DD268473A5 - Ein verfahren zur herstellung von neuen thieno-imidazo(2,1-b)thiazolderivaten - Google Patents

Ein verfahren zur herstellung von neuen thieno-imidazo(2,1-b)thiazolderivaten Download PDF

Info

Publication number: DD268473A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; hydrogen; alkyl; group; preparation
Prior art date: 1987-04-03

Application number

DD88314284A

Other languages

German (de)

English (en)

Inventor

Dieter Binder

Franz Rovenszky

Hubert P Ferber

Original Assignee

��@��@��k��

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.)

1987-04-03

Filing date

1988-03-31

Publication date

1989-05-31

1988-03-31 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1989-05-31 Publication of DD268473A5 publication Critical patent/DD268473A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 11
QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical class CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 16
150000002431 hydrogen Chemical group 0.000 claims abstract description 15
150000002148 esters Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical group 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
150000007979 thiazole derivatives Chemical class 0.000 claims abstract description 4
238000007127 saponification reaction Methods 0.000 claims abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
239000000203 mixture Substances 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
238000004440 column chromatography Methods 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000003480 eluent Substances 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
238000001953 recrystallisation Methods 0.000 claims description 3
239000000741 silica gel Substances 0.000 claims description 3
229910002027 silica gel Inorganic materials 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
-1 1H-thienoimidazole -2-yl Chemical group 0.000 abstract description 5
210000000987 immune system Anatomy 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 abstract description 3
206010028980 Neoplasm Diseases 0.000 abstract description 2
201000011510 cancer Diseases 0.000 abstract description 2
125000002883 imidazolyl group Chemical group 0.000 abstract description 2
206010039073 rheumatoid arthritis Diseases 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
230000002950 deficient Effects 0.000 abstract 1
239000012024 dehydrating agents‎ Substances 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 10
UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 10
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
239000000243 solution Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
238000003756 stirring Methods 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
WGCQNQVBMANWKZ-UHFFFAOYSA-N 1,3-dihydrothieno[2,3-d]imidazole-2-thione Chemical compound C1=CSC2=C1NC(=S)N2 WGCQNQVBMANWKZ-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OSAIIRUBPFEMEN-UHFFFAOYSA-N P(=O)(=O)CCl Chemical compound P(=O)(=O)CCl OSAIIRUBPFEMEN-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 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
230000002051 biphasic effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002519 immonomodulatory effect Effects 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
238000010874 in vitro model Methods 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
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WGUMZKCZDLPGHY-UHFFFAOYSA-N methyl 3-bromo-4-(4-chlorophenyl)-4-oxobutanoate Chemical compound COC(=O)CC(Br)C(=O)C1=CC=C(Cl)C=C1 WGUMZKCZDLPGHY-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
ARNQVEPKVKPGOJ-UHFFFAOYSA-N o-methyl 4-(4-chlorophenyl)-4-oxo-3-(1h-thieno[2,3-d]imidazol-2-yl)butanethioate Chemical compound N=1C=2SC=CC=2NC=1C(CC(=S)OC)C(=O)C1=CC=C(Cl)C=C1 ARNQVEPKVKPGOJ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000004810 partition chromatography Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000011282 treatment Methods 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000013311 vegetables Nutrition 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
- C07D513/12—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 three hetero rings
- C07D513/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD88314284A 1987-04-03 1988-03-31 Ein verfahren zur herstellung von neuen thieno-imidazo(2,1-b)thiazolderivaten DD268473A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT82187		1987-04-03

Publications (1)

Publication Number	Publication Date
DD268473A5 true DD268473A5 (de)	1989-05-31

Family

ID=3500525

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88314284A DD268473A5 (de)	1987-04-03	1988-03-31	Ein verfahren zur herstellung von neuen thieno-imidazo(2,1-b)thiazolderivaten

Country Status (13)

Country	Link
EP (1)	EP0284893A3 (fr)
JP (1)	JPS63258885A (fr)
KR (1)	KR880012614A (fr)
CN (1)	CN88101719A (fr)
AU (1)	AU1406088A (fr)
DD (1)	DD268473A5 (fr)
DK (1)	DK176888A (fr)
FI (1)	FI881505A7 (fr)
HU (1)	HUT47297A (fr)
IL (1)	IL85924A0 (fr)
NO (1)	NO881280L (fr)
PL (1)	PL271544A1 (fr)
ZA (1)	ZA882338B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT394046B (de) *	1988-09-08	1992-01-27	Chem Pharm Forsch Gmbh	Neue thieno(3',4'-4,5)imidazo(2,1-b)thiazolderivate, verfahren zu ihrer herstellung und ihre verwendung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4214089A (en) *	1978-07-18	1980-07-22	American Home Products Corporation	Thiazolo[3,2-a]benzimidazoles, imidazo [2,1-b]thiazoles, and related compounds as antineoplastic agents, and enhancers of the immune response
US4293696A (en) *	1980-12-22	1981-10-06	American Home Products Corporation	3-Substituted phenylthiazolo[3'2':1,2]imidazo[4,5-b]pyridine-2-alkanoic acids

1988
- 1988-03-16 EP EP88104164A patent/EP0284893A3/fr not_active Withdrawn
- 1988-03-23 NO NO881280A patent/NO881280L/no unknown
- 1988-03-30 DK DK176888A patent/DK176888A/da not_active Application Discontinuation
- 1988-03-30 FI FI881505A patent/FI881505A7/fi not_active Application Discontinuation
- 1988-03-30 IL IL85924A patent/IL85924A0/xx unknown
- 1988-03-31 PL PL27154488A patent/PL271544A1/xx unknown
- 1988-03-31 DD DD88314284A patent/DD268473A5/de unknown
- 1988-03-31 AU AU14060/88A patent/AU1406088A/en not_active Abandoned
- 1988-03-31 ZA ZA882338A patent/ZA882338B/xx unknown
- 1988-04-01 JP JP63078267A patent/JPS63258885A/ja active Pending
- 1988-04-01 HU HU881628A patent/HUT47297A/hu unknown
- 1988-04-02 KR KR1019880003716A patent/KR880012614A/ko not_active Withdrawn
- 1988-04-02 CN CN198888101719A patent/CN88101719A/zh active Pending

Also Published As

Publication number	Publication date
PL271544A1 (en)	1989-01-05
NO881280L (no)	1988-10-04
EP0284893A2 (fr)	1988-10-05
FI881505A0 (fi)	1988-03-30
FI881505A7 (fi)	1988-10-04
ZA882338B (en)	1988-09-23
JPS63258885A (ja)	1988-10-26
DK176888D0 (da)	1988-03-30
CN88101719A (zh)	1988-10-19
IL85924A0 (en)	1988-09-30
HUT47297A (en)	1989-02-28
AU1406088A (en)	1988-10-06
EP0284893A3 (fr)	1990-04-18
KR880012614A (ko)	1988-11-28
NO881280D0 (no)	1988-03-23
DK176888A (da)	1988-10-04

Publication	Publication Date	Title
DE2915318C2 (fr)	1990-12-13
DD146293A5 (de)	1981-02-04	Verfahren zur herstellung von 5-(4-pyridyl)-6-(4-fluorphenyl)-2,3-dihydroimidazo eckige klammer auf 2,1-b eckige klammer zu thiazol,seiner salze und seiner oxide
DE3685604T2 (de)	1993-01-28	1,7-naphthyridinderivate und diese enthaltende arzneimittel.
DE2931418C2 (fr)	1989-06-29
CH641458A5 (en)	1984-02-29	Process for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid esters
EP0665228B1 (fr)	1999-07-14	Compositions pharmaceutiques contenant 3-phenylsulfonyl-3,7-diazabicyclo 3,3,1 nonanes
EP0180834A1 (fr)	1986-05-14	Dérivés de la 4-oxopyrido[2,3-d]pyrimidine, procédé pour leur préparation et médicaments les contenant
US3853872A (en)	1974-12-10	2,3,4,5-substituted thiazoles
DE3721223C2 (fr)	1991-11-14
EP0152868A2 (fr)	1985-08-28	Dérivés d'isoxazole, procédé de préparation et médicaments contenant ces composés
EP0576906A1 (fr)	1994-01-05	Dérivés et thiénothiazine, procédé pour leur préparation et leur utilisation comme agents anti-inflammatoires et analgésiques.
DE1910930A1 (de)	1969-10-16	Verfahren zur Herstellung von neuen 1,6-Dimethyl-10alpha-ergolinderivaten
EP0328913B1 (fr)	1994-06-08	5-Halothiénoisothiazole-3(2H)-one-1,1-dioxydes à substituant basique, procédé pour leur préparation et compositions pharmaceutiques les contenant
DD268473A5 (de)	1989-05-31	Ein verfahren zur herstellung von neuen thieno-imidazo(2,1-b)thiazolderivaten
EP0213295B1 (fr)	1991-04-10	Dérivés de thiéno-1,2-thiazole, leur procédé de préparation et compositions pharmaceutiques les contenant
EP0180833B1 (fr)	1989-07-19	Dérivés de la 4-oxopyrido[2,3-d]pyrimidine, procédé pour leur préparation et médicaments les contenant
DD275689A5 (de)	1990-01-31	Verfahren zur herstellung von enolethern von 6-chlor-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno(2,3-e)-1,2-thiazin-3-carbonsaeureamid-1,1-dioxid
EP0301245B1 (fr)	1993-09-08	Composés de 3-sulfonyl-3,7-diazabicyclo-(3,3,1)nonane, leurs procédés de préparation et médicaments contenant ces composés
CH619237A5 (fr)	1980-09-15
DD150897A5 (de)	1981-09-23	Verfahren zur herstellung von neuen pyrazolo(1,5-c)chinazolinderivaten
DD284236A5 (de)	1990-11-07	Verfahren zur herstellung neuer thieno(3',4'-4,5)imidazo(2,1-b)thiazol-derivate
EP0219747B1 (fr)	1990-05-16	Dérivés de la (thiényl-2)-2 imidazo(4,5-c)pyridine et leurs sels, leur procédé de préparation et compositions pharmaceutiques les contenant
DE3248094C1 (de)	1984-06-14	7H-Dibenzo(a,c)cyclohepten-5-on(7)-Derivate,Verfahren zu deren Herstellung und deren Verwendung bei der Bekaempfung psychischer Erkrankungen und von Magen-und/oder Darmgeschwueren
EP0182271B1 (fr)	1990-01-17	Dérivés dibromo Nb-quaternaires d'ajmaline, isoajmaline, sandwicine et isosandwicine et compositions pharmaceutiques contenant ces dérivés, produits intermédiaires et procédé pour leur préparation
DE2701511A1 (de)	1977-07-28	Thieno(3,2-c)pyridinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel