IL105191A - חומצות 0 אימינואוקסימתילבנזואיות והכנתן - Google Patents

חומצות 0 אימינואוקסימתילבנזואיות והכנתן

Info

Publication number: IL105191A
Authority: IL; Israel
Prior art keywords: substituted; unsubstituted; phenyl; alkyl; optionally substituted
Prior art date: 1992-04-04

Application number

IL10519193A

Other languages

English (en)

Other versions

IL105191A0 (en

Original Assignee

Basf Ag

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.)

1992-04-04

Filing date

1993-03-29

Publication date

1998-08-16

1993-03-29 Application filed by Basf Ag filed Critical Basf Ag

1993-07-08 Publication of IL105191A0 publication Critical patent/IL105191A0/xx

1998-08-16 Publication of IL105191A publication Critical patent/IL105191A/he

Links

239000002253 acid Substances 0.000 title claims abstract description 35
150000007513 acids Chemical class 0.000 title abstract description 12
238000002360 preparation method Methods 0.000 title abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 164
-1 cyano, hydroxyl Chemical group 0.000 claims abstract description 122
238000000034 method Methods 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 16
239000003085 diluting agent Substances 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 14
125000004104 aryloxy group Chemical group 0.000 claims abstract description 13
150000002596 lactones Chemical class 0.000 claims abstract description 13
150000002923 oximes Chemical class 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 4
125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
125000005164 aryl thioalkyl group Chemical group 0.000 claims abstract description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 4
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract 8
125000003545 alkoxy group Chemical group 0.000 claims abstract 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 226
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 137
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 44
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 32
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
239000002585 base Substances 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
125000001786 isothiazolyl group Chemical group 0.000 claims description 7
125000002971 oxazolyl group Chemical group 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
125000003373 pyrazinyl group Chemical group 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
125000002098 pyridazinyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000001544 thienyl group Chemical group 0.000 claims description 7
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
229910052987 metal hydride Inorganic materials 0.000 claims description 4
150000004681 metal hydrides Chemical class 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
125000005493 quinolyl group Chemical group 0.000 claims description 4
125000004306 triazinyl group Chemical group 0.000 claims description 4
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 3
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 abstract description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 2
125000004414 alkyl thio group Chemical group 0.000 abstract 1
125000000304 alkynyl group Chemical group 0.000 abstract 1
125000005018 aryl alkenyl group Chemical group 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000004446 heteroarylalkyl group Chemical group 0.000 abstract 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 148
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 15
229940125877 compound 31 Drugs 0.000 description 15
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
XAAUYUMBCPRWED-NTMALXAHSA-N (nz)-n-[1-(4-methylphenyl)ethylidene]hydroxylamine Chemical compound O/N=C(/C)C1=CC=C(C)C=C1 XAAUYUMBCPRWED-NTMALXAHSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 4
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000002699 waste material Substances 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
239000007788 liquid Substances 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
238000003482 Pinner synthesis reaction Methods 0.000 description 1
238000006956 Pummerer reaction Methods 0.000 description 1
229910007219 SnPr Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
229940125844 compound 46 Drugs 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
DYROHZMICXBUMX-UHFFFAOYSA-N methoxymethylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=COC)C1=CC=CC=C1 DYROHZMICXBUMX-UHFFFAOYSA-N 0.000 description 1
WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 1
238000005822 methylenation reaction Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
JHNRZXQVBKRYKN-UHFFFAOYSA-N n-(1-phenylethylidene)hydroxylamine Chemical class ON=C(C)C1=CC=CC=C1 JHNRZXQVBKRYKN-UHFFFAOYSA-N 0.000 description 1
KXCHBSNEAXRGCM-UHFFFAOYSA-N n-(1-thiophen-3-ylethylidene)hydroxylamine Chemical compound ON=C(C)C=1C=CSC=1 KXCHBSNEAXRGCM-UHFFFAOYSA-N 0.000 description 1
KAXTWDXRCMICEQ-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethylidene]hydroxylamine Chemical compound ON=C(C)C1=CC=C(Cl)C=C1 KAXTWDXRCMICEQ-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
238000010943 off-gassing Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/17—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and doubly-bound oxygen atoms bound to the same acyclic carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pyridine Compounds (AREA)
Indole Compounds (AREA)

IL10519193A 1992-04-04 1993-03-29 חומצות 0 אימינואוקסימתילבנזואיות והכנתן IL105191A (he)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4211350		1992-04-04

Publications (2)

Publication Number	Publication Date
IL105191A0 IL105191A0 (en)	1993-07-08
IL105191A true IL105191A (he)	1998-08-16

Family

ID=6456083

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10519193A IL105191A (he)	1992-04-04	1993-03-29	חומצות 0 אימינואוקסימתילבנזואיות והכנתן

Country Status (14)

Country	Link
US (2)	US5393920A (he)
EP (1)	EP0564984B1 (he)
JP (1)	JP3459838B2 (he)
KR (1)	KR100286243B1 (he)
AT (1)	ATE157082T1 (he)
AU (1)	AU658280B2 (he)
CA (1)	CA2093069A1 (he)
DE (1)	DE59307141D1 (he)
DK (1)	DK0564984T3 (he)
ES (1)	ES2104988T3 (he)
GR (1)	GR3024663T3 (he)
HU (1)	HU212602B (he)
IL (1)	IL105191A (he)
TW (1)	TW272185B (he)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GEP20012438B (en) *	1994-06-10	2001-05-25	Basf Ag	Process of Preparing α-Methoxyimino-carboxylic Acid Methylamides and Intermediates Used in the Method
DE19539324A1 (de) *	1995-10-23	1997-04-24	Basf Ag	Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel
DE19548783A1 (de) *	1995-12-27	1997-07-03	Basf Ag	Cyaniminooximether, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen
KR20000005224A (ko) *	1996-04-04	2000-01-25	가와무라 요시부미	페닐알킬카르복실산 유도체_
JPWO2004080947A1 (ja) *	2003-03-13	2006-06-08	小野薬品工業株式会社	イミノエーテル誘導体化合物およびその化合物を有効成分として含有する薬剤
US7420083B2 (en) *	2003-09-25	2008-09-02	Wyeth	Substituted aryloximes
US7342039B2 (en) *	2003-09-25	2008-03-11	Wyeth	Substituted indole oximes
CN110015977B (zh)	2015-12-25	2020-09-15	沈阳中化农药化工研发有限公司	一种丙二腈肟醚类化合物及其用途

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2559486B1 (fr)	1984-02-13	1988-02-12	Roussel Uclaf	Nouveaux derives de l'acide 1-dethia 2-thia cephalosporanique, leur procede de preparation et leur application comme medicaments
US4552585A (en)	1984-10-04	1985-11-12	Fmc Corporation	Herbicidal 2-(aminophenyl)methyl derivatives of 3-isoxazolidinones or 3-oxazinones
US4843068A (en) *	1985-12-27	1989-06-27	Nihon Nohyaku Co., Ltd.	Pyrazole oxime derivatives and compositions
CA1300137C (en) *	1985-12-27	1992-05-05	Hiroshi Hamaguchi	Pyrazole oxime derivative and its production and use
JPS63132893A (ja) *	1986-11-25	1988-06-04	Mochida Pharmaceut Co Ltd	新規セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤
ES2118769T3 (es) *	1988-11-21	1998-10-01	Zeneca Ltd	Fungicidas.
DK0669319T3 (da) *	1990-06-27	1999-02-08	Basf Ag	O-benzyloximethere og plantebeskyttelsesmidler indeholdende disse forbindelser
GB9018408D0 (en) *	1990-08-22	1990-10-03	Ici Plc	Fungicides

1993
- 1993-03-29 IL IL10519193A patent/IL105191A/he not_active IP Right Cessation
- 1993-03-31 CA CA002093069A patent/CA2093069A1/en not_active Abandoned
- 1993-04-01 AT AT93105432T patent/ATE157082T1/de not_active IP Right Cessation
- 1993-04-01 TW TW082102430A patent/TW272185B/zh active
- 1993-04-01 DE DE59307141T patent/DE59307141D1/de not_active Expired - Fee Related
- 1993-04-01 ES ES93105432T patent/ES2104988T3/es not_active Expired - Lifetime
- 1993-04-01 EP EP93105432A patent/EP0564984B1/de not_active Expired - Lifetime
- 1993-04-01 DK DK93105432.4T patent/DK0564984T3/da active
- 1993-04-02 US US08/041,848 patent/US5393920A/en not_active Expired - Lifetime
- 1993-04-02 HU HU9300978A patent/HU212602B/hu not_active IP Right Cessation
- 1993-04-02 AU AU35649/93A patent/AU658280B2/en not_active Ceased
- 1993-04-02 JP JP07677993A patent/JP3459838B2/ja not_active Expired - Fee Related
- 1993-04-03 KR KR1019930005657A patent/KR100286243B1/ko not_active Expired - Fee Related
1994
- 1994-09-29 US US08/314,908 patent/US5530156A/en not_active Expired - Fee Related
1997
- 1997-09-09 GR GR970402305T patent/GR3024663T3/el unknown

