FI69841C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-fenoxi- eller fenyltio- eller fenylalkyl)-4-bensimidoylpi peaziner - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-fenoxi- eller fenyltio- eller fenylalkyl)-4-bensimidoylpi peaziner Download PDFInfo
- Publication number
- FI69841C FI69841C FI791350A FI791350A FI69841C FI 69841 C FI69841 C FI 69841C FI 791350 A FI791350 A FI 791350A FI 791350 A FI791350 A FI 791350A FI 69841 C FI69841 C FI 69841C
- Authority
- FI
- Finland
- Prior art keywords
- ppm
- group
- formula
- alkyl group
- piperazine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- DNJKAZDWTONBCX-UHFFFAOYSA-N C[SH2]C(C1=CC=CC=C1)=N Chemical compound C[SH2]C(C1=CC=CC=C1)=N DNJKAZDWTONBCX-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- -1 alkyl radical Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 206010003119 arrhythmia Diseases 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XORIAMUOPCPYFP-UHFFFAOYSA-N 1-[2-(2,6-dimethylphenoxy)ethyl]piperazine Chemical compound CC1=CC=CC(C)=C1OCCN1CCNCC1 XORIAMUOPCPYFP-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000006793 arrhythmia Effects 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- MSKAVXYLXIUCJP-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1OCCBr MSKAVXYLXIUCJP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000166550 Strophanthus gratus Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 3
- 229960003343 ouabain Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 2
- UTXHKQAZYGRDBA-UHFFFAOYSA-N 1-(2-phenylpropyl)piperazine Chemical compound C=1C=CC=CC=1C(C)CN1CCNCC1 UTXHKQAZYGRDBA-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 2
- WNBDVECWEGIBCG-UHFFFAOYSA-N IO.CSC(C1=CC=CC=C1)=N Chemical compound IO.CSC(C1=CC=CC=C1)=N WNBDVECWEGIBCG-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229960003404 mexiletine Drugs 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 206010047302 ventricular tachycardia Diseases 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical class C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- QPBMCBIEHMJXIQ-UHFFFAOYSA-N 1-(1-phenoxypropan-2-yl)piperazine Chemical compound C1CNCCN1C(C)COC1=CC=CC=C1 QPBMCBIEHMJXIQ-UHFFFAOYSA-N 0.000 description 1
- PTJSLCXRMMGRLY-UHFFFAOYSA-N 1-(2-phenoxyethyl)piperazine Chemical compound C=1C=CC=CC=1OCCN1CCNCC1 PTJSLCXRMMGRLY-UHFFFAOYSA-N 0.000 description 1
- LKUAPSRIYZLAAO-UHFFFAOYSA-N 1-(2-phenylethyl)piperazine Chemical compound C1CNCCN1CCC1=CC=CC=C1 LKUAPSRIYZLAAO-UHFFFAOYSA-N 0.000 description 1
- KVSFTLLHQGAGKB-UHFFFAOYSA-N 1-(2-phenylsulfanylethyl)piperazine Chemical compound C=1C=CC=CC=1SCCN1CCNCC1 KVSFTLLHQGAGKB-UHFFFAOYSA-N 0.000 description 1
- JCMMXVUEJTZCIS-UHFFFAOYSA-N 1-(3-phenoxypropyl)piperazine Chemical compound C1CNCCN1CCCOC1=CC=CC=C1 JCMMXVUEJTZCIS-UHFFFAOYSA-N 0.000 description 1
- LOJCUYCKDGYLJH-UHFFFAOYSA-N 1-(3-phenylpropyl)piperazine Chemical compound C=1C=CC=CC=1CCCN1CCNCC1 LOJCUYCKDGYLJH-UHFFFAOYSA-N 0.000 description 1
- NYBYNSQDRDHPMS-UHFFFAOYSA-N 1-[3-(2,6-dimethylphenoxy)propyl]piperazine Chemical compound CC1=CC=CC(C)=C1OCCCN1CCNCC1 NYBYNSQDRDHPMS-UHFFFAOYSA-N 0.000 description 1
- MWEXFYJNMHVCPG-UHFFFAOYSA-N 1-phenoxy-3-piperazin-1-ylpropan-2-ol Chemical compound C1CNCCN1CC(O)COC1=CC=CC=C1 MWEXFYJNMHVCPG-UHFFFAOYSA-N 0.000 description 1
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- GIEZSMRKYNDDTR-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC(=CC=C2)OCC2=CC=CC=C2)=N)C(=CC=C1)C Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC(=CC=C2)OCC2=CC=CC=C2)=N)C(=CC=C1)C GIEZSMRKYNDDTR-UHFFFAOYSA-N 0.000 description 1
- VWBHVPPQBBREEQ-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)C)=N)C(=CC=C1)C Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)C)=N)C(=CC=C1)C VWBHVPPQBBREEQ-UHFFFAOYSA-N 0.000 description 1
- YXUDEXCTFHGMRH-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)Cl)=N)C(=CC=C1)C Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)Cl)=N)C(=CC=C1)C YXUDEXCTFHGMRH-UHFFFAOYSA-N 0.000 description 1
- CKEMYHNEAMDBOA-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)O)=N)C(=CC=C1)C Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)O)=N)C(=CC=C1)C CKEMYHNEAMDBOA-UHFFFAOYSA-N 0.000 description 1
- WCDVINLJGIOQMG-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)OCC2=CC=CC=C2)=N)C(=CC=C1)C Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=C(C=C2)OCC2=CC=CC=C2)=N)C(=CC=C1)C WCDVINLJGIOQMG-UHFFFAOYSA-N 0.000 description 1
- KLVXGRYKJTVMEL-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C(=CC=C1)C Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C(=CC=C1)C KLVXGRYKJTVMEL-UHFFFAOYSA-N 0.000 description 1
- BQTUPPMUJWZNJK-UHFFFAOYSA-N ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=CC=C1 Chemical compound ClOCl.CC1=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=CC=C1 BQTUPPMUJWZNJK-UHFFFAOYSA-N 0.000 description 1
- FKGOMCOKUZEPNT-UHFFFAOYSA-N ClOCl.CC=1C=C(OCCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=C(C1Cl)C Chemical compound ClOCl.CC=1C=C(OCCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=C(C1Cl)C FKGOMCOKUZEPNT-UHFFFAOYSA-N 0.000 description 1
- FRHIMFHRSFRONW-UHFFFAOYSA-N ClOCl.CC=1C=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=C(C1Cl)C Chemical compound ClOCl.CC=1C=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=C(C1Cl)C FRHIMFHRSFRONW-UHFFFAOYSA-N 0.000 description 1
- GUAAWEILYHDKBP-UHFFFAOYSA-N ClOCl.ClC1=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=C(C=C1)OC Chemical compound ClOCl.ClC1=C(OCCN2CCN(CC2)C(C2=CC=CC=C2)=N)C=C(C=C1)OC GUAAWEILYHDKBP-UHFFFAOYSA-N 0.000 description 1
- BOIKSRHOAJEPDD-UHFFFAOYSA-N ClOCl.O(C1=CC=CC=C1)CCCN1CCN(CC1)C(C1=C(C=CC=C1Cl)Cl)=N Chemical compound ClOCl.O(C1=CC=CC=C1)CCCN1CCN(CC1)C(C1=C(C=CC=C1Cl)Cl)=N BOIKSRHOAJEPDD-UHFFFAOYSA-N 0.000 description 1
- LXTZNOMGWBXXCP-UHFFFAOYSA-N ClOCl.O(C1=CC=CC=C1)CCCN1CCN(CC1)C(C1=CC=C(C=C1)Cl)=N Chemical compound ClOCl.O(C1=CC=CC=C1)CCCN1CCN(CC1)C(C1=CC=C(C=C1)Cl)=N LXTZNOMGWBXXCP-UHFFFAOYSA-N 0.000 description 1
