CA1060023A - 2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones - Google Patents

2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones

Info

Publication number: CA1060023A
Authority: CA; Canada
Prior art keywords: benzophenone; chloro; ethyl; imidazol; fluoro
Prior art date: 1975-03-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA319,182A

Other languages

English (en)

Inventor

Martin Gall

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

Pharmacia and Upjohn Co

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.)

1975-03-28

Filing date

1979-01-05

Publication date

1979-08-07

1975-03-28 Priority claimed from US05/563,079 external-priority patent/US3941803A/en

1979-01-05 Application filed by Upjohn Co filed Critical Upjohn Co

1979-01-05 Priority to CA319,182A priority Critical patent/CA1060023A/fr

1979-08-07 Application granted granted Critical

1979-08-07 Publication of CA1060023A publication Critical patent/CA1060023A/fr

Status Expired legal-status Critical Current

Links

-1 2-(2-(phthalimidomethyl)imidazol-1-yl) benzophenones Chemical class 0.000 title claims description 17
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 51
239000001257 hydrogen Substances 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims abstract description 24
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims abstract description 23
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 22
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 18
150000002431 hydrogen Chemical group 0.000 claims abstract description 15
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
239000012965 benzophenone Substances 0.000 claims description 170
229940024874 benzophenone Drugs 0.000 claims description 164
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 151
238000002360 preparation method Methods 0.000 claims description 102
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 30
238000000034 method Methods 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 4
DEYONRMKFVHKOL-UHFFFAOYSA-N [2-[2-(hydroxymethyl)imidazol-1-yl]-5-nitrophenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 DEYONRMKFVHKOL-UHFFFAOYSA-N 0.000 claims description 3
TXEXTTMPGYEOPJ-UHFFFAOYSA-N 2-[[1-(2-benzoyl-4-nitrophenyl)imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C(=NC=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 TXEXTTMPGYEOPJ-UHFFFAOYSA-N 0.000 claims description 2
ZLJPKECIQQJHMW-UHFFFAOYSA-N [5-fluoro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1 ZLJPKECIQQJHMW-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 8
QAIFCVJGZRPULF-UHFFFAOYSA-N 2-[[1-[4-chloro-2-(2-chlorobenzoyl)phenyl]imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(Cl)=CC=C(N2C(=NC=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1Cl QAIFCVJGZRPULF-UHFFFAOYSA-N 0.000 claims 2
JVUZVSZGPMUUFV-UHFFFAOYSA-N 2-[[1-(2-benzoyl-4-chlorophenyl)-5-methylimidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound CC1=CN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 JVUZVSZGPMUUFV-UHFFFAOYSA-N 0.000 claims 1
CAALCJWLWAPCKK-UHFFFAOYSA-N 2-[[1-(2-benzoyl-4-chlorophenyl)imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(Cl)=CC=C(N2C(=NC=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 CAALCJWLWAPCKK-UHFFFAOYSA-N 0.000 claims 1
ZMHFFKVVGFJDKD-UHFFFAOYSA-N 2-[[1-[4-chloro-2-(2-fluorobenzoyl)phenyl]imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound FC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C(CN2C(C3=CC=CC=C3C2=O)=O)=NC=C1 ZMHFFKVVGFJDKD-UHFFFAOYSA-N 0.000 claims 1
GBRXQSGCYWGTDO-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]-phenylmethanone Chemical compound CC1=CN=C(CO)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 GBRXQSGCYWGTDO-UHFFFAOYSA-N 0.000 claims 1
SGKPJNYHQYETKT-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-(2-chlorophenyl)methanone Chemical compound OCC1=NC=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl SGKPJNYHQYETKT-UHFFFAOYSA-N 0.000 claims 1
TYFCJRKLUNMUBJ-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-(2-fluorophenyl)methanone Chemical compound OCC1=NC=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F TYFCJRKLUNMUBJ-UHFFFAOYSA-N 0.000 claims 1
SAXQXOAPEGGWSN-UHFFFAOYSA-N [5-chloro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]-phenylmethanone Chemical compound OCC1=NC=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 SAXQXOAPEGGWSN-UHFFFAOYSA-N 0.000 claims 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 10
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 abstract description 2
239000002249 anxiolytic agent Substances 0.000 abstract description 2
230000002936 tranquilizing effect Effects 0.000 abstract description 2
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 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
239000003204 tranquilizing agent Substances 0.000 abstract 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 63
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 47
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 45
239000000047 product Substances 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 24
150000002460 imidazoles Chemical class 0.000 description 22
239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
239000000243 solution Substances 0.000 description 20
239000003810 Jones reagent Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 11
229940049706 benzodiazepine Drugs 0.000 description 10
239000000203 mixture Substances 0.000 description 10
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 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 9
239000008096 xylene Substances 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 8
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 8
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 7
150000007857 hydrazones Chemical class 0.000 description 7
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000008366 benzophenones Chemical class 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
239000008098 formaldehyde solution Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000010410 layer Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229920002866 paraformaldehyde Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
125000003944 tolyl group Chemical group 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
229930040373 Paraformaldehyde Natural products 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000010936 titanium Substances 0.000 description 3
229910052719 titanium Inorganic materials 0.000 description 3
BVVSUFVLGBJYOR-UHFFFAOYSA-N (2-methyl-1,3-dioxolan-2-yl)methanamine Chemical compound NCC1(C)OCCO1 BVVSUFVLGBJYOR-UHFFFAOYSA-N 0.000 description 2
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
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 2
LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-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
JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000011717 all-trans-retinol Substances 0.000 description 2
235000019169 all-trans-retinol Nutrition 0.000 description 2
150000001557 benzodiazepines Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
LJYAJFGLPICHON-UHFFFAOYSA-N n-(2-chlorophenyl)-2-methylaniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1Cl LJYAJFGLPICHON-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000004992 toluidines Chemical class 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
NQKIGLYJDGGOPC-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-chlorophenyl)methanone;hydrazine Chemical compound NN.NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl NQKIGLYJDGGOPC-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
LSYOVJJQGCWQCV-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone;hydrazine Chemical compound NN.NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 LSYOVJJQGCWQCV-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
PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-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
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
ZTTWFFSWQSTBAU-UHFFFAOYSA-N (2-chlorophenyl)-[2-[2-(hydroxymethyl)imidazol-1-yl]-5-nitrophenyl]methanone Chemical compound OCC1=NC=CN1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl ZTTWFFSWQSTBAU-UHFFFAOYSA-N 0.000 description 1
HXNQJCCMDFMLFP-UHFFFAOYSA-N (2-chlorophenyl)-[5-fluoro-2-(5-methylimidazol-1-yl)phenyl]methanone Chemical compound CC1=CN=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl HXNQJCCMDFMLFP-UHFFFAOYSA-N 0.000 description 1
LYEMXYGTCWVIRO-UHFFFAOYSA-N (2-chlorophenyl)-[5-fluoro-2-[2-(hydroxymethyl)imidazol-1-yl]phenyl]methanone Chemical compound OCC1=NC=CN1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl LYEMXYGTCWVIRO-UHFFFAOYSA-N 0.000 description 1
LIGGTHHMIFMDSF-UHFFFAOYSA-N (2-ethyl-1,3-dioxolan-2-yl)methanamine Chemical compound CCC1(CN)OCCO1 LIGGTHHMIFMDSF-UHFFFAOYSA-N 0.000 description 1
DWFDQVMFSLLMPE-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC=CC=C1 DWFDQVMFSLLMPE-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
BXZNCJBWROPOIP-UHFFFAOYSA-N (2-imidazol-1-ylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(N2C=NC=C2)C=1C(=O)C1=CC=CC=C1 BXZNCJBWROPOIP-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
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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
QXXRLUXAOFVOTE-UHFFFAOYSA-N 1,3-dioxolan-2-ylmethanamine Chemical compound NCC1OCCO1 QXXRLUXAOFVOTE-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
ASCJVOHEMCUERB-UHFFFAOYSA-N 1h-imidazo[1,2-a][1,4]benzodiazepine Chemical compound N1=CC2=CC=CC=C2N2CC=NC2=C1 ASCJVOHEMCUERB-UHFFFAOYSA-N 0.000 description 1
ZOMATQMEHRJKLO-UHFFFAOYSA-N 1h-imidazol-2-ylmethanol Chemical compound OCC1=NC=CN1 ZOMATQMEHRJKLO-UHFFFAOYSA-N 0.000 description 1
RBHDCDKDOMIAIW-UHFFFAOYSA-N 2,6-difluoro-N-(2-methylphenyl)aniline Chemical compound FC1=C(C(=CC=C1)F)NC=1C(=CC=CC1)C RBHDCDKDOMIAIW-UHFFFAOYSA-N 0.000 description 1
UODMKOHXPZDFGW-UHFFFAOYSA-N 2-(C-phenylcarbonohydrazonoyl)-6-(trifluoromethyl)aniline Chemical compound C=1C=CC(C(F)(F)F)=C(N)C=1C(=NN)C1=CC=CC=C1 UODMKOHXPZDFGW-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
LLPGEPRZHOMDHC-UHFFFAOYSA-N 2-(c-phenylcarbonohydrazonoyl)aniline Chemical class C=1C=CC=C(N)C=1C(=NN)C1=CC=CC=C1 LLPGEPRZHOMDHC-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
LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
OCJHXJOLCAWWIK-UHFFFAOYSA-N 2-[C-(2-chlorophenyl)carbonohydrazonoyl]-4-(trifluoromethyl)aniline Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl OCJHXJOLCAWWIK-UHFFFAOYSA-N 0.000 description 1
GPOHAFSTWZTJPD-UHFFFAOYSA-N 2-[C-(2-chlorophenyl)carbonohydrazonoyl]-4-fluoroaniline Chemical compound C=1C(F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1Cl GPOHAFSTWZTJPD-UHFFFAOYSA-N 0.000 description 1
MVDCSTXXAXPPDO-UHFFFAOYSA-N 2-[C-(2-fluorophenyl)carbonohydrazonoyl]-4-(trifluoromethyl)aniline Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=NN)C1=CC=CC=C1F MVDCSTXXAXPPDO-UHFFFAOYSA-N 0.000 description 1
RFPQYYBLIHIPPI-UHFFFAOYSA-N 2-[[1-[2-(2-chlorobenzoyl)-4-fluorophenyl]imidazol-2-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(F)=CC=C(N2C(=NC=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1Cl RFPQYYBLIHIPPI-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
VLRWWADMWHAHFZ-UHFFFAOYSA-N 2-benzyl-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1CC1=CC=CC=C1 VLRWWADMWHAHFZ-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
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
UNABNMBJRCOGAD-UHFFFAOYSA-N 2-chloro-6-[C-(2-fluorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC(Cl)=C(N)C=1C(=NN)C1=CC=CC=C1F UNABNMBJRCOGAD-UHFFFAOYSA-N 0.000 description 1
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
IRDUHPSVEBCHJM-UHFFFAOYSA-N 4-bromo-2-(c-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C(Br)=CC=C(N)C=1C(=NN)C1=CC=CC=C1 IRDUHPSVEBCHJM-UHFFFAOYSA-N 0.000 description 1
QZFAAVBSUXZOIF-UHFFFAOYSA-N 4-bromo-2-[C-(2-fluorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Br)=CC=C(N)C=1C(=NN)C1=CC=CC=C1F QZFAAVBSUXZOIF-UHFFFAOYSA-N 0.000 description 1
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 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
NFETTZPRGMYVEK-UHFFFAOYSA-N 4-chloro-2-[C-(4-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(=NN)C1=CC=C(Cl)C=C1 NFETTZPRGMYVEK-UHFFFAOYSA-N 0.000 description 1
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 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-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
SWCGJJRZAVNABK-UHFFFAOYSA-N 5-bromo-2-[C-(2-chlorophenyl)carbonohydrazonoyl]aniline Chemical compound C=1C=CC=C(Cl)C=1C(=NN)C1=CC=C(Br)C=C1N SWCGJJRZAVNABK-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
FRYGXBXYFCYJRR-UHFFFAOYSA-N 5-chloro-2-(C-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C=C(Cl)C=C(N)C=1C(=NN)C1=CC=CC=C1 FRYGXBXYFCYJRR-UHFFFAOYSA-N 0.000 description 1
LRDXYWCCCNFYTO-UHFFFAOYSA-N 5-nitro-2-(C-phenylcarbonohydrazonoyl)aniline Chemical compound C=1C=C([N+]([O-])=O)C=C(N)C=1C(=NN)C1=CC=CC=C1 LRDXYWCCCNFYTO-UHFFFAOYSA-N 0.000 description 1
101100162203 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflG gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-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
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
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 1
YHESILKRLKYJDT-UHFFFAOYSA-N [2-chloro-6-[2-(hydroxymethyl)-5-methylimidazol-1-yl]phenyl]-phenylmethanone Chemical compound CC1=CN=C(CO)N1C1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 YHESILKRLKYJDT-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
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
VBFBBEDUJWNHHL-UHFFFAOYSA-N [Cl].[Cl].[Cl].[Cl].[Ti] Chemical compound [Cl].[Cl].[Cl].[Cl].[Ti] VBFBBEDUJWNHHL-UHFFFAOYSA-N 0.000 description 1
OYURBNDEUITEQS-UHFFFAOYSA-N [N-(dichloroamino)-C-phenylcarbonimidoyl]benzene Chemical compound ClN(N=C(C1=CC=CC=C1)C1=CC=CC=C1)Cl OYURBNDEUITEQS-UHFFFAOYSA-N 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000001207 fluorophenyl group Chemical group 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
239000000499 gel Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
ZPVNDJIEAXRBEX-UHFFFAOYSA-N n-(2-fluorophenyl)-2-methylaniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1F ZPVNDJIEAXRBEX-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 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
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA319,182A 1975-03-28 1979-01-05 2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones Expired CA1060023A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA319,182A CA1060023A (fr)	1975-03-28	1979-01-05	2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US05/563,079 US3941803A (en)	1975-03-28	1975-03-28	2-(Imidazol-1-yl)benzophenones
CA244,659A CA1059522A (fr)	1975-03-28	1976-01-30	Les 2-(2-(hydroxymethyl)-imidazo-1-yl) benzophenones
CA319,182A CA1060023A (fr)	1975-03-28	1979-01-05	2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones

Publications (1)

Publication Number	Publication Date
CA1060023A true CA1060023A (fr)	1979-08-07

Family

ID=27164306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA319,182A Expired CA1060023A (fr)	1975-03-28	1979-01-05	2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones

Country Status (1)

Country	Link
CA (1)	CA1060023A (fr)

1979
- 1979-01-05 CA CA319,182A patent/CA1060023A/fr not_active Expired

Publication	Publication Date	Title
RU2169143C2 (ru)	2001-06-20	Способ получения 3-галогеналкил-1н-пиразолов
JPH01157934A (ja)	1989-06-21	新規なベンゾシクロヘプテン誘導体
JPS6036469A (ja)	1985-02-25	１，２，４−トリアゾ−ル−３−オン抗うつ剤
PT92448B (pt)	1995-07-18	Processo para a preparacao de derivados de quinoxalina, quinazolina ou quinolina susbtituidas por 1h-azol-1-ilmetilo e de composicoes farmaceuticas que os contem
FR2643903A1 (fr)	1990-09-07	Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux
WO1997013755A1 (fr)	1997-04-17	Pyrazoles 1,3,5-trisubstitues pour le traitement des inflammations
JPS59101484A (ja)	1984-06-12	新規なアリ−ルフエニルエ−テル誘導体及びその製造法
HU190573B (en)	1986-09-29	Process for producing new beta-carboline derivatives and pharmaceutical compositions cintaining them
CA1060023A (fr)	1979-08-07	2-(2-phthalimidomethyl)imidazol-1-yl) benzophenones
SU643083A3 (ru)	1979-01-15	Способ получени производных 1,4-дифенил-3-пиразолин-5-она
CA1059522A (fr)	1979-07-31	Les 2-(2-(hydroxymethyl)-imidazo-1-yl) benzophenones
CZ357392A3 (en)	1993-08-11	Process for preparing mono-n-substituted tetraazamacrocycles
US3625970A (en)	1971-12-07	1-(disubstituted phenyl or benzyl)-1h-indazol-3-yloxyacetic acid
CA1241657A (fr)	1988-09-06	1-(2-aryl-2-halogeno-1-ethenyl)-1h-azoles
CA1167440A (fr)	1984-05-15	1,4,9,10-tetrahydro-pyrazolo[4,3-e]pyrido [3,2-b][1,4]diazepin-10-ones; preparation et compositions pharmaceutiques qui en renferment
CA1060027A (fr)	1979-08-07	1-(.alpha.-PHENYL-O-TOLYL) IMIDAZOLES ET 2-(IMIDAZOL-1-YL) BENZOPHENONES
US3534061A (en)	1970-10-13	N-(alpha-(p-methoxyphenyl)-beta-nitrostyryl)-phenoxyalkyl pyrroles
US4260773A (en)	1981-04-07	Intermediates for triazolobenzazepines
KR900004322B1 (ko)	1990-06-22	2-아졸릴메틸-3-디플루오로벤질옥시-2,3-디하이드로 플루오로벤조[b]티오펜 및 이의 제조방법
US4537890A (en)	1985-08-27	2-(3,5-Substituted-2-pyridylalkylamino)-5-oxopyridylmethyl-4-pyrimidones useful as histamine H1 -antagonists
FI83777C (fi)	1991-08-26	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-aryl-1-(fluorhydroxialkyl eller perfluoralkanoyl)-2-(1h-1,2,4-triazol-1-yl) etanoler.
US3992400A (en)	1976-11-16	1-(α-Phenyl-o-tolyl)imidazoles
US3712903A (en)	1973-01-23	5(1-(phenyl or benzyl)-1h-indazol-3-yloxymethyl)-tetrazoles
US4379765A (en)	1983-04-12	Pyrazolobenzazepines
US4259503A (en)	1981-03-31	Triazole intermediates for triazolobenzazepines