JPH11501905A - レボブピバカインと同類のピペリジンカルボキサニリド麻酔剤の製造に用いるラセミ化法 - Google Patents
レボブピバカインと同類のピペリジンカルボキサニリド麻酔剤の製造に用いるラセミ化法Info
- Publication number
- JPH11501905A JPH11501905A JP8522102A JP52210296A JPH11501905A JP H11501905 A JPH11501905 A JP H11501905A JP 8522102 A JP8522102 A JP 8522102A JP 52210296 A JP52210296 A JP 52210296A JP H11501905 A JPH11501905 A JP H11501905A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- bupivacaine
- aqueous medium
- solvent
- formula
- 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
- 238000000034 method Methods 0.000 title claims abstract description 29
- LEBVLXFERQHONN-INIZCTEOSA-N levobupivacaine Chemical compound CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-INIZCTEOSA-N 0.000 title claims abstract description 12
- 230000006340 racemization Effects 0.000 title claims description 12
- 229960004288 levobupivacaine Drugs 0.000 title abstract description 4
- 229940035674 anesthetics Drugs 0.000 title description 3
- 239000003193 general anesthetic agent Substances 0.000 title description 3
- UICIJOHWFFTRLI-UHFFFAOYSA-N n-phenylpiperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)NC1=CC=CC=C1 UICIJOHWFFTRLI-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000012736 aqueous medium Substances 0.000 claims abstract description 7
- -1 piperidine-2-carboxanilide compound Chemical class 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 claims description 9
- 229960003150 bupivacaine Drugs 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000006184 cosolvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- SILRCGDPZGQJOQ-UHFFFAOYSA-N 2,6-Pipecoloxylidide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1NCCCC1 SILRCGDPZGQJOQ-UHFFFAOYSA-N 0.000 claims description 3
- LEBVLXFERQHONN-MRXNPFEDSA-N dextrobupivacaine Chemical compound CCCCN1CCCC[C@@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-MRXNPFEDSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000003839 salts Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical compound CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004296 chiral HPLC Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MFCCQIZJSIYKQV-UHFFFAOYSA-N n-phenylpiperidine-2-carboxamide Chemical class C1CCCNC1C(=O)NC1=CC=CC=C1 MFCCQIZJSIYKQV-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 description 2
- 229960002409 mepivacaine Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229960001549 ropivacaine Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SILRCGDPZGQJOQ-LBPRGKRZSA-N (S)-2',6'-Pipecoloxylidide Chemical compound CC1=CC=CC(C)=C1NC(=O)[C@H]1NCCCC1 SILRCGDPZGQJOQ-LBPRGKRZSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960001813 ropivacaine hydrochloride Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Rolling Contact Bearings (AREA)
- Optical Head (AREA)
- Beans For Foods Or Fodder (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.ピペリジン環が所望によりN−アルキル化されていてもよい光学的に濃縮 されたピペリジン−2−カルボキサニリド化合物を水性媒体中で加熱することを 含む該化合物のラセミ化法(但し、該化合物がN−アルキル化されているときに は有機補助溶剤を水性媒体に含有させる)。 2.塩形態の該化合物も存在させる請求項1記載の方法。 3.pHが6よりも高い条件下でおこなう請求項1または2記載の方法。 4.酸の不存在下でおこなう請求項1から3いずれかに記載の方法。 5.該化合物が(R)−鏡像体に富む化合物である請求項1から4いずれかに記 載の方法。 6.該化合物が次式: (式中、R1はHまたは炭素原子数20までの置換基を示し、R2はC6-20アリー ル基を示す) で表される化合物である請求項1から5いずれかに記載の方法。 7.R1がHまたはC1-6アルキル基であり、R2が1個もしくはそれ以上のC1 -4 アルキル基で置換されていてもよいフェニル基である請求項6記載の方法。 8.R2が2,6−ジメチルフェニルである請求項7記載の方法。 9.水性媒体が水および有機補助溶剤を含有する請求項1から8いずれかに記 載の方法。 10.補助溶剤がアルコールまたはポリオールである請求項9記載の方法。 11.補助溶剤がエチレングリコールである請求項9記載の方法。 12.光学純度が低減したブピバカインを製造するための方法であって、R1 がn−ブチルである請求項8または請求項8を引用する請求項9から11いずれ かに記載の方法。 13.R1がn−プロピルである請求項8または請求項8を引用する請求項9か ら11いずれかに記載の方法。 14.2',6'−ジメチルピペリジン−2−カルボキサニリドをラセミ化する ための方法であって、R1がHであって請求項8記載の方法。 15.R1がHであり、水性媒体が実質的に水のみから成る請求項6、7、8 または14記載の方法。 16.ブピバカインの鏡像体混合物を分割し、(S)−ブピバカインを分離し、 残余の(R)−ブピバカインをさらに分割する前に請求項12記載の方法によって ラセミ化することを含む(S)−ブピバカインの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9501071.6 | 1995-01-18 | ||
GBGB9501071.6A GB9501071D0 (en) | 1995-01-18 | 1995-01-18 | Racemisation |
PCT/GB1996/000067 WO1996022281A1 (en) | 1995-01-18 | 1996-01-12 | Racemisation process for use in the manufacture of levobupivacaine and related piperidinecarboxanilide anaesthetic agents |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11501905A true JPH11501905A (ja) | 1999-02-16 |
JP4015696B2 JP4015696B2 (ja) | 2007-11-28 |
Family
ID=10768271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52210296A Expired - Lifetime JP4015696B2 (ja) | 1995-01-18 | 1996-01-12 | レボブピバカインと同類のピペリジンカルボキサニリド麻酔剤の製造に用いるラセミ化法 |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP0804417B1 (ja) |
JP (1) | JP4015696B2 (ja) |
KR (1) | KR100404390B1 (ja) |
CN (1) | CN1172912C (ja) |
AT (1) | ATE242214T1 (ja) |
AU (1) | AU701221B2 (ja) |
BR (1) | BR9606821A (ja) |
CA (1) | CA2208522C (ja) |
DE (1) | DE69628540T2 (ja) |
DK (1) | DK0804417T3 (ja) |
ES (1) | ES2201166T3 (ja) |
FI (1) | FI117437B (ja) |
GB (1) | GB9501071D0 (ja) |
HU (1) | HU227426B1 (ja) |
MX (1) | MX9705428A (ja) |
NO (1) | NO308843B1 (ja) |
PL (1) | PL184091B1 (ja) |
PT (1) | PT804417E (ja) |
WO (1) | WO1996022281A1 (ja) |
ZA (1) | ZA96403B (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0002246A (pt) * | 2000-04-06 | 2003-04-15 | Cristalia Prod Quimicos Farm | Processo de obtenção dos enantiÈmeros da bupivacaìna racêmica, processo de obtenção de composições farmacêuticas a base de levobupivacaìna: composições farmacêuticas a base de levobupivacaìna formuladas nas formas básicas ou sais farmaceuticamente aceitáveis e utilização das composições farmacêuticas a base de levobupivacaìna formuladas nas formas básicas ou sais farmaceuticamente aceitáveis |
US20040001889A1 (en) | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
SI1575569T1 (sl) | 2002-12-13 | 2010-12-31 | Durect Corp | Oralni sistem dostave zdravila, ki obsega visokoviskozne tekoče nosilne materiale |
EP2415484B1 (en) | 2004-09-17 | 2014-06-18 | Durect Corporation | Sustained local anesthetic composition containing SAIB |
US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
DK2117521T3 (da) | 2006-11-03 | 2012-09-03 | Durect Corp | Transdermale indgivelsessystemer omfattende bupivacain |
CA2706931C (en) | 2007-12-06 | 2015-05-12 | Durect Corporation | Oral pharmaceutical dosage forms |
US20100260844A1 (en) | 2008-11-03 | 2010-10-14 | Scicinski Jan J | Oral pharmaceutical dosage forms |
CN102093284B (zh) * | 2010-12-29 | 2013-05-08 | 宜昌人福药业有限责任公司 | 富集哌啶-2-甲酰苯胺类旋光化合物的方法 |
EP2983468A4 (en) | 2013-03-15 | 2016-09-07 | Durect Corp | COMPOSITIONS WITH RHEOLOGY MODIFIER TO REDUCE RESOLUTION VARIABILITY |
CN106187864B (zh) * | 2016-07-11 | 2018-11-23 | 江苏天和制药有限公司 | 一种由盐酸布比卡因制备高纯度布比卡因碱的方法 |
CA3167217A1 (en) | 2020-01-13 | 2021-07-22 | Durect Corporation | Sustained release drug delivery systems with reduced impurities and related methods |
WO2023158722A2 (en) * | 2022-02-16 | 2023-08-24 | Teva Pharmaceuticals International Gmbh | Processes for preparation of avacopan and intermediates thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2301498A1 (fr) * | 1975-02-20 | 1976-09-17 | Maggioni & C Spa | Methode pour la racemisation d'une lysine optiquement active |
-
1995
- 1995-01-18 GB GBGB9501071.6A patent/GB9501071D0/en active Pending
-
1996
- 1996-01-12 BR BR9606821A patent/BR9606821A/pt unknown
- 1996-01-12 CA CA002208522A patent/CA2208522C/en not_active Expired - Lifetime
- 1996-01-12 JP JP52210296A patent/JP4015696B2/ja not_active Expired - Lifetime
- 1996-01-12 EP EP96900349A patent/EP0804417B1/en not_active Expired - Lifetime
- 1996-01-12 KR KR1019970704822A patent/KR100404390B1/ko not_active IP Right Cessation
- 1996-01-12 HU HU9901418A patent/HU227426B1/hu unknown
- 1996-01-12 CN CNB961915242A patent/CN1172912C/zh not_active Expired - Lifetime
- 1996-01-12 DE DE69628540T patent/DE69628540T2/de not_active Expired - Lifetime
- 1996-01-12 ES ES96900349T patent/ES2201166T3/es not_active Expired - Lifetime
- 1996-01-12 WO PCT/GB1996/000067 patent/WO1996022281A1/en active IP Right Grant
- 1996-01-12 DK DK96900349T patent/DK0804417T3/da active
- 1996-01-12 PT PT96900349T patent/PT804417E/pt unknown
- 1996-01-12 AT AT96900349T patent/ATE242214T1/de active
- 1996-01-12 PL PL96321378A patent/PL184091B1/pl unknown
- 1996-01-12 AU AU43948/96A patent/AU701221B2/en not_active Expired
- 1996-01-12 MX MX9705428A patent/MX9705428A/es unknown
- 1996-01-18 ZA ZA96403A patent/ZA96403B/xx unknown
-
1997
- 1997-07-17 NO NO973312A patent/NO308843B1/no not_active IP Right Cessation
- 1997-07-17 FI FI973040A patent/FI117437B/fi not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP4015696B2 (ja) | 2007-11-28 |
CA2208522A1 (en) | 1996-07-25 |
BR9606821A (pt) | 1997-12-23 |
NO973312L (no) | 1997-07-17 |
DK0804417T3 (da) | 2003-10-06 |
KR100404390B1 (ko) | 2004-01-31 |
CN1168134A (zh) | 1997-12-17 |
HU227426B1 (en) | 2011-05-30 |
HUP9901418A2 (hu) | 1999-08-30 |
CN1172912C (zh) | 2004-10-27 |
CA2208522C (en) | 2007-03-13 |
DE69628540T2 (de) | 2004-01-08 |
FI973040A (fi) | 1997-07-17 |
PT804417E (pt) | 2003-09-30 |
AU4394896A (en) | 1996-08-07 |
EP0804417A1 (en) | 1997-11-05 |
PL321378A1 (en) | 1997-12-08 |
ATE242214T1 (de) | 2003-06-15 |
WO1996022281A1 (en) | 1996-07-25 |
AU701221B2 (en) | 1999-01-21 |
NO308843B1 (no) | 2000-11-06 |
KR19980701432A (ko) | 1998-05-15 |
ES2201166T3 (es) | 2004-03-16 |
PL184091B1 (pl) | 2002-08-30 |
ZA96403B (en) | 1997-01-20 |
FI117437B (fi) | 2006-10-13 |
MX9705428A (es) | 1997-11-29 |
EP0804417B1 (en) | 2003-06-04 |
GB9501071D0 (en) | 1995-03-08 |
HUP9901418A3 (en) | 2001-01-29 |
NO973312D0 (no) | 1997-07-17 |
FI973040A0 (fi) | 1997-07-17 |
DE69628540D1 (de) | 2003-07-10 |
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