GB2086885A - Imidazoles - Google Patents
Imidazoles Download PDFInfo
- Publication number
- GB2086885A GB2086885A GB8127115A GB8127115A GB2086885A GB 2086885 A GB2086885 A GB 2086885A GB 8127115 A GB8127115 A GB 8127115A GB 8127115 A GB8127115 A GB 8127115A GB 2086885 A GB2086885 A GB 2086885A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- alkyl
- maleate
- compound according
- 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.)
- Withdrawn
Links
- 150000002460 imidazoles Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 20
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 arylhydroxymethylene Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 3
- OEYZGSRLAGSENP-UHFFFAOYSA-N 1-(2-bromoethoxy)-2,4-dichlorobenzene Chemical compound ClC1=CC=C(OCCBr)C(Cl)=C1 OEYZGSRLAGSENP-UHFFFAOYSA-N 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 3
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 3
- 229960003147 reserpine Drugs 0.000 description 3
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YYFLBDSMQRWARK-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-chlorobenzene Chemical compound ClC1=CC=C(OCCBr)C=C1 YYFLBDSMQRWARK-UHFFFAOYSA-N 0.000 description 2
- QVEAVDHTWIVBSX-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-chlorobenzene Chemical compound ClC1=CC=C(OCCCBr)C=C1 QVEAVDHTWIVBSX-UHFFFAOYSA-N 0.000 description 2
- DPTVPYBSBNIACI-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-chlorobenzene Chemical compound ClC1=CC=C(OCCCCBr)C=C1 DPTVPYBSBNIACI-UHFFFAOYSA-N 0.000 description 2
- ZSUYJPUZAAYCTF-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenoxy)ethyl]-2-methylimidazole Chemical compound CC1=NC=CN1CCOC1=CC=C(Cl)C=C1Cl ZSUYJPUZAAYCTF-UHFFFAOYSA-N 0.000 description 2
- RMXXADCHVRTBSY-UHFFFAOYSA-N 1-[3-(4-chlorophenoxy)propyl]-2-methylimidazole Chemical compound CC1=NC=CN1CCCOC1=CC=C(Cl)C=C1 RMXXADCHVRTBSY-UHFFFAOYSA-N 0.000 description 2
- HRCJSNNEDGJCJZ-UHFFFAOYSA-N 1-[4-(4-chlorophenoxy)butyl]-2-methylimidazole Chemical compound CC1=NC=CN1CCCCOC1=CC=C(Cl)C=C1 HRCJSNNEDGJCJZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GSYCWDDWMQXSAY-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2,4-dichlorophenoxy)ethyl]-2-ethylimidazole Chemical compound OC(=O)\C=C/C(O)=O.CCC1=NC=CN1CCOC1=CC=C(Cl)C=C1Cl GSYCWDDWMQXSAY-BTJKTKAUSA-N 0.000 description 1
- ZUWWMHULLUAESW-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2,4-dichlorophenoxy)ethyl]-2-methylimidazole Chemical compound OC(=O)\C=C/C(O)=O.CC1=NC=CN1CCOC1=CC=C(Cl)C=C1Cl ZUWWMHULLUAESW-BTJKTKAUSA-N 0.000 description 1
- OJPYYJLRDGJCAR-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2,6-dichlorophenoxy)ethyl]-2-methylimidazole Chemical compound OC(=O)\C=C/C(O)=O.CC1=NC=CN1CCOC1=C(Cl)C=CC=C1Cl OJPYYJLRDGJCAR-BTJKTKAUSA-N 0.000 description 1
- HTXJNAGFRWBFIZ-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(3,5-dichlorophenoxy)ethyl]-2-methylimidazole Chemical compound OC(=O)\C=C/C(O)=O.CC1=NC=CN1CCOC1=CC(Cl)=CC(Cl)=C1 HTXJNAGFRWBFIZ-BTJKTKAUSA-N 0.000 description 1
- QIIKXVMKJGEPHG-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(4-chloro-2-methylphenoxy)ethyl]-2-methylimidazole Chemical compound OC(=O)\C=C/C(O)=O.CC1=NC=CN1CCOC1=CC=C(Cl)C=C1C QIIKXVMKJGEPHG-BTJKTKAUSA-N 0.000 description 1
- JPUNJRMHRCQICJ-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-methyl-1-[2-[3-(trifluoromethyl)phenoxy]ethyl]imidazole Chemical compound OC(=O)\C=C/C(O)=O.CC1=NC=CN1CCOC1=CC=CC(C(F)(F)F)=C1 JPUNJRMHRCQICJ-BTJKTKAUSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- IFTYLSWVLWWBMR-UHFFFAOYSA-N 1-(2-bromoethyl)-2-methylimidazole Chemical compound CC1=NC=CN1CCBr IFTYLSWVLWWBMR-UHFFFAOYSA-N 0.000 description 1
- UDWDCVUPUDZZOM-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)ethyl]-2-methylimidazole Chemical compound CC1=NC=CN1CCOC1=CC=C(Cl)C(Cl)=C1 UDWDCVUPUDZZOM-UHFFFAOYSA-N 0.000 description 1
- SNVRUWNTTJNUOM-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)ethyl]-2-methylimidazole Chemical compound CC1=NC=CN1CCOC1=CC=C(Cl)C=C1 SNVRUWNTTJNUOM-UHFFFAOYSA-N 0.000 description 1
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical group CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
- LQODJJDSWBDZMB-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)ethanol Chemical compound OCCOC1=CC=C(Cl)C(Cl)=C1 LQODJJDSWBDZMB-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- SNIXRMIHFOIVBB-UHFFFAOYSA-N N-Hydroxyl-tryptamine Chemical compound C1=CC=C2C(CCNO)=CNC2=C1 SNIXRMIHFOIVBB-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 108010069102 Thromboxane-A synthase Proteins 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 238000009115 maintenance therapy Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108010064377 prostacyclin synthetase Proteins 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013037 reversible inhibitor Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- 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
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8029682 | 1980-09-13 | ||
| GB8101924 | 1981-01-22 | ||
| GB8109167 | 1981-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2086885A true GB2086885A (en) | 1982-05-19 |
Family
ID=27261008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8127115A Withdrawn GB2086885A (en) | 1980-09-13 | 1981-09-08 | Imidazoles |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0049060A1 (enExample) |
| AU (1) | AU7517481A (enExample) |
| DK (1) | DK406781A (enExample) |
| ES (1) | ES8301931A1 (enExample) |
| GB (1) | GB2086885A (enExample) |
| GR (1) | GR75820B (enExample) |
| NO (1) | NO813107L (enExample) |
| PT (1) | PT73642B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT377514B (de) * | 1978-08-08 | 1985-03-25 | Wellcome Found | Verfahren zur herstellung von neuen imidazolderivaten und deren salzen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61268674A (ja) * | 1985-05-22 | 1986-11-28 | Nippon Tokushu Noyaku Seizo Kk | フエノキシアルキルトリアゾ−ル類、その製法及び農園芸用殺菌剤 |
| US4851423A (en) * | 1986-12-10 | 1989-07-25 | Schering Corporation | Pharmaceutically active compounds |
| US5750532A (en) * | 1986-12-10 | 1998-05-12 | Schering Corporation | Pharmaceutically active compounds |
| AU6062590A (en) * | 1989-07-07 | 1991-02-06 | Schering Corporation | Pharmaceutically active compounds |
| JPH07179457A (ja) * | 1993-11-08 | 1995-07-18 | Mitsubishi Chem Corp | Ｎ−置換イミダゾール誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2705677A1 (de) * | 1977-02-11 | 1978-08-17 | Bayer Ag | 2,4-dichlorphenyl-imidazolyl-aethanone(ole), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1981
- 1981-09-08 EP EP81304085A patent/EP0049060A1/en not_active Withdrawn
- 1981-09-08 GB GB8127115A patent/GB2086885A/en not_active Withdrawn
- 1981-09-09 PT PT73642A patent/PT73642B/pt unknown
- 1981-09-11 GR GR66020A patent/GR75820B/el unknown
- 1981-09-11 DK DK406781A patent/DK406781A/da not_active Application Discontinuation
- 1981-09-11 ES ES505433A patent/ES8301931A1/es not_active Expired
- 1981-09-11 AU AU75174/81A patent/AU7517481A/en not_active Abandoned
- 1981-09-11 NO NO813107A patent/NO813107L/no unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT377514B (de) * | 1978-08-08 | 1985-03-25 | Wellcome Found | Verfahren zur herstellung von neuen imidazolderivaten und deren salzen |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0049060A1 (en) | 1982-04-07 |
| PT73642A (en) | 1981-10-01 |
| GR75820B (enExample) | 1984-08-02 |
| DK406781A (da) | 1982-03-14 |
| PT73642B (en) | 1982-11-17 |
| ES505433A0 (es) | 1983-01-01 |
| NO813107L (no) | 1982-03-15 |
| ES8301931A1 (es) | 1983-01-01 |
| AU7517481A (en) | 1982-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4374990A (en) | Cyclic diamine derivatives | |
| KR100244626B1 (ko) | 5-ht1a 길항제로서의 피페라진 유도체, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
| US4059621A (en) | Substituted benzamido propanolamines | |
| US5614518A (en) | Morpholine derivatives as dopamine receptor subtype ligands | |
| PL178546B1 (pl) | Nowe, zasadniczo czyste optycznie, enancjomery prawoskrętne lub lewoskrętne 1-[(4-chlorofenylo)fenylometylo] piperazyny i sposób ich wytwarzania | |
| US4575508A (en) | 2-Substituted 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-β-carbolines, and their use as antiarrhythmic agents | |
| US4138494A (en) | 3-Phenylindolines | |
| IE901665L (en) | Arylthiazolylmethylimidazoles | |
| EP0006614A2 (en) | Pyridyl- and imidazopyridyloxypropanolamines, process for preparing the same and pharmaceutical compositions containing the same | |
| US5356916A (en) | 1,2,4-oxadiazole derivatives having monoamine oxidase B enzyme-inhibitory activity | |
| GB2086885A (en) | Imidazoles | |
| US4115569A (en) | Cyclic diamine derivatives | |
| US4539318A (en) | Tertiary aminohydroxypropoxy substituted thiadiazoles, pharmaceutical compositions and use | |
| US4616017A (en) | Aminohydroxypropoxy substituted aryl compounds | |
| US5214053A (en) | Thiourea derivatives and antimicrobial agent and antiulcer agent containing the same | |
| CH654001A5 (de) | Benzothiazolin-verbindungen. | |
| PL137682B1 (en) | Method of obtaining novel derivatives of 4a,9b-trans-hexahydro-1h-pyridinol and 2,3,4,5-tetrahydro-1h-pyridinol | |
| US3931222A (en) | Tetrahydro-carbazole derivates | |
| US4110472A (en) | Derivatives of 1-(disubstituted phenoxy)-3-amino-2-hydroxypropanes | |
| US4448777A (en) | 1-Phenylindazole-3-one compounds, process and intermediates for their preparation, and pharmaceutical compositions containing same | |
| US4237311A (en) | 2-Methyl-1-(substituted)phenyl-2-propyl esters of 2-aminopropanoic acid | |
| US3984558A (en) | 1,3,5-Trisubstituted-1,2,4-triazole compounds used as bronchodilators | |
| US4499095A (en) | Indolizine derivatives and their use in treating heart ailments | |
| US4505918A (en) | 4-[2-Pyridinylthio(oxy or amino)methyl]-1H-imidazoles and derivatives | |
| US4333929A (en) | Carboxamidine derivatives and hypoglycemical use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |