UA78662C2 - Cis-trans-isomerization of semicarbazone compounds - Google Patents

Cis-trans-isomerization of semicarbazone compounds Download PDF

Info

Publication number: UA78662C2
Authority: UA; Ukraine
Prior art keywords: isomer; isomerization; differs; alkyl; formula
Prior art date: 2003-11-14

Application number

UAA200606379A

Other languages

English (en)

Ukrainian (uk)

Inventor

Phil Harrington

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.)

2003-11-14

Filing date

2004-12-11

Publication date

2007-04-10

2004-12-11 Application filed by Basf Ag filed Critical Basf Ag

2007-04-10 Publication of UA78662C2 publication Critical patent/UA78662C2/uk

Links

-1 semicarbazone compounds Chemical class 0.000 title claims abstract description 39
238000007697 cis-trans-isomerization reaction Methods 0.000 title 1
238000006317 isomerization reaction Methods 0.000 claims abstract description 23
150000001875 compounds Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 16
229910052740 iodine Inorganic materials 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
239000011630 iodine Substances 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
230000003993 interaction Effects 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
239000003701 inert diluent Substances 0.000 claims 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
239000011541 reaction mixture Substances 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012535 impurity Substances 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000007858 starting material Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000003849 aromatic solvent Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 2
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012467 final product Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 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
238000002955 isolation Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000007659 semicarbazones Chemical class 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
125000006083 1-bromoethyl group Chemical group 0.000 description 1
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UAA200606379A 2003-11-14 2004-12-11 Cis-trans-isomerization of semicarbazone compounds UA78662C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US51962103P	2003-11-14	2003-11-14
PCT/EP2004/012872 WO2005047235A1 (en)	2003-11-14	2004-11-12	Cis-trans isomerisation of semicarbazone compounds

Publications (1)

Publication Number	Publication Date
UA78662C2 true UA78662C2 (en)	2007-04-10

Family

ID=34590435

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200606379A UA78662C2 (en)	2003-11-14	2004-12-11	Cis-trans-isomerization of semicarbazone compounds

Country Status (20)

Country	Link
US (1)	US7371885B2 (de)
EP (1)	EP1687263B1 (de)
JP (1)	JP4362517B2 (de)
KR (1)	KR20060134930A (de)
CN (1)	CN100417642C (de)
AR (1)	AR047122A1 (de)
AT (1)	ATE409689T1 (de)
AU (1)	AU2004289444A1 (de)
BR (1)	BRPI0416484A (de)
CA (1)	CA2545011A1 (de)
DE (1)	DE602004016879D1 (de)
DK (1)	DK1687263T3 (de)
EA (1)	EA200600888A1 (de)
ES (1)	ES2311880T3 (de)
IL (1)	IL175224A (de)
PL (1)	PL1687263T3 (de)
SI (1)	SI1687263T1 (de)
UA (1)	UA78662C2 (de)
WO (1)	WO2005047235A1 (de)
ZA (1)	ZA200604804B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE602006009513D1 (de)	2005-06-16	2009-11-12	Basf Se	Verwendung von phenylsemicarbazonen für die saatgutbeizung
US20110105794A1 (en) *	2008-06-30	2011-05-05	Basf Se	Process for the Isomerization of Semicarbazone Compounds
US9125411B2 (en) *	2010-04-15	2015-09-08	Basf Se	UV absorbers for reducing the E/Z isomerization of pesticides
DE102010020882A1 (de) *	2010-05-18	2011-11-24	Alzchem Trostberg Gmbh	Semicarbazone zur Härtung von Epoxidharzen
DE102011118501A1 (de) *	2011-11-15	2013-05-16	Alzchem Ag	Alkyl- oder Dialkyl-Semicarbazone als Härter für Epoxidharze
CN103193684B (zh) *	2013-04-08	2016-06-22	杭州宇龙化工有限公司	一种缩氨基脲的制备方法
CN103342666A (zh) *	2013-07-18	2013-10-09	桂林理工大学	3-乙氧基水杨醛缩碳酰肼双希夫碱的合成方法
CN104592059B (zh) *	2015-01-07	2016-07-06	青岛农业大学	3-酰腙二苯脲衍生物及其制备方法和应用
CN105037331B (zh) *	2015-06-17	2018-02-09	浙江科技学院	瑞舒伐他汀中间体的制备方法
CN106674069B (zh) *	2016-12-06	2018-05-11	上海博志研新药物技术有限公司	Gft505及其中间体的制备方法
CN108129358B (zh) *	2018-02-05	2020-03-24	扬州工业职业技术学院	一种清洁高效的氰氟虫腙合成工艺

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3136794A (en)	1962-02-02	1964-06-09	Pfizer & Co C	Stabilization of iodine isomerized vitamin a esters
NL131506C (de)	1966-01-28	1900-01-01
DE69119301T2 (de)	1990-06-16	1996-10-17	Nihon Nohyaku Co Ltd	Hydrazincarboxamidderivate, Verfahren für ihre Herstellung und ihre Verwendung
JP5093429B2 (ja) *	2000-10-18	2012-12-12	日本農薬株式会社	動物用外部寄生性害虫防除剤及びその使用方法
TW200609203A (en) *	2004-03-17	2006-03-16	Basf Ag	Preparation of semicarbazones

2004
- 2004-11-12 PL PL04818397T patent/PL1687263T3/pl unknown
- 2004-11-12 KR KR1020067009271A patent/KR20060134930A/ko not_active Abandoned
- 2004-11-12 DK DK04818397T patent/DK1687263T3/da active
- 2004-11-12 CA CA002545011A patent/CA2545011A1/en not_active Abandoned
- 2004-11-12 DE DE602004016879T patent/DE602004016879D1/de not_active Expired - Lifetime
- 2004-11-12 AR ARP040104192A patent/AR047122A1/es unknown
- 2004-11-12 EP EP04818397A patent/EP1687263B1/de not_active Expired - Lifetime
- 2004-11-12 EA EA200600888A patent/EA200600888A1/ru unknown
- 2004-11-12 US US10/578,465 patent/US7371885B2/en not_active Expired - Fee Related
- 2004-11-12 BR BRPI0416484-9A patent/BRPI0416484A/pt not_active IP Right Cessation
- 2004-11-12 AU AU2004289444A patent/AU2004289444A1/en not_active Abandoned
- 2004-11-12 ES ES04818397T patent/ES2311880T3/es not_active Expired - Lifetime
- 2004-11-12 WO PCT/EP2004/012872 patent/WO2005047235A1/en not_active Ceased
- 2004-11-12 CN CNB2004800333644A patent/CN100417642C/zh not_active Expired - Lifetime
- 2004-11-12 JP JP2006538809A patent/JP4362517B2/ja not_active Expired - Fee Related
- 2004-11-12 AT AT04818397T patent/ATE409689T1/de not_active IP Right Cessation
- 2004-11-12 SI SI200430877T patent/SI1687263T1/sl unknown
- 2004-12-11 UA UAA200606379A patent/UA78662C2/uk unknown
2006
- 2006-04-26 IL IL175224A patent/IL175224A/en active IP Right Grant
- 2006-06-12 ZA ZA200604804A patent/ZA200604804B/xx unknown

Also Published As

Publication number	Publication date
WO2005047235A1 (en)	2005-05-26
AR047122A1 (es)	2006-01-11
ES2311880T3 (es)	2009-02-16
KR20060134930A (ko)	2006-12-28
CA2545011A1 (en)	2005-05-26
ZA200604804B (en)	2007-11-28
CN1878752A (zh)	2006-12-13
EP1687263B1 (de)	2008-10-01
DK1687263T3 (da)	2009-02-02
EA200600888A1 (ru)	2006-10-27
IL175224A0 (en)	2006-09-05
HK1099276A1 (zh)	2007-08-10
BRPI0416484A (pt)	2007-03-27
DE602004016879D1 (de)	2008-11-13
SI1687263T1 (sl)	2008-12-31
PL1687263T3 (pl)	2009-04-30
US20070135520A1 (en)	2007-06-14
ATE409689T1 (de)	2008-10-15
JP4362517B2 (ja)	2009-11-11
AU2004289444A1 (en)	2005-05-26
EP1687263A1 (de)	2006-08-09
IL175224A (en)	2010-11-30
CN100417642C (zh)	2008-09-10
US7371885B2 (en)	2008-05-13
JP2007511483A (ja)	2007-05-10

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RU2138489C1 (ru)	1999-09-27	Способ получения производных оксадиазина и промежуточные продукты
UA78662C2 (en)	2007-04-10	Cis-trans-isomerization of semicarbazone compounds
CN102076635B (zh)	2013-12-25	缩氨基脲化合物的异构化方法
KR101207668B1 (ko)	2012-12-03	세미카르바존의 제조 방법
MXPA06005193A (en)	2006-10-17	Cis-trans isomerisation of semicarbazone compounds
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HK1099276B (en)	2009-02-13	Cis-trans isomerisation of semicarbazone compounds
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