- NBLTZZBZUPUELS-UHFFFAOYSA-N ClOCl.O(C1=CC=CC=C1)CCCN1CCN(CC1)C(C1=CC=CC=C1)=N Chemical compound ClOCl.O(C1=CC=CC=C1)CCCN1CCN(CC1)C(C1=CC=CC=C1)=N NBLTZZBZUPUELS-UHFFFAOYSA-N 0.000 description 1
- FMBJJCCIZYLUMV-UHFFFAOYSA-N ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=C(C=CC=C1Cl)Cl)=N Chemical compound ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=C(C=CC=C1Cl)Cl)=N FMBJJCCIZYLUMV-UHFFFAOYSA-N 0.000 description 1
- JYVMWXASNQVYEZ-UHFFFAOYSA-N ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=CC=C(C=C1)Cl)=N Chemical compound ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=CC=C(C=C1)Cl)=N JYVMWXASNQVYEZ-UHFFFAOYSA-N 0.000 description 1
- GLRRTVNZWOYZNE-UHFFFAOYSA-N ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=CC=CC=C1)=N Chemical compound ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=CC=CC=C1)=N GLRRTVNZWOYZNE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
- CSNNZISOGOXLNV-UHFFFAOYSA-N [4-[2-(2,6-dimethylphenoxy)ethyl]piperazin-1-yl]-[3-(trifluoromethyl)phenyl]methanimine Chemical compound CC1=CC=CC(C)=C1OCCN1CCN(C(=N)C=2C=C(C=CC=2)C(F)(F)F)CC1 CSNNZISOGOXLNV-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OXOPPLHLNNIPQL-UHFFFAOYSA-N chloro hypochlorite [4-(2-phenoxyethyl)piperazin-1-yl]-[3-(trifluoromethyl)phenyl]methanimine Chemical compound ClOCl.O(C1=CC=CC=C1)CCN1CCN(CC1)C(C1=CC(=CC=C1)C(F)(F)F)=N OXOPPLHLNNIPQL-UHFFFAOYSA-N 0.000 description 1
- ZCMBPGQPLLJWRX-UHFFFAOYSA-N chloro hypochlorite [4-[3-(2,6-dimethylphenoxy)propyl]piperazin-1-yl]-[3-(trifluoromethyl)phenyl]methanimine Chemical compound ClOCl.CC1=C(OCCCN2CCN(CC2)C(C2=CC(=CC=C2)C(F)(F)F)=N)C(=CC=C1)C ZCMBPGQPLLJWRX-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 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
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 208000036501 vesicoureteral reflux 7 Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1674478 | 1978-04-27 | ||
| GB1674478 | 1978-04-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI791350A7 FI791350A7 (fi) | 1979-10-28 |
| FI69841B FI69841B (fi) | 1985-12-31 |
| FI69841C true FI69841C (fi) | 1986-05-26 |
Family
ID=10082882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI791350A FI69841C (fi) | 1978-04-27 | 1979-04-25 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-fenoxi- eller fenyltio- eller fenylalkyl)-4-bensimidoylpi peaziner |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4259334A (cs) |
| EP (1) | EP0005385B1 (cs) |
| JP (1) | JPS55370A (cs) |
| AT (1) | AT375358B (cs) |
| AU (1) | AU521238B2 (cs) |
| CA (1) | CA1127156A (cs) |
| CS (1) | CS226185B2 (cs) |
| DE (1) | DE2963600D1 (cs) |
| ES (2) | ES480637A0 (cs) |
| FI (1) | FI69841C (cs) |
| HU (1) | HU178272B (cs) |
| IE (1) | IE47950B1 (cs) |
| NZ (1) | NZ190293A (cs) |
| OA (1) | OA06247A (cs) |
| PH (1) | PH15270A (cs) |
| ZA (1) | ZA791944B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374837A (en) * | 1981-07-31 | 1983-02-22 | Laroche Navarron, S.A. | Piperazine derivatives of theobromine |
