JP2009280577A - マンデル酸のピペリジルエステルの第４級塩を製造する方法 - Google Patents
マンデル酸のピペリジルエステルの第４級塩を製造する方法 Download PDFInfo
- Publication number
- JP2009280577A JP2009280577A JP2009106522A JP2009106522A JP2009280577A JP 2009280577 A JP2009280577 A JP 2009280577A JP 2009106522 A JP2009106522 A JP 2009106522A JP 2009106522 A JP2009106522 A JP 2009106522A JP 2009280577 A JP2009280577 A JP 2009280577A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- piperidyl
- solvent
- group
- alkylating agent
- 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.)
- Pending
Links
- -1 piperidyl mandelate Chemical compound 0.000 title claims abstract description 16
- 150000003839 salts Chemical group 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 12
- 239000002168 alkylating agent Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 6
- 229960002510 mandelic acid Drugs 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical group BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 5
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000007858 starting material Substances 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000005936 piperidyl group Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008020746A DE102008020746A1 (de) | 2008-04-25 | 2008-04-25 | Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014222950A Division JP2015063530A (ja) | 2008-04-25 | 2014-10-31 | マンデル酸のピペリジルエステルの第４級塩を製造する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009280577A true JP2009280577A (ja) | 2009-12-03 |
| JP2009280577A5 JP2009280577A5 (enExample) | 2012-06-07 |
Family
ID=40848413
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009106522A Pending JP2009280577A (ja) | 2008-04-25 | 2009-04-24 | マンデル酸のピペリジルエステルの第４級塩を製造する方法 |
| JP2014222950A Pending JP2015063530A (ja) | 2008-04-25 | 2014-10-31 | マンデル酸のピペリジルエステルの第４級塩を製造する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014222950A Pending JP2015063530A (ja) | 2008-04-25 | 2014-10-31 | マンデル酸のピペリジルエステルの第４級塩を製造する方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8309732B2 (enExample) |
| EP (1) | EP2112137A1 (enExample) |
| JP (2) | JP2009280577A (enExample) |
| DE (1) | DE102008020746A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015063530A (ja) * | 2008-04-25 | 2015-04-09 | サルティゴ・ゲーエムベーハー | マンデル酸のピペリジルエステルの第４級塩を製造する方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002004402A1 (en) * | 2000-07-11 | 2002-01-17 | Banyu Pharmaceutical Co., Ltd. | Ester derivatives |
| WO2007123465A1 (en) * | 2006-04-24 | 2007-11-01 | Astrazeneca Ab | New alkyl esters of cyclic amino alcohols with muscarinic m3 receptor antagonist activity, useful for treating e.g. chronic bronchial obstruction, asthma and overactive bladder |
| WO2007141289A1 (en) * | 2006-06-09 | 2007-12-13 | Beiersdorf Ag | Piperidinium compounds and cosmetic compositions containing them |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB788126A (en) | 1955-09-29 | 1957-12-23 | Schering Corp | Quaternary salts of piperidyl esters |
| US2956062A (en) | 1959-02-26 | 1960-10-11 | Robins Co Inc A H | Esters of amino alcohols |
| US4022787A (en) | 1975-07-18 | 1977-05-10 | Carter-Wallace, Inc. | Anticholinergic ester and salts thereof |
| DE19605526A1 (de) * | 1996-02-15 | 1997-08-21 | Hoechst Ag | Ammoniumnitrile und deren Verwendung als Bleichaktivatoren |
| EP1131290B1 (en) * | 1998-11-20 | 2008-02-20 | F. Hoffmann-La Roche Ag | Piperidine ccr-3 receptor antagonists |
| GB0428418D0 (en) | 2004-12-24 | 2005-02-02 | Novartis Ag | Organic compounds |
| DE102008020746A1 (de) * | 2008-04-25 | 2009-10-29 | Saltigo Gmbh | Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure |
-
2008
- 2008-04-25 DE DE102008020746A patent/DE102008020746A1/de not_active Withdrawn
-
2009
- 2009-04-06 US US12/418,847 patent/US8309732B2/en not_active Expired - Fee Related
- 2009-04-09 EP EP09157753A patent/EP2112137A1/de not_active Withdrawn
- 2009-04-24 JP JP2009106522A patent/JP2009280577A/ja active Pending
-
2014
- 2014-10-31 JP JP2014222950A patent/JP2015063530A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002004402A1 (en) * | 2000-07-11 | 2002-01-17 | Banyu Pharmaceutical Co., Ltd. | Ester derivatives |
| WO2007123465A1 (en) * | 2006-04-24 | 2007-11-01 | Astrazeneca Ab | New alkyl esters of cyclic amino alcohols with muscarinic m3 receptor antagonist activity, useful for treating e.g. chronic bronchial obstruction, asthma and overactive bladder |
| WO2007141289A1 (en) * | 2006-06-09 | 2007-12-13 | Beiersdorf Ag | Piperidinium compounds and cosmetic compositions containing them |
Non-Patent Citations (1)
| Title |
|---|
| JPN6013050003; Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ａｍｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ Ｓｏｃｉｅｔｙ ７８, 1956, ｐｐ３７０１-３７０３ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015063530A (ja) * | 2008-04-25 | 2015-04-09 | サルティゴ・ゲーエムベーハー | マンデル酸のピペリジルエステルの第４級塩を製造する方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8309732B2 (en) | 2012-11-13 |
| DE102008020746A1 (de) | 2009-10-29 |
| US20090270629A1 (en) | 2009-10-29 |
| JP2015063530A (ja) | 2015-04-09 |
| EP2112137A1 (de) | 2009-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5398539B2 (ja) | ２−アミノ−５−シアノ安息香酸誘導体を調製するためのプロセス | |
| EP2231592B1 (en) | Process for preparing 2-amino-5-cyanobenzoic acid derivatives | |
| KR101609891B1 (ko) | 2-아미노-5-시아노벤조산 유도체의 제조 방법 | |
| JP2014001226A (ja) | ３−ジハロメチルピラゾール−４−カルボン酸誘導体の調製方法 | |
| JP6001112B2 (ja) | １−（２−ハロビフェニル−４−イル）−シクロプロパンカルボン酸の誘導体の調製方法 | |
| TWI610922B (zh) | 製造醯胺之方法 | |
| CN102775271B (zh) | 由卤代苯衍生物制备烷基n-酰苯胺的方法 | |
| JP2009280577A (ja) | マンデル酸のピペリジルエステルの第４級塩を製造する方法 | |
| Verma et al. | CDI-mediated monoacylation of symmetrical diamines and selective acylation of primary amines of unsymmetrical diamines | |
| JP3459892B2 (ja) | フッ素系界面活性化合物及びその製造方法 | |
| JP5140776B1 (ja) | １−置換−３−フルオロアルキルピラゾール−４−カルボン酸エステルの製造方法 | |
| KR20250044809A (ko) | 치환된 피라졸의 제조 및 안트라닐아미드 전구체로서의 그의 용도 | |
| JP2009507867A (ja) | ５−フルオロ−１，３−ジアルキル−１ｈ−ピラゾール−４−カルボニルフルオリドの製造方法 | |
| CN108026017B (zh) | 酰卤溶液的制造方法、混合溶液及单酯化合物的制造方法 | |
| JP2016522199A (ja) | 特定のオキシムおよびオキシムエーテルの改善された製造方法 | |
| CN107556320B (zh) | 一种合成6H-异吲哚并[2,1-a]吲哚-6-酮衍生物的方法 | |
| WO2015150302A1 (en) | Process for the preparation of n-[3-(benzylcarbamoyl)phenyl]-1 h-pyrazole-5-carboxamides | |
| JP5468400B2 (ja) | ４−クロロピリジン−２−カルボン酸クロリドの製造方法 | |
| JP6809485B2 (ja) | 酸ハライド溶液の製造方法、及びモノエステル化合物の製造方法 | |
| JP2014208604A (ja) | 芳香族アシル化合物の製造方法 | |
| JP6286968B2 (ja) | パーフルオロ分岐アルキルアニリン類の製造方法 | |
| CN109096324B (zh) | 一种二烷基酰基氯化锗合成方法与应用 | |
| JP6349329B2 (ja) | ５−フルオロ−１−メチル−３−ジフルオロメチル−１ｈ−ピラゾール−４−カルバルデヒドを調製する方法 | |
| JP5132238B2 (ja) | フッ素化アダマンタン化合物の製造方法 | |
| EP3406595B1 (en) | Method for producing 2-aminonicotinic acid benzyl ester derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120423 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120423 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20131008 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20131010 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140108 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140114 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140210 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140214 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140307 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140701 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141031 |
|
| A911 | Transfer of reconsideration by examiner before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20141114 |
|
| A912 | Removal of reconsideration by examiner before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20150116 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160404 |