KR880009955A - 피페라진 유도체 및 그의 제조방법 - Google Patents
피페라진 유도체 및 그의 제조방법 Download PDFInfo
- Publication number
- KR880009955A KR880009955A KR1019880001939A KR880001939A KR880009955A KR 880009955 A KR880009955 A KR 880009955A KR 1019880001939 A KR1019880001939 A KR 1019880001939A KR 880001939 A KR880001939 A KR 880001939A KR 880009955 A KR880009955 A KR 880009955A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- process according
- acid addition
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims 38
- 150000004885 piperazines Chemical class 0.000 title claims 3
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- 239000002253 acid Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- 238000005984 hydrogenation reaction Methods 0.000 claims 4
- 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 claims 4
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- VKFAUCPBMAGVRG-UHFFFAOYSA-N dipivefrin hydrochloride Chemical class [Cl-].C[NH2+]CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 VKFAUCPBMAGVRG-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- YRTHJMQKDCXPAY-UHFFFAOYSA-N azaspirodecanedione Chemical compound C1C(=O)NC(=O)CC11CCCC1 YRTHJMQKDCXPAY-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229940046892 lead acetate Drugs 0.000 claims 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 claims 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229920002866 paraformaldehyde Polymers 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 claims 1
- -1 propargyl halide Chemical class 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU71687A HU197313B (en) | 1987-02-25 | 1987-02-25 | Process for producing 8-azaspiro <4.5> decane-7,9-dione-8-propine-/2/ |
| HU717/87 | 1987-02-25 | ||
| HU71787A HU198204B (en) | 1987-02-25 | 1987-02-25 | Process for production of derivatives of piperasine |
| HU71887A HU198477B (en) | 1987-02-25 | 1987-02-25 | Process for producing pyrimidinyl piperazine derivatives |
| HU718/87 | 1987-02-25 | ||
| HU716/87 | 1987-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR880009955A true KR880009955A (ko) | 1988-10-06 |
Family
ID=27269942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880001939A Ceased KR880009955A (ko) | 1987-02-25 | 1988-02-25 | 피페라진 유도체 및 그의 제조방법 |
Country Status (20)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU217129B (hu) * | 1993-07-16 | 1999-11-29 | EGIS Gyógyszergyár Rt. | Eljárás nagy tisztaságú buspiron gyógyászati hatóanyag előállítására |
| KR950014099A (ko) * | 1993-11-10 | 1995-06-15 | 장기하 | N-(2-피리미딜)피페라지닐 부틸아미드의 제조방법 |
| CN119409681A (zh) * | 2024-03-28 | 2025-02-11 | 北京华素制药股份有限公司 | 一种盐酸丁螺环酮的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE300422B (enrdf_load_stackoverflow) * | 1964-07-03 | 1968-04-29 | Astra Ab | |
| DE1545543B1 (de) * | 1964-07-03 | 1970-01-22 | Astra Apotekarnes Kem Fab | 4-Aminobutinylimide,ihre Salze und Verfahren zu deren Herstellung |
| US3354178A (en) * | 1965-04-09 | 1967-11-21 | Sterling Drug Inc | Nu-(4-amino-2-butynyl)-nu-alkylcarboxamides |
| BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
| JPS6310786A (ja) * | 1986-07-01 | 1988-01-18 | Sumitomo Pharmaceut Co Ltd | 新規イミド誘導体およびその製造法 |
| JPS6310760A (ja) * | 1986-07-01 | 1988-01-18 | Sumitomo Pharmaceut Co Ltd | イミド誘導体の新規製造法 |
-
1988
- 1988-02-23 PL PL1988270815A patent/PL152958B1/pl unknown
- 1988-02-23 CH CH675/88A patent/CH677924A5/de not_active IP Right Cessation
- 1988-02-24 CN CN198888100923A patent/CN88100923A/zh active Pending
- 1988-02-25 IT IT19545/88A patent/IT1217342B/it active
- 1988-02-25 ES ES8800543A patent/ES2009236A6/es not_active Expired
- 1988-02-25 CS CS122288A patent/CS274423B2/cs unknown
- 1988-02-25 KR KR1019880001939A patent/KR880009955A/ko not_active Ceased
- 1988-02-25 FI FI880895A patent/FI880895A7/fi not_active Application Discontinuation
- 1988-02-25 DK DK099388A patent/DK99388A/da not_active Application Discontinuation
- 1988-02-25 GB GB8804385A patent/GB2201417B/en not_active Expired - Lifetime
- 1988-02-25 YU YU36288A patent/YU46441B/sh unknown
- 1988-02-25 SE SE8800651A patent/SE8800651L/xx not_active Application Discontinuation
- 1988-02-25 GR GR880100108A patent/GR1002245B/el unknown
- 1988-02-25 AT AT0047688A patent/AT395851B/de not_active IP Right Cessation
- 1988-02-25 DE DE3806009A patent/DE3806009C2/de not_active Expired - Fee Related
- 1988-02-25 NL NL8800484A patent/NL8800484A/nl not_active Application Discontinuation
- 1988-02-25 IL IL85545A patent/IL85545A/xx not_active IP Right Cessation
- 1988-02-25 BE BE8800218A patent/BE1001464A3/fr not_active IP Right Cessation
- 1988-02-25 FR FR888802286A patent/FR2615853B1/fr not_active Expired - Lifetime
- 1988-02-25 CA CA000559846A patent/CA1300141C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE1001464A3 (fr) | 1989-11-07 |
| IT8819545A0 (it) | 1988-02-25 |
| DE3806009A1 (de) | 1988-09-08 |
| GR880100108A (el) | 1988-12-16 |
| SE8800651D0 (sv) | 1988-02-25 |
| FR2615853B1 (fr) | 1991-01-04 |
| IL85545A0 (en) | 1988-08-31 |
| ATA47688A (de) | 1992-08-15 |
| PL270815A1 (en) | 1989-04-03 |
| AT395851B (de) | 1993-03-25 |
| CN88100923A (zh) | 1988-09-28 |
| ES2009236A6 (es) | 1989-09-16 |
| GB8804385D0 (en) | 1988-03-23 |
| YU36288A (en) | 1989-10-31 |
| GR1002245B (en) | 1996-04-22 |
| FI880895A0 (fi) | 1988-02-25 |
| GB2201417B (en) | 1990-10-31 |
| PL152958B1 (en) | 1991-02-28 |
| FI880895A7 (fi) | 1988-08-26 |
| GB2201417A (en) | 1988-09-01 |
| CH677924A5 (enrdf_load_stackoverflow) | 1991-07-15 |
| DK99388A (da) | 1988-08-26 |
| FR2615853A1 (fr) | 1988-12-02 |
| YU46441B (sh) | 1993-10-20 |
| NL8800484A (nl) | 1988-09-16 |
| CA1300141C (en) | 1992-05-05 |
| SE8800651L (sv) | 1988-08-26 |
| IT1217342B (it) | 1990-03-22 |
| IL85545A (en) | 1992-05-25 |
| DE3806009C2 (de) | 1996-09-12 |
| DK99388D0 (da) | 1988-02-25 |
| CS274423B2 (en) | 1991-04-11 |
| CS122288A2 (en) | 1990-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19880224 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19930224 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19880224 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19951129 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 19960305 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19951129 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |