IL121031A - Process and intermediates for the preparation of 5 - (alkoxymethyl) -2, 3 - pyridinedicarboximide compounds and their use in the preparation of herbicidal imidazolinone compounds - Google Patents

Process and intermediates for the preparation of 5 - (alkoxymethyl) -2, 3 - pyridinedicarboximide compounds and their use in the preparation of herbicidal imidazolinone compounds

Info

Publication number: IL121031A
Authority: IL; Israel
Prior art keywords: halogen; compound; optionally substituted; alkyl; alkoxy
Prior art date: 1996-06-10

Application number

IL12103197A

Other languages

English (en)

Other versions

IL121031A0 (en

Original Assignee

American Cyanamid 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.)

1996-06-10

Filing date

1997-06-08

Publication date

2001-04-30

1997-06-08 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1997-11-20 Publication of IL121031A0 publication Critical patent/IL121031A0/xx

2001-04-30 Publication of IL121031A publication Critical patent/IL121031A/en

Links

238000000034 method Methods 0.000 title claims abstract description 45
238000002360 preparation method Methods 0.000 title claims abstract description 24
125000004849 alkoxymethyl group Chemical group 0.000 title claims description 21
230000002363 herbicidal effect Effects 0.000 title claims description 6
239000000543 intermediate Substances 0.000 title abstract description 6
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 34
-1 C(O)R2 Chemical group 0.000 claims abstract description 31
229910052736 halogen Inorganic materials 0.000 claims abstract description 27
150000002367 halogens Chemical class 0.000 claims abstract description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 23
239000000203 mixture Substances 0.000 claims abstract description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 16
239000002904 solvent Substances 0.000 claims abstract description 16
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 12
239000002585 base Substances 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
150000001412 amines Chemical class 0.000 claims abstract description 7
150000002923 oximes Chemical class 0.000 claims abstract description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 20
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 10
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000003444 phase transfer catalyst Substances 0.000 claims description 7
239000001632 sodium acetate Substances 0.000 claims description 6
235000017281 sodium acetate Nutrition 0.000 claims description 6
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
235000011056 potassium acetate Nutrition 0.000 claims description 3
VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
150000002431 hydrogen Chemical group 0.000 abstract 1
125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 62
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
GXIKFQDWFQDJMU-UHFFFAOYSA-N 2-(methoxymethyl)prop-2-enal Chemical compound COCC(=C)C=O GXIKFQDWFQDJMU-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000010586 diagram Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
UFUQBRMYERTCQH-UHFFFAOYSA-N 3-bromo-1-methylpyrrole-2,5-dione Chemical compound CN1C(=O)C=C(Br)C1=O UFUQBRMYERTCQH-UHFFFAOYSA-N 0.000 description 2
XPWBLMOTTABVDZ-UHFFFAOYSA-N 3-bromo-1-phenylpyrrole-2,5-dione Chemical compound O=C1C(Br)=CC(=O)N1C1=CC=CC=C1 XPWBLMOTTABVDZ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 1
VCJAXUAZKWUPSH-UHFFFAOYSA-N 3-chloro-1-methylpyrrole-2,5-dione Chemical group CN1C(=O)C=C(Cl)C1=O VCJAXUAZKWUPSH-UHFFFAOYSA-N 0.000 description 1
ZKKDYLHSRWLPSP-UHFFFAOYSA-N 3-chloro-1-phenylpyrrole-2,5-dione Chemical group O=C1C(Cl)=CC(=O)N1C1=CC=CC=C1 ZKKDYLHSRWLPSP-UHFFFAOYSA-N 0.000 description 1
IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011133 lead Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 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
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
ZRKGTINFVOLLNT-UHFFFAOYSA-N pyrrolo[3,4-b]pyridine-5,7-dione Chemical class C1=CC=C2C(=O)NC(=O)C2=N1 ZRKGTINFVOLLNT-UHFFFAOYSA-N 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Pyrrole Compounds (AREA)

IL12103197A 1996-06-10 1997-06-08 Process and intermediates for the preparation of 5 - (alkoxymethyl) -2, 3 - pyridinedicarboximide compounds and their use in the preparation of herbicidal imidazolinone compounds IL121031A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US66128996A	1996-06-10	1996-06-10

Publications (2)

