DE2505068A1 - Imidazo eckige klammer auf 2,1-b eckige klammer zu thiazole - Google Patents
Imidazo eckige klammer auf 2,1-b eckige klammer zu thiazoleInfo
- Publication number
- DE2505068A1 DE2505068A1 DE19752505068 DE2505068A DE2505068A1 DE 2505068 A1 DE2505068 A1 DE 2505068A1 DE 19752505068 DE19752505068 DE 19752505068 DE 2505068 A DE2505068 A DE 2505068A DE 2505068 A1 DE2505068 A1 DE 2505068A1
- Authority
- DE
- Germany
- Prior art keywords
- imidazo
- thiazole
- methyl
- carbomethoxy
- general formula
- 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.)
- Withdrawn
Links
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 9
- 239000000243 solution Substances 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000002904 solvent Substances 0.000 claims description 61
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000725 suspension Substances 0.000 claims description 18
- -1 hydrogen atom inorganic cation Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 12
- UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical class C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 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
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 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 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001767 cationic compounds Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 4
- XNMXTGLJKDSVOT-UHFFFAOYSA-N 2-ethyl-3-methylimidazo[2,1-b][1,3]thiazole-6-carboxylic acid Chemical compound OC(=O)C1=CN2C(C)=C(CC)SC2=N1 XNMXTGLJKDSVOT-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- MICLHMNRMZVOHO-UHFFFAOYSA-N ethyl 3,5-dimethylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound S1C=C(C)N2C(C)=C(C(=O)OCC)N=C21 MICLHMNRMZVOHO-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical class SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 claims description 2
- FQIBVYSYFWBQHP-UHFFFAOYSA-N 2-imidazo[2,1-b][1,3]thiazol-6-ylacetic acid Chemical compound C1=CSC2=NC(CC(=O)O)=CN21 FQIBVYSYFWBQHP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- NVPIFUFXNOYQHH-UHFFFAOYSA-N [NH3+]C.[NH3+]C.CC([O-])=O.[O-]C(=O)C1=CN2C(C)=CSC2=N1 Chemical compound [NH3+]C.[NH3+]C.CC([O-])=O.[O-]C(=O)C1=CN2C(C)=CSC2=N1 NVPIFUFXNOYQHH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- DSVFDEWSKWCGEY-UHFFFAOYSA-N ethyl 2-imidazo[2,1-b][1,3]thiazol-6-ylacetate Chemical compound C1=CSC2=NC(CC(=O)OCC)=CN21 DSVFDEWSKWCGEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004997 halocarbonyl group Chemical group 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 2
- GGVWMZCCBKWYQO-UHFFFAOYSA-N methyl 2-ethyl-3-methylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound COC(=O)C1=CN2C(C)=C(CC)SC2=N1 GGVWMZCCBKWYQO-UHFFFAOYSA-N 0.000 claims description 2
- QGJVKOZSXAOSBH-UHFFFAOYSA-N methyl 3-methyl-2-phenylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound S1C2=NC(C(=O)OC)=CN2C(C)=C1C1=CC=CC=C1 QGJVKOZSXAOSBH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- CTGIMFUPVPDASG-UHFFFAOYSA-N (3-methylimidazo[2,1-b][1,3]thiazol-6-yl)methanol Chemical compound OCC1=CN2C(C)=CSC2=N1 CTGIMFUPVPDASG-UHFFFAOYSA-N 0.000 claims 1
- QNAXDPCUSZBVFW-UHFFFAOYSA-N 2-(2h-1,3-thiazol-3-yl)acetic acid Chemical compound OC(=O)CN1CSC=C1 QNAXDPCUSZBVFW-UHFFFAOYSA-N 0.000 claims 1
- GLXBNIGDYPJBIZ-UHFFFAOYSA-N 3-methyl-6-(trifluoromethyl)imidazo[2,1-b][1,3]thiazole Chemical compound FC(F)(F)C1=CN2C(C)=CSC2=N1 GLXBNIGDYPJBIZ-UHFFFAOYSA-N 0.000 claims 1
- KFUOGWCJHOVQIL-UHFFFAOYSA-N 3-o-ethyl 6-o-methyl imidazo[2,1-b][1,3]thiazole-3,6-dicarboxylate Chemical compound COC(=O)C1=CN2C(C(=O)OCC)=CSC2=N1 KFUOGWCJHOVQIL-UHFFFAOYSA-N 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- AFFBYDXLBUZWKD-UHFFFAOYSA-N ethyl 2,3,5-trimethylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound S1C(C)=C(C)N2C(C)=C(C(=O)OCC)N=C21 AFFBYDXLBUZWKD-UHFFFAOYSA-N 0.000 claims 1
- FGEFIPHMJNKEET-UHFFFAOYSA-N ethyl 2-butyl-3-methylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound CCOC(=O)C1=CN2C(C)=C(CCCC)SC2=N1 FGEFIPHMJNKEET-UHFFFAOYSA-N 0.000 claims 1
- JYSJPPICBHCSNR-UHFFFAOYSA-N ethyl 3-methyl-2-propylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound CCOC(=O)C1=CN2C(C)=C(CCC)SC2=N1 JYSJPPICBHCSNR-UHFFFAOYSA-N 0.000 claims 1
- OBUVCJKNVNDWCT-UHFFFAOYSA-N ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-5-carboxylate Chemical compound N1=C2SC=CN2C(C(=O)OCC)=C1C1=CC=CC=C1 OBUVCJKNVNDWCT-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 119
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 108
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 229910000029 sodium carbonate Inorganic materials 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 206010012601 diabetes mellitus Diseases 0.000 description 14
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 12
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 11
- 229960003243 phenformin Drugs 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 239000008280 blood Substances 0.000 description 10
- 210000004369 blood Anatomy 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000031709 bromination Effects 0.000 description 8
- 238000005893 bromination reaction Methods 0.000 description 8
- 239000012458 free base Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- VLVVCQMANMWJSH-UHFFFAOYSA-N 3-methylimidazo[2,1-b][1,3]thiazole-6-carboxylic acid Chemical compound OC(=O)C1=CN2C(C)=CSC2=N1 VLVVCQMANMWJSH-UHFFFAOYSA-N 0.000 description 5
- 239000003472 antidiabetic agent Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
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- 238000001035 drying Methods 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 235000019890 Amylum Nutrition 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- KZJCIJLYDYYWEU-UHFFFAOYSA-N methyl 3-methylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound CC1=CSC2=NC(C(=O)OC)=CN21 KZJCIJLYDYYWEU-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- NWJWTTJFADBMAQ-UHFFFAOYSA-N 2,3-dimethylimidazo[2,1-b][1,3]thiazole-6-carboxylic acid Chemical compound OC(=O)C1=CN2C(C)=C(C)SC2=N1 NWJWTTJFADBMAQ-UHFFFAOYSA-N 0.000 description 2
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- 229960005371 tolbutamide Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 230000004580 weight loss Effects 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL44161A IL44161A (en) | 1974-02-07 | 1974-02-07 | Pharmaceutical compositions containing 6-substituted imidazo (2,1-b)thiazoles, some new compounds of this type and type and their preparation |
| IL4512774A IL45127A (en) | 1974-06-26 | 1974-06-26 | Imidazo(2,1)thiazole-6-carboxylic or alkanoic salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2505068A1 true DE2505068A1 (de) | 1975-08-14 |
Family
ID=26320498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752505068 Withdrawn DE2505068A1 (de) | 1974-02-07 | 1975-02-06 | Imidazo eckige klammer auf 2,1-b eckige klammer zu thiazole |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4267339A (en, 2012) |
| CA (1) | CA1053239A (en, 2012) |
| CH (1) | CH621126A5 (en, 2012) |
| DE (1) | DE2505068A1 (en, 2012) |
| DK (1) | DK42175A (en, 2012) |
| FR (1) | FR2260344B1 (en, 2012) |
| GB (1) | GB1493048A (en, 2012) |
| NL (1) | NL7501449A (en, 2012) |
| SE (1) | SE7501334L (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981002013A1 (en) * | 1980-01-16 | 1981-07-23 | Yoshitomi Pharmaceutical | Hetero ring-substituted oxoalkanoic acid derivatives |
| US7994336B2 (en) | 2006-08-15 | 2011-08-09 | Actelion Pharmaceuticals Ltd. | Azetidine compounds as orexin receptor antagonists |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2410001A1 (fr) * | 1977-11-24 | 1979-06-22 | Synthelabo | Derives bicycliques de thiazole et leur application en therapeutique |
| EP0002400A1 (fr) * | 1977-11-24 | 1979-06-13 | Synthelabo | Dérivés de thiazole, leur préparation, intermédiaires et leur application en thérapeutique |
| GB8724566D0 (en) * | 1987-10-20 | 1987-11-25 | Roussel Lab Ltd | Chemical compounds |
| JP2726999B2 (ja) * | 1988-06-22 | 1998-03-11 | 日研化学株式会社 | イミダゾ［２，１−ｂ］ベンゾチアゾール誘導体及び該化合物を有効成分とする抗潰瘍剤 |
| EP0463212A1 (en) * | 1990-06-27 | 1992-01-02 | Nikken Chemicals Co., Ltd. | Imidazo[2,1-b]thiazole compound anti-ulcer agent containing the same |
| EP2094685B1 (en) | 2006-12-01 | 2011-01-19 | Actelion Pharmaceuticals Ltd. | 3-heteroaryl (amino or amido)-1- (biphenyl or phenylthiazolyl) carbonylpiperdine derivatives as orexin receptor inhibitors |
| AR064561A1 (es) | 2006-12-28 | 2009-04-08 | Actelion Pharmaceuticals Ltd | Derivados de 2-aza-biciclo[3.1.0]hexano y su uso en la preparacion de un medicamento para el tratamiento de enfermedades relacionadas con disfunciones generales del sistema de la orexina. |
| WO2009133522A1 (en) * | 2008-04-30 | 2009-11-05 | Actelion Pharmaceuticals Ltd | Piperidine and pyrrolidine compounds |
| EP2682395A1 (en) | 2012-07-04 | 2014-01-08 | Laboratorios Del. Dr. Esteve, S.A. | Imidazo[2,1-b]thiazole derivatives, their preparation and use as medicaments |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445669A1 (de) * | 1964-03-26 | 1969-03-13 | Akad Wissenschaften Ddr | Verfahren zur Herstellung von in 7-Stellung substituierten 2,3,5,6-Tetrahydro-imidazo[2,1-b]thiazolium-Salzen |
-
1975
- 1975-02-03 CH CH122175A patent/CH621126A5/de not_active IP Right Cessation
- 1975-02-04 CA CA219,342A patent/CA1053239A/en not_active Expired
- 1975-02-06 FR FR7503680A patent/FR2260344B1/fr not_active Expired
- 1975-02-06 DE DE19752505068 patent/DE2505068A1/de not_active Withdrawn
- 1975-02-06 NL NL7501449A patent/NL7501449A/xx not_active Application Discontinuation
- 1975-02-06 SE SE7501334A patent/SE7501334L/xx not_active Application Discontinuation
- 1975-02-06 DK DK42175*#A patent/DK42175A/da not_active Application Discontinuation
- 1975-02-06 GB GB5060/75A patent/GB1493048A/en not_active Expired
-
1976
- 1976-12-28 US US05/755,031 patent/US4267339A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981002013A1 (en) * | 1980-01-16 | 1981-07-23 | Yoshitomi Pharmaceutical | Hetero ring-substituted oxoalkanoic acid derivatives |
| US7994336B2 (en) | 2006-08-15 | 2011-08-09 | Actelion Pharmaceuticals Ltd. | Azetidine compounds as orexin receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7501334L (en, 2012) | 1975-08-08 |
| GB1493048A (en) | 1977-11-23 |
| DK42175A (en, 2012) | 1975-10-06 |
| CH621126A5 (en, 2012) | 1981-01-15 |
| NL7501449A (nl) | 1975-08-11 |
| FR2260344B1 (en, 2012) | 1979-01-05 |
| FR2260344A1 (en, 2012) | 1975-09-05 |
| CA1053239A (en) | 1979-04-24 |
| US4267339A (en) | 1981-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |