CH618687A5 - - Google Patents

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Publication number: CH618687A5
Authority: CH; Switzerland
Prior art keywords: formula; chloro; compound; tolyl; imidazole
Prior art date: 1975-04-04

Application number

CH361676A

Other languages

German (de)

English (en)

Inventor

Martin Gall

Original Assignee

Upjohn Co

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.)

1975-04-04

Filing date

1976-03-23

Publication date

1980-08-15

1976-03-23 Application filed by Upjohn Co filed Critical Upjohn Co

1980-08-15 Publication of CH618687A5 publication Critical patent/CH618687A5/de

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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 154
150000001875 compounds Chemical class 0.000 claims description 104
238000000034 method Methods 0.000 claims description 71
238000002360 preparation method Methods 0.000 claims description 55
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 30
239000000460 chlorine Substances 0.000 claims description 25
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 20
229910052731 fluorine Inorganic materials 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
229910052801 chlorine Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000011737 fluorine Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
-1 alkyl radical Chemical class 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 4
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 3
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 3
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
GFEBYYXDXMODAG-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C=1C(Cl)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 GFEBYYXDXMODAG-UHFFFAOYSA-N 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
239000000047 product Substances 0.000 description 37
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 18
239000000203 mixture Substances 0.000 description 16
239000003153 chemical reaction reagent Substances 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 13
QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 10
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
239000012965 benzophenone Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000010410 layer Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000002936 tranquilizing effect Effects 0.000 description 4
VLRWWADMWHAHFZ-UHFFFAOYSA-N 2-benzyl-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1 VLRWWADMWHAHFZ-UHFFFAOYSA-N 0.000 description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000003810 Jones reagent Substances 0.000 description 3
239000000538 analytical sample Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DUMGVPIXKALANS-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2,6-difluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=C(F)C=CC=C1F DUMGVPIXKALANS-UHFFFAOYSA-N 0.000 description 2
BXZNCJBWROPOIP-UHFFFAOYSA-N (2-imidazol-1-ylphenyl)-phenylmethanone Chemical class C=1C=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 BXZNCJBWROPOIP-UHFFFAOYSA-N 0.000 description 2
BVVSUFVLGBJYOR-UHFFFAOYSA-N (2-methyl-1,3-dioxolan-2-yl)methanamine Chemical compound NCC1(C)OCCO1 BVVSUFVLGBJYOR-UHFFFAOYSA-N 0.000 description 2
LLPGEPRZHOMDHC-SSZFMOIBSA-N 2-[(z)-c-phenylcarbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(N)C=1C(=N/N)\C1=CC=CC=C1 LLPGEPRZHOMDHC-SSZFMOIBSA-N 0.000 description 2
UYHUMDTXZYZFSO-UHFFFAOYSA-N 2-[c-(2-chlorophenyl)carbonohydrazonoyl]-4-nitroaniline Chemical compound C=1C([N+]([O-])=O)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl UYHUMDTXZYZFSO-UHFFFAOYSA-N 0.000 description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
WPRRWTZCKYTGRJ-UHFFFAOYSA-N 4-chloro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 WPRRWTZCKYTGRJ-UHFFFAOYSA-N 0.000 description 2
QUEGNOLKMASBPU-UHFFFAOYSA-N 4-chloro-2-[c-(2-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(Cl)C=1C(=NN)C1=CC(Cl)=CC=C1N QUEGNOLKMASBPU-UHFFFAOYSA-N 0.000 description 2
PWQAIHNPIZFUPY-UHFFFAOYSA-N 4-chloro-2-[c-(2-fluorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NN)C1=CC=CC=C1F PWQAIHNPIZFUPY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
NRMOBHGSHDKJLW-UHFFFAOYSA-N [2-amino-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 NRMOBHGSHDKJLW-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002460 imidazoles Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
KWZYIAJRFJVQDO-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl KWZYIAJRFJVQDO-UHFFFAOYSA-N 0.000 description 1
