IL139174A - Intermediate product in the preparation of compounds 2 - chlorothiazole - Google Patents

Intermediate product in the preparation of compounds 2 - chlorothiazole

Info

Publication number: IL139174A
Authority: IL; Israel
Prior art keywords: noz; och3; cehs; ch2c6h4; unsubstituted
Prior art date: 1995-12-01

Application number

IL13917496A

Other languages

English (en)

Hebrew (he)

Other versions

IL139174A0 (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.)

1995-12-01

Filing date

1996-12-02

Publication date

2004-01-04

1996-12-02 Application filed by Novartis Ag filed Critical Novartis Ag

2001-11-25 Publication of IL139174A0 publication Critical patent/IL139174A0/xx

2004-01-04 Publication of IL139174A publication Critical patent/IL139174A/en

Links

KLEYVGWAORGTIT-UHFFFAOYSA-N 2-chlorothiazole Chemical class ClC1=NC=CS1 KLEYVGWAORGTIT-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 88
125000005842 heteroatom Chemical group 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
239000003513 alkali Substances 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 abstract description 17
125000003118 aryl group Chemical group 0.000 abstract description 14
125000003107 substituted aryl group Chemical group 0.000 abstract description 11
229910052757 nitrogen Inorganic materials 0.000 abstract description 9
125000002947 alkylene group Chemical group 0.000 abstract description 7
125000000217 alkyl group Chemical group 0.000 abstract description 6
229910052717 sulfur Inorganic materials 0.000 abstract description 6
101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 abstract description 3
101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 abstract description 3
150000001340 alkali metals Chemical class 0.000 abstract description 3
229910052783 alkali metal Inorganic materials 0.000 abstract description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 376
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 133
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 53
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 47
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 33
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 31
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
238000000034 method Methods 0.000 description 20
125000006412 propinylene group Chemical group [H]C#CC([H])([H])* 0.000 description 20
239000000203 mixture Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 16
239000000543 intermediate Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
239000003085 diluting agent Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
-1 (alkylene)SR7- is Chemical class 0.000 description 7
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
229910052736 halogen Inorganic materials 0.000 description 7
150000002367 halogens Chemical class 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000007858 starting material Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000012320 chlorinating reagent Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
101100005001 Caenorhabditis elegans cah-5 gene Proteins 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
HCKYRLWYBRUAHE-UHFFFAOYSA-N 2-benzylsulfanyl-5-(chloromethyl)-1,3-thiazole Chemical compound S1C(CCl)=CN=C1SCC1=CC=CC=C1 HCKYRLWYBRUAHE-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 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
NEKLRVZZAZHDGT-UHFFFAOYSA-N n-[3-[(2-benzylsulfanyl-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(C)COCN1CC(S1)=CN=C1SCC1=CC=CC=C1 NEKLRVZZAZHDGT-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
229950011008 tetrachloroethylene Drugs 0.000 description 2
NWWZPOKUUAIXIW-UHFFFAOYSA-N thiamethoxam Chemical compound O=N(=O)N=C1N(C)COCN1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-UHFFFAOYSA-N 0.000 description 2
229960002415 trichloroethylene Drugs 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
YQRRLOOOZNMRIP-UHFFFAOYSA-N 5-methylidene-1,3-thiazolidine-2-thione Chemical compound C=C1CNC(=S)S1 YQRRLOOOZNMRIP-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
101000756400 Human T-cell leukemia virus 2 Protein Rex Proteins 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
101100365003 Mus musculus Scel gene Proteins 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
238000009835 boiling Methods 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
229940010415 calcium hydride Drugs 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
229920006038 crystalline resin Polymers 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
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic 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
150000004678 hydrides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
GAYLOVDFGKQKCJ-UHFFFAOYSA-N n-(3-methyl-2,6-dihydro-1,3,5-oxadiazin-4-yl)nitramide Chemical compound CN1COCN=C1N[N+]([O-])=O GAYLOVDFGKQKCJ-UHFFFAOYSA-N 0.000 description 1
QICLRFNQZLRLMF-UHFFFAOYSA-N n-[3-[(2-cyclohexylsulfanyl-1,3-thiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(C)COCN1CC(S1)=CN=C1SC1CCCCC1 QICLRFNQZLRLMF-UHFFFAOYSA-N 0.000 description 1
DPRKJAQMHKISEQ-UHFFFAOYSA-N n-[3-methyl-5-[(2-phenylsulfanyl-1,3-thiazol-5-yl)methyl]-1,3,5-oxadiazinan-4-ylidene]nitramide Chemical compound [O-][N+](=O)N=C1N(C)COCN1CC(S1)=CN=C1SC1=CC=CC=C1 DPRKJAQMHKISEQ-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl 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
150000002826 nitrites Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

IL13917496A 1995-12-01 1996-12-02 Intermediate product in the preparation of compounds 2 - chlorothiazole IL139174A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH341295		1995-12-01
IL12431196A IL124311A0 (en)	1995-12-01	1996-12-02	Process for preparing 2-chlorothiazole compounds
PCT/IB1996/001329 WO1997020829A1 (en)	1995-12-01	1996-12-02	Process for preparing 2-chlorothiazole compounds

Publications (2)

Publication Number	Publication Date
IL139174A0 IL139174A0 (en)	2001-11-25
IL139174A true IL139174A (en)	2004-01-04

Family

ID=4255435

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
IL13917496A IL139174A (en)	1995-12-01	1996-12-02	Intermediate product in the preparation of compounds 2 - chlorothiazole
IL13917596A IL139175A (en)	1995-12-01	1996-12-02	An intermediate compound in the process of making compounds of 2-chlorothiazole
IL12431196A IL124311A0 (en)	1995-12-01	1996-12-02	Process for preparing 2-chlorothiazole compounds

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
IL13917596A IL139175A (en)	1995-12-01	1996-12-02	An intermediate compound in the process of making compounds of 2-chlorothiazole
IL12431196A IL124311A0 (en)	1995-12-01	1996-12-02	Process for preparing 2-chlorothiazole compounds

Country Status (21)

Country	Link
US (1)	US6211381B1 (de)
EP (1)	EP0873326B1 (de)
JP (1)	JP4142100B2 (de)
KR (2)	KR100489160B1 (de)
CN (2)	CN1083446C (de)
AR (1)	AR004984A1 (de)
AT (1)	ATE309230T1 (de)
AU (1)	AU7636896A (de)
BR (1)	BR9611666A (de)
CA (2)	CA2591794A1 (de)
CZ (2)	CZ301539B6 (de)
DE (1)	DE69635421T2 (de)
DK (1)	DK0873326T3 (de)
ES (1)	ES2252762T3 (de)
HU (1)	HUP9903701A3 (de)
IL (3)	IL139174A (de)
MX (1)	MX9804301A (de)
PL (1)	PL189519B1 (de)
TW (1)	TW480255B (de)
WO (1)	WO1997020829A1 (de)
ZA (1)	ZA9610046B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW240163B (en) *	1992-07-22	1995-02-11	Syngenta Participations Ag	Oxadiazine derivatives
DE4425145A1 (de) *	1994-07-15	1996-01-18	Basf Ag	Verwendung von Thiazol- und Thiadiazolverbindungen
DE69734479T2 (de)	1996-12-19	2006-06-29	Syngenta Participations Ag	Herstellung von Thiazolen
JP4275742B2 (ja) *	1996-12-19	2009-06-10	シンジェンタパーティシペーションズアクチェンゲゼルシャフト	チアゾール誘導体の製造方法
TWI287007B (en) *	2000-08-23	2007-09-21	Syngenta Participations Ag	Continuous process for the preparation of pesticides
TWI359810B (en)	2004-11-04	2012-03-11	Mitsubishi Tanabe Pharma Corp	Carboxylic acid derivative containing thiazole rin
WO2007126043A1 (ja) *	2006-04-27	2007-11-08	Mitsubishi Tanabe Pharma Corporation	チアゾール環を含むカルボン酸誘導体の医薬用途
EP2065374A1 (de) *	2007-11-30	2009-06-03	Bayer CropScience AG	2-(Benzyl- und 1H-pyrazol-4-ylmethyl)sulfinyl-Thiazol-Derivate als Herbizide und Pflanzenwachstumsregulatoren
AU2015203829B2 (en) *	2007-11-30	2017-02-23	Bayer Intellectual Property Gmbh	2-(benzyl- and 1H-pyrazol-4-ylmethyl)sulfinyl thiazole derivatives as herbicides and plant growth regulators
JP2011193857A (ja) *	2010-03-24	2011-10-06	Sumitomo Chemical Co Ltd	Ｎ−カルバモイルアミノ化合物の製造方法
GB2514927B (en) *	2014-05-28	2019-04-17	Rotam Agrochem Int Co Ltd	Thiamethoxam and uses thereof
WO2016057931A1 (en)	2014-10-10	2016-04-14	The Research Foundation For The State University Of New York	Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration
CN110325518A (zh) *	2017-02-26	2019-10-11	日本欧爱特农业科技株式会社	噻唑化合物及除草剂
CN107474022B (zh) *	2017-09-07	2020-06-26	连云港立本作物科技有限公司	噻唑基新烟碱化合物及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE67493T1 (de) *	1985-02-04	1991-10-15	Bayer Agrochem Kk	Heterocyclische verbindungen.
DE3712307A1 (de) *	1987-04-10	1988-10-20	Bayer Ag	3-substituierte 1-(2-chlor-thiazol-5-yl-methyl)-2- nitroimino-1,3-diazacycloalkane
IE960441L (en) *	1988-12-27	1990-06-27	Takeda Chemical Industries Ltd	Guanidine derivatives, their production and insecticides
AU640239B2 (en) *	1990-06-18	1993-08-19	Mitsubishi Chemical Corporation	Pyrazolecarboxamide, insecticidal and miticidal composition, and fungicidal composition for use in agriculture and horticulture
IL99161A (en) *	1990-08-17	1996-11-14	Takeda Chemical Industries Ltd	History of guanidine A process for their preparation and preparations from pesticides that contain them

1996
- 1996-11-29 ZA ZA9610046A patent/ZA9610046B/xx unknown
- 1996-12-01 TW TW085114834A patent/TW480255B/zh not_active IP Right Cessation
- 1996-12-02 IL IL13917496A patent/IL139174A/en not_active IP Right Cessation
- 1996-12-02 EP EP96939236A patent/EP0873326B1/de not_active Expired - Lifetime
- 1996-12-02 HU HU9903701A patent/HUP9903701A3/hu unknown
- 1996-12-02 US US09/077,569 patent/US6211381B1/en not_active Expired - Lifetime
- 1996-12-02 KR KR10-1998-0704017A patent/KR100489160B1/ko not_active Expired - Fee Related
- 1996-12-02 CZ CZ20033398A patent/CZ301539B6/cs not_active IP Right Cessation
- 1996-12-02 DK DK96939236T patent/DK0873326T3/da active
- 1996-12-02 CA CA002591794A patent/CA2591794A1/en not_active Abandoned
- 1996-12-02 AR ARP960105458A patent/AR004984A1/es active IP Right Grant
- 1996-12-02 KR KR10-2004-7015572A patent/KR100519189B1/ko not_active Expired - Fee Related
- 1996-12-02 IL IL13917596A patent/IL139175A/en not_active IP Right Cessation
- 1996-12-02 CA CA002237348A patent/CA2237348C/en not_active Expired - Fee Related
- 1996-12-02 IL IL12431196A patent/IL124311A0/xx not_active IP Right Cessation
- 1996-12-02 PL PL96326973A patent/PL189519B1/pl not_active IP Right Cessation
- 1996-12-02 DE DE69635421T patent/DE69635421T2/de not_active Expired - Lifetime
- 1996-12-02 ES ES96939236T patent/ES2252762T3/es not_active Expired - Lifetime
- 1996-12-02 CN CN96198745A patent/CN1083446C/zh not_active Expired - Fee Related
- 1996-12-02 AU AU76368/96A patent/AU7636896A/en not_active Abandoned
- 1996-12-02 BR BR9611666A patent/BR9611666A/pt not_active IP Right Cessation
- 1996-12-02 WO PCT/IB1996/001329 patent/WO1997020829A1/en not_active Ceased
- 1996-12-02 AT AT96939236T patent/ATE309230T1/de active
- 1996-12-02 JP JP52111697A patent/JP4142100B2/ja not_active Expired - Fee Related
- 1996-12-02 CZ CZ19981664A patent/CZ295996B6/cs not_active IP Right Cessation
1998
- 1998-05-29 MX MX9804301A patent/MX9804301A/es unknown
2001
- 2001-05-18 CN CNB011195185A patent/CN1219773C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DK0873326T3 (da)	2006-03-27
IL139175A0 (en)	2001-11-25
DE69635421D1 (de)	2005-12-15
HUP9903701A2 (hu)	2000-03-28
CZ301539B6 (cs)	2010-04-07
ES2252762T3 (es)	2006-05-16
AR004984A1 (es)	1999-04-07
DE69635421T2 (de)	2006-06-14
KR100489160B1 (ko)	2005-10-19
IL139175A (en)	2004-01-04
AU7636896A (en)	1997-06-27
ZA9610046B (en)	1997-07-10
BR9611666A (pt)	1999-02-23
JP2000501413A (ja)	2000-02-08
EP0873326A1 (de)	1998-10-28
CN1203593A (zh)	1998-12-30
PL326973A1 (en)	1998-11-09
PL189519B1 (pl)	2005-08-31
EP0873326B1 (de)	2005-11-09
CZ295996B6 (cs)	2005-12-14
CN1083446C (zh)	2002-04-24
IL124311A0 (en)	1998-12-06
CA2591794A1 (en)	1997-06-12
IL139174A0 (en)	2001-11-25
ATE309230T1 (de)	2005-11-15
WO1997020829A1 (en)	1997-06-12
KR19990071739A (ko)	1999-09-27
KR20040089750A (ko)	2004-10-21
HUP9903701A3 (en)	2002-01-28
MX9804301A (es)	1998-09-30
CN1219773C (zh)	2005-09-21
TW480255B (en)	2002-03-21
CA2237348A1 (en)	1997-06-12
US6211381B1 (en)	2001-04-03
CA2237348C (en)	2007-08-21
CZ166498A3 (cs)	1998-08-12
CN1327982A (zh)	2001-12-26
KR100519189B1 (ko)	2005-10-07
JP4142100B2 (ja)	2008-08-27

Legal Events

Date	Code	Title
2004-02-19	HP	Change in proprietorship
2004-06-01	FF	Patent granted
2004-06-20	KB	Patent renewed
2007-07-24	MM9K	Patent not in force due to non-payment of renewal fees
2015-07-30	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0873326B1 (de)	2005-11-09	Verfahren zur herstellung von 2-chlorthiazolderivaten
SE456581B (sv)	1988-10-17	Mellanprodukter for framstellning av 3,4-disubstituerade 1,2,5-tiadiazol-1-oxider och -1,1-dioxider som er h 71-receptorantagonister
US20110306772A1 (en)	2011-12-15	Process for the preparation of 2-chloro-5-chloromethyl-thiazole
EP0946531B1 (de)	2005-11-02	Verfahren zur herstellung von thiazolederivaten
KR100520249B1 (ko)	2005-10-12	티아졸 유도체의 제조 방법
US12565493B2 (en)	2026-03-03	Method for preparing 2-[2-(2-chlorothiazol-5-yl)-2-oxo-ethyl]sulfanyl-6-hydroxy-3-methyl-5-phenyl-pyrimidin-4-one
WO1997023469A9 (en)	1998-11-26	Process for the preparation of 2-chloro-5-chloromethyl-thiazole
Lee et al.	1993	Reactions of 5-(arylimino)-4-chloro-5H-1, 2, 3-dithiazoles with primary and secondary alkylamines: Novel synthesis of (arylimino) cyanomethyl alkylamino disulfides and their mechanisms of formation
Heimgartner	1986	2-Thiazolin-5-thiones, a New Type of Sulfur Heterocycle Synthesis and Reactions
AU2006200339B2 (en)	2008-03-06	Process for preparing 2-chlorothiazole compounds
AU2002300672B2 (en)	2006-02-16	Process for preparing 2-chlorothiazole compounds
US6462043B1 (en)	2002-10-08	Method for producing substituted-2-nitroguanidine derivatives
CZ2000568A3 (cs)	2000-05-17	Způsob výroby substituovaných 2- nitroguanidinových derivátů