DE1795651C3 - Verfahren zur Herstellung von 6-substituierten 233,6-Tetrahydroimidazo [2,1-b] thiazolen - Google Patents
Verfahren zur Herstellung von 6-substituierten 233,6-Tetrahydroimidazo [2,1-b] thiazolenInfo
- Publication number
- DE1795651C3 DE1795651C3 DE1795651A DE1795651A DE1795651C3 DE 1795651 C3 DE1795651 C3 DE 1795651C3 DE 1795651 A DE1795651 A DE 1795651A DE 1795651 A DE1795651 A DE 1795651A DE 1795651 C3 DE1795651 C3 DE 1795651C3
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- hydrochloride
- phenyl
- reaction
- stirring
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003557 thiazoles Chemical class 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 41
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 35
- 238000003756 stirring Methods 0.000 description 31
- 239000000047 product Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 23
- -1 furyl radical Chemical group 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- HXCSOQNQZVYAJC-UHFFFAOYSA-N 2-(2-amino-4,5-dihydro-1,3-thiazol-3-ium-3-yl)-1-phenylethanol;chloride Chemical compound Cl.C=1C=CC=CC=1C(O)CN1CCSC1=N HXCSOQNQZVYAJC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 239000003054 catalyst Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- LYWIFGDFJLWXHK-UHFFFAOYSA-N 2-(aziridin-1-yl)-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)CN1CC1 LYWIFGDFJLWXHK-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000003113 alkalizing effect Effects 0.000 description 5
- 150000001541 aziridines Chemical class 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 241000534944 Thia Species 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 108010047623 iridine Proteins 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- VQCBPRUALIUOQA-UHFFFAOYSA-N 2-[(2-hydroxy-2-phenylethyl)amino]ethyl carbamimidothioate Chemical compound NC(=N)SCCNCC(O)C1=CC=CC=C1 VQCBPRUALIUOQA-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- PVMWFCUPSUANSK-UHFFFAOYSA-N 3-(2-chloro-2-phenylethyl)-1,3-thiazolidin-2-imine Chemical compound C=1C=CC=CC=1C(Cl)CN1CCSC1=N PVMWFCUPSUANSK-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- LAZPBGZRMVRFKY-UHFFFAOYSA-N Tetramisole hydrochloride Chemical compound Cl.N1=C2SCCN2CC1C1=CC=CC=C1 LAZPBGZRMVRFKY-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000009738 saturating Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZEJWZIZFOBFKOC-SCSAIBSYSA-N (1R)-1-(aziridin-1-yl)ethanol Chemical class C[C@@H](O)N1CC1 ZEJWZIZFOBFKOC-SCSAIBSYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- NGKOCETVOBCCII-UHFFFAOYSA-N 2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical class C1CN=C2SCCN21 NGKOCETVOBCCII-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical group C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- UTHQDRBQLOYOFO-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)CN1CCSC1=N UTHQDRBQLOYOFO-UHFFFAOYSA-N 0.000 description 1
- MCTPEMSIZLTTCE-UHFFFAOYSA-N 2-(2-imino-1,3-thiazolidin-3-yl)-1-phenylethanol;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C=1C=CC=CC=1C(O)CN1CCSC1=N MCTPEMSIZLTTCE-UHFFFAOYSA-N 0.000 description 1
- JVKAAEKOBOXXEW-UHFFFAOYSA-N 2-(aziridin-1-yl)-1-(4-nitrophenyl)ethanol Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)CN1CC1 JVKAAEKOBOXXEW-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- MPJAJMDNZRZOFM-UHFFFAOYSA-N 6-thiophen-2-yl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SCCN2CC1C1=CC=CS1 MPJAJMDNZRZOFM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KDUFKIIMEWLUSX-UHFFFAOYSA-N C1CN1.C1CN1 Chemical compound C1CN1.C1CN1 KDUFKIIMEWLUSX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- IRSCLJADMXHRLY-UHFFFAOYSA-N N=C1SCCN1CC(C1=CC=CC=C1)O.N#CS Chemical compound N=C1SCCN1CC(C1=CC=CC=C1)O.N#CS IRSCLJADMXHRLY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 229910052804 chromium Chemical group 0.000 description 1
- 235000019987 cider Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- LNQCUTNLHUQZLR-OZJWLQQPSA-N iridin Chemical compound OC1=C(OC)C(OC)=CC(C=2C(C3=C(O)C(OC)=C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=C3OC=2)=O)=C1 LNQCUTNLHUQZLR-OZJWLQQPSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000012071 phase 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
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XJVIPPHGDPEDJL-UHFFFAOYSA-N thiourea;hydrochloride Chemical compound Cl.NC(N)=S XJVIPPHGDPEDJL-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/10—Radicals substituted by singly bound 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU61653/65A AU409983B2 (en) | 1965-07-19 | 1965-07-19 | Process for the manufacture of thia zolidines and thiazolidines produced thereby |
| AU6193165 | 1965-07-26 | ||
| AU6341565 | 1965-08-31 | ||
| AU6378665 | 1965-09-08 | ||
| US56509266A | 1966-07-14 | 1966-07-14 | |
| US240827A US3862166A (en) | 1965-07-19 | 1972-04-03 | Certain 3-haloethyl-2-iminothiazolidine |
| US00240773A US3828061A (en) | 1965-07-19 | 1972-04-03 | Multi-step process for preparing 2,3,5,6-tetrahydroimidazo(2,1-b)thiazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795651A1 DE1795651A1 (de) | 1973-04-12 |
| DE1795651B2 DE1795651B2 (de) | 1979-01-04 |
| DE1795651C3 true DE1795651C3 (de) | 1979-09-13 |
Family
ID=27560622
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1795651A Expired DE1795651C3 (de) | 1965-07-19 | 1966-07-13 | Verfahren zur Herstellung von 6-substituierten 233,6-Tetrahydroimidazo [2,1-b] thiazolen |
| DE19661795650 Pending DE1795650A1 (de) | 1965-07-19 | 1966-07-13 | Verfahren zur herstellung von biologisch aktiven verbindungen |
| DE19661695249 Pending DE1695249A1 (de) | 1965-07-19 | 1966-07-13 | Verfahren zur Herstellung von biologisch wirksamen Verbindungen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661795650 Pending DE1795650A1 (de) | 1965-07-19 | 1966-07-13 | Verfahren zur herstellung von biologisch aktiven verbindungen |
| DE19661695249 Pending DE1695249A1 (de) | 1965-07-19 | 1966-07-13 | Verfahren zur Herstellung von biologisch wirksamen Verbindungen |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US3759937A (enExample) |
| AU (1) | AU409983B2 (enExample) |
| BE (1) | BE684340A (enExample) |
| BR (1) | BR6681363D0 (enExample) |
| CH (2) | CH562233A5 (enExample) |
| CS (2) | CS155142B2 (enExample) |
| DE (3) | DE1795651C3 (enExample) |
| DK (1) | DK125996B (enExample) |
| FR (1) | FR1502712A (enExample) |
| GB (3) | GB1131798A (enExample) |
| IL (3) | IL34051A (enExample) |
| NL (1) | NL6610166A (enExample) |
| SE (2) | SE323382B (enExample) |
| YU (2) | YU32997B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04567A (fr) * | 1972-11-30 | 1980-05-31 | Rhone Poulenc Sa | Nouveaux dérivés de l'imidazo (2,1-b) thiazole et leur préparation. |
| GB1475891A (en) * | 1973-06-18 | 1977-06-10 | American Cyanamid Co | Method of preparing dl-or l-tetramisole and acid addition salts thereof |
| US4107170A (en) * | 1975-10-29 | 1978-08-15 | American Cyanamid Company | Method of preparing dl 6-phenyl-2,3,5,6-tetrahydroimidazo-[2,1-b]thiazole and acid addition salts thereof |
| GB1533347A (en) * | 1976-10-22 | 1978-11-22 | Pfizer Ltd | Anthelmintic compounds |
| CA2028756A1 (en) * | 1989-11-24 | 1991-05-25 | Alfons H. M. Raeymaekers | Immunostimulating 6-aryl-5,6-dihydro-imidazo[2,1-b]thiazole derivatives |
| US6291370B1 (en) * | 1999-09-01 | 2001-09-18 | Harodite Industries, Inc. | Chopped fiberglass laminate for automotive headliners and method of fabrication |
| EP2298337B1 (en) * | 2003-12-09 | 2017-02-22 | Novo Nordisk A/S | Regulation of food preference using GLP-1 agonists |
| CN1950078A (zh) * | 2004-06-11 | 2007-04-18 | 诺和诺德公司 | 使用glp－1激动剂抵抗药物诱发的肥胖 |
| CN111377949B (zh) * | 2020-03-18 | 2021-05-14 | 山东国邦药业有限公司 | 一种四咪唑游离碱制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547996A (en) * | 1965-10-05 | 1970-12-15 | American Cyanamid Co | Di 2 - (2 - ((beta - hydroxyphenethyl)amino)ethyl) - 2 - thiopseudourea and hydrochloride salt thereof |
| US3679696A (en) * | 1965-10-05 | 1972-07-25 | American Cyanamid Co | METHOD OF PREPARING d1 6-PHENYL-2,3,5,6-TETRAHYDROIMIDAZO {8 2,1-b{9 -THIAZOLE HYDROCHLORIDE |
| US3642809A (en) * | 1965-10-05 | 1972-02-15 | American Cyanamid Co | Method for producing 2 3 5 6-tetra hydroimidazo-(2 1-b)thiazoles |
| US3624099A (en) * | 1965-10-05 | 1971-11-30 | American Cyanamid Co | Process of preparing 2 -imino-{60 phenyl 3-thiazolidineethanol acid salts |
| US3297708A (en) * | 1965-10-06 | 1967-01-10 | American Cyanamid Co | Method of preparing thiazolidines |
| NL129632C (enExample) * | 1965-12-10 |
-
1965
- 1965-07-19 AU AU61653/65A patent/AU409983B2/en not_active Expired
-
1966
- 1966-07-04 GB GB29834/66A patent/GB1131798A/en not_active Expired
- 1966-07-04 GB GB33971/67A patent/GB1131799A/en not_active Expired
- 1966-07-04 GB GB33972/67A patent/GB1131800A/en not_active Expired
- 1966-07-11 IL IL34051A patent/IL34051A/xx unknown
- 1966-07-11 IL IL34052A patent/IL34052A/en unknown
- 1966-07-11 IL IL26123A patent/IL26123A/xx unknown
- 1966-07-13 DE DE1795651A patent/DE1795651C3/de not_active Expired
- 1966-07-13 DE DE19661795650 patent/DE1795650A1/de active Pending
- 1966-07-13 DE DE19661695249 patent/DE1695249A1/de active Pending
- 1966-07-14 US US00565092A patent/US3759937A/en not_active Expired - Lifetime
- 1966-07-18 SE SE9822/66A patent/SE323382B/xx unknown
- 1966-07-18 FR FR69792A patent/FR1502712A/fr not_active Expired
- 1966-07-18 BR BR181363/66A patent/BR6681363D0/pt unknown
- 1966-07-18 SE SE13384/68A patent/SE370078B/xx unknown
- 1966-07-19 BE BE684340D patent/BE684340A/xx unknown
- 1966-07-19 NL NL6610166A patent/NL6610166A/xx unknown
- 1966-07-19 YU YU1401/66A patent/YU32997B/xx unknown
- 1966-07-19 CH CH1104069A patent/CH562233A5/xx not_active IP Right Cessation
- 1966-07-19 CS CS487666A patent/CS155142B2/cs unknown
- 1966-07-19 CS CS348072*1A patent/CS155143B2/cs unknown
- 1966-07-19 CH CH1040966A patent/CH490376A/de not_active IP Right Cessation
-
1969
- 1969-09-17 DK DK496169AA patent/DK125996B/da unknown
-
1971
- 1971-12-08 US US206155A patent/US3927097A/en not_active Expired - Lifetime
-
1972
- 1972-04-03 US US240827A patent/US3862166A/en not_active Expired - Lifetime
- 1972-04-03 US US00240773A patent/US3828061A/en not_active Expired - Lifetime
-
1973
- 1973-03-13 YU YU00654/73A patent/YU65473A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU140166A (en) | 1975-08-31 |
| YU65473A (en) | 1982-05-31 |
| AU409983B2 (en) | 1970-12-31 |
| CS155143B2 (enExample) | 1974-05-30 |
| DE1795651B2 (de) | 1979-01-04 |
| US3927097A (en) | 1975-12-16 |
| DE1795651A1 (de) | 1973-04-12 |
| YU32997B (en) | 1976-03-31 |
| US3759937A (en) | 1973-09-18 |
| CS155142B2 (enExample) | 1974-05-30 |
| GB1131799A (en) | 1968-10-30 |
| CH562233A5 (enExample) | 1975-05-30 |
| IL34052A (en) | 1970-08-19 |
| CH490376A (de) | 1970-05-15 |
| DE1795652A1 (de) | 1972-10-26 |
| SE370078B (enExample) | 1974-09-30 |
| DE1695249A1 (de) | 1970-09-17 |
| US3862166A (en) | 1975-01-21 |
| NL6610166A (enExample) | 1967-01-20 |
| DK125996B (da) | 1973-05-28 |
| DE1795650A1 (de) | 1973-05-24 |
| DE1795652B2 (de) | 1977-01-20 |
| GB1131798A (en) | 1968-10-30 |
| FR1502712A (fr) | 1967-11-24 |
| GB1131800A (en) | 1968-10-30 |
| IL26123A (en) | 1970-08-19 |
| BR6681363D0 (pt) | 1973-12-27 |
| SE323382B (enExample) | 1970-05-04 |
| AU6165365A (en) | 1968-01-18 |
| IL34051A (en) | 1970-08-19 |
| US3828061A (en) | 1974-08-06 |
| BE684340A (enExample) | 1967-01-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |