DD274618A5 - Verfahren zum herstellen von halogenalkylthiazolen - Google Patents

Verfahren zum herstellen von halogenalkylthiazolen Download PDF

Info

Publication number: DD274618A5
Authority: DD; German Democratic Republic
Prior art keywords: substituents; ring; alkyl; substituted; chlorine
Prior art date: 1987-09-16

Application number

DD88319830A

Other languages

German (de)

English (en)

Inventor

Banavara L Mylari

William J Zembrowski

Original Assignee

��@��Kk��

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.)

1987-09-16

Filing date

1988-09-15

Publication date

1989-12-27

1988-09-15 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1989-12-27 Publication of DD274618A5 publication Critical patent/DD274618A5/de

Links

238000000034 method Methods 0.000 title claims description 31
238000004519 manufacturing process Methods 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 34
125000001424 substituent group Chemical group 0.000 claims abstract description 22
239000000460 chlorine Substances 0.000 claims abstract description 20
229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052794 bromium Inorganic materials 0.000 claims abstract description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 11
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
239000011737 fluorine Substances 0.000 claims abstract description 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 5
239000012433 hydrogen halide Substances 0.000 claims abstract description 5
229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 5
229910052740 iodine Inorganic materials 0.000 claims abstract description 5
239000011630 iodine Substances 0.000 claims abstract description 5
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical group ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 claims description 3
150000001555 benzenes Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
LCMLYTXTONRGSW-UHFFFAOYSA-N 2-(bromomethyl)-4,5-dichloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(CBr)=NC2=C1Cl LCMLYTXTONRGSW-UHFFFAOYSA-N 0.000 claims 1
125000005999 2-bromoethyl group Chemical group 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
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 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
-1 Halomethyl thiazoles Chemical class 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000002904 solvent Substances 0.000 description 5
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
102000016912 Aldehyde Reductase Human genes 0.000 description 3
108010053754 Aldehyde reductase Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WFLCAOGKZQTOIG-UHFFFAOYSA-N 2-(bromomethyl)-1,3-benzothiazole Chemical class C1=CC=C2SC(CBr)=NC2=C1 WFLCAOGKZQTOIG-UHFFFAOYSA-N 0.000 description 2
SERUZNHRWBXDOX-UHFFFAOYSA-N 2-(chloromethyl)-1,3-benzothiazole Chemical class C1=CC=C2SC(CCl)=NC2=C1 SERUZNHRWBXDOX-UHFFFAOYSA-N 0.000 description 2
PEDOSWZBWWCOAY-UHFFFAOYSA-N 2-aminobenzenethiol;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1S PEDOSWZBWWCOAY-UHFFFAOYSA-N 0.000 description 2
DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
206010007749 Cataract diabetic Diseases 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
201000007025 diabetic cataract Diseases 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002997 ophthalmic solution Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
PQXMQZYDBQBWNL-UHFFFAOYSA-N 1,3-benzothiazol-2-ylmethanol Chemical compound C1=CC=C2SC(CO)=NC2=C1 PQXMQZYDBQBWNL-UHFFFAOYSA-N 0.000 description 1
OKIWVOUYVNGXOK-UHFFFAOYSA-N 2-(1-chloroethyl)-5-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2SC(C(Cl)C)=NC2=C1 OKIWVOUYVNGXOK-UHFFFAOYSA-N 0.000 description 1
VMJOGHYLJSXTDW-UHFFFAOYSA-N 2-(bromomethyl)-1,3-thiazole Chemical class BrCC1=NC=CS1 VMJOGHYLJSXTDW-UHFFFAOYSA-N 0.000 description 1
VHXMEOSCYRMMCS-UHFFFAOYSA-N 2-(bromomethyl)-4,5-difluoro-1,3-benzothiazole Chemical compound FC1=CC=C2SC(CBr)=NC2=C1F VHXMEOSCYRMMCS-UHFFFAOYSA-N 0.000 description 1
PHWNPTNPAZHYEU-UHFFFAOYSA-N 2-(bromomethyl)-5,7-dichloro-1,3-benzothiazole Chemical compound ClC1=CC(Cl)=C2SC(CBr)=NC2=C1 PHWNPTNPAZHYEU-UHFFFAOYSA-N 0.000 description 1
KIRNDFQEFIIAGQ-UHFFFAOYSA-N 2-(bromomethyl)-5,7-difluoro-1,3-benzothiazole Chemical compound FC1=CC(F)=C2SC(CBr)=NC2=C1 KIRNDFQEFIIAGQ-UHFFFAOYSA-N 0.000 description 1
KUAVZYOLZWNIMY-UHFFFAOYSA-N 2-(bromomethyl)-5-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2SC(CBr)=NC2=C1 KUAVZYOLZWNIMY-UHFFFAOYSA-N 0.000 description 1
ZHAKAIBZKYHXJS-UHFFFAOYSA-N 2-(chloromethyl)-1,3-thiazole Chemical class ClCC1=NC=CS1 ZHAKAIBZKYHXJS-UHFFFAOYSA-N 0.000 description 1
PYQMHQZKNVMNAV-UHFFFAOYSA-N 3-amino-1h-pyridine-2-thione;hydrochloride Chemical compound Cl.NC1=CC=CN=C1S PYQMHQZKNVMNAV-UHFFFAOYSA-N 0.000 description 1
125000004008 6 membered carbocyclic group Chemical group 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
208000032131 Diabetic Neuropathies Diseases 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical class BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
FIAGYDIJZOWVAB-UHFFFAOYSA-N [2-sulfanyl-5-(trifluoromethyl)phenyl]azanium;chloride Chemical compound Cl.NC1=CC(C(F)(F)F)=CC=C1S FIAGYDIJZOWVAB-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
238000003287 bathing Methods 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
GAWAXYCUBKOJQP-UHFFFAOYSA-N methyl 2-chloroethanimidate Chemical compound COC(=N)CCl GAWAXYCUBKOJQP-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000002798 polar solvent Substances 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
239000012429 reaction media Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000011200 topical administration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD88319830A 1987-09-16 1988-09-15 Verfahren zum herstellen von halogenalkylthiazolen DD274618A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US9703387A	1987-09-16	1987-09-16

