CH621126A5 - - Google Patents

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Info

Publication number: CH621126A5
Authority: CH; Switzerland
Prior art keywords: thiazole; solution; imidazo; methyl; hours
Prior art date: 1974-02-07

Application number

CH122175A

Other languages

German (de)

English (en)

Inventor

Enzo Dr Tedeschi

Original Assignee

Plantex Ltd

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.)

1974-02-07

Filing date

1975-02-03

Publication date

1981-01-15

1974-02-07 Priority claimed from IL44161A external-priority patent/IL44161A/xx

1974-06-26 Priority claimed from IL4512774A external-priority patent/IL45127A/xx

1975-02-03 Application filed by Plantex Ltd filed Critical Plantex Ltd

1981-01-15 Publication of CH621126A5 publication Critical patent/CH621126A5/de

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 121
239000000243 solution Substances 0.000 description 109
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 108
239000002904 solvent Substances 0.000 description 59
150000001875 compounds Chemical class 0.000 description 55
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 49
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 49
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
238000000034 method Methods 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
238000002360 preparation method Methods 0.000 description 23
229910000029 sodium carbonate Inorganic materials 0.000 description 22
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000725 suspension Substances 0.000 description 20
239000002253 acid Substances 0.000 description 19
125000000217 alkyl group Chemical group 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
206010012601 diabetes mellitus Diseases 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
230000008569 process Effects 0.000 description 15
238000010992 reflux Methods 0.000 description 15
150000003839 salts Chemical class 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
125000001424 substituent group Chemical group 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
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
239000008103 glucose Substances 0.000 description 12
125000003118 aryl group Chemical group 0.000 description 11
239000002585 base Substances 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
125000003710 aryl alkyl group Chemical group 0.000 description 10
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
229910000041 hydrogen chloride Inorganic materials 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
239000002244 precipitate Substances 0.000 description 10
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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
241000700159 Rattus Species 0.000 description 8
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
230000008020 evaporation Effects 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000012458 free base Substances 0.000 description 8
ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 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
125000003282 alkyl amino group Chemical group 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
-1 aromatic sulfuric acids Chemical class 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
150000001767 cationic compounds Chemical group 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910001411 inorganic cation Inorganic materials 0.000 description 6
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 6
150000002500 ions Chemical group 0.000 description 6
150000003242 quaternary ammonium salts Chemical class 0.000 description 6
125000005157 alkyl carboxy group Chemical group 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000006482 condensation reaction Methods 0.000 description 5
238000006297 dehydration reaction Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000006386 neutralization reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
150000003557 thiazoles Chemical class 0.000 description 5
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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 4
241001465754 Metazoa Species 0.000 description 4
125000002723 alicyclic group Chemical group 0.000 description 4
239000003472 antidiabetic agent Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
102000004877 Insulin Human genes 0.000 description 3
108090001061 Insulin Proteins 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
125000003545 alkoxy group Chemical group 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000004104 aryloxy group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium 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
230000018044 dehydration Effects 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000002768 hydroxyalkyl group Chemical group 0.000 description 3
229940125396 insulin Drugs 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-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
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
208000013016 Hypoglycemia Diseases 0.000 description 2
208000007976 Ketosis Diseases 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001263 acyl chlorides Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
150000004283 biguanides Chemical class 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
MGDWUTQKXCZNAJ-UHFFFAOYSA-N ethyl 4-bromo-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CBr MGDWUTQKXCZNAJ-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
230000002608 insulinlike Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
VMUCTYJACNFNHF-UHFFFAOYSA-N nitric acid 1,3-thiazole Chemical compound [N+](=O)(O)[O-].S1C=NC=C1 VMUCTYJACNFNHF-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000004044 response Effects 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
239000000829 suppository Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical class SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 description 1
BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
CCXQVBSQUQCEEO-UHFFFAOYSA-N 1-bromobutan-2-one Chemical compound CCC(=O)CBr CCXQVBSQUQCEEO-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
XNHTZBFSFZSWOO-UHFFFAOYSA-N 1-bromopentan-2-one Chemical compound CCCC(=O)CBr XNHTZBFSFZSWOO-UHFFFAOYSA-N 0.000 description 1
GZOWUFLRGAWBAM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazol-2-ol Chemical class OC1NC=CS1 GZOWUFLRGAWBAM-UHFFFAOYSA-N 0.000 description 1
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 1
QNAXDPCUSZBVFW-UHFFFAOYSA-N 2-(2h-1,3-thiazol-3-yl)acetic acid Chemical compound OC(=O)CN1CSC=C1 QNAXDPCUSZBVFW-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
DOGFOANXOUKFEC-UHFFFAOYSA-N 2-bromopentanal Chemical compound CCCC(Br)C=O DOGFOANXOUKFEC-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 1
XWHNHJPGYRNPKT-UHFFFAOYSA-N 6-(chloromethyl)-3-methylimidazo[2,1-b][1,3]thiazole Chemical compound ClCC1=CN2C(C)=CSC2=N1 XWHNHJPGYRNPKT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
206010010071 Coma Diseases 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
206010018473 Glycosuria Diseases 0.000 description 1
206010021000 Hypoglycaemic coma Diseases 0.000 description 1
206010023379 Ketoacidosis Diseases 0.000 description 1
206010024264 Lethargy Diseases 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
229940127003 anti-diabetic drug Drugs 0.000 description 1
230000003178 anti-diabetic effect Effects 0.000 description 1
230000002686 anti-diuretic effect Effects 0.000 description 1
230000002058 anti-hyperglycaemic effect Effects 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
229960001761 chlorpropamide Drugs 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
QJFUMFCCMJJLIE-UHFFFAOYSA-N ethanethial Chemical compound CC=S QJFUMFCCMJJLIE-UHFFFAOYSA-N 0.000 description 1
VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
YGYOGBSHUMVUNY-UHFFFAOYSA-N ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-5-carboxylate;hydrobromide Chemical compound Br.N1=C2SC=CN2C(C(=O)OCC)=C1C1=CC=CC=C1 YGYOGBSHUMVUNY-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
206010019465 hemiparesis Diseases 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000003345 hyperglycaemic effect Effects 0.000 description 1
ZRNNBFWNIKQYNW-UHFFFAOYSA-N hypochlorous acid methyl 2-aminoacetate Chemical compound ClO.COC(CN)=O ZRNNBFWNIKQYNW-UHFFFAOYSA-N 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 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
230000004140 ketosis Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
PVKOTKNHMWTSGT-UHFFFAOYSA-N methyl 2,3-dimethylimidazo[2,1-b][1,3]thiazole-6-carboxylate Chemical compound CC1=C(C)SC2=NC(C(=O)OC)=CN21 PVKOTKNHMWTSGT-UHFFFAOYSA-N 0.000 description 1
GWGCHVPWLBTRSK-UHFFFAOYSA-N methyl 3-propylimidazo[2,1-b][1,3]thiazole-5-carboxylate Chemical compound C1=C(C(=O)OC)N2C(CCC)=CSC2=N1 GWGCHVPWLBTRSK-UHFFFAOYSA-N 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000008693 nausea Effects 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000008188 pellet Substances 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 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
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000007979 thiazole derivatives Chemical class 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229960002277 tolazamide Drugs 0.000 description 1
OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
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
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
210000002700 urine Anatomy 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)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (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)

CH122175A 1974-02-07 1975-02-03 CH621126A5 (ru)

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
CH621126A5 true CH621126A5 (ru)	1981-01-15

Family

ID=26320498

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH122175A CH621126A5 (ru)	1974-02-07	1975-02-03

Country Status (9)

Country	Link
US (1)	US4267339A (ru)
CA (1)	CA1053239A (ru)
CH (1)	CH621126A5 (ru)
DE (1)	DE2505068A1 (ru)
DK (1)	DK42175A (ru)
FR (1)	FR2260344B1 (ru)
GB (1)	GB1493048A (ru)
NL (1)	NL7501449A (ru)
SE (1)	SE7501334L (ru)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
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
JPS56100784A (en) *	1980-01-16	1981-08-12	Yoshitomi Pharmaceut Ind Ltd	Indolizine derivative
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
WO2008020405A2 (en)	2006-08-15	2008-02-21	Actelion Pharmaceuticals Ltd	Azetidine compounds as orexin receptor antagonists
DE602007012142D1 (en)	2006-12-01	2011-03-03	Actelion Pharmaceuticals Ltd	3-heteroaryl (amino bzw. amido)-1- (biphenyl bzw. phenylthiazolyl) carbonylpiperdinderivate als orexinrezeptor-inhibitoren
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.
CN102015645B (zh) *	2008-04-30	2012-11-14	埃科特莱茵药品有限公司	哌啶和吡咯烷化合物
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)

* Cited by examiner, † Cited by third party
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 NL NL7501449A patent/NL7501449A/xx not_active Application Discontinuation
- 1975-02-06 DE DE19752505068 patent/DE2505068A1/de not_active Withdrawn
- 1975-02-06 DK DK42175*#A patent/DK42175A/da not_active Application Discontinuation
- 1975-02-06 FR FR7503680A patent/FR2260344B1/fr not_active Expired
- 1975-02-06 SE SE7501334A patent/SE7501334L/xx 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

Also Published As

Publication number	Publication date
DE2505068A1 (de)	1975-08-14
FR2260344B1 (ru)	1979-01-05
CA1053239A (en)	1979-04-24
US4267339A (en)	1981-05-12
GB1493048A (en)	1977-11-23
NL7501449A (nl)	1975-08-11
DK42175A (ru)	1975-10-06
FR2260344A1 (ru)	1975-09-05
SE7501334L (ru)	1975-08-08

Publication	Publication Date	Title
DE2155558C2 (de)	1982-08-26	Trifluormethyl-diphenyl-imidazole und deren Verwendung
DE3008056C2 (ru)	1988-07-21
DE1795792A1 (de)	1975-06-19	Die serumlipoidkonzentration vermindernde arzneimittel
EP0041215B1 (de)	1986-01-29	Imidazoazolalkensäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
DE69222459T2 (de)	1998-02-05	Thiazolidindionderivate, ihre Herstellung und Anwendung
CH621126A5 (ru)	1981-01-15
AT376976B (de)	1985-01-25	Verfahren zur herstellung von neuen 5-substituierten oxazolidin-2,4-dionen und ihren salzen
DE2634903C2 (de)	1985-08-14	Tetrahydrothieno-[3,2-c]-pyridin-Derivate und sie enthaltende Arzneimittel
DE2716837A1 (de)	1977-11-10	Adenin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE3218055C2 (ru)	1991-07-11
DE2321518C2 (de)	1986-07-31	Sulfamylbenzoesäuren und deren Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
CH618439A5 (ru)	1980-07-31
DE2746550C2 (ru)	1987-10-15
US4137320A (en)	1979-01-30	Pharmaceutical compositions containing imidazo(2,1-b)thiazoles and process for reducing blood sugar levels therewith
DE2404050A1 (de)	1974-08-08	Neue heterocyclische vrbindungen und verfahren zu deren herstellung
DE1934392C3 (de)	1974-05-30	Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung
DE2805167A1 (de)	1978-08-10	Entzuendungshemmende imidazole, verfahren zu ihrer herstellung und sie entheltende arzneimittel
EP0088323B1 (de)	1987-05-06	Imidazothiadiazolalkencarbonsäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln
DE3017977A1 (de)	1981-11-19	Neue substituierte 2(3h)-benzothiazolone
DE3337925C2 (de)	1994-11-24	N-(6-Aminopurinyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazin-3-carboxamid-1,1-dioxid, Verfahren zu dessen Herstellung und seine Verwendung
DE2121694B2 (de)	1977-08-18	Diamino-s-triazinderivate, ein verfahren zu deren herstellung und diese enthaltende therapeutische zubereitungen
DE3020421A1 (de)	1981-12-10	Imidazoazolalkensaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln
DE1695560B2 (de)	1980-12-04	Pyrid-2-thione und diese enthaltende pharmazeutische Zusammensetzungen
DE2232098A1 (de)	1974-01-17	2-alkyl-4(3h)-pteridinone und verfahren zu ihrer herstellung
DE2247828A1 (de)	1974-04-04	Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung

Legal Events

Date	Code	Title	Description
1981-10-30	PL	Patent ceased
2024-10-31	PL	Patent ceased