IL108767A - Process for Preparation 6 - Alkyl - 4 -) Pyridine - 3 - Il - Methylamino (- 4, 5 - Dihydro - 1, 2, 4 - Triazine - H) 23 (- On - Google Patents

Process for Preparation 6 - Alkyl - 4 -) Pyridine - 3 - Il - Methylamino (- 4, 5 - Dihydro - 1, 2, 4 - Triazine - H) 23 (- On

Info

Publication number: IL108767A
Authority: IL; Israel
Prior art keywords: process according; formula; reaction; alkyl; carboxylic acid
Prior art date: 1993-03-02

Application number

IL10876794A

Other languages

English (en)

Hebrew (he)

Other versions

IL108767A0 (en

Original Assignee

Novartis 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.)

1993-03-02

Filing date

1994-02-24

Publication date

1999-03-12

1994-02-24 Application filed by Novartis Ag filed Critical Novartis Ag

1994-06-24 Publication of IL108767A0 publication Critical patent/IL108767A0/xx

1999-03-12 Publication of IL108767A publication Critical patent/IL108767A/en

Links

238000000034 method Methods 0.000 title claims abstract description 32
238000002360 preparation method Methods 0.000 title claims abstract description 13
238000006243 chemical reaction Methods 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims abstract description 10
229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 9
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 5
230000001476 alcoholic effect Effects 0.000 claims abstract description 4
229910052799 carbon Inorganic materials 0.000 claims abstract description 3
229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
VKJMPYGLTDMUPZ-UHFFFAOYSA-N 5-amino-1h-triazin-6-one Chemical compound NC1=CN=NNC1=O VKJMPYGLTDMUPZ-UHFFFAOYSA-N 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
239000006174 pH buffer Substances 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
-1 carboxylic acid alkali metal salt Chemical class 0.000 claims 1
239000001632 sodium acetate Substances 0.000 claims 1
235000017281 sodium acetate Nutrition 0.000 claims 1
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical group [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 claims 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
150000001735 carboxylic acids Chemical class 0.000 description 5
239000007858 starting material Substances 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000005260 corrosion Methods 0.000 description 4
230000007797 corrosion Effects 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
239000010948 rhodium Substances 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
WJWZRUMTLNWEBP-UHFFFAOYSA-N 5-amino-1h-triazin-6-one;hydrochloride Chemical compound Cl.NC1=CN=NNC1=O WJWZRUMTLNWEBP-UHFFFAOYSA-N 0.000 description 2
QHMTXANCGGJZRX-UHFFFAOYSA-N 6-methyl-4-(pyridin-3-ylmethylideneamino)-2,5-dihydro-1,2,4-triazin-3-one Chemical compound C1C(C)=NNC(=O)N1N=CC1=CC=CN=C1 QHMTXANCGGJZRX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
238000010792 warming Methods 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001447 alkali salts 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
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
OOTKJPZEEVPWCR-UHFFFAOYSA-N n-methyl-1-pyridin-2-ylmethanamine Chemical compound CNCC1=CC=CC=N1 OOTKJPZEEVPWCR-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000007974 sodium acetate buffer Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1

Classifications

- 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
- C07D401/12—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 chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

IL10876794A 1993-03-02 1994-02-24 Process for Preparation 6 - Alkyl - 4 -) Pyridine - 3 - Il - Methylamino (- 4, 5 - Dihydro - 1, 2, 4 - Triazine - H) 23 (- On IL108767A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939304178A GB9304178D0 (en)	1993-03-02	1993-03-02	Process for the preparation of 6-alkyl-4-(pyridin-3-yl-methyleneamino),5-dihydro-1,2,4-triazin-3(2h)-one

Publications (2)

Publication Number	Publication Date
IL108767A0 IL108767A0 (en)	1994-06-24
IL108767A true IL108767A (en)	1999-03-12

Family

ID=10731281

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10876794A IL108767A (en)	1993-03-02	1994-02-24	Process for Preparation 6 - Alkyl - 4 -) Pyridine - 3 - Il - Methylamino (- 4, 5 - Dihydro - 1, 2, 4 - Triazine - H) 23 (- On

Country Status (15)

Country	Link
US (1)	US5606057A (fr)
EP (1)	EP0613895B1 (fr)
JP (1)	JP3314219B2 (fr)
KR (1)	KR100286120B1 (fr)
CN (1)	CN1041089C (fr)
AT (1)	ATE172729T1 (fr)
BR (1)	BR9400770A (fr)
CA (1)	CA2116632C (fr)
DE (1)	DE69414155T2 (fr)
DK (1)	DK0613895T3 (fr)
ES (1)	ES2123113T3 (fr)
GB (1)	GB9304178D0 (fr)
IL (1)	IL108767A (fr)
TW (1)	TW391966B (fr)
ZA (1)	ZA941410B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2959397A (en) *	1996-05-31	1998-01-05	Novartis Ag	Process for the preparation of hydrazine derivatives useful as intermediates for the preparation of peptide analogues
AR040073A1 (es)	2002-05-07	2005-03-16	Syngenta Participations Ag	Derivados de 4''-desoxi-4''-(s)-amido avermectina y su uso como plaguicidas
CN102250030B (zh) *	2010-05-17	2013-01-30	中国中化股份有限公司	一种4-氨基-6-甲基-1,2,4三嗪-3-酮制备方法
CN102491952A (zh) *	2011-12-09	2012-06-13	四川省乐山市福华通达农药科技有限公司	一种三嗪酰胺的合成工艺
CN102763669A (zh) *	2012-07-04	2012-11-07	河北威远生物化工股份有限公司	一种杀虫农药组合物
CN103222466A (zh) *	2013-04-26	2013-07-31	南通金陵农化有限公司	一种吡蚜酮和甲氧虫酰肼的复配农药
CN103271074B (zh) *	2013-06-18	2014-09-03	陕西农心作物科技有限公司	一种含环氧虫啉和吡蚜酮的杀虫组合物
CN105028442A (zh) *	2015-08-24	2015-11-11	江阴苏利化学股份有限公司	一种含有除虫脲和吡蚜酮的杀虫组合物及其用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE43047C (de) *			E. DUCRETET und E. PlNEL, in Firma : E. DUCRETET & CO. in Paris, rue Claude-Bernard 75	Vorrichtung, um die mit optischen Telegraphen abgesandten Depeschen automatisch zu fixiren
DE43044C (de) *			V. PFEIFFER in München.	Befeuchtungsvorrichtung für Schleifapparate.
US2798077A (en) *	1954-09-24	1957-07-02	Hoffmann La Roche	Preparation of methyl-(beta-picolyl)-amine
US2945862A (en) *	1957-04-12	1960-07-19	Cfmc	Process for the production of aldehydes
US3274206A (en) *	1964-03-06	1966-09-20	Nepera Chemical Co Inc	Process for the production of pyridine aldehydes
ES2070861T3 (es) *	1987-10-16	1995-06-16	Ciba Geigy Ag	Compuestos antiparasitarios.
US5179094A (en) *	1989-04-06	1993-01-12	Ciba-Geigy Corporation	Pest control agents
EP0391849B1 (fr) *	1989-04-06	1995-04-19	Ciba-Geigy Ag	Pyridyl-méthylène amino-1,2,4-triazinones
TW199149B (fr) *	1989-11-15	1993-02-01	Ciba Geigy Ag
EP0548233B1 (fr) *	1990-08-10	1997-10-22	Reilly Industries, Inc.	Procedes de synthese d'imines, d'aldehydes et d'amines secondaires non symetriques