Publications (1)

Publication Number	Publication Date
DD274618A5 true DD274618A5 (de)	1989-12-27

Family

ID=22260469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88319830A DD274618A5 (de)	1987-09-16	1988-09-15	Verfahren zum herstellen von halogenalkylthiazolen

Country Status (19)

Country	Link
EP (1)	EP0313202A3 (fr)
JP (1)	JPH01104060A (fr)
KR (1)	KR910000443B1 (fr)
CN (1)	CN1032007A (fr)
AU (1)	AU597513B2 (fr)
CA (1)	CA1336193C (fr)
DD (1)	DD274618A5 (fr)
DK (1)	DK513888A (fr)
EG (1)	EG18451A (fr)
FI (1)	FI884258A7 (fr)
HU (1)	HU198701B (fr)
IL (1)	IL87709A (fr)
NO (1)	NO884100L (fr)
NZ (1)	NZ226194A (fr)
PL (1)	PL160202B1 (fr)
PT (1)	PT88504B (fr)
SU (1)	SU1683498A3 (fr)
YU (1)	YU46886B (fr)
ZA (1)	ZA886874B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL89351A0 (en) *	1988-03-14	1989-09-10	Lundbeck & Co As H	4,5,6,7-tetrahydroisothiazolo(4,5-c)pyridines,process for their preparation and pharmaceutical compositions containing them
TWI302911B (en) *	2000-04-03	2008-11-11		Process for production of substituted alkylamine derivative
TWI545119B (zh) *	2011-08-04	2016-08-11	住友化學股份有限公司	稠合雜環化合物及其在病蟲害防制上之用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1077177A (en) *	1964-04-23	1967-07-26	Monsanto Chem Australia Ltd	New benzthiazole compounds and their application
US4581457A (en) *	1984-09-21	1986-04-08	American Home Products Corporation	Heterocyclic sulfonamides
CA1299178C (fr) *	1985-11-07	1992-04-21	Banavara Lakshmana Mylari	Acides oxophtalazinylacetiques heterocycliques
DE3684410D1 (de) *	1985-11-07	1992-04-23	Pfizer	Heterocyclische oxophthalazinylessigsaeure.

1988
- 1988-09-08 IL IL87709A patent/IL87709A/xx not_active IP Right Cessation
- 1988-09-09 EP EP88308358A patent/EP0313202A3/fr not_active Withdrawn
- 1988-09-14 PT PT88504A patent/PT88504B/pt not_active IP Right Cessation
- 1988-09-14 EG EG482/88A patent/EG18451A/xx active
- 1988-09-15 NO NO88884100A patent/NO884100L/no unknown
- 1988-09-15 DD DD88319830A patent/DD274618A5/de not_active IP Right Cessation
- 1988-09-15 NZ NZ226194A patent/NZ226194A/xx unknown
- 1988-09-15 DK DK513888A patent/DK513888A/da not_active Application Discontinuation
- 1988-09-15 CA CA000577516A patent/CA1336193C/fr not_active Expired - Fee Related
- 1988-09-15 FI FI884258A patent/FI884258A7/fi not_active Application Discontinuation
- 1988-09-15 YU YU174188A patent/YU46886B/sh unknown
- 1988-09-15 SU SU884356639A patent/SU1683498A3/ru active
- 1988-09-15 ZA ZA886874A patent/ZA886874B/xx unknown
- 1988-09-15 HU HU884860A patent/HU198701B/hu not_active IP Right Cessation
- 1988-09-15 AU AU22303/88A patent/AU597513B2/en not_active Ceased
- 1988-09-15 KR KR1019880011905A patent/KR910000443B1/ko not_active Expired
- 1988-09-15 CN CN88106789A patent/CN1032007A/zh active Pending
- 1988-09-16 PL PL1988274709A patent/PL160202B1/pl unknown
- 1988-09-16 JP JP63232149A patent/JPH01104060A/ja active Pending

Also Published As

Publication number	Publication date
PT88504A (pt)	1988-10-01
FI884258A0 (fi)	1988-09-15
HU198701B (en)	1989-11-28
DK513888D0 (da)	1988-09-15
NO884100D0 (no)	1988-09-15
YU46886B (sh)	1994-06-24
HUT48877A (en)	1989-07-28
IL87709A (en)	1992-11-15
KR910000443B1 (ko)	1991-01-25
PL274709A1 (en)	1989-05-16
EP0313202A2 (fr)	1989-04-26
ZA886874B (en)	1990-04-25
CA1336193C (fr)	1995-07-04
YU174188A (en)	1990-02-28
PL160202B1 (pl)	1993-02-26
JPH01104060A (ja)	1989-04-21
AU2230388A (en)	1989-03-16
DK513888A (da)	1989-03-17
PT88504B (pt)	1992-11-30
KR890005126A (ko)	1989-05-11
SU1683498A3 (ru)	1991-10-07
FI884258A7 (fi)	1989-03-17
IL87709A0 (en)	1989-02-28
NZ226194A (en)	1991-05-28
EG18451A (en)	1993-02-28
NO884100L (no)	1989-03-17
EP0313202A3 (fr)	1989-12-13
CN1032007A (zh)	1989-03-29
AU597513B2 (en)	1990-05-31

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

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USRE36575E (en)	2000-02-15	Pyridine and thiazolidinedione derivatives
DE2814556C2 (de)	1987-03-12	Substituierte Phenylessigsäurederivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE69118565T2 (de)	1997-01-09	Thiazolidinderivate mit antidiabetischer Wirkung, ihre Herstellung und Anwendung
DE69231886T2 (de)	2002-03-28	Thiazolidindionderivate, herstellung und anwendung
DE69721134T2 (de)	2004-03-04	Verfahren zur Herstellung von 4-(2-(2-Pyridyl)Ethoxy)Benzaldehyd-Derivate
DE69434020T2 (de)	2005-09-29	Verfahren und zwischenprodukte für die herstellung von 5-[4-(benzisothiazol-3-yl)-piperazin-1-yl)ethyl]-6 chlor-1,3-dihydro-indol-2-one
DE69018876T2 (de)	1995-08-24	Pyridazinon-Derivate.
DE69432542T2 (de)	2004-03-04	Tetraderivate, ihre Herstellung und Verwendung
DE69225123T2 (de)	1998-12-24	Thiazolidinederivate, die eine Quinone-Gruppe enthalten, ihre Herstellung und therapeutische Anwendung
DE69530988T2 (de)	2003-12-04	Benzimidazolderivate mit dopaminerger wirkung
DD280320A5 (de)	1990-07-04	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol oder anderen heterocyclischen seitenketten
DE69007846T2 (de)	1994-07-28	Verfahren und Zwischenprodukte zur Herstellung von Oxophthalazinyl-Essigsäuren und deren Analogen.
DD274618A5 (de)	1989-12-27	Verfahren zum herstellen von halogenalkylthiazolen
DE1695516A1 (de)	1971-04-15	Aromatische Sulfone
DE2828578A1 (de)	1979-01-11	Thiazolidine und ihre salze sowie verfahren zu ihrer herstellung
DE69026087T2 (de)	1996-08-29	Substituierte 2-imidazoline und verfahren zur herstellung sowie deren verwendung
DE2841644C2 (fr)	1989-09-21
DE9290035U1 (de)	1993-11-18	Pyridazinonessigsäuren
EP0137426A2 (fr)	1985-04-17	Dérivés de 2-mercaptothiazole, procédé pour les préparer et utilisation de dérivés de 2-mercaptothiazole dans des médicaments
EP0011282B1 (fr)	1983-02-16	Dérivés de l'acide thiénylbenzoique, procédé pour leur préparation, préparations pharmaceutiques à base de ces composés
US3350407A (en)	1967-10-31	Sulfur containing pyrazole derivatives
MC1135A1 (fr)	1977-11-18	Derives de thiazine
DE4417705A1 (de)	1995-11-23	Substituierte Furoxane
EP0115811B1 (fr)	1990-04-18	2,4-Dichloro-5-thiazole carboxaldehyde, et un procédé pour le préparer