ZA200201110B - Process for the preparation of thiazole derivatives. - Google Patents
Process for the preparation of thiazole derivatives. Download PDFInfo
- Publication number
- ZA200201110B ZA200201110B ZA200201110A ZA200201110A ZA200201110B ZA 200201110 B ZA200201110 B ZA 200201110B ZA 200201110 A ZA200201110 A ZA 200201110A ZA 200201110 A ZA200201110 A ZA 200201110A ZA 200201110 B ZA200201110 B ZA 200201110B
- Authority
- ZA
- South Africa
- Prior art keywords
- acid
- chloride
- formula
- compound
- addition salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 5
- 150000007979 thiazole derivatives Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- -1 S-hydroxythiazole-2-diazonium salt compound Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 7
- JIADEYNEMBZHIG-UHFFFAOYSA-N 5-(hydroxymethyl)-3h-1,3-thiazol-2-one Chemical compound OCC1=CN=C(O)S1 JIADEYNEMBZHIG-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- CLXRVGDJXKDDRJ-UHFFFAOYSA-N 5-(hydroxymethyl)-1,3-thiazole-2-diazonium Chemical class OCC1=CN=C([N+]#N)S1 CLXRVGDJXKDDRJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003841 chloride salts Chemical class 0.000 claims description 3
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 claims description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 2
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- 239000012954 diazonium Substances 0.000 description 16
- VRMUIVKEHJSADG-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CN=C(Cl)S1 VRMUIVKEHJSADG-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- TZEMBFLDHOUKNI-UHFFFAOYSA-N (2-amino-1,3-thiazol-5-yl)methanol Chemical compound NC1=NC=C(CO)S1 TZEMBFLDHOUKNI-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PEOOQVDIOJQJHW-UHFFFAOYSA-N (2-chloro-1,3-thiazol-5-yl)methanol Chemical class OCC1=CN=C(Cl)S1 PEOOQVDIOJQJHW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004304 potassium nitrite Substances 0.000 description 3
- 235000010289 potassium nitrite Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 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
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- JFTZOKQGKPIYBB-UHFFFAOYSA-N 2-amino-1,3-thiazol-5-ol Chemical compound NC1=NC=C(O)S1 JFTZOKQGKPIYBB-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- SYGOJCPWJYTHOC-UHFFFAOYSA-N 5-hydroxy-4-methyl-3h-1,3-thiazol-2-one Chemical class CC=1N=C(O)SC=1O SYGOJCPWJYTHOC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012948 isocyanate 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
- 238000010992 reflux Methods 0.000 description 1
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RYXNTTXRPACDJA-UHFFFAOYSA-N sulfanyl carbonochloridate Chemical compound SOC(Cl)=O RYXNTTXRPACDJA-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 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
- C07D277/34—Oxygen 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- 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
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/371,180 US6265553B1 (en) | 1999-08-10 | 1999-08-10 | Intermediate thiazoles and process for the preparation of 2-chloro-5-chloromethyl-thiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201110B true ZA200201110B (en) | 2002-11-27 |
Family
ID=23462834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201110A ZA200201110B (en) | 1999-08-10 | 2002-02-08 | Process for the preparation of thiazole derivatives. |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US6265553B1 (es) |
| EP (1) | EP1202979B1 (es) |
| JP (1) | JP2003506444A (es) |
| KR (1) | KR20020022796A (es) |
| CN (2) | CN1169800C (es) |
| AR (1) | AR030258A1 (es) |
| AT (1) | ATE294166T1 (es) |
| AU (1) | AU778367B2 (es) |
| BR (1) | BR0013235A (es) |
| CA (1) | CA2380838A1 (es) |
| CZ (1) | CZ2002483A3 (es) |
| DE (1) | DE60019763D1 (es) |
| ES (1) | ES2238029T3 (es) |
| HU (1) | HUP0202819A3 (es) |
| MX (1) | MXPA02001246A (es) |
| RU (1) | RU2002105516A (es) |
| TR (2) | TR200200304T2 (es) |
| WO (1) | WO2001010852A1 (es) |
| ZA (1) | ZA200201110B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100878737B1 (ko) | 2003-08-29 | 2009-01-14 | 미쓰이 가가쿠 가부시키가이샤 | 농업용 또는 원예용 살충제 및 그의 이용 방법 |
| US8754053B2 (en) * | 2010-02-17 | 2014-06-17 | Syngenta Crop Protection Llc | Isoxazoline derivatives as insecticides |
| TW201202179A (en) * | 2010-02-26 | 2012-01-16 | Sumitomo Chemical Co | Process for production of cyclopropanecarboxylic acid ester compound |
| EP2751070A4 (en) * | 2011-09-01 | 2015-04-22 | Biotelliga Holdings Ltd | INSULATED LIPIDIC AGENTS ISOLATED IN ENTOMOPATHOGENIC FUNGI AND USES THEREOF |
| CN106749086B (zh) * | 2016-12-27 | 2019-05-24 | 江苏振方生物化学有限公司 | 一种农药中间体2-氯-5-氯甲基噻唑的制备方法 |
| CN111036158A (zh) * | 2019-12-28 | 2020-04-21 | 邯郸市瑞田农药有限公司 | 一种2氯-5氯甲基噻唑合成反应系统 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3631538A1 (de) * | 1986-09-17 | 1988-03-24 | Bayer Ag | Verfahren zur herstellung von 2-chlor-5-chlormethylthiazol |
| EP0775700B1 (en) * | 1995-11-22 | 2000-03-22 | Kureha Chemical Industry Co., Ltd. | Process for the replacement of a primary amino group by a chlorine atom and utilization of this process for the preparation of 2-chloro-5-chloromethyl-thiazol |
| IL130766A0 (en) * | 1997-01-22 | 2001-01-28 | Novartis Ag | Process for the preparation of thiazole derivatives |
| US5773625A (en) * | 1997-10-02 | 1998-06-30 | Abbott Laboratories | Process for the preparation of disubstituted carbonates |
| US6407251B1 (en) * | 2000-12-28 | 2002-06-18 | Takeda Chemical Industries, Ltd. | Process for preparing 2-chloro-5-chloromethylthiazole |
-
1999
- 1999-08-10 US US09/371,180 patent/US6265553B1/en not_active Expired - Fee Related
-
2000
- 2000-08-08 US US10/049,073 patent/US6476230B1/en not_active Expired - Fee Related
- 2000-08-08 CA CA002380838A patent/CA2380838A1/en not_active Abandoned
- 2000-08-08 AU AU68364/00A patent/AU778367B2/en not_active Ceased
- 2000-08-08 AT AT00956412T patent/ATE294166T1/de not_active IP Right Cessation
- 2000-08-08 EP EP00956412A patent/EP1202979B1/en not_active Expired - Lifetime
- 2000-08-08 BR BR0013235-7A patent/BR0013235A/pt not_active IP Right Cessation
- 2000-08-08 RU RU2002105516/04A patent/RU2002105516A/ru not_active Application Discontinuation
- 2000-08-08 WO PCT/EP2000/007709 patent/WO2001010852A1/en active Search and Examination
- 2000-08-08 ES ES00956412T patent/ES2238029T3/es not_active Expired - Lifetime
- 2000-08-08 KR KR1020027001623A patent/KR20020022796A/ko not_active Application Discontinuation
- 2000-08-08 DE DE60019763T patent/DE60019763D1/de not_active Expired - Lifetime
- 2000-08-08 TR TR2002/00304T patent/TR200200304T2/xx unknown
- 2000-08-08 CZ CZ2002483A patent/CZ2002483A3/cs unknown
- 2000-08-08 CN CNB008114455A patent/CN1169800C/zh not_active Expired - Fee Related
- 2000-08-08 CN CNA2004100566415A patent/CN1626525A/zh active Pending
- 2000-08-08 AR ARP000104086A patent/AR030258A1/es not_active Application Discontinuation
- 2000-08-08 TR TR2002/02474T patent/TR200202474T2/xx unknown
- 2000-08-08 JP JP2001515318A patent/JP2003506444A/ja active Pending
- 2000-08-08 HU HU0202819A patent/HUP0202819A3/hu not_active Application Discontinuation
- 2000-08-08 MX MXPA02001246A patent/MXPA02001246A/es unknown
-
2002
- 2002-02-08 ZA ZA200201110A patent/ZA200201110B/en unknown
- 2002-09-16 US US10/244,236 patent/US6566530B2/en not_active Expired - Fee Related
-
2003
- 2003-05-07 US US10/431,100 patent/US6710182B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001010852A1 (en) | 2001-02-15 |
| US6710182B2 (en) | 2004-03-23 |
| HUP0202819A3 (en) | 2004-03-01 |
| MXPA02001246A (es) | 2002-07-22 |
| US20030191321A1 (en) | 2003-10-09 |
| DE60019763D1 (de) | 2005-06-02 |
| US20030055229A1 (en) | 2003-03-20 |
| CN1169800C (zh) | 2004-10-06 |
| CA2380838A1 (en) | 2001-02-15 |
| ES2238029T3 (es) | 2005-08-16 |
| JP2003506444A (ja) | 2003-02-18 |
| EP1202979B1 (en) | 2005-04-27 |
| CN1368966A (zh) | 2002-09-11 |
| KR20020022796A (ko) | 2002-03-27 |
| RU2002105516A (ru) | 2003-09-20 |
| US6566530B2 (en) | 2003-05-20 |
| AU778367B2 (en) | 2004-12-02 |
| TR200200304T2 (tr) | 2002-06-21 |
| CZ2002483A3 (cs) | 2002-05-15 |
| US6476230B1 (en) | 2002-11-05 |
| CN1626525A (zh) | 2005-06-15 |
| TR200202474T2 (tr) | 2003-01-21 |
| HUP0202819A2 (hu) | 2002-12-28 |
| BR0013235A (pt) | 2002-04-23 |
| US6265553B1 (en) | 2001-07-24 |
| AR030258A1 (es) | 2003-08-20 |
| EP1202979A1 (en) | 2002-05-08 |
| ATE294166T1 (de) | 2005-05-15 |
| AU6836400A (en) | 2001-03-05 |
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