SK36694A3 - Method of preparation of aminotriazine derivatives - Google Patents

Method of preparation of aminotriazine derivatives Download PDF

Info

Publication number: SK36694A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; alkyl; phenyl; hydrogen
Prior art date: 1993-03-31

Application number

SK366-94A

Other languages

English (en)

Slovak (sk)

Inventor

Thomas Rapold

Marcel Senn

Original Assignee

Ciba Geigy 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.)

1993-03-31

Filing date

1994-03-28

Publication date

1995-02-08

1994-03-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1995-02-08 Publication of SK36694A3 publication Critical patent/SK36694A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 38
238000002360 preparation method Methods 0.000 title claims abstract description 14
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 title abstract description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 34
150000001875 compounds Chemical class 0.000 claims abstract description 23
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 19
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 19
230000001476 alcoholic effect Effects 0.000 claims abstract description 10
238000003797 solvolysis reaction Methods 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
-1 phenylbutyl Chemical group 0.000 claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 claims description 10
125000004344 phenylpropyl group Chemical group 0.000 claims description 10
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 9
125000001188 haloalkyl group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 8
VKJMPYGLTDMUPZ-UHFFFAOYSA-N 5-amino-1h-triazin-6-one Chemical compound NC1=CN=NNC1=O VKJMPYGLTDMUPZ-UHFFFAOYSA-N 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
229910000564 Raney nickel Inorganic materials 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
239000007868 Raney catalyst Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
NYEPBMRXVGDUEZ-UHFFFAOYSA-N 5-acetyl-1h-triazin-6-one Chemical compound CC(=O)C1=CN=NNC1=O NYEPBMRXVGDUEZ-UHFFFAOYSA-N 0.000 claims description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
238000010531 catalytic reduction reaction Methods 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
150000003138 primary alcohols Chemical class 0.000 claims description 2
238000006722 reduction reaction Methods 0.000 claims description 2
150000003333 secondary alcohols Chemical class 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
150000003509 tertiary alcohols Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 2
125000002837 carbocyclic group Chemical group 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
238000010992 reflux Methods 0.000 claims 1
239000002917 insecticide Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
229910052759 nickel Inorganic materials 0.000 description 10
239000003054 catalyst Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
FIFXOUHQMGZUTO-UHFFFAOYSA-N 4-amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-one Chemical compound CC1=NNC(=O)N(N)C1 FIFXOUHQMGZUTO-UHFFFAOYSA-N 0.000 description 7
VSMQHCXCTMWZGY-UHFFFAOYSA-N 4-amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-one;hydrochloride Chemical compound Cl.CC1=NNC(=O)N(N)C1 VSMQHCXCTMWZGY-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
238000001212 derivatisation Methods 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000002609 medium Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
150000001735 carboxylic acids Chemical group 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
NCSCAWXVGUIUEY-UHFFFAOYSA-N n-(6-methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4-yl)acetamide Chemical compound CC(=O)NN1CC(C)=NNC1=O NCSCAWXVGUIUEY-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
IFLRITVIVMSVTL-UHFFFAOYSA-N 4-amino-2,5-dihydro-1,2,4-triazin-3-one Chemical class NN1CC=NNC1=O IFLRITVIVMSVTL-UHFFFAOYSA-N 0.000 description 1
PFNTVCXZEZYYQE-UHFFFAOYSA-N 4-amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-one;5-amino-1h-triazin-6-one Chemical compound NC1=CN=NNC1=O.CC1=NNC(=O)N(N)C1 PFNTVCXZEZYYQE-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052758 niobium Inorganic materials 0.000 description 1
239000010955 niobium Substances 0.000 description 1
GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

SK366-94A 1993-03-31 1994-03-28 Method of preparation of aminotriazine derivatives SK36694A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4069193A	1993-03-31	1993-03-31

Publications (1)

Publication Number	Publication Date
SK36694A3 true SK36694A3 (en)	1995-02-08

Family

ID=21912393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK366-94A SK36694A3 (en)	1993-03-31	1994-03-28	Method of preparation of aminotriazine derivatives

Country Status (20)

Country	Link
US (2)	US5384403A (de)
EP (1)	EP0618200B1 (de)
JP (1)	JP3668899B2 (de)
KR (2)	KR100306200B1 (de)
CN (2)	CN1144802C (de)
AT (1)	ATE157971T1 (de)
AU (1)	AU689459B2 (de)
BR (1)	BR9401346A (de)
CA (1)	CA2120164C (de)
CZ (2)	CZ287169B6 (de)
DE (1)	DE69405439T2 (de)
DK (1)	DK0618200T3 (de)
ES (1)	ES2110206T3 (de)
HU (1)	HU214018B (de)
IL (1)	IL109116A (de)
NZ (2)	NZ260211A (de)
PH (1)	PH30984A (de)
PL (1)	PL185421B1 (de)
SG (1)	SG46219A1 (de)
SK (1)	SK36694A3 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9304191D0 (en) *	1993-03-02	1993-04-21	Ciba Geigy Ag	Process for the preparation of aqueous nicotinaldehyde
CO5210907A1 (es) *	1999-05-12	2002-10-30	Novartis Ag	Solvatos de pometrozina, insecticidamente activos, composiciones que contienen estos compuestos y metodos tanto para producir dichos compuestos y composiciones como para controlar plagas animales con estas composiciones
JP2006213674A (ja) *	2005-02-07	2006-08-17	Ube Ind Ltd	４−ホルミルテトラヒドロピラン化合物の製法
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
JP6063953B2 (ja)	2011-11-29	2017-01-18	シンジェンタパーティシペーションズアーゲー	殺虫性トリアジノン誘導体
CN112028876B (zh) *	2020-09-18	2021-04-20	河北威远生物化工有限公司	一种回收吡蚜酮的方法
CN114573561B (zh) *	2022-03-21	2023-07-18	中国农业大学	含有苄基或杂环取代的三嗪酮类化合物及其制备方法与应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE121742T1 (de) *	1987-10-16	1995-05-15	Ciba Geigy Ag	Schädlingsbekämpfungsmittel.
DK0391849T3 (da) *	1989-04-06	1995-06-26	Ciba Geigy Ag	Pyridyl-methylenamino-1,2,4-triazinoner
DE4011740A1 (de) *	1989-04-14	1990-10-18	Ciba Geigy Ag	1,2,4-triazinonderivate
US5324842A (en) *	1989-11-15	1994-06-28	Ciba-Geigy Corporation	Process for the preparation of aminotriazine derivatives
TW199149B (de) *	1989-11-15	1993-02-01	Ciba Geigy Ag
GB9304191D0 (en) *	1993-03-02	1993-04-21	Ciba Geigy Ag	Process for the preparation of aqueous nicotinaldehyde

1994
- 1994-02-09 US US08/194,185 patent/US5384403A/en not_active Expired - Lifetime
- 1994-02-15 PH PH47771A patent/PH30984A/en unknown
- 1994-03-21 PL PL94302711A patent/PL185421B1/pl not_active IP Right Cessation
- 1994-03-22 AT AT94810174T patent/ATE157971T1/de active
- 1994-03-22 ES ES94810174T patent/ES2110206T3/es not_active Expired - Lifetime
- 1994-03-22 DK DK94810174.6T patent/DK0618200T3/da active
- 1994-03-22 SG SG1996001018A patent/SG46219A1/en unknown
- 1994-03-22 DE DE69405439T patent/DE69405439T2/de not_active Expired - Lifetime
- 1994-03-22 EP EP94810174A patent/EP0618200B1/de not_active Expired - Lifetime
- 1994-03-24 IL IL10911694A patent/IL109116A/en not_active IP Right Cessation
- 1994-03-25 KR KR1019940006216A patent/KR100306200B1/ko not_active Expired - Fee Related
- 1994-03-28 SK SK366-94A patent/SK36694A3/sk unknown
- 1994-03-29 CA CA002120164A patent/CA2120164C/en not_active Expired - Fee Related
- 1994-03-29 AU AU59140/94A patent/AU689459B2/en not_active Ceased
- 1994-03-29 CZ CZ1994739A patent/CZ287169B6/cs not_active IP Right Cessation
- 1994-03-29 NZ NZ260211A patent/NZ260211A/en unknown
- 1994-03-29 NZ NZ286194A patent/NZ286194A/en unknown
- 1994-03-29 CN CNB001010360A patent/CN1144802C/zh not_active Expired - Lifetime
- 1994-03-29 CN CN94103768A patent/CN1058713C/zh not_active Expired - Lifetime
- 1994-03-30 JP JP08535094A patent/JP3668899B2/ja not_active Expired - Fee Related
- 1994-03-30 BR BR9401346A patent/BR9401346A/pt not_active IP Right Cessation
- 1994-03-30 HU HU9400917A patent/HU214018B/hu not_active IP Right Cessation
1995
- 1995-06-06 US US08/468,507 patent/US5514795A/en not_active Expired - Lifetime
1997
- 1997-10-07 CZ CZ19973174A patent/CZ287227B6/cs not_active IP Right Cessation
2001
- 2001-02-12 KR KR1020010006700A patent/KR100303593B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUT66867A (en)	1995-01-30
NZ260211A (en)	1996-08-27
CN1275570A (zh)	2000-12-06
CN1144802C (zh)	2004-04-07
DK0618200T3 (da)	1998-02-16
JPH06321919A (ja)	1994-11-22
JP3668899B2 (ja)	2005-07-06
NZ286194A (en)	1996-08-27
KR100306200B1 (ko)	2001-12-28
AU5914094A (en)	1994-10-06
ES2110206T3 (es)	1998-02-01
IL109116A0 (en)	1994-06-24
US5384403A (en)	1995-01-24
ATE157971T1 (de)	1997-09-15
EP0618200B1 (de)	1997-09-10
CN1104638A (zh)	1995-07-05
KR940021538A (ko)	1994-10-19
SG46219A1 (en)	1998-02-20
HU9400917D0 (en)	1994-06-28
CN1058713C (zh)	2000-11-22
EP0618200A1 (de)	1994-10-05
DE69405439D1 (de)	1997-10-16
CZ287227B6 (cs)	2000-10-11
BR9401346A (pt)	1994-11-01
IL109116A (en)	1999-07-14
CA2120164C (en)	2004-12-21
PH30984A (en)	1997-12-23
KR100303593B1 (ko)	2001-09-24
HU214018B (en)	1997-12-29
AU689459B2 (en)	1998-04-02
CA2120164A1 (en)	1994-10-01
CZ287169B6 (en)	2000-10-11
US5514795A (en)	1996-05-07
PL185421B1 (pl)	2003-05-30
CZ73994A3 (en)	1994-10-19
DE69405439T2 (de)	1998-02-12

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US5514795A (en)	1996-05-07	Process for the preparation of aminotriazine derivatives
US5484918A (en)	1996-01-16	Process for the preparation of aqueous nicotinaldehyde
EP1985614B1 (de)	2013-09-25	Verbessertes verfahren zur herstellung eines nitroguanidinderivats
EP0653421B1 (de)	1997-01-15	Verfahren zur Herstellung 2-cyanoimidazol Derivate
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SK285728B6 (sk)	2007-07-06	Spôsob prípravy substituovaných pyrimidínov
SU545258A3 (ru)	1977-01-30	Способ получени 1-замещенных пиразолонов-5 или их солей
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