CS236894B2 - Processing of 5,11-dihydro-11-(4-methyl-1-piperazinyl)acetyl)-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-one - Google Patents
Processing of 5,11-dihydro-11-(4-methyl-1-piperazinyl)acetyl)-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-one Download PDFInfo
- Publication number
- CS236894B2 CS236894B2 CS837048A CS704883A CS236894B2 CS 236894 B2 CS236894 B2 CS 236894B2 CS 837048 A CS837048 A CS 837048A CS 704883 A CS704883 A CS 704883A CS 236894 B2 CS236894 B2 CS 236894B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- piperazinyl
- dihydro
- pyrido
- benzodiazepin
- Prior art date
Links
- -1 4-Methyl-1-piperazinyl Chemical group 0.000 claims abstract description 9
- MIRBIZDDMSFTKY-UHFFFAOYSA-N 5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2NC2=CC=CC=C12 MIRBIZDDMSFTKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 6
- JCXZKUZXVQKENT-UHFFFAOYSA-N 2-(4-methylpiperazin-1-ium-1-yl)acetate Chemical compound CN1CCN(CC(O)=O)CC1 JCXZKUZXVQKENT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000006184 cosolvent Substances 0.000 claims description 2
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 abstract description 12
- 229960004633 pirenzepine Drugs 0.000 abstract description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- QETJQVJIERQYIQ-UHFFFAOYSA-N ethyl 2-(4-methylpiperazin-1-yl)acetate Chemical compound CCOC(=O)CN1CCN(C)CC1 QETJQVJIERQYIQ-UHFFFAOYSA-N 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PWDSJBHSKYBUEX-UHFFFAOYSA-N 1,4-benzodiazepin-5-one Chemical compound O=C1N=CC=NC2=CC=CC=C12 PWDSJBHSKYBUEX-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- PHGMLCRXRGZJCD-UHFFFAOYSA-N 3-phenylpropyl 2-(4-methylpiperazin-1-yl)acetate Chemical compound CN1CCN(CC1)CC(=O)OCCCC1=CC=CC=C1 PHGMLCRXRGZJCD-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SQJBXGFHLHCFKR-UHFFFAOYSA-N benzyl 2-(4-methylpiperazin-1-yl)acetate Chemical compound C1CN(C)CCN1CC(=O)OCC1=CC=CC=C1 SQJBXGFHLHCFKR-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- QSOFJTPEADTCHW-UHFFFAOYSA-N hexyl 2-(4-methylpiperazin-1-yl)acetate Chemical compound CCCCCCOC(=O)CN1CCN(C)CC1 QSOFJTPEADTCHW-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RJYUOFUCWIYMCZ-UHFFFAOYSA-N propyl 2-(4-methylpiperazin-1-yl)acetate Chemical compound CCCOC(=O)CN1CCN(C)CC1 RJYUOFUCWIYMCZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823235795 DE3235795A1 (de) | 1982-09-28 | 1982-09-28 | Neues verfahren zur herstellung von 5,11-dihydro-11-((4-methyl-1-piperazinyl)- acetyl)- 6h-pyrido(2,3-b)(1,4)- benzodiazepin-6-on |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236894B2 true CS236894B2 (en) | 1985-05-15 |
Family
ID=6174310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS837048A CS236894B2 (en) | 1982-09-28 | 1983-09-27 | Processing of 5,11-dihydro-11-(4-methyl-1-piperazinyl)acetyl)-6h-pyrido(2,3-b)-(1,4)benzodiazepine-6-one |
Country Status (16)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3735895A1 (de) * | 1987-10-23 | 1989-05-03 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| IT1225729B (it) * | 1988-08-12 | 1990-11-26 | Menarini S A S Firenze A | Derivati della 5,5-diossido-6,11-diidrodibenzo (c,f)(1,2,5) tiadiazepina, loro sali e relativi procedimenti di fabbricazione |
| US7123562B2 (en) | 2002-06-20 | 2006-10-17 | Koninklijke Philips Electronics N. V. | Method and device for determining a set of recording pulse series parameters for optical carrier recording and optical record carrier |
| CN103044419A (zh) * | 2012-09-04 | 2013-04-17 | 苏州弘森药业有限公司 | 一种合成盐酸哌仑西平的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1130973B (it) * | 1980-03-17 | 1986-06-18 | Microsules Argentina Sa De S C | Processo per la preparazione di derivati di 5,11-di-idro-6h-pirido(2,3-b) (1,4)-benzodiazepin-6-one,derivati finali ed intermedi di sintesi in tal modo ottenuti |
-
1982
- 1982-09-28 DE DE19823235795 patent/DE3235795A1/de not_active Withdrawn
-
1983
- 1983-09-17 DE DE8383109230T patent/DE3369847D1/de not_active Expired
- 1983-09-17 EP EP83109230A patent/EP0104566B1/de not_active Expired
- 1983-09-17 AT AT83109230T patent/ATE25524T1/de not_active IP Right Cessation
- 1983-09-20 FI FI833349A patent/FI73680C/fi not_active IP Right Cessation
- 1983-09-24 KR KR1019830004476A patent/KR840006244A/ko not_active Withdrawn
- 1983-09-26 DD DD83255117A patent/DD211350A5/de unknown
- 1983-09-26 GR GR72533A patent/GR79679B/el unknown
- 1983-09-27 ES ES525969A patent/ES525969A0/es active Granted
- 1983-09-27 CS CS837048A patent/CS236894B2/cs unknown
- 1983-09-27 CA CA000437625A patent/CA1202625A/en not_active Expired
- 1983-09-27 PL PL1983243918A patent/PL139939B1/pl unknown
- 1983-09-27 NO NO833474A patent/NO833474L/no unknown
- 1983-09-27 HU HU833352A patent/HU187976B/hu unknown
- 1983-09-27 DK DK441183A patent/DK441183A/da not_active Application Discontinuation
- 1983-09-27 PT PT77401A patent/PT77401B/pt unknown
- 1983-09-27 JP JP58179100A patent/JPS5980684A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0104566B1 (de) | 1987-02-25 |
| DD211350A5 (de) | 1984-07-11 |
| ES8405793A1 (es) | 1984-06-16 |
| PL243918A1 (en) | 1984-09-10 |
| GR79679B (enrdf_load_stackoverflow) | 1984-10-31 |
| FI73680B (fi) | 1987-07-31 |
| PT77401A (de) | 1983-10-01 |
| FI833349L (fi) | 1984-03-29 |
| FI833349A0 (fi) | 1983-09-20 |
| CA1202625A (en) | 1986-04-01 |
| PL139939B1 (en) | 1987-03-31 |
| NO833474L (no) | 1984-03-29 |
| PT77401B (de) | 1986-03-20 |
| EP0104566A2 (de) | 1984-04-04 |
| EP0104566A3 (en) | 1985-05-15 |
| ATE25524T1 (de) | 1987-03-15 |
| KR840006244A (ko) | 1984-11-22 |
| FI73680C (fi) | 1987-11-09 |
| DK441183D0 (da) | 1983-09-27 |
| ES525969A0 (es) | 1984-06-16 |
| DE3369847D1 (en) | 1987-04-02 |
| DE3235795A1 (de) | 1984-03-29 |
| DK441183A (da) | 1984-03-29 |
| JPS5980684A (ja) | 1984-05-10 |
| HU187976B (en) | 1986-03-28 |
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