GTGMXPIQRQSORU-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F GTGMXPIQRQSORU-UHFFFAOYSA-N 0.000 description 1
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
HJEITXVKEVSIQM-UHFFFAOYSA-N (2-amino-5-fluorophenyl)-(2,6-difluorophenyl)methanone Chemical compound NC1=CC=C(F)C=C1C(=O)C1=C(F)C=CC=C1F HJEITXVKEVSIQM-UHFFFAOYSA-N 0.000 description 1
OTBMFWQZXXWHOO-UHFFFAOYSA-N (2-amino-5-fluorophenyl)-phenylmethanone Chemical compound NC1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 OTBMFWQZXXWHOO-UHFFFAOYSA-N 0.000 description 1
GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 1
JUXQFXDPNVXNEN-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(3-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC(Cl)=C1 JUXQFXDPNVXNEN-UHFFFAOYSA-N 0.000 description 1
PKSVTEMCGNQIMD-UHFFFAOYSA-N (2-aminophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl PKSVTEMCGNQIMD-UHFFFAOYSA-N 0.000 description 1
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
YKKLPDOLJVNCBF-UHFFFAOYSA-N (2-chlorophenyl)-(2-imidazol-1-yl-5-nitrophenyl)methanone Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1Cl YKKLPDOLJVNCBF-UHFFFAOYSA-N 0.000 description 1
FWUIPAWWNQQLIR-UHFFFAOYSA-N (2-chlorophenyl)-(2-imidazol-1-ylphenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1N1C=NC=C1 FWUIPAWWNQQLIR-UHFFFAOYSA-N 0.000 description 1
ZFUFQUSCTWEWFI-UHFFFAOYSA-N (2-chlorophenyl)-(5-fluoro-2-imidazol-1-ylphenyl)methanone Chemical compound C=1C(F)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1Cl ZFUFQUSCTWEWFI-UHFFFAOYSA-N 0.000 description 1
OILBXOJSIGAQOI-UHFFFAOYSA-N (2-chlorophenyl)-[2-(4,5-dipropylimidazol-1-yl)-5-fluorophenyl]methanone Chemical compound CCCC1=C(CCC)N=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl OILBXOJSIGAQOI-UHFFFAOYSA-N 0.000 description 1
WOOJTMHSUDJUJL-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]methanone Chemical compound CC1=CN=CN1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1Cl WOOJTMHSUDJUJL-UHFFFAOYSA-N 0.000 description 1
JKRMSXLLMZSUGG-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-methylimidazol-1-yl)-5-nitrophenyl]methanone Chemical compound CC1=CN=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl JKRMSXLLMZSUGG-UHFFFAOYSA-N 0.000 description 1
YJPYETRZDQKHIT-UHFFFAOYSA-N (2-chlorophenyl)-[2-(5-methylimidazol-1-yl)phenyl]methanone Chemical compound CC1=CN=CN1C1=CC=CC=C1C(=O)C1=CC=CC=C1Cl YJPYETRZDQKHIT-UHFFFAOYSA-N 0.000 description 1
IBSPDPJEJHESCG-UHFFFAOYSA-N (2-imidazol-1-yl-5-nitrophenyl)-phenylmethanone Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 IBSPDPJEJHESCG-UHFFFAOYSA-N 0.000 description 1
SVSOYMDJIIENBL-UHFFFAOYSA-N (3-chlorophenyl)-(2-imidazol-1-ylphenyl)methanone Chemical compound ClC1=CC=CC(C(=O)C=2C(=CC=CC=2)N2C=NC=C2)=C1 SVSOYMDJIIENBL-UHFFFAOYSA-N 0.000 description 1
VHVFCDKTZVYYLO-UHFFFAOYSA-N (4-chloro-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C1=CN=CN1C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VHVFCDKTZVYYLO-UHFFFAOYSA-N 0.000 description 1
TXEOFLUVGBQJHF-UHFFFAOYSA-N (5-bromo-2-imidazol-1-ylphenyl)-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC(Br)=CC=C1N1C=NC=C1 TXEOFLUVGBQJHF-UHFFFAOYSA-N 0.000 description 1
GLGWWOSDQYYULY-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(2,6-difluorophenyl)methanone Chemical compound FC1=CC=CC(F)=C1C(=O)C1=CC(Cl)=CC=C1N1C=NC=C1 GLGWWOSDQYYULY-UHFFFAOYSA-N 0.000 description 1
URKLWYBPBQWGTG-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(2-chlorophenyl)methanone Chemical compound C=1C(Cl)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1Cl URKLWYBPBQWGTG-UHFFFAOYSA-N 0.000 description 1
HVSGXVNTRJXGBF-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C=NC=C1 HVSGXVNTRJXGBF-UHFFFAOYSA-N 0.000 description 1
BSNOZFQHWKCAJO-UHFFFAOYSA-N (5-chloro-2-imidazol-1-ylphenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C=NC=C1 BSNOZFQHWKCAJO-UHFFFAOYSA-N 0.000 description 1
IDCNTSHPGWMKBB-UHFFFAOYSA-N (5-fluoro-2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C=1C(F)=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 IDCNTSHPGWMKBB-UHFFFAOYSA-N 0.000 description 1
DAEXNIJXVASTAB-UHFFFAOYSA-N 1-(2-ethyl-1,3-dioxolan-2-yl)propan-1-amine Chemical compound CCC(N)C1(CC)OCCO1 DAEXNIJXVASTAB-UHFFFAOYSA-N 0.000 description 1
XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 description 1
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
CWLUWEMZOXJTET-UHFFFAOYSA-N 2-(c-phenylcarbonohydrazonoyl)-4-(trifluoromethyl)aniline Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 CWLUWEMZOXJTET-UHFFFAOYSA-N 0.000 description 1
