DE102008020746A1 - Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure - Google Patents
Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure Download PDFInfo
- Publication number
- DE102008020746A1 DE102008020746A1 DE102008020746A DE102008020746A DE102008020746A1 DE 102008020746 A1 DE102008020746 A1 DE 102008020746A1 DE 102008020746 A DE102008020746 A DE 102008020746A DE 102008020746 A DE102008020746 A DE 102008020746A DE 102008020746 A1 DE102008020746 A1 DE 102008020746A1
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- formula
- general formula
- mandelic acid
- preparation
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract 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 title description 11
- 229960002510 mandelic acid Drugs 0.000 title description 11
- 125000005936 piperidyl group Chemical class 0.000 title description 9
- 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 title description 8
- 150000003839 salts Chemical group 0.000 title description 8
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 8
- 239000002168 alkylating agent Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 15
- -1 cycloalkyl radical Chemical class 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[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
- 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
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical group BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 5
- 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
- 239000000126 substance 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
- 230000002152 alkylating effect Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 0 *C1(C(OC2CC[N+](*)CC2)=*1)c1ccccc1 Chemical compound *C1(C(OC2CC[N+](*)CC2)=*1)c1ccccc1 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003905 agrochemical Substances 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
- 230000015572 biosynthetic process Effects 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
- 150000002148 esters Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 239000007858 starting material 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
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- 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
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 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
- 229960002903 benzyl benzoate Drugs 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229920000642 polymer Polymers 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
- 238000010626 work up procedure 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)
Priority Applications (5)
| 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 |
| US12/418,847 US8309732B2 (en) | 2008-04-25 | 2009-04-06 | Process for preparing quaternary salts of piperidyl esters of mandelic acid |
| EP09157753A EP2112137A1 (de) | 2008-04-25 | 2009-04-09 | Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure |
| JP2009106522A 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 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 |
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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102008020746A1 true DE102008020746A1 (de) | 2009-10-29 |
Family
ID=40848413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102008020746A Withdrawn DE102008020746A1 (de) | 2008-04-25 | 2008-04-25 | Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8309732B2 (https=) |
| EP (1) | EP2112137A1 (https=) |
| JP (2) | JP2009280577A (https=) |
| DE (1) | DE102008020746A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008020746A1 (de) * | 2008-04-25 | 2009-10-29 | Saltigo Gmbh | Verfahren zur Herstellung von quarternären Salzen von Piperidyl Estern der Mandelsäure |
Citations (2)
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP3421323B2 (ja) * | 1998-11-20 | 2003-06-30 | エフ．ホフマン−ラ ロシュ アーゲー | ピペリジンｃｃｒ−３受容体拮抗薬 |
| EP1302458A4 (en) | 2000-07-11 | 2005-10-19 | Banyu Pharma Co Ltd | ESTERDERIVATE |
| GB0428418D0 (en) | 2004-12-24 | 2005-02-02 | Novartis Ag | Organic compounds |
| EP2013172A4 (en) * | 2006-04-24 | 2010-08-04 | Astrazeneca Ab | NEW ALKYLESTERS FROM CYCLIC AMINO ALCOHOLS WITH MUSCARIN M3 RECEPTORANTAGONOSTIC ACTIVITY FOR THE TREATMENT OF CHRONIC BRONCHIA SUPPRESSION, ASTHMA OR OVERACTIVE HARNBASE |
| US7851633B2 (en) | 2006-06-09 | 2010-12-14 | Beiersdorf Ag | Piperidinium compounds and cosmetic compositions containing them |
| 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 (2)
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| Journal of the American Chemical Society 1956, 78, 3701 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2112137A1 (de) | 2009-10-28 |
| US20090270629A1 (en) | 2009-10-29 |
| US8309732B2 (en) | 2012-11-13 |
| JP2015063530A (ja) | 2015-04-09 |
| JP2009280577A (ja) | 2009-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20131101 |