IL103532A - Preparation of a history of 6-trifluoromethyl-1,3,5-triazine - Google Patents

Preparation of a history of 6-trifluoromethyl-1,3,5-triazine

Info

Publication number: IL103532A
Authority: IL; Israel
Prior art keywords: trifluoromethyl; triazine; organic radical; formula; vii
Prior art date: 1991-11-30

Application number

IL10353292A

Other languages

English (en)

Hebrew (he)

Other versions

IL103532A0 (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.)

1991-11-30

Filing date

1992-10-23

Publication date

1996-10-31

1992-10-23 Application filed by Basf Ag filed Critical Basf Ag

1993-03-15 Publication of IL103532A0 publication Critical patent/IL103532A0/xx

1996-10-31 Publication of IL103532A publication Critical patent/IL103532A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 16
CYCJLDRPFYTAMJ-UHFFFAOYSA-N 2-(trifluoromethyl)-1,3,5-triazine Chemical class FC(F)(F)C1=NC=NC=N1 CYCJLDRPFYTAMJ-UHFFFAOYSA-N 0.000 title claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 12
238000000034 method Methods 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 17
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 3
241000257303 Hymenoptera Species 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
239000011814 protection agent Substances 0.000 abstract description 2
150000001298 alcohols Chemical class 0.000 abstract 1
150000003918 triazines Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 14
239000002585 base Substances 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
150000003254 radicals Chemical class 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
-1 6-Trichloromethyl-substituted 1,3, 5-triazines Chemical class 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
SCRPYPQDRSFLLF-UHFFFAOYSA-N 4-methylsulfanyl-6-(trifluoromethyl)-1,3,5-triazin-2-amine Chemical compound CSC1=NC(N)=NC(C(F)(F)F)=N1 SCRPYPQDRSFLLF-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000010949 copper Substances 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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 3
VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 description 3
PGWVITGVIBSMTK-UHFFFAOYSA-N methyl n-(diaminomethylidene)carbamimidothioate;hydroiodide Chemical compound [I-].CSC(=[NH2+])N=C(N)N PGWVITGVIBSMTK-UHFFFAOYSA-N 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000000182 1,3,5-triazines Chemical class 0.000 description 2
RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000376 reactant Substances 0.000 description 2
125000001424 substituent group Chemical group 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
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
CYPWEVNLBQKLEU-UHFFFAOYSA-N 2-methylsulfanyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound CSC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 CYPWEVNLBQKLEU-UHFFFAOYSA-N 0.000 description 1
YXUPRFHQQYZYNZ-UHFFFAOYSA-N 4-methylsulfanyl-6-(trichloromethyl)-1,3,5-triazin-2-amine Chemical compound CSC1=NC(N)=NC(C(Cl)(Cl)Cl)=N1 YXUPRFHQQYZYNZ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
LVMZCNBYTSGGIQ-UHFFFAOYSA-N methyl n-(diaminomethylidene)carbamimidothioate Chemical compound CSC(=N)N=C(N)N LVMZCNBYTSGGIQ-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL10353292A 1991-11-30 1992-10-23 Preparation of a history of 6-trifluoromethyl-1,3,5-triazine IL103532A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4139624A DE4139624A1 (de)	1991-11-30	1991-11-30	Verfahren zur herstellung von derivaten des 6-trifluormethyl-1,3,5-triazins

Publications (2)

Publication Number	Publication Date
IL103532A0 IL103532A0 (en)	1993-03-15
IL103532A true IL103532A (en)	1996-10-31

Family

ID=6446037

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10353292A IL103532A (en)	1991-11-30	1992-10-23	Preparation of a history of 6-trifluoromethyl-1,3,5-triazine

Country Status (9)

Country	Link
EP (1)	EP0545149B1 (fr)
JP (1)	JP3192783B2 (fr)
KR (1)	KR100255570B1 (fr)
AT (1)	ATE111088T1 (fr)
CA (1)	CA2081413C (fr)
DE (2)	DE4139624A1 (fr)
ES (1)	ES2060443T3 (fr)
HU (1)	HU212346B (fr)
IL (1)	IL103532A (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4335497A1 (de) *	1993-10-19	1995-04-20	Basf Ag	Verfahren zur Herstellung unsymmetrisch substituierter Triazine
DE19830902A1 (de)	1998-07-10	2000-01-13	Hoechst Schering Agrevo Gmbh	Verfahren zur Herstellung von 2-Amino-4-chlor-1,3,5-triazinen
RU2371435C2 (ru) *	2006-07-24	2009-10-27	Федеральное государственное научное учреждение "Научно-исследовательский институт проблем конверсии и высоких технологий"	Способ получения 2,4-диалкокси-6-тринитрометил-1,3,5-триазинов
ES2702362T3 (es)	2007-01-31	2019-02-28	Ym Biosciences Australia Pty	Compuestos a base de tiopirimidina y usos de los mismos
US10479777B2 (en)	2013-07-16	2019-11-19	Basf Se	Herbicidal azines
EP3126348B1 (fr)	2014-04-03	2017-11-29	Basf Se	Compose de diaminotriazine utile comme herbicide
EP2930174A1 (fr)	2014-04-07	2015-10-14	Basf Se	Dérivés de diaminotriazine en tant qu'herbicides
US10941122B2 (en)	2014-04-11	2021-03-09	Basf Se	Diaminotriazine derivatives as herbicides
EP3129360B1 (fr)	2014-04-11	2018-10-17	Basf Se	Dérivés de diaminotriazine comme herbicides
CN106232595B (zh)	2014-04-23	2020-01-14	巴斯夫欧洲公司	作为除草剂的二氨基三嗪化合物
WO2015162166A1 (fr)	2014-04-23	2015-10-29	Basf Se	Composés de diaminotriazine et leur utilisation en tant qu'herbicides
KR102022323B1 (ko) *	2018-03-30	2019-09-18	정하윤	트리아진 화합물 및 이의 용도

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1670147A1 (de) *	1966-09-10	1970-10-29	Basf Ag	Verfahren zur Herstellung von Amino-alkylmercapto-s-triazinen
DE4034078A1 (de) *	1990-10-26	1992-04-30	Basf Ag	Verfahren zur herstellung von 6-trifluormethyl-1,3,5-triazinen

1991
- 1991-11-30 DE DE4139624A patent/DE4139624A1/de not_active Withdrawn
1992
- 1992-10-23 IL IL10353292A patent/IL103532A/en not_active IP Right Cessation
- 1992-10-26 CA CA002081413A patent/CA2081413C/fr not_active Expired - Fee Related
- 1992-11-19 AT AT92119689T patent/ATE111088T1/de not_active IP Right Cessation
- 1992-11-19 EP EP92119689A patent/EP0545149B1/fr not_active Expired - Lifetime
- 1992-11-19 ES ES92119689T patent/ES2060443T3/es not_active Expired - Lifetime
- 1992-11-19 DE DE59200474T patent/DE59200474D1/de not_active Expired - Lifetime
- 1992-11-27 HU HU9203764A patent/HU212346B/hu not_active IP Right Cessation
- 1992-11-28 KR KR1019920022749A patent/KR100255570B1/ko not_active Expired - Fee Related
- 1992-11-30 JP JP31988792A patent/JP3192783B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH05262749A (ja)	1993-10-12
KR100255570B1 (ko)	2000-05-01
CA2081413A1 (fr)	1993-05-31
EP0545149B1 (fr)	1994-09-07
JP3192783B2 (ja)	2001-07-30
DE59200474D1 (de)	1994-10-13
DE4139624A1 (de)	1993-06-03
CA2081413C (fr)	2003-02-25
IL103532A0 (en)	1993-03-15
ATE111088T1 (de)	1994-09-15
HUT62568A (en)	1993-05-28
EP0545149A1 (fr)	1993-06-09
ES2060443T3 (es)	1994-11-16
HU9203764D0 (en)	1993-03-29
HU212346B (en)	1996-05-28

Legal Events

Date	Code	Title
1997-03-18	FF	Patent granted
1997-07-13	KB	Patent renewed
1999-04-11	KB	Patent renewed
2002-12-01	KB	Patent renewed
2006-12-07	KB	Patent renewed
2011-06-30	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0251859B1 (fr)	1990-11-22	Procédé de préparation d'imidazopyridines
CA2081413C (fr)	2003-02-25	Preparation de derives de 6-(trifluoromethyl)-1,3,5-triazine
HU204506B (en)	1992-01-28	Process for producing phenyl-hydrazine derivatives
JP3342057B2 (ja)	2002-11-05	置換ｎ−（アリール）−１，２，４−トリアゾロピリミジン−２−スルホンアミド類の製造方法
US5093532A (en)	1992-03-03	Process for the preparation of halogenomethylketones, in particular of 1,1,1-trifluoroacetone
US5739328A (en)	1998-04-14	Preparation of asymmetrically substituted triazines
deStevens et al.	1964	Investigations in Heterocycles. XVI. 1 A New Synthesis of 1, 2-Disubstituted 4-Thiopyrimidines via Enamines
KR100429082B1 (ko)	2004-08-25	1,2-벤즈이소티아졸린-3-온의제조방법
CA1063109A (fr)	1979-09-25	Derives de la n-(1,2,4,-triazin-5-on-4-yl)-glycine, procede pour leur preparation et leur utilisation comme herbicides
EP0556156B1 (fr)	1996-09-25	Procédé pour la préparation de 2-hydroxy-4,6-diaryl-1,3,5-triazine
CS224607B2 (en)	1984-01-16	Method for producing 1-amino-1,3,5-triazine-2,4(1h,3h) dione
PL190872B1 (pl)	2006-02-28	Sposób wytwarzania amidów i estrów kwasu heteroarylokarboksylowego oraz nowe związki
US5130428A (en)	1992-07-14	Preparation of 6-trifluoromethyl-1,3,5-triazines
Okabe et al.	1973	Reaction of 2-Amino-5-Substituted-l, 3, 4-Thiadiazole with 1, 3-Dicarbonyl Compound
US5739329A (en)	1998-04-14	Process for producing hexahydropyridazine and hexahydropyridazine-1,2-dicarboxy derivative
US5214143A (en)	1993-05-25	2-amino-4-fluoroalkoxy-1,3,5-triazines and the preparation thereof
CA2174332C (fr)	2006-02-07	Procede de preparation de triazines substituees asymetriquement
US5280118A (en)	1994-01-18	Trifluoro-and chlorodifluoromethoxy-1,3,5-triazines
CS224639B2 (en)	1984-01-16	Method for producing 3,6-disubstituted 4-amino-1,2,4-triazine-5-one
US4524205A (en)	1985-06-18	Process for the preparation of 1-amino-1,3,5-triazine-2,4(1H,3H)-diones
JP3376481B2 (ja)	2003-02-10	ヘキサヒドロピリダジンの製造法
JPH03123768A (ja)	1991-05-27	ビスアルキルスルホノキシメチルエーテル類あるいはビスアリールスルホノキシメチルエーテル類の製造方法
JPH08245595A (ja)	1996-09-24	ピラゾールの製造方法
BE677858A (fr)	1966-09-15
BE552215A (fr)