IL132077A - Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride - Google Patents
Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochlorideInfo
- Publication number
- IL132077A IL132077A IL13207798A IL13207798A IL132077A IL 132077 A IL132077 A IL 132077A IL 13207798 A IL13207798 A IL 13207798A IL 13207798 A IL13207798 A IL 13207798A IL 132077 A IL132077 A IL 132077A
- Authority
- IL
- Israel
- Prior art keywords
- piperidinopiperidine
- chlorocarbonyl
- hydrochloride
- represented
- reacting
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title abstract description 21
- YDNSNQRKIINKPV-UHFFFAOYSA-N 4-piperidin-1-ylpiperidine-1-carbonyl chloride Chemical compound C1CN(C(=O)Cl)CCC1N1CCCCC1 YDNSNQRKIINKPV-UHFFFAOYSA-N 0.000 title abstract description 9
- -1 trialkylsilyl halide Chemical class 0.000 claims abstract description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims abstract description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- VBXXNCHZAMNCBX-UHFFFAOYSA-N 4-piperidin-1-ylpiperidine-1-carbonyl chloride;hydrochloride Chemical compound Cl.C1CN(C(=O)Cl)CCC1N1CCCCC1 VBXXNCHZAMNCBX-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 14
- 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 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PCQUGYRNPPGYRK-UHFFFAOYSA-N 1-piperidin-4-ylpiperidine;hydrochloride Chemical compound Cl.C1CCCCN1C1CCNCC1 PCQUGYRNPPGYRK-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 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
- 244000309464 bull Species 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration 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
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000020138 yakult Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9093723A JP3046258B2 (ja) | 1997-04-11 | 1997-04-11 | １−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法 |
| PCT/JP1998/001465 WO1998046568A1 (en) | 1997-04-11 | 1998-03-31 | Process for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL132077A0 IL132077A0 (en) | 2001-03-19 |
| IL132077A true IL132077A (en) | 2002-11-10 |
Family
ID=14090343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13207798A IL132077A (en) | 1997-04-11 | 1998-03-31 | Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6147215A (da) |
| EP (1) | EP0976733B1 (da) |
| JP (1) | JP3046258B2 (da) |
| CN (1) | CN1110479C (da) |
| AT (1) | ATE232517T1 (da) |
| AU (1) | AU723133B2 (da) |
| BR (1) | BR9808105B1 (da) |
| CA (1) | CA2286914C (da) |
| DE (1) | DE69811358T2 (da) |
| DK (1) | DK0976733T3 (da) |
| EA (1) | EA001696B1 (da) |
| ES (1) | ES2192765T3 (da) |
| IL (1) | IL132077A (da) |
| TW (1) | TW419476B (da) |
| WO (1) | WO1998046568A1 (da) |
| ZA (1) | ZA982960B (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3046258B2 (ja) | 1997-04-11 | 2000-05-29 | 株式会社ヤクルト本社 | １−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法 |
| CA2591071C (en) * | 2005-02-08 | 2014-04-29 | Fermion Oy | Process for producing [1,4'] bipiperidinyl-1'-carbonyl chloride or hydrochloride thereof |
| US8546573B2 (en) * | 2009-11-18 | 2013-10-01 | Cadila Healthcare Limited | Process for the preparation of 7-ethyl-10-[4-(1-piperidino)-1-piperdino] carbonyloxy-camptothecin hydrochloride trihydrate |
| CN102869747B (zh) | 2009-12-30 | 2017-06-30 | 普拉德研究及开发股份有限公司 | 在井下应用中的流体系统内流体段塞固结的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5540754A (en) * | 1978-09-19 | 1980-03-22 | Mitsubishi Electric Corp | Electrodeposition coating |
| JPS6019790A (ja) * | 1983-07-14 | 1985-01-31 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体 |
| JPS6150984A (ja) * | 1984-07-05 | 1986-03-13 | Yakult Honsha Co Ltd | 新規なカンプトテシン誘導体 |
| IE913790A1 (en) * | 1990-10-31 | 1992-05-22 | Smithkline Beecham Corp | SUBSTITUTED INDOLIZINO [1,2-b]QUINOLINONES |
| JP3046258B2 (ja) | 1997-04-11 | 2000-05-29 | 株式会社ヤクルト本社 | １−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法 |
-
1997
- 1997-04-11 JP JP9093723A patent/JP3046258B2/ja not_active Expired - Fee Related
-
1998
- 1998-03-31 ES ES98911123T patent/ES2192765T3/es not_active Expired - Lifetime
- 1998-03-31 WO PCT/JP1998/001465 patent/WO1998046568A1/ja not_active Ceased
- 1998-03-31 CN CN98804019A patent/CN1110479C/zh not_active Expired - Fee Related
- 1998-03-31 DE DE69811358T patent/DE69811358T2/de not_active Expired - Lifetime
- 1998-03-31 DK DK98911123T patent/DK0976733T3/da active
- 1998-03-31 AT AT98911123T patent/ATE232517T1/de active
- 1998-03-31 US US09/402,470 patent/US6147215A/en not_active Expired - Lifetime
- 1998-03-31 BR BRPI9808105-5A patent/BR9808105B1/pt not_active IP Right Cessation
- 1998-03-31 EP EP98911123A patent/EP0976733B1/en not_active Expired - Lifetime
- 1998-03-31 IL IL13207798A patent/IL132077A/en not_active IP Right Cessation
- 1998-03-31 AU AU65206/98A patent/AU723133B2/en not_active Ceased
- 1998-03-31 CA CA002286914A patent/CA2286914C/en not_active Expired - Fee Related
- 1998-03-31 EA EA199900926A patent/EA001696B1/ru not_active IP Right Cessation
- 1998-04-02 TW TW087105000A patent/TW419476B/zh not_active IP Right Cessation
- 1998-04-07 ZA ZA982960A patent/ZA982960B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA982960B (en) | 1998-10-09 |
| EP0976733A1 (en) | 2000-02-02 |
| IL132077A0 (en) | 2001-03-19 |
| JP3046258B2 (ja) | 2000-05-29 |
| CA2286914C (en) | 2005-07-26 |
| EP0976733A4 (en) | 2001-05-09 |
| TW419476B (en) | 2001-01-21 |
| ES2192765T3 (es) | 2003-10-16 |
| AU6520698A (en) | 1998-11-11 |
| JPH10287650A (ja) | 1998-10-27 |
| DE69811358D1 (de) | 2003-03-20 |
| EA199900926A1 (ru) | 2000-04-24 |
| DE69811358T2 (de) | 2003-10-16 |
| BR9808105B1 (pt) | 2008-11-18 |
| ATE232517T1 (de) | 2003-02-15 |
| WO1998046568A1 (en) | 1998-10-22 |
| EP0976733B1 (en) | 2003-02-12 |
| AU723133B2 (en) | 2000-08-17 |
| CA2286914A1 (en) | 1998-10-22 |
| EA001696B1 (ru) | 2001-06-25 |
| BR9808105A (pt) | 2000-03-08 |
| US6147215A (en) | 2000-11-14 |
| DK0976733T3 (da) | 2003-03-31 |
| CN1252055A (zh) | 2000-05-03 |
| CN1110479C (zh) | 2003-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |