PL97129B1 - Sposob wytwarzania nowych n-benzhydrylo-n'-p-hydroksybenzylopiperazyn - Google Patents
Sposob wytwarzania nowych n-benzhydrylo-n'-p-hydroksybenzylopiperazyn Download PDFInfo
- Publication number
- PL97129B1 PL97129B1 PL1973186638A PL18663873A PL97129B1 PL 97129 B1 PL97129 B1 PL 97129B1 PL 1973186638 A PL1973186638 A PL 1973186638A PL 18663873 A PL18663873 A PL 18663873A PL 97129 B1 PL97129 B1 PL 97129B1
- Authority
- PL
- Poland
- Prior art keywords
- general formula
- benzhydryl
- piperazine
- radical
- cleaved
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- -1 acyl radical Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical class C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- KBSZKZDILXBWMX-UHFFFAOYSA-N 4-[(4-benzhydrylpiperazin-1-yl)methyl]phenol Chemical class C1=CC(O)=CC=C1CN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 KBSZKZDILXBWMX-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 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 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 125000006178 methyl benzyl group Chemical group 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 210000004556 brain Anatomy 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000036770 blood supply Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 238000005661 deetherification reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
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- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 229910021653 sulphate ion Inorganic materials 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- SPVWZCMIKICRCY-UHFFFAOYSA-N Cl.Cl.OC1=CC=C(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)C=C1 Chemical compound Cl.Cl.OC1=CC=C(CN2CCN(CC2)C(C2=CC=CC=C2)C2=CC=C(Cl)C=C2)C=C1 SPVWZCMIKICRCY-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- MZJAGMCMEKGGPE-UHFFFAOYSA-N 4-[[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]methyl]phenol Chemical compound C1=CC(O)=CC=C1CN1CCN(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)CC1 MZJAGMCMEKGGPE-UHFFFAOYSA-N 0.000 description 2
- SEVSMVUOKAMPDO-UHFFFAOYSA-N 4-acetoxy benzaldehyde Chemical compound CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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 2
- KYZWJGYDXCOKRS-UHFFFAOYSA-N (4-formylphenyl) benzoate Chemical compound C1=CC(C=O)=CC=C1OC(=O)C1=CC=CC=C1 KYZWJGYDXCOKRS-UHFFFAOYSA-N 0.000 description 1
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 1
- PEQBRKNCMMXMMZ-UHFFFAOYSA-N 1-benzhydryl-2-benzyl-4-hydroxypiperazine Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C(CN(CC1)O)CC1=CC=CC=C1 PEQBRKNCMMXMMZ-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- CNRXJITXJZQWPJ-UHFFFAOYSA-N 4-(piperazin-1-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CN1CCNCC1 CNRXJITXJZQWPJ-UHFFFAOYSA-N 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
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- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
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- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
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- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
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- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
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- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
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- 229940105631 nembutal Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
-
- 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
- C07D295/06—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 halogen atoms or nitro radicals
- C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2226767A DE2226767A1 (de) | 1972-06-02 | 1972-06-02 | N-benzhydryl-n'-p-hydroxybenzylpiperazin und verfahren zu seiner herstellung |
| DE19732312212 DE2312212A1 (de) | 1973-03-12 | 1973-03-12 | N-(p-chlorbenzhydryl)-n'-p-hydroxybenzyl-piperazin und verfahren zu seiner herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL97129B1 true PL97129B1 (pl) | 1978-02-28 |
Family
ID=25763357
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973186638A PL97129B1 (pl) | 1972-06-02 | 1973-05-31 | Sposob wytwarzania nowych n-benzhydrylo-n'-p-hydroksybenzylopiperazyn |
| PL1973186639A PL94759B1 (pl) | 1972-06-02 | 1973-05-31 | Sposob wytwarzania nowych n-benzhydrylo-n'-p-hydroksybenzylopiperazyn |
| PL1973162986A PL91050B1 (forum.php) | 1972-06-02 | 1973-05-31 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973186639A PL94759B1 (pl) | 1972-06-02 | 1973-05-31 | Sposob wytwarzania nowych n-benzhydrylo-n'-p-hydroksybenzylopiperazyn |
| PL1973162986A PL91050B1 (forum.php) | 1972-06-02 | 1973-05-31 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3868377A (forum.php) |
| JP (1) | JPS4948687A (forum.php) |
| AR (5) | AR196936A1 (forum.php) |
| AT (3) | AT331802B (forum.php) |
| AU (1) | AU470393B2 (forum.php) |
| BG (3) | BG20371A3 (forum.php) |
| CA (1) | CA980347A (forum.php) |
| CH (4) | CH579064A5 (forum.php) |
| CS (4) | CS178429B2 (forum.php) |
| DD (1) | DD106644A5 (forum.php) |
| DK (1) | DK139751C (forum.php) |
| EG (1) | EG11434A (forum.php) |
| ES (3) | ES415465A1 (forum.php) |
| FI (1) | FI55656C (forum.php) |
| FR (1) | FR2186265B1 (forum.php) |
| GB (1) | GB1386916A (forum.php) |
| HU (1) | HU165312B (forum.php) |
| IE (1) | IE37717B1 (forum.php) |
| IL (1) | IL42384A (forum.php) |
| NL (1) | NL7306771A (forum.php) |
| NO (1) | NO138026C (forum.php) |
| PH (1) | PH9485A (forum.php) |
| PL (3) | PL97129B1 (forum.php) |
| RO (3) | RO68378A (forum.php) |
| SE (1) | SE396385B (forum.php) |
| SU (4) | SU507238A3 (forum.php) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59101475A (ja) * | 1982-12-02 | 1984-06-12 | Nippon Chemiphar Co Ltd | 新規ピペラジン誘導体およびその製造法ならびにこれを含有する脳循環改善剤 |
| HU186656B (en) * | 1982-12-28 | 1985-09-30 | Richter Gedeon Vegyeszet | Process for producing new benzhydryl-piperazine derivatives, acid additionak salts and pharmaceutical compositions containing them |
| GB8320701D0 (en) * | 1983-08-01 | 1983-09-01 | Wellcome Found | Chemotherapeutic agent |
| JPS60222472A (ja) * | 1984-03-30 | 1985-11-07 | Kanebo Ltd | 新規なピペラジン誘導体および該化合物を有効成分とする医薬組成物 |
| US4978666A (en) * | 1988-08-05 | 1990-12-18 | Nippon Chemiphar Co., Ltd. | Optically active piperazine derivative |
| FR2661176B1 (fr) * | 1990-04-20 | 1992-06-12 | Adir | Nouveau procede de preparation de la 1-(2,3,4-trimethoxybenzyl) piperazine en amination reductive. |
| EP0711289B1 (en) * | 1993-07-30 | 2000-08-23 | Delta Pharmaceuticals, Inc. | Piperazine compounds used in therapy |
| BR9406080A (pt) * | 1993-12-08 | 1996-02-06 | Alcon Lab Inc | Compostos que tem tanto antividade de anaonista potente de calcio como de antioxidante e uso dos mesmos como agentes citoprotetores |
| EP2307392A2 (en) * | 2008-06-02 | 2011-04-13 | Cipla Limited | Processes for the synthesis of levocetirizine and intermediates for use therein |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2709169A (en) * | 1955-05-24 | X c chs | ||
| US3051710A (en) * | 1959-12-21 | 1962-08-28 | Lakeside Lab Inc | Glycolic acid amide derivatives of piperazine and use thereof |
-
1973
- 1973-05-15 NL NL7306771A patent/NL7306771A/xx not_active Application Discontinuation
- 1973-05-28 IE IE855/73A patent/IE37717B1/xx unknown
- 1973-05-29 CS CS3877A patent/CS178429B2/cs unknown
- 1973-05-29 BG BG026973A patent/BG20371A3/xx unknown
- 1973-05-29 RO RO7382539A patent/RO68378A/ro unknown
- 1973-05-29 IL IL42384A patent/IL42384A/en unknown
- 1973-05-29 RO RO7382540A patent/RO68379A/ro unknown
- 1973-05-29 CS CS7300003883A patent/CS182234B2/cs unknown
- 1973-05-29 CS CS7600004284A patent/CS182248B2/cs unknown
- 1973-05-29 RO RO7374944A patent/RO62900A/ro unknown
- 1973-05-29 US US364764A patent/US3868377A/en not_active Expired - Lifetime
- 1973-05-29 BG BG023741A patent/BG20595A3/xx unknown
- 1973-05-29 CS CS3878A patent/CS178430B2/cs unknown
- 1973-05-29 BG BG026972A patent/BG20596A3/xx unknown
- 1973-05-30 GB GB2571073A patent/GB1386916A/en not_active Expired
- 1973-05-30 SE SE7307692A patent/SE396385B/xx unknown
- 1973-05-31 CA CA172,824A patent/CA980347A/en not_active Expired
- 1973-05-31 SU SU1926939A patent/SU507238A3/ru active
- 1973-05-31 SU SU1926942A patent/SU530644A3/ru active
- 1973-05-31 AR AR248325A patent/AR196936A1/es active
- 1973-05-31 SU SU1926943A patent/SU508196A3/ru active
- 1973-05-31 EG EG206/73A patent/EG11434A/xx active
- 1973-05-31 AU AU56343/73A patent/AU470393B2/en not_active Expired
- 1973-05-31 PL PL1973186638A patent/PL97129B1/pl unknown
- 1973-05-31 AR AR248326A patent/AR194688A1/es active
- 1973-05-31 PH PH14678*UA patent/PH9485A/en unknown
- 1973-05-31 JP JP48060375A patent/JPS4948687A/ja active Pending
- 1973-05-31 DD DD171224A patent/DD106644A5/xx unknown
- 1973-05-31 HU HUCA347A patent/HU165312B/hu unknown
- 1973-05-31 PL PL1973186639A patent/PL94759B1/pl unknown
- 1973-05-31 AR AR248327A patent/AR201001A1/es active
- 1973-05-31 PL PL1973162986A patent/PL91050B1/pl unknown
- 1973-06-01 DK DK304673A patent/DK139751C/da active
- 1973-06-01 ES ES73415465A patent/ES415465A1/es not_active Expired
- 1973-06-01 AT AT483173A patent/AT331802B/de not_active IP Right Cessation
- 1973-06-01 FI FI1797/73A patent/FI55656C/fi active
- 1973-06-01 AT AT483273A patent/AT331252B/de not_active IP Right Cessation
- 1973-06-01 NO NO2303/73A patent/NO138026C/no unknown
- 1973-06-01 AT AT483073A patent/AT331801B/de not_active IP Right Cessation
- 1973-06-01 ES ES415466A patent/ES415466A1/es not_active Expired
- 1973-06-01 FR FR7319998A patent/FR2186265B1/fr not_active Expired
- 1973-06-01 ES ES415464A patent/ES415464A1/es not_active Expired
- 1973-06-04 CH CH802973A patent/CH579064A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH803073A patent/CH593959A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH802873A patent/CH574949A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH1193576A patent/CH594651A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR252417A patent/AR204987A1/es active
- 1974-02-18 AR AR252416A patent/AR200764A1/es active
- 1974-12-13 SU SU7402082532A patent/SU577995A3/ru active
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