IKJHNXGQANRXPN-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CC1=CC=CC=C1Cl IKJHNXGQANRXPN-UHFFFAOYSA-N 0.000 description 1
PFFRXFWDKDIUNS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1Cl PFFRXFWDKDIUNS-UHFFFAOYSA-N 0.000 description 1
VQFDEFHCQYNKMP-UHFFFAOYSA-N 2-[c-(2-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(Cl)C=1C(=NN)C1=CC=CC=C1N VQFDEFHCQYNKMP-UHFFFAOYSA-N 0.000 description 1
GVPWLVRPBMAMPV-UHFFFAOYSA-N 2-[c-(3-chlorophenyl)carbonohydrazonoyl]-4-nitroaniline Chemical compound C=1C([N+]([O-])=O)=CC=C(N)C=1C(=NN)C1=CC=CC(Cl)=C1 GVPWLVRPBMAMPV-UHFFFAOYSA-N 0.000 description 1
SRLZVIVUBOKWHU-UHFFFAOYSA-N 2-benzyl-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CC1=CC=CC=C1 SRLZVIVUBOKWHU-UHFFFAOYSA-N 0.000 description 1
DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 1
XFHXIBYEHIGZCR-UHFFFAOYSA-N 4-bromo-2-[(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC=C(Br)C=C1CC1=CC=CC=C1Cl XFHXIBYEHIGZCR-UHFFFAOYSA-N 0.000 description 1
NLYWPPDPZODCIP-UHFFFAOYSA-N 4-chloro-2-[(2-chlorophenyl)methyl]aniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1Cl NLYWPPDPZODCIP-UHFFFAOYSA-N 0.000 description 1
KAGSTLRMFPEMCJ-UHFFFAOYSA-N 4-chloro-2-[(2-fluorophenyl)methyl]aniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1F KAGSTLRMFPEMCJ-UHFFFAOYSA-N 0.000 description 1
STVQQHQEABMMKA-UHFFFAOYSA-N 4-chloro-2-[c-(2,6-difluorophenyl)carbonohydrazonoyl]aniline Chemical compound FC=1C=CC=C(F)C=1C(=NN)C1=CC(Cl)=CC=C1N STVQQHQEABMMKA-UHFFFAOYSA-N 0.000 description 1
AQKILPKBICMNAC-UHFFFAOYSA-N 4-fluoro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 AQKILPKBICMNAC-UHFFFAOYSA-N 0.000 description 1
VUFGVUILECQMHD-UHFFFAOYSA-N 4-nitro-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C([N+]([O-])=O)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 VUFGVUILECQMHD-UHFFFAOYSA-N 0.000 description 1
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
BSFQEKVYNAAAAG-UHFFFAOYSA-N [2-(4,5-dimethylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound CC1=C(C)N=CN1C1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 BSFQEKVYNAAAAG-UHFFFAOYSA-N 0.000 description 1
LONJJRQATHIDBZ-UHFFFAOYSA-N [2-(5-methylimidazol-1-yl)-5-nitrophenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 LONJJRQATHIDBZ-UHFFFAOYSA-N 0.000 description 1
ITFGTBNIEOFDIE-UHFFFAOYSA-N [2-(5-methylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=CC=C1C(=O)C1=CC=CC=C1 ITFGTBNIEOFDIE-UHFFFAOYSA-N 0.000 description 1
MAOMTOGDSCHWON-UHFFFAOYSA-N [2-imidazol-1-yl-3-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound C1=CN=CN1C=1C(C(F)(F)F)=CC=CC=1C(=O)C1=CC=CC=C1 MAOMTOGDSCHWON-UHFFFAOYSA-N 0.000 description 1
LNGNXXKFSQOJLY-UHFFFAOYSA-N [5-bromo-2-(5-methylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound CC1=CN=CN1C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1Cl LNGNXXKFSQOJLY-UHFFFAOYSA-N 0.000 description 1
USYMRGJCKQXLKD-UHFFFAOYSA-N [5-chloro-2-(4-ethyl-5-methylimidazol-1-yl)phenyl]-(2,6-difluorophenyl)methanone Chemical compound CC1=C(CC)N=CN1C1=CC=C(Cl)C=C1C(=O)C1=C(F)C=CC=C1F USYMRGJCKQXLKD-UHFFFAOYSA-N 0.000 description 1
QLKVVQKZOSBAGN-UHFFFAOYSA-N [5-chloro-2-(5-methylimidazol-1-yl)phenyl]-(2-chlorophenyl)methanone Chemical compound CC1=CN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl QLKVVQKZOSBAGN-UHFFFAOYSA-N 0.000 description 1
FTNATJWGJDWTID-UHFFFAOYSA-N [5-chloro-2-(5-methylimidazol-1-yl)phenyl]-(2-fluorophenyl)methanone Chemical compound CC1=CN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F FTNATJWGJDWTID-UHFFFAOYSA-N 0.000 description 1
RTFYHPFOFWDGRX-UHFFFAOYSA-N [5-chloro-2-(5-methylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CC1=CN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 RTFYHPFOFWDGRX-UHFFFAOYSA-N 0.000 description 1
OKNYYHGNXHEYON-UHFFFAOYSA-N [5-nitro-2-(5-propylimidazol-1-yl)phenyl]-phenylmethanone Chemical compound CCCC1=CN=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 OKNYYHGNXHEYON-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001845 chromium compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
KLNFAMGHSZQYHR-UHFFFAOYSA-N imidazo[4,5-i][1,2]benzodiazepine Chemical class C1=CC=NN=C2C3=NC=NC3=CC=C21 KLNFAMGHSZQYHR-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D233/56—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- 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
- 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
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH361676A 1975-04-04 1976-03-23 CH618687A5 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/565,107 US3941802A (en)	1975-04-04	1975-04-04	2-(Imidazol-1-yl)benzophenones

Publications (1)

Publication Number	Publication Date
CH618687A5 true CH618687A5 (pl)	1980-08-15

Family

ID=24257237

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH361676A CH618687A5 (pl)	1975-04-04	1976-03-23

Country Status (7)

Country	Link
US (1)	US3941802A (pl)
JP (1)	JPS51127073A (pl)
CA (1)	CA1060027A (pl)
CH (1)	CH618687A5 (pl)
DE (1)	DE2611345A1 (pl)
MX (1)	MX3167E (pl)
PL (1)	PL100372B1 (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4281142A (en) *	1979-03-29	1981-07-28	Hoffmann-La Roche Inc.	Imidazolecarboxaldehydes
EP0757988A4 (en) *	1994-04-27	2000-07-26	Nippon Soda Co	IMIDAZOLE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
AU2001241084A1 (en) *	2000-03-13	2001-09-24	Taisho Pharmaceutical Co. Ltd.	Imidazolylbenzophenone derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3534061A (en) *	1967-12-04	1970-10-13	Parke Davis & Co	N-(alpha-(p-methoxyphenyl)-beta-nitrostyryl)-phenoxyalkyl pyrroles
US3526636A (en) *	1968-01-16	1970-09-01	Sandoz Ag	Imidazoisoindoles
US3763178A (en) *	1968-09-05	1973-10-02	American Home Prod	Imidazolinyl phenyl carbonyl acid addition salts and related compounds
US3763179A (en) *	1972-05-05	1973-10-02	Upjohn Co	2-imidazol-1-yl benzophenones

1975
- 1975-04-04 US US05/565,107 patent/US3941802A/en not_active Expired - Lifetime
1976
- 1976-03-01 MX MX000030U patent/MX3167E/es unknown
- 1976-03-04 CA CA247,105A patent/CA1060027A/en not_active Expired
- 1976-03-18 DE DE19762611345 patent/DE2611345A1/de not_active Withdrawn
- 1976-03-23 CH CH361676A patent/CH618687A5/de not_active IP Right Cessation
- 1976-03-29 JP JP51035106A patent/JPS51127073A/ja active Pending
- 1976-04-02 PL PL1976188457A patent/PL100372B1/pl unknown

Also Published As

Publication number	Publication date
US3941802A (en)	1976-03-02
DE2611345A1 (de)	1976-10-14
PL100372B1 (pl)	1978-09-30
JPS51127073A (en)	1976-11-05
MX3167E (es)	1980-06-02
CA1060027A (en)	1979-08-07

Legal Events

Date	Code	Title	Description
1983-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2235544A1 (de)	1973-03-15	1-alkyl-3,5-disubstituierte 1,2,4triazolderivate und verfahren zu deren herstellung
DE3780669T2 (de)	1993-01-21	2-pyrazolin-5-ones und ein verfahren zu deren herstellung.
EP0475122A1 (de)	1992-03-18	Verfahren zur Herstellung von Zwischenprodukten
DE2733868A1 (de)	1978-02-02	Neue 1,2,4,5-tetrahydro-3h-2-benzazepin-3-one, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
FR2711993A1 (fr)	1995-05-12	Médicaments contenant des dérivés de 7H-imidazol[1,2-a]pyrazine-8-one, les nouveaux composés et leur préparation.
DE2430237A1 (de)	1975-01-16	Aethanolaminderivate und verfahren zur herstellung derselben
EP0112284A2 (de)	1984-06-27	Neue Arylphenylether-derivate
CH630231A5 (en)	1982-06-15	Fungicidal composition and process for its preparation
DE2149249A1 (de)	1972-04-13	6-Arylpyrimidine
DE3902031A1 (de)	1990-07-26	Substituierte azolylmethylcycloalkan-derivate, ihre herstellung und verwendung sowie diese enthaltende arzneimittel
DE2633679A1 (de)	1977-02-17	4,5-dihydro-2-niederalkoxycarbonylamino-4-phenylimidazole und derivate davon mit substituierter phenylgruppe
EP1071670A1 (de)	2001-01-31	Diphenyl-substituierte 5-ring-heterocyclen, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel
FR2696466A1 (fr)	1994-04-08	Dérivés de 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant.
EP0560109B1 (de)	1996-07-17	Verfahren zur Herstellung von 1-Fluorcyclopropyl-methyl-keton
CH618687A5 (pl)	1980-08-15
CH626892A5 (pl)	1981-12-15
EP0088874A2 (de)	1983-09-21	Azolyl-phenoxy-tetrahydrofuran-2-yliden-methane, Verfahren zu ihrer Herstellung sowie antimikrobielle Mittel, die diese Stoffe enthalten
DE2242454A1 (de)	1974-03-07	1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
CH620205A5 (pl)	1980-11-14
EP0057863B1 (de)	1984-06-13	Antimikrobielle Mittel
EP0045521B1 (de)	1984-06-27	Pyrazolobenzazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE3012770A1 (de)	1981-10-08	Biphenylyl-azolylethan-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US3992400A (en)	1976-11-16	1-(α-Phenyl-o-tolyl)imidazoles
EP1419160B1 (de)	2008-12-10	Verfahren zur herstellung von 6-(4-chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl-essigsäure
DE2143646A1 (de)	1972-03-09	2-Amino-l,5-benzodiazocinderivate und Verfahren zu ihrer Herstellung