CS226185B2 - Method of preparig new piperazinemethanimine derivatives - Google Patents
Method of preparig new piperazinemethanimine derivatives Download PDFInfo
- Publication number
- CS226185B2 CS226185B2 CS792952A CS295279A CS226185B2 CS 226185 B2 CS226185 B2 CS 226185B2 CS 792952 A CS792952 A CS 792952A CS 295279 A CS295279 A CS 295279A CS 226185 B2 CS226185 B2 CS 226185B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ppm
- piperazine
- formula
- dihydrochloride
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- BZGNKKZWBCFYBQ-UHFFFAOYSA-N piperazin-1-ylmethanimine Chemical class N=CN1CCNCC1 BZGNKKZWBCFYBQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 ethylene, trimethylene Chemical group 0.000 claims description 24
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ULUFNLOLSKSXTH-UHFFFAOYSA-N methanimine;piperazine Chemical class N=C.C1CNCCN1 ULUFNLOLSKSXTH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000243 solution 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
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 206010003119 arrhythmia Diseases 0.000 description 5
- 230000006793 arrhythmia Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 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
- 239000004480 active ingredient Substances 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 3
- 230000033764 rhythmic process Effects 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 230000036982 action potential Effects 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HWCQDABKUTZAIZ-UHFFFAOYSA-N (2,6-dichlorophenyl)-[4-(3-phenoxypropyl)piperazin-1-yl]methanimine;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=CC(Cl)=C1C(=N)N1CCN(CCCOC=2C=CC=CC=2)CC1 HWCQDABKUTZAIZ-UHFFFAOYSA-N 0.000 description 1
- YFRFXDQCRJCYKN-UHFFFAOYSA-N (2,6-dichlorophenyl)-[4-[2-(2,6-dimethylphenoxy)ethyl]piperazin-1-yl]methanimine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(C)=C1OCCN1CCN(C(=N)C=2C(=CC=CC=2Cl)Cl)CC1 YFRFXDQCRJCYKN-UHFFFAOYSA-N 0.000 description 1
- OVDCMLKSYABCDE-UHFFFAOYSA-N (4-chlorophenyl)-[4-(2-phenoxyethyl)piperazin-1-yl]methanimine;dihydrochloride Chemical compound Cl.Cl.C1=CC(Cl)=CC=C1C(=N)N1CCN(CCOC=2C=CC=CC=2)CC1 OVDCMLKSYABCDE-UHFFFAOYSA-N 0.000 description 1
- YFUVOAAWOJLXFS-UHFFFAOYSA-N (4-chlorophenyl)-[4-(2-phenylethyl)piperazin-1-yl]methanimine;dihydrochloride Chemical compound Cl.Cl.C1=CC(Cl)=CC=C1C(=N)N1CCN(CCC=2C=CC=CC=2)CC1 YFUVOAAWOJLXFS-UHFFFAOYSA-N 0.000 description 1
- GAKZJBKJLVTYCY-UHFFFAOYSA-N (4-phenylmethoxyphenyl)-[4-(2-phenylpropyl)piperazin-1-yl]methanimine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1C(C)CN(CC1)CCN1C(=N)C(C=C1)=CC=C1OCC1=CC=CC=C1 GAKZJBKJLVTYCY-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
- XORIAMUOPCPYFP-UHFFFAOYSA-N 1-[2-(2,6-dimethylphenoxy)ethyl]piperazine Chemical compound CC1=CC=CC(C)=C1OCCN1CCNCC1 XORIAMUOPCPYFP-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
- XJWVCWQKZQENDS-UHFFFAOYSA-N 1-bromopropan-2-ylbenzene Chemical compound BrCC(C)C1=CC=CC=C1 XJWVCWQKZQENDS-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- RTDPAOVHEOTNRL-UHFFFAOYSA-N [4-(2-phenoxyethyl)piperazin-1-yl]-[3-(trifluoromethyl)phenyl]methanimine;dihydrochloride Chemical compound Cl.Cl.FC(F)(F)C1=CC=CC(C(=N)N2CCN(CCOC=3C=CC=CC=3)CC2)=C1 RTDPAOVHEOTNRL-UHFFFAOYSA-N 0.000 description 1
- FVIGVNDNHBHCQV-UHFFFAOYSA-N [4-[2-(2,6-dimethylphenoxy)ethyl]piperazin-1-yl]-(3-methylphenyl)methanimine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(C(=N)N2CCN(CCOC=3C(=CC=CC=3C)C)CC2)=C1 FVIGVNDNHBHCQV-UHFFFAOYSA-N 0.000 description 1
- ALJBTMUXNJKPTG-UHFFFAOYSA-N [4-[2-(2,6-dimethylphenoxy)ethyl]piperazin-1-yl]-(4-phenylmethoxyphenyl)methanimine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(C)=C1OCCN1CCN(C(=N)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC1 ALJBTMUXNJKPTG-UHFFFAOYSA-N 0.000 description 1
- ZVRGKDGFSMFUCY-UHFFFAOYSA-N [4-[3-(2,6-dimethylphenoxy)propyl]piperazin-1-yl]-[3-(trifluoromethyl)phenyl]methanimine dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(C)=C1OCCCN1CCN(C(=N)C=2C=C(C=CC=2)C(F)(F)F)CC1 ZVRGKDGFSMFUCY-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WDXLNYMNQNOOPZ-UHFFFAOYSA-N phenyl-[4-(2-phenylpropyl)piperazin-1-yl]methanimine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1C(C)CN(CC1)CCN1C(=N)C1=CC=CC=C1 WDXLNYMNQNOOPZ-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 238000005406 washing Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1674478 | 1978-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226185B2 true CS226185B2 (en) | 1984-03-19 |
Family
ID=10082882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS792952A CS226185B2 (en) | 1978-04-27 | 1979-04-27 | Method of preparig new piperazinemethanimine derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4259334A (fi) |
| EP (1) | EP0005385B1 (fi) |
| JP (1) | JPS55370A (fi) |
| AT (1) | AT375358B (fi) |
| AU (1) | AU521238B2 (fi) |
| CA (1) | CA1127156A (fi) |
| CS (1) | CS226185B2 (fi) |
| DE (1) | DE2963600D1 (fi) |
| ES (2) | ES480637A0 (fi) |
| FI (1) | FI69841C (fi) |
| HU (1) | HU178272B (fi) |
| IE (1) | IE47950B1 (fi) |
| NZ (1) | NZ190293A (fi) |
| OA (1) | OA06247A (fi) |
| PH (1) | PH15270A (fi) |
| ZA (1) | ZA791944B (fi) |
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 |
| FI69841C (fi) | 1986-05-26 |
| 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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