JP2013512276A5 - - Google Patents
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- Publication number
- JP2013512276A5 JP2013512276A5 JP2012541614A JP2012541614A JP2013512276A5 JP 2013512276 A5 JP2013512276 A5 JP 2013512276A5 JP 2012541614 A JP2012541614 A JP 2012541614A JP 2012541614 A JP2012541614 A JP 2012541614A JP 2013512276 A5 JP2013512276 A5 JP 2013512276A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- formula
- anhydride
- alkyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 24
- 238000000034 method Methods 0.000 claims 21
- 150000008064 anhydrides Chemical class 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 6
- 150000004820 halides Chemical class 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- KWTWDQCKEHXFFR-SMDDNHRTSA-N tapentadol Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-SMDDNHRTSA-N 0.000 claims 6
- 229960005126 tapentadol Drugs 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- -1 aliphatic ketones Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 150000007524 organic acids Chemical class 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 238000006193 diazotization reaction Methods 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002524 organometallic group Chemical group 0.000 claims 3
- 239000002798 polar solvent Substances 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 2
- 239000012954 diazonium Substances 0.000 claims 2
- 150000001989 diazonium salts Chemical class 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 235000006408 oxalic acid Nutrition 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- RWOLDZZTBNYTMS-SSDOTTSWSA-N (2r)-2-(2-chlorophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1Cl RWOLDZZTBNYTMS-SSDOTTSWSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
- 229940106681 chloroacetic acid Drugs 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 0 CCC(*)([C@](C)(CN(C)C)[Si])c1cccc(N*)c1 Chemical compound CCC(*)([C@](C)(CN(C)C)[Si])c1cccc(N*)c1 0.000 description 2
- SCZGQTRPAVMTQE-SMDDNHRTSA-N CC[C@@]([C@@H](C)CN(C)C)(c1cccc(N)c1)O Chemical compound CC[C@@]([C@@H](C)CN(C)C)(c1cccc(N)c1)O SCZGQTRPAVMTQE-SMDDNHRTSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A002110A IT1397189B1 (it) | 2009-12-01 | 2009-12-01 | Nuovo processo per la preparazione di tapentadol e suoi intermedi. |
| ITMI2009A002110 | 2009-12-01 | ||
| PCT/IB2010/055499 WO2011067714A1 (en) | 2009-12-01 | 2010-11-30 | New process for the preparation of tapentadol and intermediates thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013512276A JP2013512276A (ja) | 2013-04-11 |
| JP2013512276A5 true JP2013512276A5 (enExample) | 2014-01-09 |
| JP5901534B2 JP5901534B2 (ja) | 2016-04-13 |
Family
ID=42309693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012541614A Expired - Fee Related JP5901534B2 (ja) | 2009-12-01 | 2010-11-30 | タペンタドールおよびその中間体を調製するための新しい方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8729308B2 (enExample) |
| EP (1) | EP2507203B1 (enExample) |
| JP (1) | JP5901534B2 (enExample) |
| KR (1) | KR101766503B1 (enExample) |
| CN (1) | CN102869644B (enExample) |
| BR (1) | BR112012013302A2 (enExample) |
| CA (1) | CA2780842C (enExample) |
| ES (1) | ES2640313T3 (enExample) |
| IL (1) | IL219913A (enExample) |
| IT (1) | IT1397189B1 (enExample) |
| WO (1) | WO2011067714A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2674414A1 (en) | 2012-06-15 | 2013-12-18 | Siegfried AG | Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds |
| CN102924303B (zh) * | 2012-10-31 | 2013-11-20 | 合肥市新星医药化工有限公司 | 盐酸他喷他多晶型c及其制备方法和应用 |
| US9090539B2 (en) | 2013-05-24 | 2015-07-28 | Ampac Fine Chemicals Llc | Compounds and methods for preparing substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds |
| CN103254088B (zh) * | 2013-05-24 | 2014-08-06 | 合肥市新星医药化工有限公司 | 盐酸他喷他多晶型d及其制备方法和应用 |
| WO2015075678A1 (en) | 2013-11-21 | 2015-05-28 | Unimark Remedies Ltd. | A novel process for the preparation of 1-phenyl-3-aminopropane derivatives |
| CN104803861B (zh) * | 2014-01-27 | 2017-05-24 | 上海博邦医药科技有限公司 | 一种合成盐酸他喷他多的方法 |
| GB2539442A (en) * | 2015-06-16 | 2016-12-21 | Azad Pharmaceutical Ingredients Ag | New synthesis of tapentadol-HCI intermediates |
| SK812017A3 (sk) | 2017-08-18 | 2019-03-01 | Saneca Pharmaceuticals A. S. | Spôsob prípravy tapentadolu a jeho medziproduktov |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3888901A (en) | 1972-07-20 | 1975-06-10 | American Cyanamid Co | Process of preparing 3-alkyl-3-(benzoyl)propionitriles |
| US3824271A (en) * | 1972-07-20 | 1974-07-16 | American Cyanamid Co | 3-alkyl-3-(benzoyl)propionitriles |
| WO1992001661A1 (en) | 1990-07-25 | 1992-02-06 | Mobil Oil Corporation | Reactor quenching for catalytic olefin hydration in ether production |
| DE4426245A1 (de) | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| DE10326097A1 (de) * | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
| WO2006012283A1 (en) | 2004-06-25 | 2006-02-02 | Ranpak Corporation | Dunnage conversion machine with floating guides |
| DE102005033732B4 (de) * | 2005-05-27 | 2014-02-13 | Grünenthal GmbH | Trennung stereoisomerer N,N-Dialkylamino-2-alkyl-3-hydroxy-3-phenyl-alkane |
| ATE455752T1 (de) * | 2006-07-24 | 2010-02-15 | Janssen Pharmaceutica Nv | Herstellung von (2r,3r)-3-(3-methoxyphenyl)-n,n,2-trimethylpent namin |
| TWI401237B (zh) * | 2006-07-24 | 2013-07-11 | ３-〔（１ｒ，２ｒ）-３-（二甲基氨基）-１-乙基-２-甲基丙基〕酚之製備 | |
| TWI496762B (zh) * | 2006-07-24 | 2015-08-21 | 製備（１ｒ，２ｒ）-３-（３-二甲胺基-１-乙基-２-甲基-丙基）-酚之方法 |
-
2009
- 2009-12-01 IT ITMI2009A002110A patent/IT1397189B1/it active
-
2010
- 2010-11-30 WO PCT/IB2010/055499 patent/WO2011067714A1/en not_active Ceased
- 2010-11-30 KR KR1020127016688A patent/KR101766503B1/ko active Active
- 2010-11-30 JP JP2012541614A patent/JP5901534B2/ja not_active Expired - Fee Related
- 2010-11-30 US US13/512,989 patent/US8729308B2/en active Active
- 2010-11-30 CN CN201080052937.3A patent/CN102869644B/zh not_active Expired - Fee Related
- 2010-11-30 CA CA2780842A patent/CA2780842C/en active Active
- 2010-11-30 ES ES10805326.5T patent/ES2640313T3/es active Active
- 2010-11-30 BR BR112012013302A patent/BR112012013302A2/pt not_active Application Discontinuation
- 2010-11-30 EP EP10805326.5A patent/EP2507203B1/en active Active
-
2012
- 2012-05-21 IL IL219913A patent/IL219913A/en active IP Right Grant
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