Publication Number	Publication Date
IL121031A0 IL121031A0 (en)	1997-11-20
IL121031A true IL121031A (en)	2001-04-30

Family

ID=24652984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12103197A IL121031A (en)	1996-06-10	1997-06-08	Process and intermediates for the preparation of 5 - (alkoxymethyl) -2, 3 - pyridinedicarboximide compounds and their use in the preparation of herbicidal imidazolinone compounds

Country Status (28)

Country	Link
EP (1)	EP0812842B1 (fr)
JP (1)	JPH1059960A (fr)
KR (1)	KR980002048A (fr)
CN (2)	CN1068882C (fr)
AR (1)	AR007522A1 (fr)
AT (1)	ATE215086T1 (fr)
AU (1)	AU712138B2 (fr)
BR (1)	BR9703504A (fr)
CA (1)	CA2207453A1 (fr)
CO (1)	CO4790132A1 (fr)
CZ (1)	CZ288287B6 (fr)
DE (1)	DE69711265T2 (fr)
DK (1)	DK0812842T3 (fr)
ES (1)	ES2175273T3 (fr)
HU (1)	HU218980B (fr)
IL (1)	IL121031A (fr)
MX (1)	MX9704257A (fr)
NZ (1)	NZ328042A (fr)
PL (1)	PL320468A1 (fr)
PT (1)	PT812842E (fr)
RU (1)	RU2186771C2 (fr)
SG (1)	SG63714A1 (fr)
SK (1)	SK283182B6 (fr)
TR (1)	TR199700475A2 (fr)
TW (1)	TW442467B (fr)
UA (1)	UA54380C2 (fr)
YU (1)	YU24097A (fr)
ZA (1)	ZA975078B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1326849C (zh) *	2005-09-23	2007-07-18	南开大学	六氢酞酰亚胺类化合物及其制备和用途
CN102875548A (zh) *	2011-07-14	2013-01-16	中国科学院大连化学物理研究所	一类基于肟的通过[2+2+2]环加成合成吡啶衍生物的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU175454B (hu) *	1977-07-25	1980-08-28	Chinoin Gyogyszer Es Vegyeszet	Sposob poluchenija novykh predel'nykh i chastichno predel'nykh n-acil-pirrol-2,5-dionov
IL62794A0 (en) *	1980-06-02	1981-07-31	American Cyanamid Co	Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents
US4754033A (en) *	1984-08-10	1988-06-28	Ciba-Geigy Corporation	Process for producing pyridine-2,3-dicarboxylic acid derivatives; and novel 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives and 1,4-dihydropyridine-2,3-dicarboxylic acid derivatives
US4709036A (en) *	1985-06-13	1987-11-24	American Cyanamid Company	Process for the preparation of herbicidal 2-(4,4-disubstituted-5-oxo-2-imidazolin-2-yl)benzoic, nicotinic and quinoline-3-carboxylic acids, esters and salts
GB8721986D0 (en) *	1987-09-18	1987-10-28	Ici Plc	Pyridine derivative
EP0461401A1 (fr) *	1990-06-15	1991-12-18	American Cyanamid Company	Procédé pour la préparation des esters dialcoyliques 2,3-dicarboxy-pyridine et leurs dérivés à partir des esters dichloromaléiques
ATE205831T1 (de) *	1995-06-05	2001-10-15	Basf Ag	Verbessertes verfahren zur herstellung von 5- (alkoxymethyl)-pyridin-2,3-dicarboxylat salz
US5925764A (en) *	1998-06-15	1999-07-20	Wu; Wen-Xue	Process and intermediated for the manufacture of pyridine-2, 3-dicarboxylate compounds

1997
- 1997-05-27 TW TW086107151A patent/TW442467B/zh active
- 1997-06-03 CZ CZ19971707A patent/CZ288287B6/cs not_active IP Right Cessation
- 1997-06-05 UA UA97062647A patent/UA54380C2/uk unknown
- 1997-06-06 CO CO97031482A patent/CO4790132A1/es unknown
- 1997-06-06 TR TR97/00475A patent/TR199700475A2/xx unknown
- 1997-06-06 AU AU24748/97A patent/AU712138B2/en not_active Ceased
- 1997-06-06 JP JP9164985A patent/JPH1059960A/ja active Pending
- 1997-06-06 CA CA002207453A patent/CA2207453A1/fr not_active Abandoned
- 1997-06-06 AR ARP970102485A patent/AR007522A1/es not_active Application Discontinuation
- 1997-06-08 IL IL12103197A patent/IL121031A/en not_active IP Right Cessation
- 1997-06-09 KR KR1019970023564A patent/KR980002048A/ko not_active Ceased
- 1997-06-09 RU RU97109817/04A patent/RU2186771C2/ru not_active IP Right Cessation
- 1997-06-09 ES ES97303987T patent/ES2175273T3/es not_active Expired - Lifetime
- 1997-06-09 NZ NZ328042A patent/NZ328042A/xx unknown
- 1997-06-09 DK DK97303987T patent/DK0812842T3/da active
- 1997-06-09 AT AT97303987T patent/ATE215086T1/de not_active IP Right Cessation
- 1997-06-09 SK SK739-97A patent/SK283182B6/sk unknown
- 1997-06-09 DE DE69711265T patent/DE69711265T2/de not_active Expired - Lifetime
- 1997-06-09 EP EP97303987A patent/EP0812842B1/fr not_active Expired - Lifetime
- 1997-06-09 BR BR9703504A patent/BR9703504A/pt not_active IP Right Cessation
- 1997-06-09 ZA ZA975078A patent/ZA975078B/xx unknown
- 1997-06-09 MX MX9704257A patent/MX9704257A/es not_active IP Right Cessation
- 1997-06-09 HU HU9701021A patent/HU218980B/hu not_active IP Right Cessation
- 1997-06-09 PL PL97320468A patent/PL320468A1/xx unknown
- 1997-06-09 YU YU24097A patent/YU24097A/sh unknown
- 1997-06-09 PT PT97303987T patent/PT812842E/pt unknown
- 1997-06-10 SG SG1997002002A patent/SG63714A1/en unknown
- 1997-06-10 CN CN97112766A patent/CN1068882C/zh not_active Expired - Fee Related
2000
- 2000-11-17 CN CN00133923A patent/CN1319599A/zh active Pending

Also Published As

Publication number	Publication date
CO4790132A1 (es)	1999-05-31
HUP9701021A3 (en)	1998-09-28
ES2175273T3 (es)	2002-11-16
EP0812842B1 (fr)	2002-03-27
ZA975078B (en)	1998-12-09
AU712138B2 (en)	1999-10-28
EP0812842A3 (fr)	1998-04-15
DE69711265D1 (de)	2002-05-02
DK0812842T3 (da)	2002-06-17
PT812842E (pt)	2002-09-30
RU2186771C2 (ru)	2002-08-10
PL320468A1 (en)	1997-12-22
MX9704257A (es)	1998-07-31
SK73997A3 (en)	1998-01-14
CN1169995A (zh)	1998-01-14
EP0812842A2 (fr)	1997-12-17
IL121031A0 (en)	1997-11-20
TW442467B (en)	2001-06-23
KR980002048A (ko)	1998-03-30
UA54380C2 (uk)	2003-03-17
ATE215086T1 (de)	2002-04-15
SG63714A1 (en)	1999-03-30
AU2474897A (en)	1997-12-18
HUP9701021A2 (hu)	1998-04-28
CZ170797A3 (en)	1997-12-17
BR9703504A (pt)	1998-10-06
HU9701021D0 (en)	1997-08-28
JPH1059960A (ja)	1998-03-03
CZ288287B6 (en)	2001-05-16
YU24097A (sh)	1999-07-28
NZ328042A (en)	1999-11-29
CN1319599A (zh)	2001-10-31
HU218980B (hu)	2001-01-29
CA2207453A1 (fr)	1997-12-10
DE69711265T2 (de)	2002-09-12
TR199700475A2 (xx)	1997-12-21
AR007522A1 (es)	1999-11-10
SK283182B6 (sk)	2003-03-04
CN1068882C (zh)	2001-07-25

Legal Events

Date	Code	Title
2001-10-31	FF	Patent granted
2001-11-25	KB	Patent renewed
2003-07-31	KB	Patent renewed
2008-02-10	MM9K	Patent not in force due to non-payment of renewal fees

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