JP2003026658A5 - - Google Patents
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- Publication number
- JP2003026658A5 JP2003026658A5 JP2002143142A JP2002143142A JP2003026658A5 JP 2003026658 A5 JP2003026658 A5 JP 2003026658A5 JP 2002143142 A JP2002143142 A JP 2002143142A JP 2002143142 A JP2002143142 A JP 2002143142A JP 2003026658 A5 JP2003026658 A5 JP 2003026658A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- complex
- palladium
- copper
- group
- 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
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 18
- 238000000034 method Methods 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 4
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 4
- 229960003592 fexofenadine Drugs 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- HTENDICUTNSELD-UHFFFAOYSA-N acetic acid triphenylphosphane Chemical compound CC(O)=O.CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 HTENDICUTNSELD-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
Claims (12)
- a)式(１)：
b)得られる式(３)：
c)得られる式(５)：
- 段階a)の反応を、プロトン性溶媒、双極性非プロトン性溶媒、エーテル、エステル、芳香族溶媒、塩素化溶媒またはこれらの混合物中、無機または有機塩基の存在下で、２０℃から溶媒の還流温度までの範囲の温度で行なう、請求項１に記載の方法。
- 段階b)で使用するＰd(０)触媒が、０の酸化状態のパラジウム、元素パラジウム、担持パラジウム、適当なリガンドと錯体化したパラジウム、またはＰd(II)塩の還元によりその場で発生するパラジウムを含む、請求項１または２に記載の方法。
- Ｃu(Ｉ)触媒が、酸化銅(Ｉ)、塩化銅(Ｉ)、臭化銅(Ｉ)、ヨウ化銅(Ｉ)、酢酸銅(Ｉ)からなる群から選択される、請求項１または２に記載の方法。
- Ｐd(０)錯体が：ビス−(トリフェニルホスフィン)−ジクロロ錯体ビス−(トリブチルホスフィン)−ジクロロ錯体ジ−アリルトリフェニルホスフィン−ジクロロ錯体テトラキス−(トリフェニルホスフィン)錯体トリフェニルホスフィン−ピペリジン−ジクロロ錯体ビス−(トリフェニルホスフィン)−二酢酸錯体２,４−ペンタンジオン錯体１,２−ビス−(ジフェニルホスフィン)−エタン錯体ビス−ベンゾニトリル−ジクロロ錯体からなる群から選択される、請求項３に記載の方法。
- Ｐd：リガンド：Ｃuモル比が１：４：２であり、使用するパラジウムのモル量が化合物(３)に対して０.０１から０.１である、請求項１から４のいずれかに記載の方法。
- 反応を所望により、化合物(３)に対して１から５容量の範囲の量の水混和性アルコールまたはそれらと水との混合物からなる群から選択される溶媒の存在下、２０から１５０℃、好ましくは６０から１２０℃の範囲の温度で行なう、請求項３から５のいずれかに記載の方法。
- 塩基がピリジン、ピペリジン、ピペラジン、モルホリン、ジイソプロピルエチルアミン、トリエチルアミン、n−オクチルアミンからなる群から選択される、請求項３から６のいずれかに記載の方法。
- 塩基がトリエチルアミンである、請求項７に記載の方法。
- 化合物(５)を化合物(６)：
- 化合物(６)をフェキソフェナジン(７)に、金属ハイドライドでの還元およびエステル基の加水分解により変換する、請求項１から１０のいずれかに記載の方法。
- 新規化合物としての化合物(３)：
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001RM000260A ITRM20010260A1 (it) | 2001-05-17 | 2001-05-17 | Processo per la preparazione della fexofenadina o acido 4 1-idrossi-4-4- (idrossidifenilmetil)-1-piperidinil|-butil|-alfa,alfa-dimetilbenz |
| IT2001A000260 | 2001-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003026658A JP2003026658A (ja) | 2003-01-29 |
| JP2003026658A5 true JP2003026658A5 (ja) | 2005-09-08 |
Family
ID=11455529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002143142A Ceased JP2003026658A (ja) | 2001-05-17 | 2002-05-17 | ４−［１−ヒドロキシ−４−［４−（ヒドロキシジフェニルメチル）−１−ピペリジニル］−ブチル］−アルファ，アルファ−ジメチルベンゼン酢酸の製造法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6815549B2 (ja) |
| EP (1) | EP1260505B1 (ja) |
| JP (1) | JP2003026658A (ja) |
| AT (1) | ATE290528T1 (ja) |
| CA (1) | CA2386452A1 (ja) |
| CZ (1) | CZ295949B6 (ja) |
| DE (1) | DE60203142T2 (ja) |
| ES (1) | ES2237631T3 (ja) |
| HU (1) | HUP0201673A3 (ja) |
| IT (1) | ITRM20010260A1 (ja) |
| PL (1) | PL353977A1 (ja) |
| PT (1) | PT1260505E (ja) |
| SI (1) | SI1260505T1 (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE03757471T1 (de) * | 2002-06-10 | 2005-09-01 | Teva Pharmaceutical Industries Ltd. | Polymorphe form xvi von fexofenadin-hydrochlorid |
| EP1616861A3 (en) * | 2004-06-15 | 2006-02-08 | Dipharma S.p.A. | A process for the preparation of keto compounds |
| ITMI20041568A1 (it) * | 2004-07-30 | 2004-10-30 | Dipharma Spa | "polimorfi di fexofenadina base" |
| ITMI20061492A1 (it) * | 2006-07-27 | 2008-01-28 | Archimica Srl | Processo per la preparazione di fexofenadina. |
| ITMI20070987A1 (it) * | 2007-05-16 | 2008-11-17 | Dipharma Francis Srl | Procedimento per la preparazione di composti chetonici |
| IT1395337B1 (it) * | 2009-03-04 | 2012-09-14 | Dipharma Francis Srl | Procedimento per la preparazione di intermedi chetonici |
| WO2011158262A1 (en) * | 2010-06-15 | 2011-12-22 | Chemelectiva S.R.L. | Polymorphic form of fexofenadine hydrochloride, intermediates and process for its preparation |
| CN102079708B (zh) * | 2011-02-11 | 2013-10-02 | 浙江启明药业有限公司 | 4-(4-卤丁酰基)-α,α-二甲基苯乙酸酯的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU671822B2 (en) | 1992-04-10 | 1996-09-12 | Aventisub Ii Inc. | 4-diphenylmethyl piperidine derivatives and process for their preparation |
| US6147216A (en) * | 1993-06-25 | 2000-11-14 | Merrell Pharmaceuticals Inc. | Intermediates useful for the preparation of antihistaminic piperidine derivatives |
| US6153754A (en) | 1995-12-21 | 2000-11-28 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
| US6201124B1 (en) | 1995-12-21 | 2001-03-13 | Albany Molecular Research, Inc. | Process for production of piperidine derivatives |
-
2001
- 2001-05-17 IT IT2001RM000260A patent/ITRM20010260A1/it unknown
-
2002
- 2002-05-15 CA CA002386452A patent/CA2386452A1/en not_active Abandoned
- 2002-05-16 PT PT02010234T patent/PT1260505E/pt unknown
- 2002-05-16 SI SI200230095T patent/SI1260505T1/xx unknown
- 2002-05-16 ES ES02010234T patent/ES2237631T3/es not_active Expired - Lifetime
- 2002-05-16 HU HU0201673A patent/HUP0201673A3/hu unknown
- 2002-05-16 EP EP02010234A patent/EP1260505B1/en not_active Expired - Lifetime
- 2002-05-16 DE DE60203142T patent/DE60203142T2/de not_active Expired - Fee Related
- 2002-05-16 AT AT02010234T patent/ATE290528T1/de not_active IP Right Cessation
- 2002-05-16 US US10/145,765 patent/US6815549B2/en not_active Expired - Fee Related
- 2002-05-17 PL PL02353977A patent/PL353977A1/xx not_active Application Discontinuation
- 2002-05-17 CZ CZ20021726A patent/CZ295949B6/cs not_active IP Right Cessation
- 2002-05-17 JP JP2002143142A patent/JP2003026658A/ja not_active Ceased
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