CN1951916A - Process for preparing argatroban intermediates - Google Patents
Process for preparing argatroban intermediates Download PDFInfo
- Publication number
- CN1951916A CN1951916A CN 200610129331 CN200610129331A CN1951916A CN 1951916 A CN1951916 A CN 1951916A CN 200610129331 CN200610129331 CN 200610129331 CN 200610129331 A CN200610129331 A CN 200610129331A CN 1951916 A CN1951916 A CN 1951916A
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- nitro
- reaction
- methyl
- arginine
- tboc
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- KXNPVXPOPUZYGB-XYVMCAHJSA-N argatroban Chemical compound OC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C1=CC=CC2=C1NC[C@H](C)C2 KXNPVXPOPUZYGB-XYVMCAHJSA-N 0.000 title claims abstract description 20
- 229960003856 argatroban Drugs 0.000 title claims abstract description 20
- 239000000543 intermediate Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000007787 solid Substances 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 239000012044 organic layer Substances 0.000 claims abstract description 5
- 239000012265 solid product Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 32
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 238000009833 condensation Methods 0.000 claims description 15
- 230000005494 condensation Effects 0.000 claims description 15
- GHBNOCBWSUHAAA-HTQZYQBOSA-N ethyl (2r,4r)-4-methylpiperidine-2-carboxylate Chemical compound CCOC(=O)[C@H]1C[C@H](C)CCN1 GHBNOCBWSUHAAA-HTQZYQBOSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 5
- 238000001816 cooling Methods 0.000 abstract description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 8
- VJDOLBUUJRHCPC-UHFFFAOYSA-N quinoline;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.N1=CC=CC2=CC=CC=C21 VJDOLBUUJRHCPC-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000004445 quantitative analysis Methods 0.000 description 5
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
- 229930064664 L-arginine Natural products 0.000 description 3
- 235000014852 L-arginine Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004019 antithrombin Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DZAHXNNEQCZPGJ-UHFFFAOYSA-N CCCCOC(OC)=O.COC(O)=O Chemical compound CCCCOC(OC)=O.COC(O)=O DZAHXNNEQCZPGJ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- IYLPVOSBXVRRJZ-QAKAPOOCSA-N (2R,4R)-1-[(2S)-5-(hydrazinylmethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid Chemical compound NN=CNCCC[C@@H](C(=O)N1[C@H](C[C@@H](CC1)C)C(=O)O)NS(=O)(=O)C=1C=CC=C2CC(CNC=12)C IYLPVOSBXVRRJZ-QAKAPOOCSA-N 0.000 description 1
- QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical group CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2006101293310A CN100465161C (en) | 2006-11-10 | 2006-11-10 | Process for preparing argatroban intermediates |
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---|---|---|---|
CNB2006101293310A CN100465161C (en) | 2006-11-10 | 2006-11-10 | Process for preparing argatroban intermediates |
Publications (2)
Publication Number | Publication Date |
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CN1951916A true CN1951916A (en) | 2007-04-25 |
CN100465161C CN100465161C (en) | 2009-03-04 |
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CNB2006101293310A Active CN100465161C (en) | 2006-11-10 | 2006-11-10 | Process for preparing argatroban intermediates |
Country Status (1)
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CN (1) | CN100465161C (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101348463B (en) * | 2007-12-25 | 2010-06-02 | 天津泰普药品科技发展有限公司 | Synthetic method of argatroban and intermediate thereof |
CN101560244B (en) * | 2009-04-21 | 2011-05-25 | 深圳翰宇药业股份有限公司 | New method for synthesizing argatroban by combining solid phase method and liquid phase method |
CN101914133B (en) * | 2008-03-07 | 2013-01-30 | 天津市炜杰科技有限公司 | Directional synthesis method for 21(S) argatroban |
CN101712645B (en) * | 2009-11-20 | 2013-08-28 | 重庆威尔德·浩瑞医药化工有限公司 | Preparation method for (2R, 4R)-4-substituted-2-piperidine carboxylic acid compound and intermediate thereof |
CN103570803A (en) * | 2012-08-30 | 2014-02-12 | 上海科胜药物研发有限公司 | Preparation method of argatroban intermediate |
CN104059125A (en) * | 2014-06-20 | 2014-09-24 | 天津市亨必达化学合成物有限公司 | Method for preparing argatroban intermediate amidate |
CN104672132A (en) * | 2013-11-28 | 2015-06-03 | 四川科瑞德制药有限公司 | Synthesis method of argatroban intermediate |
CN111471085A (en) * | 2020-04-16 | 2020-07-31 | 江巨东 | Method for continuously preparing argatroban |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101519429B (en) * | 2009-03-31 | 2012-07-25 | 深圳翰宇药业股份有限公司 | Solid phase method for synchronizing Argatroban |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4201863A (en) * | 1974-11-08 | 1980-05-06 | Mitsubishi Chemical Industries, Limited | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
US4258192A (en) * | 1977-12-16 | 1981-03-24 | Mitsubishi Chemical Industries Limited | N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof |
ATE207482T1 (en) * | 1996-08-07 | 2001-11-15 | Mitsubishi Chem Corp | METHOD FOR PRODUCING N2-ARYLSULFONYL-L-ARGININE AMIDES |
US6440417B1 (en) * | 1998-11-06 | 2002-08-27 | Conjuchem, Inc. | Antibodies to argatroban derivatives and their use in therapeutic and diagnostic treatments |
-
2006
- 2006-11-10 CN CNB2006101293310A patent/CN100465161C/en active Active
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101348463B (en) * | 2007-12-25 | 2010-06-02 | 天津泰普药品科技发展有限公司 | Synthetic method of argatroban and intermediate thereof |
CN101914133B (en) * | 2008-03-07 | 2013-01-30 | 天津市炜杰科技有限公司 | Directional synthesis method for 21(S) argatroban |
CN101560244B (en) * | 2009-04-21 | 2011-05-25 | 深圳翰宇药业股份有限公司 | New method for synthesizing argatroban by combining solid phase method and liquid phase method |
CN101712645B (en) * | 2009-11-20 | 2013-08-28 | 重庆威尔德·浩瑞医药化工有限公司 | Preparation method for (2R, 4R)-4-substituted-2-piperidine carboxylic acid compound and intermediate thereof |
CN103570803A (en) * | 2012-08-30 | 2014-02-12 | 上海科胜药物研发有限公司 | Preparation method of argatroban intermediate |
CN103570803B (en) * | 2012-08-30 | 2015-06-03 | 上海科胜药物研发有限公司 | Preparation method of argatroban intermediate |
CN104672132A (en) * | 2013-11-28 | 2015-06-03 | 四川科瑞德制药有限公司 | Synthesis method of argatroban intermediate |
CN104672132B (en) * | 2013-11-28 | 2017-06-16 | 四川科瑞德制药股份有限公司 | The synthetic method of argatroban intermediate |
CN104059125A (en) * | 2014-06-20 | 2014-09-24 | 天津市亨必达化学合成物有限公司 | Method for preparing argatroban intermediate amidate |
CN111471085A (en) * | 2020-04-16 | 2020-07-31 | 江巨东 | Method for continuously preparing argatroban |
Also Published As
Publication number | Publication date |
---|---|
CN100465161C (en) | 2009-03-04 |
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