1993
- 1993-03-02 GB GB939304178A patent/GB9304178D0/en active Pending
1994
- 1994-02-05 TW TW083100983A patent/TW391966B/zh not_active IP Right Cessation
- 1994-02-09 US US08/194,183 patent/US5606057A/en not_active Expired - Lifetime
- 1994-02-21 ES ES94810101T patent/ES2123113T3/es not_active Expired - Lifetime
- 1994-02-21 DE DE69414155T patent/DE69414155T2/de not_active Expired - Lifetime
- 1994-02-21 EP EP94810101A patent/EP0613895B1/fr not_active Expired - Lifetime
- 1994-02-21 AT AT94810101T patent/ATE172729T1/de active
- 1994-02-21 DK DK94810101T patent/DK0613895T3/da active
- 1994-02-24 IL IL10876794A patent/IL108767A/en not_active IP Right Cessation
- 1994-02-26 KR KR1019940003645A patent/KR100286120B1/ko not_active Expired - Fee Related
- 1994-02-28 CA CA002116632A patent/CA2116632C/fr not_active Expired - Fee Related
- 1994-03-01 BR BR9400770A patent/BR9400770A/pt not_active IP Right Cessation
- 1994-03-01 ZA ZA941410A patent/ZA941410B/xx unknown
- 1994-03-01 CN CN94102546A patent/CN1041089C/zh not_active Expired - Fee Related
- 1994-03-02 JP JP05661694A patent/JP3314219B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BR9400770A (pt)	1994-10-11
GB9304178D0 (en)	1993-04-21
KR100286120B1 (ko)	2001-04-16
JP3314219B2 (ja)	2002-08-12
IL108767A0 (en)	1994-06-24
EP0613895A1 (fr)	1994-09-07
US5606057A (en)	1997-02-25
CN1041089C (zh)	1998-12-09
ATE172729T1 (de)	1998-11-15
DE69414155T2 (de)	1999-04-08
ES2123113T3 (es)	1999-01-01
DE69414155D1 (de)	1998-12-03
CA2116632A1 (fr)	1994-09-03
DK0613895T3 (da)	1999-07-05
EP0613895B1 (fr)	1998-10-28
CN1124736A (zh)	1996-06-19
CA2116632C (fr)	2005-01-04
JPH06316575A (ja)	1994-11-15
TW391966B (en)	2000-06-01
ZA941410B (en)	1994-09-02

Legal Events

Date	Code	Title
1999-09-22	FF	Patent granted
2000-02-29	KB	Patent renewed
2000-08-13	KB	Patent renewed
2004-02-19	HP	Change in proprietorship
2004-03-28	KB	Patent renewed
2008-03-23	KB	Patent renewed
2012-02-29	KB	Patent renewed
2014-09-30	EXP	Patent expired

Publication	Publication Date	Title
EP0613895B1 (fr)	1998-10-28	Procédé pour la préparation de 6-alkyl-4-(pyridin-3-yl-méthylèneamino)-4,5-dihydro-1,2,4-triazin-3(2H)-one
US7977496B2 (en)	2011-07-12	Process for producing nitroguanidine derivatives
US5484918A (en)	1996-01-16	Process for the preparation of aqueous nicotinaldehyde
JP3166125B2 (ja)	2001-05-14	インドール誘導体の製法
JP3668899B2 (ja)	2005-07-06	アミノトリアジン誘導体の製造方法
RU2213728C2 (ru)	2003-10-10	Способ получения аминоцианацетамида
EP0990646B1 (fr)	2004-04-28	Procede de preparation de derives d'acide 3-(7-amidino-2-naphthyl)-2-phenylpropionique
US6340773B1 (en)	2002-01-22	Preparation of halogenated primary amines
US5936119A (en)	1999-08-10	Chemical process
US6194600B1 (en)	2001-02-27	Method of producing aminocyanoacetamide
KR100856891B1 (ko)	2008-09-05	수마트립탄의 제조방법
JP2004099454A (ja)	2004-04-02	Ｎ−置換イミダゾールカルボン酸類の製造方法
JPH0237912B2 (fr)	1990-08-28