IL44122A - 2-(1-piperazinyl)-thiazole derivatives their preparation and pharmaceutical compositions containing them - Google Patents
2-(1-piperazinyl)-thiazole derivatives their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL44122A IL44122A IL44122A IL4412274A IL44122A IL 44122 A IL44122 A IL 44122A IL 44122 A IL44122 A IL 44122A IL 4412274 A IL4412274 A IL 4412274A IL 44122 A IL44122 A IL 44122A
- Authority
- IL
- Israel
- Prior art keywords
- piperazinyl
- thiazole
- methyl
- formula
- butyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- WQFWIVTXNKRNJZ-UHFFFAOYSA-N 2-piperazin-1-yl-1,3-thiazole Chemical class C1CNCCN1C1=NC=CS1 WQFWIVTXNKRNJZ-UHFFFAOYSA-N 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 4-methyl-l-piperazinyl Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 18
- 239000012458 free base Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 10
- QOJMQILDLLFGEE-UHFFFAOYSA-N 2-butyl-1,3-thiazole Chemical compound CCCCC1=NC=CS1 QOJMQILDLLFGEE-UHFFFAOYSA-N 0.000 claims description 9
- 150000004885 piperazines Chemical class 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- UWMDQTMFXHJUTA-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-4-(2-methylpropyl)-1,3-thiazole Chemical compound CC(C)CC1=CSC(N2CCN(C)CC2)=N1 UWMDQTMFXHJUTA-UHFFFAOYSA-N 0.000 claims 1
- SDFYSFFQVDSUAT-UHFFFAOYSA-N 2-[4-(4-cyclopentyl-1,3-thiazol-2-yl)piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=NC(C2CCCC2)=CS1 SDFYSFFQVDSUAT-UHFFFAOYSA-N 0.000 claims 1
- WESBELJEHGVYTH-UHFFFAOYSA-N 4-butyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound CCCCC1=CSC(N2CCN(C)CC2)=N1 WESBELJEHGVYTH-UHFFFAOYSA-N 0.000 claims 1
- NFOMOYGKMHHXPB-UHFFFAOYSA-N 4-cyclobutyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound C1CN(C)CCN1C1=NC(C2CCC2)=CS1 NFOMOYGKMHHXPB-UHFFFAOYSA-N 0.000 claims 1
- YRLWABAEYGSYNI-UHFFFAOYSA-N 4-cycloheptyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound C1CN(C)CCN1C1=NC(C2CCCCCC2)=CS1 YRLWABAEYGSYNI-UHFFFAOYSA-N 0.000 claims 1
- LPEMVPRIOYIWTO-UHFFFAOYSA-N 4-cyclopentyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound C1CN(C)CCN1C1=NC(C2CCCC2)=CS1 LPEMVPRIOYIWTO-UHFFFAOYSA-N 0.000 claims 1
- HOVLVYBDSFSDDF-UHFFFAOYSA-N 4-cyclopropyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound C1CN(C)CCN1C1=NC(C2CC2)=CS1 HOVLVYBDSFSDDF-UHFFFAOYSA-N 0.000 claims 1
- RIPVINIOQMAQDP-UHFFFAOYSA-N 4-heptyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound CCCCCCCC1=CSC(N2CCN(C)CC2)=N1 RIPVINIOQMAQDP-UHFFFAOYSA-N 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000000243 solution Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 5
- QFACSDPLAUCZBD-UHFFFAOYSA-N 4-methylpiperazine-1-carbothioamide Chemical compound CN1CCN(C(N)=S)CC1 QFACSDPLAUCZBD-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ULSAJQMHTGKPIY-UHFFFAOYSA-N 1-chloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CCl ULSAJQMHTGKPIY-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- CFURXPUTJPGOEI-UHFFFAOYSA-N 2-butyl-1,3-thiazol-3-ium chloride Chemical compound [Cl-].C(CCC)C=1SC=C[NH+]1 CFURXPUTJPGOEI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- PVIJLUXKGBJNNI-UHFFFAOYSA-N piperazine-1-carbothioamide Chemical compound NC(=S)N1CCNCC1 PVIJLUXKGBJNNI-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- WPASOZFIBCYNCU-UHFFFAOYSA-N 1-methylpiperazin-1-ium;thiocyanate Chemical compound [S-]C#N.C[NH+]1CCNCC1 WPASOZFIBCYNCU-UHFFFAOYSA-N 0.000 description 1
- XINLLYHPMGDSMW-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-4-propan-2-yl-1,3-thiazole Chemical compound CC(C)C1=CSC(N2CCN(C)CC2)=N1 XINLLYHPMGDSMW-UHFFFAOYSA-N 0.000 description 1
- POMJGYGECRNWEK-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-4-propan-2-yl-1,3-thiazole;dihydrochloride Chemical compound Cl.Cl.CC(C)C1=CSC(N2CCN(C)CC2)=N1 POMJGYGECRNWEK-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
- DYBYFYWEGZGUPG-UHFFFAOYSA-N 2-[4-(4-cyclopentyl-1,3-thiazol-2-yl)piperazin-1-yl]ethanol;dihydrochloride Chemical compound Cl.Cl.C1CN(CCO)CCN1C1=NC(C2CCCC2)=CS1 DYBYFYWEGZGUPG-UHFFFAOYSA-N 0.000 description 1
- FCMSADORJFIRBT-UHFFFAOYSA-N 2-butyl-5-methyl-1,3-thiazole Chemical compound CCCCC1=NC=C(C)S1 FCMSADORJFIRBT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- TYBLNRMADGOJIC-UHFFFAOYSA-N 4-(2-hydroxyethyl)piperazine-1-carbothioamide Chemical compound NC(=S)N1CCN(CCO)CC1 TYBLNRMADGOJIC-UHFFFAOYSA-N 0.000 description 1
- ZBNQVYYPSOUTOC-UHFFFAOYSA-N 4-benzylpiperazine-1-carbothioamide Chemical compound C1CN(C(=S)N)CCN1CC1=CC=CC=C1 ZBNQVYYPSOUTOC-UHFFFAOYSA-N 0.000 description 1
- AVYQKJMCSGDSRP-UHFFFAOYSA-N 4-cyclohexyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole Chemical compound C1CN(C)CCN1C1=NC(C2CCCCC2)=CS1 AVYQKJMCSGDSRP-UHFFFAOYSA-N 0.000 description 1
- RXIWMKWCYLOMOX-UHFFFAOYSA-N 4-cyclohexyl-2-(4-methylpiperazin-1-yl)-1,3-thiazole;hydrochloride Chemical compound Cl.C1CN(C)CCN1C1=NC(C2CCCCC2)=CS1 RXIWMKWCYLOMOX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002891 anorexigenic effect Effects 0.000 description 1
- 229940125684 antimigraine agent Drugs 0.000 description 1
- 239000002282 antimigraine agent Substances 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH156373A CH583232A5 (da) | 1973-02-02 | 1973-02-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44122A0 IL44122A0 (en) | 1974-05-16 |
| IL44122A true IL44122A (en) | 1977-05-31 |
Family
ID=4213345
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL50304A IL50304A (en) | 1973-02-02 | 1974-01-31 | 2-(4-methyl-1-piperazinyl)-4-tert butylthiazole its preparation and pharmaceutical compositions containing it |
| IL44122A IL44122A (en) | 1973-02-02 | 1974-01-31 | 2-(1-piperazinyl)-thiazole derivatives their preparation and pharmaceutical compositions containing them |
| IL50304A IL50304A0 (en) | 1973-02-02 | 1976-08-19 | A new 2-(1-piperazinyl)-thiazole derivative its preparation and pharmaceutical compositions containing it |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL50304A IL50304A (en) | 1973-02-02 | 1974-01-31 | 2-(4-methyl-1-piperazinyl)-4-tert butylthiazole its preparation and pharmaceutical compositions containing it |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL50304A IL50304A0 (en) | 1973-02-02 | 1976-08-19 | A new 2-(1-piperazinyl)-thiazole derivative its preparation and pharmaceutical compositions containing it |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4064244A (da) |
| JP (1) | JPS49102682A (da) |
| AT (1) | AT348531B (da) |
| BE (1) | BE810467A (da) |
| CA (1) | CA1018168A (da) |
| CH (1) | CH583232A5 (da) |
| DD (1) | DD109390A5 (da) |
| DE (1) | DE2404050A1 (da) |
| ES (3) | ES422886A1 (da) |
| FR (1) | FR2215960B1 (da) |
| GB (1) | GB1461874A (da) |
| HU (1) | HU167399B (da) |
| IE (1) | IE40253B1 (da) |
| IL (3) | IL50304A (da) |
| NL (1) | NL7401253A (da) |
| PH (1) | PH13708A (da) |
| PL (1) | PL88592B1 (da) |
| SE (1) | SE404801B (da) |
| SU (1) | SU513624A3 (da) |
| ZA (1) | ZA74679B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1518559A (en) * | 1976-04-12 | 1978-07-19 | Science Union & Cie | Naphthyl derivatives processes for their preparation an pharmaceutical compositions containing them |
| NZ187474A (en) * | 1977-06-10 | 1981-03-16 | Science Union & Cie | 4-heterocyclyl-piperazine-i-carbodithioic acids and salts and pharmaceutical compositions thereof |
| EP0094498A3 (en) * | 1982-05-06 | 1985-04-03 | American Cyanamid Company | Antiatherosclerotic 1-piperazine derivatives |
| NL8601494A (nl) * | 1985-06-22 | 1987-01-16 | Sandoz Ag | Thiazolen, hun bereiding en farmaceutische preparaten die ze bevatten. |
| IT1191845B (it) * | 1986-01-20 | 1988-03-23 | Dompe Farmaceutici Spa | Alchiloli derivati farmacologicamente attivi |
| US5232921A (en) * | 1987-03-12 | 1993-08-03 | Sanofi | Thiazole derivatives active on the cholinergic system, process for obtention and pharmaceutical compositions |
| FR2612187B1 (fr) * | 1987-03-12 | 1989-07-21 | Sanofi Sa | Derives du thiazole actifs sur le systeme cholinergique, leur procede de preparation et compositions pharmaceutiques en contenant |
| DE4136579A1 (de) * | 1991-11-07 | 1993-05-13 | Rewo Chemische Werke Gmbh | Polyolpolyethersulfosuccinate, verfahren zu ihrer herstelllung und ihre verwendung |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE485737A (da) * | 1947-11-12 | |||
| US2606906A (en) * | 1948-10-14 | 1952-08-12 | American Cyanamid Co | 1-(2-pyridyl) piperazine and process of preparing same |
| BE577438A (da) * | 1958-04-07 | |||
| US2975182A (en) * | 1959-11-16 | 1961-03-14 | Paul A J Janssen | 1-(aroylalkyl)-4-(heterocyclyl) piperazines |
| DE1595923A1 (de) * | 1965-02-20 | 1969-11-27 | Merck Ag E | 1-Aralkyl-4-(thiazolyl-2)-piperazine und Verfahren zu ihrer Herstellung |
-
1973
- 1973-02-02 CH CH156373A patent/CH583232A5/xx not_active IP Right Cessation
-
1974
- 1974-01-24 SE SE7400917A patent/SE404801B/xx unknown
- 1974-01-29 GB GB409074A patent/GB1461874A/en not_active Expired
- 1974-01-29 DE DE2404050A patent/DE2404050A1/de active Pending
- 1974-01-30 FR FR7403094A patent/FR2215960B1/fr not_active Expired
- 1974-01-30 NL NL7401253A patent/NL7401253A/xx not_active Application Discontinuation
- 1974-01-31 PL PL1974168473A patent/PL88592B1/pl unknown
- 1974-01-31 JP JP49012296A patent/JPS49102682A/ja active Pending
- 1974-01-31 IE IE187/74A patent/IE40253B1/xx unknown
- 1974-01-31 IL IL50304A patent/IL50304A/en unknown
- 1974-01-31 IL IL44122A patent/IL44122A/en unknown
- 1974-01-31 CA CA191,436A patent/CA1018168A/en not_active Expired
- 1974-01-31 PH PH15462A patent/PH13708A/en unknown
- 1974-01-31 DD DD176293A patent/DD109390A5/xx unknown
- 1974-01-31 BE BE140433A patent/BE810467A/xx unknown
- 1974-02-01 ZA ZA00740679A patent/ZA74679B/xx unknown
- 1974-02-01 AT AT80674A patent/AT348531B/de not_active IP Right Cessation
- 1974-02-01 HU HUWA291A patent/HU167399B/hu unknown
- 1974-02-02 ES ES422886A patent/ES422886A1/es not_active Expired
- 1974-12-12 SU SU2082480A patent/SU513624A3/ru active
-
1975
- 1975-06-18 US US05/588,002 patent/US4064244A/en not_active Expired - Lifetime
-
1976
- 1976-03-16 ES ES446077A patent/ES446077A1/es not_active Expired
- 1976-03-16 ES ES446076A patent/ES446076A1/es not_active Expired
- 1976-08-19 IL IL50304A patent/IL50304A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE404801B (sv) | 1978-10-30 |
| IL50304A (en) | 1977-05-31 |
| FR2215960B1 (da) | 1976-12-03 |
| AU6506574A (en) | 1975-07-31 |
| AT348531B (de) | 1979-02-26 |
| GB1461874A (en) | 1977-01-19 |
| SU513624A3 (ru) | 1976-05-05 |
| US4064244A (en) | 1977-12-20 |
| DD109390A5 (da) | 1974-11-05 |
| IL44122A0 (en) | 1974-05-16 |
| IL50304A0 (en) | 1976-10-31 |
| IE40253B1 (en) | 1979-04-25 |
| ZA74679B (en) | 1975-09-24 |
| FR2215960A1 (da) | 1974-08-30 |
| BE810467A (fr) | 1974-07-31 |
| CA1018168A (en) | 1977-09-27 |
| IE40253L (en) | 1974-08-02 |
| PL88592B1 (da) | 1976-09-30 |
| JPS49102682A (da) | 1974-09-27 |
| CH583232A5 (da) | 1976-12-31 |
| DE2404050A1 (de) | 1974-08-08 |
| ES446077A1 (es) | 1977-10-01 |
| PH13708A (en) | 1980-09-08 |
| ATA80674A (de) | 1978-07-15 |
| NL7401253A (da) | 1974-08-06 |
| ES446076A1 (es) | 1977-09-01 |
| HU167399B (da) | 1975-09-27 |
| ES422886A1 (es) | 1976-09-16 |
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