| US4400381A (en) * | 1981-07-31 | 1983-08-23 | Laroche-Navarron, S.A. | Piperazine derivatives of theophylline |
| US4515947A (en) * | 1982-08-11 | 1985-05-07 | Eastman Kodak Company | Cyanoalkylpiperazines and methods for their preparation and use |
| US4713382A (en) * | 1985-05-30 | 1987-12-15 | Syntex (U.S.A.) Inc. | N-phenyl-4-phenyl-1-piperazinecarboxamidines and related compounds as antiarrhythmic agents |
| AU7446900A (en) * | 1999-09-28 | 2001-04-30 | Nihon Nohyaku Co., Ltd. | Thioalkylamine derivatives and process for the preparation thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1810836A1 (de) * | 1967-12-28 | 1970-01-08 | Chinoin Gyogyszer Es Vegyeszet | Neue Benzamidinderivate und Verfahren zur Herstellung derselben |
| US4115569A (en) * | 1971-11-19 | 1978-09-19 | Hoechst Aktiengesellschaft | Cyclic diamine derivatives |
| CA1012540A (en) * | 1972-06-17 | 1977-06-21 | Sumitomo Chemical Company | 2-propanol derivatives and preparation thereof |
| US3793322A (en) * | 1972-12-15 | 1974-02-19 | Usv Pharma Corp | 1,4-disubstituted piperazines |
-
1979
- 1979-04-03 DE DE7979400214T patent/DE2963600D1/de not_active Expired
- 1979-04-03 EP EP79400214A patent/EP0005385B1/fr not_active Expired
- 1979-04-04 CA CA324,866A patent/CA1127156A/en not_active Expired
- 1979-04-05 US US06/027,475 patent/US4259334A/en not_active Expired - Lifetime
- 1979-04-18 AT AT0291379A patent/AT375358B/de not_active IP Right Cessation
- 1979-04-24 AU AU46331/79A patent/AU521238B2/en not_active Ceased
- 1979-04-24 ZA ZA791944A patent/ZA791944B/xx unknown
- 1979-04-25 HU HU79LA954A patent/HU178272B/hu unknown
- 1979-04-25 FI FI791350A patent/FI69841C/fi not_active IP Right Cessation
- 1979-04-26 PH PH22424A patent/PH15270A/en unknown
- 1979-04-26 NZ NZ190293A patent/NZ190293A/xx unknown
- 1979-04-26 JP JP5093779A patent/JPS55370A/ja active Pending
- 1979-04-26 ES ES480637A patent/ES480637A0/es active Granted
- 1979-04-26 OA OA56798A patent/OA06247A/xx unknown
- 1979-04-27 CS CS792952A patent/CS226185B2/cs unknown
- 1979-08-08 IE IE872/79A patent/IE47950B1/en unknown
-
1980
- 1980-01-31 ES ES488835A patent/ES488835A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8103740A1 (es) | 1981-03-16 |
| PH15270A (en) | 1982-11-02 |
| IE47950B1 (en) | 1984-07-25 |
| EP0005385A1 (fr) | 1979-11-14 |
| US4259334A (en) | 1981-03-31 |
| DE2963600D1 (en) | 1982-10-28 |
| ES8100282A1 (es) | 1980-11-01 |
| AU521238B2 (en) | 1982-03-25 |
| HU178272B (en) | 1982-04-28 |
| ES488835A0 (es) | 1981-03-16 |
| AT375358B (de) | 1984-07-25 |
| ZA791944B (en) | 1980-04-30 |
| JPS55370A (en) | 1980-01-05 |
| ES480637A0 (es) | 1980-11-01 |
| IE790872L (en) | 1978-10-27 |
| NZ190293A (en) | 1980-11-28 |
| CS226185B2 (en) | 1984-03-19 |
| CA1127156A (en) | 1982-07-06 |
| FI791350A7 (fi) | 1979-10-28 |
| FI69841B (fi) | 1985-12-31 |
| AU4633179A (en) | 1979-11-01 |
| ATA291379A (de) | 1983-12-15 |
| OA06247A (fr) | 1981-06-30 |
| EP0005385B1 (fr) | 1982-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: LAROCHE NAVARRON S.A. |