Also Published As

Publication number	Publication date
US5393920A (en)	1995-02-28
TW272185B (he)	1996-03-11
EP0564984A3 (en)	1995-03-22
GR3024663T3 (en)	1997-12-31
CA2093069A1 (en)	1993-10-05
HU9300978D0 (en)	1993-07-28
DE59307141D1 (de)	1997-09-25
KR930021608A (ko)	1993-11-22
JPH0665178A (ja)	1994-03-08
JP3459838B2 (ja)	2003-10-27
HU212602B (en)	1996-09-30
ATE157082T1 (de)	1997-09-15
US5530156A (en)	1996-06-25
AU658280B2 (en)	1995-04-06
KR100286243B1 (ko)	2001-04-16
HUT64015A (en)	1993-11-29
EP0564984A2 (de)	1993-10-13
IL105191A0 (en)	1993-07-08
EP0564984B1 (de)	1997-08-20
AU3564993A (en)	1993-10-07
DK0564984T3 (da)	1997-09-15
ES2104988T3 (es)	1997-10-16

Legal Events

Date	Code	Title
1998-12-27	FF	Patent granted
1999-10-28	KB	Patent renewed
2003-06-24	KB	Patent renewed
2008-01-06	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
KR100314118B1 (ko)	2002-02-19	N-페닐아세트아미노니트릴
JP4353633B2 (ja)	2009-10-28	（ヘテロ）芳香族ヒドロキシルアミンの製造方法
AU2008255284B9 (en)	2013-01-24	Process for the production of pyrazoles
KR101364292B1 (ko)	2014-02-18	치환된 2-플루오로아크릴산 유도체의 제조
IL105191A (he)	1998-08-16	חומצות 0 אימינואוקסימתילבנזואיות והכנתן
CA1200813A (en)	1986-02-18	Process for producing 3-oxo-nitriles
US6657085B2 (en)	2003-12-02	Process for the preparation of aniline compounds
US5157119A (en)	1992-10-20	Process for preparing sulfonylureas
EP0511019B1 (en)	1999-06-23	Method of producing keto acids
JP3481623B2 (ja)	2003-12-22	ヒドロキシルアミンエーテルおよびその塩の製造方法ならびにそのための中間生成物
US4327033A (en)	1982-04-27	Process for the production of methomyl oxime
JP2609966B2 (ja)	1997-05-14	２−置換ベンゾ［ｂ］チオフェンおよびその中間体の製造方法
EP1202949B1 (en)	2004-04-21	Process for the preparation of acylated 1,3-dicarbonyl compounds
CN101410386B (zh)	2013-07-24	2-链烯基-3-氨基噻吩衍生物及其制备方法
EP0537585B1 (en)	1997-08-20	Process for preparing sulfonylureas
JP3118596B2 (ja)	2000-12-18	アリールジアルキルチオカルバマート、２−メルカプトベンズアルデヒドおよび２−置換ベンゾ［ｂ］チオフェンの製造方法
KR0162645B1 (ko)	1999-01-15	아실시클로헥사디온티오카르복실산 s-에스테르의 제조방법 및 이것의 중간체
CA2577942A1 (en)	2006-03-09	Chiral 3-halophthalic acid derivatives
WO2001000580A1 (en)	2001-01-04	2-(optionally substituted benzoylamino)-6-(optionally substituted phenoxy)pyridine derivatives, process for the preparation thereof and herbicides
WO2025124942A1 (en)	2025-06-19	Process for preparing a saflufenacil intermediate
JPH08151354A (ja)	1996-06-11	アミノアセトアミド誘導体の製造法
KR20020051926A (ko)	2002-06-29	2-(2-하이드록시페닐)-2-(알콕시이미노)-ｎ-메틸아세트아미드 유도체의 제조방법
MXPA00002189A (en)	2001-03-05	Method for producing (hetero)aromatic hydroxylamines