129661A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4129661A (en) | 1978-12-12 |
| FR2319349B1 (enExample) | 1979-07-13 |
| GB1519689A (en) | 1978-08-02 |
| BE844515A (fr) | 1977-01-26 |
| AU1622176A (en) | 1978-02-02 |
| AU504595B2 (en) | 1979-10-18 |
| ATA554876A (de) | 1979-04-15 |
| US4080335A (en) | 1978-03-21 |
| NL7608383A (nl) | 1977-02-01 |
| AT353263B (de) | 1979-11-12 |
| DE2633679A1 (de) | 1977-02-17 |
| FR2319349A1 (fr) | 1977-02-25 |
| SE7608479L (sv) | 1977-01-29 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |