CA1323629C - Process for the preparation of 5-arylidene and alkylidene-substituted hydantoins - Google Patents

Process for the preparation of 5-arylidene and alkylidene-substituted hydantoins

Info

Publication number: CA1323629C
Authority: CA; Canada
Prior art keywords: phosphonate; hydantoin; alkyl; methyl; hydrogen
Prior art date: 1986-09-29
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 - Fee Related

Application number

CA000548024A

Other languages

English (en)

French (fr)

Inventor

John J. Wright

Nicholas A. Meanwell

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.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb 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.)

1986-09-29

Filing date

1987-09-28

Publication date

1993-10-26

1987-09-28 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1993-10-26 Application granted granted Critical

1993-10-26 Publication of CA1323629C publication Critical patent/CA1323629C/en

2010-10-26 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 67
150000001469 hydantoins Chemical class 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims abstract description 7
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract description 44
229940091173 hydantoin Drugs 0.000 claims abstract description 30
150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 17
150000002576 ketones Chemical class 0.000 claims abstract description 16
125000001931 aliphatic group Chemical group 0.000 claims abstract description 11
238000010168 coupling process Methods 0.000 claims abstract description 8
230000008878 coupling Effects 0.000 claims abstract description 7
238000005859 coupling reaction Methods 0.000 claims abstract description 7
-1 ali-phatic aldehyde Chemical class 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
150000001299 aldehydes Chemical class 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 4
SAFCTMWBPBVFII-UHFFFAOYSA-N 5-bromoimidazolidine-2,4-dione Chemical compound BrC1NC(=O)NC1=O SAFCTMWBPBVFII-UHFFFAOYSA-N 0.000 claims description 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 3
150000003997 cyclic ketones Chemical class 0.000 claims description 2
LIRDJALZRPAZOR-UHFFFAOYSA-N indolin-3-one Chemical compound C1=CC=C2C(=O)CNC2=C1 LIRDJALZRPAZOR-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
RSRLEAGQLHAZEZ-UHFFFAOYSA-N (3-methyl-2,5-dioxoimidazolidin-4-yl)phosphonic acid Chemical compound CN1C(C(=O)NC1=O)P(=O)(O)O RSRLEAGQLHAZEZ-UHFFFAOYSA-N 0.000 claims 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 1
230000000875 corresponding effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 15
239000000543 intermediate Substances 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 3
238000003786 synthesis reaction Methods 0.000 abstract description 3
BINWKEIURMBREF-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical class C1=CC=C2N=C(NC(=O)N3)C3=CC2=C1 BINWKEIURMBREF-UHFFFAOYSA-N 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
229910001868 water Inorganic materials 0.000 description 68
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
239000000203 mixture Substances 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
PNQYQNIOVAYJJG-UHFFFAOYSA-N 5-diethoxyphosphorylimidazolidine-2,4-dione Chemical compound CCOP(=O)(OCC)C1NC(=O)NC1=O PNQYQNIOVAYJJG-UHFFFAOYSA-N 0.000 description 38
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 37
229960004756 ethanol Drugs 0.000 description 26
235000019441 ethanol Nutrition 0.000 description 26
239000007787 solid Substances 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 22
239000000243 solution Substances 0.000 description 22
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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 11
229940095076 benzaldehyde Drugs 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
239000011734 sodium Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000000538 analytical sample Substances 0.000 description 10
125000004429 atom Chemical group 0.000 description 10
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
239000000284 extract Substances 0.000 description 8
XLYPHUGUKGMURE-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C(C=O)=C1 XLYPHUGUKGMURE-UHFFFAOYSA-N 0.000 description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 5
KXIFFDHDTNVQPJ-UHFFFAOYSA-N 5-diethoxyphosphoryl-1-methylimidazolidine-2,4-dione Chemical compound CCOP(=O)(OCC)C1N(C)C(=O)NC1=O KXIFFDHDTNVQPJ-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
150000003254 radicals Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 4
CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 4
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 4
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
SEVSMVUOKAMPDO-UHFFFAOYSA-N 4-acetoxy benzaldehyde Chemical compound CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000002152 alkylating effect Effects 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 4
WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
LBHWNZFYCKTRFN-UHFFFAOYSA-N 2-methyl-6-nitrobenzaldehyde Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C=O LBHWNZFYCKTRFN-UHFFFAOYSA-N 0.000 description 3
RQMQLOBCUISWAW-UHFFFAOYSA-N 5-[[2-nitro-5-[(2-oxo-3-propan-2-yl-1,3-oxazolidin-5-yl)methoxy]phenyl]methylidene]imidazolidine-2,4-dione Chemical compound O1C(=O)N(C(C)C)CC1COC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=C1 RQMQLOBCUISWAW-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ANCFEHFRUKZNRS-UHFFFAOYSA-N P(O)(O)=O.N1C(=O)NC(=O)C1 Chemical class P(O)(O)=O.N1C(=O)NC(=O)C1 ANCFEHFRUKZNRS-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229940053195 antiepileptics hydantoin derivative Drugs 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
DJLUGWFUVRDHLO-UHFFFAOYSA-N ethyl 4,5-dimethyl-6-oxo-7-propyl-7,8-dihydrocyclopenta[e][1]benzofuran-2-carboxylate Chemical class O=C1C(CCC)CC2=C1C(C)=C(C)C1=C2C=C(C(=O)OCC)O1 DJLUGWFUVRDHLO-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
238000002955 isolation Methods 0.000 description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
229940100595 phenylacetaldehyde Drugs 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
238000010992 reflux Methods 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
DAFTVVBQFUITOL-UHFFFAOYSA-N (4-formylphenyl) butanoate Chemical compound CCCC(=O)OC1=CC=C(C=O)C=C1 DAFTVVBQFUITOL-UHFFFAOYSA-N 0.000 description 2
ITNVPNIQTLUFOP-UHFFFAOYSA-N (4-formylphenyl) formate Chemical compound O=COC1=CC=C(C=O)C=C1 ITNVPNIQTLUFOP-UHFFFAOYSA-N 0.000 description 2
CWKXDPPQCVWXAG-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde Chemical compound O1CCOC2=CC(C=O)=CC=C21 CWKXDPPQCVWXAG-UHFFFAOYSA-N 0.000 description 2
YNGGRNROMJXLCP-UHFFFAOYSA-N 2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound O=CC1=CC=C2CCCC2=C1 YNGGRNROMJXLCP-UHFFFAOYSA-N 0.000 description 2
DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 2
VEENASAWEHHFHV-UHFFFAOYSA-N 2-(propan-2-ylamino)benzaldehyde Chemical compound CC(C)NC1=CC=CC=C1C=O VEENASAWEHHFHV-UHFFFAOYSA-N 0.000 description 2
JODRRPJMQDFCBJ-UHFFFAOYSA-N 2-Hydroxy-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(O)=C1 JODRRPJMQDFCBJ-UHFFFAOYSA-N 0.000 description 2
FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 2
ZVDXHSUCDWVQEY-UHFFFAOYSA-N 2-cyclopropylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1CC1 ZVDXHSUCDWVQEY-UHFFFAOYSA-N 0.000 description 2
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
DHEJIZSVHGOKMJ-UHFFFAOYSA-N 2-ethenylbenzaldehyde Chemical compound C=CC1=CC=CC=C1C=O DHEJIZSVHGOKMJ-UHFFFAOYSA-N 0.000 description 2
HHDPXULKSZZACU-UHFFFAOYSA-N 2-hydroxy-4-nitrobenzaldehyde Chemical compound OC1=CC([N+]([O-])=O)=CC=C1C=O HHDPXULKSZZACU-UHFFFAOYSA-N 0.000 description 2
IYWHFRWDWDMYOY-UHFFFAOYSA-N 2-nitro-5-[(2-oxo-3-propan-2-yl-1,3-oxazolidin-5-yl)methoxy]benzaldehyde Chemical compound O1C(=O)N(C(C)C)CC1COC1=CC=C([N+]([O-])=O)C(C=O)=C1 IYWHFRWDWDMYOY-UHFFFAOYSA-N 0.000 description 2
AIQRXNNMBUMUCO-UHFFFAOYSA-N 2-nitro-5-piperidin-1-ylbenzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC=C1N1CCCCC1 AIQRXNNMBUMUCO-UHFFFAOYSA-N 0.000 description 2
239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 2
FZTDYEUXQXNEER-UHFFFAOYSA-N 2-prop-2-enylbenzaldehyde Chemical compound C=CCC1=CC=CC=C1C=O FZTDYEUXQXNEER-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDUPASLURGOXGD-UHFFFAOYSA-N 2-propoxybenzaldehyde Chemical compound CCCOC1=CC=CC=C1C=O CDUPASLURGOXGD-UHFFFAOYSA-N 0.000 description 2
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
LIYGCLJYTHRBQV-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(C=O)C=C1Cl LIYGCLJYTHRBQV-UHFFFAOYSA-N 0.000 description 2
QMPNFQLVIGPNEI-UHFFFAOYSA-N 3-bromo-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1Br QMPNFQLVIGPNEI-UHFFFAOYSA-N 0.000 description 2
CATOVPRCMWIZLR-UHFFFAOYSA-N 3-ethenylbenzaldehyde Chemical compound C=CC1=CC=CC(C=O)=C1 CATOVPRCMWIZLR-UHFFFAOYSA-N 0.000 description 2
QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 description 2
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
YWSPWKXREVSQCA-UHFFFAOYSA-N 4,5-dimethoxy-2-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=C([N+]([O-])=O)C=C1OC YWSPWKXREVSQCA-UHFFFAOYSA-N 0.000 description 2
IVNWLIBLNSKBSD-UHFFFAOYSA-N 4-(2-phenylethyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1CCC1=CC=CC=C1 IVNWLIBLNSKBSD-UHFFFAOYSA-N 0.000 description 2
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FOBQFDVPYJEMFC-UHFFFAOYSA-N 5-[(5-methoxy-2-nitrophenyl)methylidene]-1-methylimidazolidine-2,4-dione Chemical compound COC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2C)=O)=C1 FOBQFDVPYJEMFC-UHFFFAOYSA-N 0.000 description 1
HQENOYHDYVTCFV-UHFFFAOYSA-N 5-[3-(benzenesulfonyl)propoxy]-2-nitrobenzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC=C1OCCCS(=O)(=O)C1=CC=CC=C1 HQENOYHDYVTCFV-UHFFFAOYSA-N 0.000 description 1
NWVHTRKZGOREJS-UHFFFAOYSA-N 5-[3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-4-nitrophenoxy]pentanoic acid Chemical compound OC(=O)CCCCOC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=C1 NWVHTRKZGOREJS-UHFFFAOYSA-N 0.000 description 1
UZLWGHOXIOJFKX-UHFFFAOYSA-N 5-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-2-nitrobenzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC=C1OCCCCC1=NN=NN1C1CCCCC1 UZLWGHOXIOJFKX-UHFFFAOYSA-N 0.000 description 1
UKPQJLLKUVDORB-UHFFFAOYSA-N 5-[[2-nitro-5-(4-phenylpiperazin-1-yl)phenyl]methylidene]imidazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=C(N2CCN(CC2)C=2C=CC=CC=2)C=C1C=C1NC(=O)NC1=O UKPQJLLKUVDORB-UHFFFAOYSA-N 0.000 description 1
KLVRHZIOWMWJOC-UHFFFAOYSA-N 5-[[4-(dimethylamino)phenyl]methylidene]imidazolidine-2,4-dione Chemical compound C1=CC(N(C)C)=CC=C1C=C1C(=O)NC(=O)N1 KLVRHZIOWMWJOC-UHFFFAOYSA-N 0.000 description 1
LTYMLJJPOAJMTB-UHFFFAOYSA-N 5-[[5-(2-ethoxyethoxy)-2-nitrophenyl]methylidene]imidazolidine-2,4-dione Chemical compound CCOCCOC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=C1 LTYMLJJPOAJMTB-UHFFFAOYSA-N 0.000 description 1
SOZKQNSFTKVLAG-UHFFFAOYSA-N 5-[[5-(4-benzoylpiperazin-1-yl)-2-nitrophenyl]methylidene]imidazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=C(N2CCN(CC2)C(=O)C=2C=CC=CC=2)C=C1C=C1NC(=O)NC1=O SOZKQNSFTKVLAG-UHFFFAOYSA-N 0.000 description 1
WNXNUPJZWYOKMW-UHFFFAOYSA-M 5-bromopentanoate Chemical compound [O-]C(=O)CCCCBr WNXNUPJZWYOKMW-UHFFFAOYSA-M 0.000 description 1
KCNCFTOZLKHIPY-UHFFFAOYSA-N 5-cyclohexylideneimidazolidine-2,4-dione Chemical compound N1C(=O)NC(=O)C1=C1CCCCC1 KCNCFTOZLKHIPY-UHFFFAOYSA-N 0.000 description 1
UGIOACMSGGVRIA-UHFFFAOYSA-N 5-ethylideneimidazolidine-2,4-dione Chemical compound CC=C1NC(=O)NC1=O UGIOACMSGGVRIA-UHFFFAOYSA-N 0.000 description 1
PBNUPOARCGPMPA-UHFFFAOYSA-N 5-hydroxy-1,2-dimethyl-4,6-dinitro-3-indolecarboxylic acid ethyl ester Chemical compound [O-][N+](=O)C1=C(O)C([N+]([O-])=O)=C2C(C(=O)OCC)=C(C)N(C)C2=C1 PBNUPOARCGPMPA-UHFFFAOYSA-N 0.000 description 1
FMXYJKCMPKALDQ-UHFFFAOYSA-N 5-methoxy-2-nitro-4-piperidin-1-ylbenzaldehyde Chemical compound COC1=CC(C=O)=C([N+]([O-])=O)C=C1N1CCCCC1 FMXYJKCMPKALDQ-UHFFFAOYSA-N 0.000 description 1
BNTDDWPHSMILHQ-UHFFFAOYSA-N 5-methoxy-2-nitrobenzaldehyde Chemical compound COC1=CC=C([N+]([O-])=O)C(C=O)=C1 BNTDDWPHSMILHQ-UHFFFAOYSA-N 0.000 description 1
KDPBSDXZXZCLNA-UHFFFAOYSA-N 5-morpholin-4-yl-2-nitrobenzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC=C1N1CCOCC1 KDPBSDXZXZCLNA-UHFFFAOYSA-N 0.000 description 1
102100033393 Anillin Human genes 0.000 description 1
XDHGWTMTPYAADO-CMDGGOBGSA-N CN1C(\C(\C2=CC=CC=C12)=C\1/C(NC(N/1)=O)=O)=O Chemical compound CN1C(\C(\C2=CC=CC=C12)=C\1/C(NC(N/1)=O)=O)=O XDHGWTMTPYAADO-CMDGGOBGSA-N 0.000 description 1
UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
RUYQOESPHQQCBM-UHFFFAOYSA-N O.O=C(C=C1C(NC(N1)=O)=O)C1=CC=CC=C1 Chemical compound O.O=C(C=C1C(NC(N1)=O)=O)C1=CC=CC=C1 RUYQOESPHQQCBM-UHFFFAOYSA-N 0.000 description 1
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101100327794 Penaeus monodon CHH2 gene Proteins 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
108010061189 anillin Proteins 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
244000309464 bull Species 0.000 description 1
HJZVHUQSQGITAM-UHFFFAOYSA-N butanamide Chemical compound CC[CH]C(N)=O HJZVHUQSQGITAM-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
SERARPRVBWDEBA-GXDHUFHOSA-N chembl1994738 Chemical compound OC1=CC=CC=C1\C=N\NC1=CC=CC=C1 SERARPRVBWDEBA-GXDHUFHOSA-N 0.000 description 1
238000009838 combustion analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
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238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
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238000004042 decolorization Methods 0.000 description 1
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DTSZRRKKKNLUQL-UHFFFAOYSA-N ethyl 4-(3-formyl-4-nitrophenoxy)pentanoate Chemical compound CCOC(=O)CCC(C)OC1=CC=C([N+]([O-])=O)C(C=O)=C1 DTSZRRKKKNLUQL-UHFFFAOYSA-N 0.000 description 1
HKXQWBCNCDWHCP-UHFFFAOYSA-N ethyl 5-[3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-4-nitrophenoxy]pentanoate Chemical compound CCOC(=O)CCCCOC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=C1 HKXQWBCNCDWHCP-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
DWRDBJCTLDOPFZ-UHFFFAOYSA-N imidazole-2,4-dione Chemical compound O=C1NC(=O)N=C1 DWRDBJCTLDOPFZ-UHFFFAOYSA-N 0.000 description 1
RYEZWKNZOAAHPL-UHFFFAOYSA-N imidazolidine-2,4-dione;hydrate Chemical compound O.O=C1CNC(=O)N1 RYEZWKNZOAAHPL-UHFFFAOYSA-N 0.000 description 1
OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
230000002101 lytic effect Effects 0.000 description 1
OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
VZXMZMJSGLFKQI-ABVWVHJUSA-N midafotel Chemical compound OC(=O)[C@H]1CN(C\C=C\P(O)(O)=O)CCN1 VZXMZMJSGLFKQI-ABVWVHJUSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
HTOLGGNSOCNPBR-UHFFFAOYSA-N n,n'-bis(4-nitrophenyl)ethane-1,2-diamine Chemical compound C1=CC([N+](=O)[O-])=CC=C1NCCNC1=CC=C([N+]([O-])=O)C=C1 HTOLGGNSOCNPBR-UHFFFAOYSA-N 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
YWXCPBOLRPNSNZ-UHFFFAOYSA-N n-(1-hydroxypyridin-4-ylidene)hydroxylamine Chemical compound ON=C1C=CN(O)C=C1 YWXCPBOLRPNSNZ-UHFFFAOYSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
VHJKCRCIFSUGTL-UHFFFAOYSA-N n-cyclohexyl-1-(3-formyl-4-nitrophenyl)-n-methylpiperidine-4-carboxamide Chemical compound C1CN(C=2C=C(C=O)C(=CC=2)[N+]([O-])=O)CCC1C(=O)N(C)C1CCCCC1 VHJKCRCIFSUGTL-UHFFFAOYSA-N 0.000 description 1
IVVZWQLJVYMFMO-UHFFFAOYSA-N n-cyclohexyl-5-[3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-4-nitrophenoxy]-n-methylpentanamide Chemical compound C=1C=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=CC=1OCCCCC(=O)N(C)C1CCCCC1 IVVZWQLJVYMFMO-UHFFFAOYSA-N 0.000 description 1
YZVISYMZPOAAGL-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-[3-[(3-methyl-2,5-dioxoimidazolidin-4-ylidene)methyl]-4-nitrophenoxy]butanamide Chemical compound C=1C=C([N+]([O-])=O)C(C=C2C(NC(=O)N2C)=O)=CC=1OCCCC(=O)N(C)C1CCCCC1 YZVISYMZPOAAGL-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
AEABQBMUYZBBCW-UHFFFAOYSA-N pentanamide Chemical compound CC[CH]CC(N)=O AEABQBMUYZBBCW-UHFFFAOYSA-N 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
235000008729 phenylalanine Nutrition 0.000 description 1
150000002994 phenylalanines Chemical class 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000548024A 1986-09-29 1987-09-28 Process for the preparation of 5-arylidene and alkylidene-substituted hydantoins Expired - Fee Related CA1323629C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US91304186A	1986-09-29	1986-09-29
US913,041		1986-09-29

Publications (1)

Publication Number	Publication Date
CA1323629C true CA1323629C (en)	1993-10-26

Family

ID=25432878

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000548024A Expired - Fee Related CA1323629C (en)	1986-09-29	1987-09-28	Process for the preparation of 5-arylidene and alkylidene-substituted hydantoins

Country Status (10)

Country	Link
KR (1)	KR880003919A (es)
AT (1)	AT398566B (es)
CA (1)	CA1323629C (es)
CH (1)	CH676846A5 (es)
ES (1)	ES2007116A6 (es)
FI (1)	FI874212L (es)
GR (1)	GR871506B (es)
HU (2)	HU208426B (es)
IT (1)	IT1222755B (es)
PT (1)	PT85805B (es)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011103289A3 (en) *	2010-02-17	2012-01-19	Jasco Pharmaceuticals, LLC	Imidazole-2, 4-dione inhibitors of casein kinase 1
RU2781135C1 (ru) *	2022-02-18	2022-10-06	Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет"	Бензиламмонийная соль 4-этоксикарбонил-5-оксо-2-(2-оксо-2-фенилэтилиден)-2,5-дигидро-1h-пиррол-3-олата, проявляющая противомикробную активность

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK0581250T3 (da) *	1992-07-31	1999-09-27	Hoechst Ag	Fremgangsmåde til bioteknisk fremstilling af L-thienylalaniner i enantiomerren form ud fra 2-hydroxy-3-thienyl-acrylsyrer o
ATE553160T1 (de)	2002-02-21	2012-04-15	Basf Se	Pigmente auf basis von lactam und deren verwendung in der herstellung gefärbter kunststoffe oder polymerer farbpartikel
EA200700117A1 (ru)	2004-06-24	2007-06-29	Инсайт Корпорейшн	N-замещенные пиперидины и их применение в качестве фармацевтических препаратов

1987
- 1987-09-25 FI FI874212A patent/FI874212L/fi not_active Application Discontinuation
- 1987-09-28 CA CA000548024A patent/CA1323629C/en not_active Expired - Fee Related
- 1987-09-28 CH CH3753/87A patent/CH676846A5/de not_active IP Right Cessation
- 1987-09-28 PT PT85805A patent/PT85805B/pt not_active IP Right Cessation
- 1987-09-28 ES ES8702767A patent/ES2007116A6/es not_active Expired
- 1987-09-28 IT IT22055/87A patent/IT1222755B/it active
- 1987-09-28 HU HU874330A patent/HU208426B/hu not_active IP Right Cessation
- 1987-09-28 KR KR870010728A patent/KR880003919A/ko not_active Ceased
- 1987-09-29 GR GR871506A patent/GR871506B/el unknown
- 1987-09-29 AT AT0247687A patent/AT398566B/de not_active IP Right Cessation
1992
- 1992-04-07 HU HU9201172A patent/HU9201172D0/hu unknown

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011103289A3 (en) *	2010-02-17	2012-01-19	Jasco Pharmaceuticals, LLC	Imidazole-2, 4-dione inhibitors of casein kinase 1
US9073903B2 (en)	2010-02-17	2015-07-07	Jasco Pharmaceuticals, LLC	Imidazole-2,4-dione inhibitors of casein kinase 1
RU2781135C1 (ru) *	2022-02-18	2022-10-06	Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет"	Бензиламмонийная соль 4-этоксикарбонил-5-оксо-2-(2-оксо-2-фенилэтилиден)-2,5-дигидро-1h-пиррол-3-олата, проявляющая противомикробную активность

Also Published As

Publication number	Publication date
FI874212A0 (fi)	1987-09-25
PT85805B (pt)	1990-08-31
HU208426B (en)	1993-10-28
GR871506B (en)	1988-01-20
CH676846A5 (en)	1991-03-15
PT85805A (en)	1987-10-01
IT8722055A0 (it)	1987-09-28
KR880003919A (ko)	1988-05-31
HUT49858A (en)	1989-11-28
IT1222755B (it)	1990-09-12
AT398566B (de)	1994-12-27
FI874212A7 (fi)	1988-03-30
HU9201172D0 (en)	1992-07-28
ATA247687A (de)	1994-05-15
FI874212L (fi)	1988-03-30
ES2007116A6 (es)	1989-06-01

Legal Events

Date	Code	Title	Description
1996-04-28	MKLA	Lapsed

Publication	Publication Date	Title
CA1120481A (en)	1982-03-23	Aryl hydantoins
US4470989A (en)	1984-09-11	Neuroleptic n-oxacyclyl-alkylpiperidine derivatives
CH643545A5 (de)	1984-06-15	Verfahren zur herstellung chiral substituierter 2-imidazolin-5-one und deren verwendung.
CH633266A5 (en)	1982-11-30	Process for preparing 1,4-dihydropyridine compounds
US4535073A (en)	1985-08-13	Antihypertensive phosphono derivatives of hantzsch dihydropyridines
CH642353A5 (de)	1984-04-13	2-methyl-dihydropyridin-verbindung, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel.
EP0004358B1 (de)	1982-01-06	N-Oxacyclyl-alkyl-piperidine, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen
EP0282502B1 (de)	1991-05-15	Imidazol-derivate
US4699914A (en)	1987-10-13	Imidazole group containing 2(1H)-pyridones and method for treating heart insufficiencies in humans
US4463001A (en)	1984-07-31	6-Substituted 6H-dibenzo[b,d]pyran derivatives and process for their preparation
NO860471L (no)	1986-08-12	Fremgangsmaate for fremstilling av nye heterocykliske derivater.
EP0093945B1 (en)	1988-11-23	1,4-dihydropyridine derivatives
AT398566B (de)	1994-12-27	Verfahren zur herstellung von 5-aryliden- und -alkylidensubstituierten hydantoinen
US4358450A (en)	1982-11-09	O-Alkylated oximes and pharmaceutical composition thereof
SU1572415A3 (ru)	1990-06-15	Способ получени производных имидазола или их фармацевтически приемлемых солей присоединени кислот
US4831046A (en)	1989-05-16	Tetrazole derivatives of 1,3-dioxane and thromboxane A2 antigonizing use thereof
EP0134096B1 (en)	1989-02-01	Aminopyrimidinone derivatives as histamine h2-antagonists
RU2049776C1 (ru)	1995-12-10	Производное хинона или его фармакологически приемлемые соли
EP0090275B1 (en)	1987-10-28	Isoxazole (5,4-b) pyridines
US4039670A (en)	1977-08-02	Butyrophenone compounds as psychotropics
NO860462L (no)	1986-08-12	Fremgangsmaate for fremstilling av et dihydropyridin.
NL8002853A (nl)	1980-11-20	Pyrazool(1,5-c)chinazolinen, werkwijze voor de bereiding van dergelijke verbindingen en geneesmiddel met als werkzaam bestanddeel een dergelijke verbinding.
US6132286A (en)	2000-10-17	Preparation of 1,2,5,6-tetra-hydro-3-carboalkoxypridines such as arecoline and salts of 1,2,5,6-tetrahydro-3-carboalkoxypridines and arecoline hydrobromide
RU2207340C2 (ru)	2003-06-27	Способ получения 1,2,3,9-тетрагидро-9-метил-3-[(2-метил-1н-имидазол-1-ил)метил]-4н-карбазол -4-она или его фармацевтически приемлемых солей
SU422157A3 (ru)	1974-03-30	Способ получения производных 4(зн)-хиназолинона