DE2114563A1 - Substituierte 6 Phenyl imidazo eckige Klammer auf 2,1 b eckige Klammer zu thiazole - Google Patents
Substituierte 6 Phenyl imidazo eckige Klammer auf 2,1 b eckige Klammer zu thiazoleInfo
- Publication number
- DE2114563A1 DE2114563A1 DE19712114563 DE2114563A DE2114563A1 DE 2114563 A1 DE2114563 A1 DE 2114563A1 DE 19712114563 DE19712114563 DE 19712114563 DE 2114563 A DE2114563 A DE 2114563A DE 2114563 A1 DE2114563 A1 DE 2114563A1
- Authority
- DE
- Germany
- Prior art keywords
- degrees
- acid
- compound
- product
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 4
- -1 alkyl radical Chemical class 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 25
- 239000000243 solution Substances 0.000 claims description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 239000001119 stannous chloride Substances 0.000 claims description 3
- 235000011150 stannous chloride Nutrition 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
- 241000341511 Nematodes Species 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 19
- ZYVPOPWDOQZIQC-UHFFFAOYSA-N 1,3-thiazole;dihydrochloride Chemical compound Cl.Cl.C1=CSC=N1 ZYVPOPWDOQZIQC-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000012458 free base Substances 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 7
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 7
- 229960001614 levamisole Drugs 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- IBMUCSJKSQYUIB-UHFFFAOYSA-N n-[3-(2-bromoacetyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C(=O)CBr)=C1 IBMUCSJKSQYUIB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 230000000507 anthelmentic effect Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- MYLUSPDQXBKXTC-UHFFFAOYSA-N n-phenylacetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=CC=C1 MYLUSPDQXBKXTC-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000007920 subcutaneous administration Methods 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229940124339 anthelmintic agent Drugs 0.000 description 4
- 239000000921 anthelmintic agent Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 208000006968 Helminthiasis Diseases 0.000 description 3
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 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
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229960001270 d- tartaric acid Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001638368 Trichuris vulpis Species 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 244000000013 helminth Species 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- AFZTYHRVDOKRKV-UHFFFAOYSA-N n-(3-acetylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C(C)=O)=C1 AFZTYHRVDOKRKV-UHFFFAOYSA-N 0.000 description 2
- FEBUIQFEAMOVKJ-UHFFFAOYSA-N n-phenylacetamide;hydrobromide Chemical compound Br.CC(=O)NC1=CC=CC=C1 FEBUIQFEAMOVKJ-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- SFJHFRRWUVGMRX-UHFFFAOYSA-N 2-(2H-imidazo[4,5-d][1,3]thiazol-2-yl)-N-phenylacetamide Chemical compound S1C(N=C2C1=NC=N2)CC(=O)NC2=CC=CC=C2 SFJHFRRWUVGMRX-UHFFFAOYSA-N 0.000 description 1
- AAKDYELXCQTRBF-UHFFFAOYSA-N 2-phenyl-2H-imidazo[4,5-d][1,3]thiazol-5-amine Chemical compound S1C2=NC(N)=NC2=NC1C1=CC=CC=C1 AAKDYELXCQTRBF-UHFFFAOYSA-N 0.000 description 1
- KWGAILXIRDXFSQ-UHFFFAOYSA-N 3-(2H-imidazo[4,5-d][1,3]thiazol-2-yl)-N-methylaniline Chemical compound CNC=1C=C(C=CC1)C1SC=2C(=N1)N=CN2 KWGAILXIRDXFSQ-UHFFFAOYSA-N 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- 241000253350 Capillaria Species 0.000 description 1
- 241000242722 Cestoda Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241001446276 Helia <angisperm> Species 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000243774 Trichinella Species 0.000 description 1
- 241001489151 Trichuris Species 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical group OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WOUIHWHNWKWHPT-UHFFFAOYSA-N n-(3-acetylphenyl)formamide Chemical compound CC(=O)C1=CC=CC(NC=O)=C1 WOUIHWHNWKWHPT-UHFFFAOYSA-N 0.000 description 1
- WPKYWZVHSQINPX-UHFFFAOYSA-N n-(3-acetylphenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(C(C)=O)=C1 WPKYWZVHSQINPX-UHFFFAOYSA-N 0.000 description 1
- MUUQHCOAOLLHIL-UHFFFAOYSA-N n-(3-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(Cl)=C1 MUUQHCOAOLLHIL-UHFFFAOYSA-N 0.000 description 1
- ALKIXOSJRUZYPH-UHFFFAOYSA-N n-phenylpropanamide;hydrochloride Chemical compound Cl.CCC(=O)NC1=CC=CC=C1 ALKIXOSJRUZYPH-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 238000001665 trituration 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2270170A | 1970-03-25 | 1970-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2114563A1 true DE2114563A1 (de) | 1971-10-14 |
Family
ID=21810982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712114563 Pending DE2114563A1 (de) | 1970-03-25 | 1971-03-25 | Substituierte 6 Phenyl imidazo eckige Klammer auf 2,1 b eckige Klammer zu thiazole |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3673205A (enExample) |
| AU (1) | AU2571671A (enExample) |
| BE (1) | BE764755A (enExample) |
| DE (1) | DE2114563A1 (enExample) |
| ES (3) | ES389573A1 (enExample) |
| FR (1) | FR2085742B1 (enExample) |
| IT (1) | IT1008517B (enExample) |
| NL (1) | NL7104032A (enExample) |
| PH (1) | PH10140A (enExample) |
| ZA (1) | ZA71969B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718976A1 (de) * | 1976-05-01 | 1977-11-17 | Pfizer | Neue 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo eckige klammer auf 2,1-b eckige klammer zu thiazol-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4014892A (en) * | 1972-09-14 | 1977-03-29 | American Cyanamid Company | 6-Substituted amino phenyl-2,3,5,6-tetrahydro[2,1-b]thiazoles |
| EP0041322A1 (en) * | 1980-05-30 | 1981-12-09 | Beecham Group Plc | m-Pyrazolylamido tetramisole derivatives, compositions thereof, processes for production of such compounds and compositions and their use in treating helminthiasis |
| IL123922A (en) * | 1996-08-01 | 2005-07-25 | Dale Wallis | Detection, prevention and treatment of papillomatous digital dermatitis in ruminants comprising a therapeutically effective amount of serpens spp |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131034C (enExample) * | 1964-05-11 | |||
| US3547996A (en) * | 1965-10-05 | 1970-12-15 | American Cyanamid Co | Di 2 - (2 - ((beta - hydroxyphenethyl)amino)ethyl) - 2 - thiopseudourea and hydrochloride salt thereof |
-
1970
- 1970-03-25 US US22701A patent/US3673205A/en not_active Expired - Lifetime
-
1971
- 1971-02-16 ZA ZA710969A patent/ZA71969B/xx unknown
- 1971-02-22 AU AU25716/71A patent/AU2571671A/en not_active Expired
- 1971-03-24 BE BE764755A patent/BE764755A/xx not_active IP Right Cessation
- 1971-03-24 IT IT49286/71A patent/IT1008517B/it active
- 1971-03-25 ES ES389573A patent/ES389573A1/es not_active Expired
- 1971-03-25 FR FR7110657A patent/FR2085742B1/fr not_active Expired
- 1971-03-25 NL NL7104032A patent/NL7104032A/xx not_active Application Discontinuation
- 1971-03-25 DE DE19712114563 patent/DE2114563A1/de active Pending
- 1971-09-03 PH PH12838A patent/PH10140A/en unknown
- 1971-10-22 ES ES396287A patent/ES396287A1/es not_active Expired
- 1971-11-09 ES ES396836A patent/ES396836A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718976A1 (de) * | 1976-05-01 | 1977-11-17 | Pfizer | Neue 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo eckige klammer auf 2,1-b eckige klammer zu thiazol-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| BE764755A (fr) | 1971-09-24 |
| ZA71969B (en) | 1971-12-29 |
| FR2085742B1 (enExample) | 1975-10-31 |
| PH10140A (en) | 1976-09-06 |
| FR2085742A1 (enExample) | 1971-12-31 |
| AU2571671A (en) | 1972-08-24 |
| ES396836A1 (es) | 1975-03-16 |
| ES396287A1 (es) | 1975-01-01 |
| ES389573A1 (es) | 1975-05-16 |
| NL7104032A (enExample) | 1971-09-28 |
| US3673205A (en) | 1972-06-27 |
| IT1008517B (it) | 1976-11-30 |
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