CN1280286C - 工业合成取代的噻吩甲酸酯的新方法和该化合物的应用 - Google Patents
工业合成取代的噻吩甲酸酯的新方法和该化合物的应用 Download PDFInfo
- Publication number
- CN1280286C CN1280286C CNB031348122A CN03134812A CN1280286C CN 1280286 C CN1280286 C CN 1280286C CN B031348122 A CNB031348122 A CN B031348122A CN 03134812 A CN03134812 A CN 03134812A CN 1280286 C CN1280286 C CN 1280286C
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- synthetic method
- oxoethyl
- amino
- 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.)
- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 9
- 239000002253 acid Substances 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title abstract description 10
- KNPBNTMMZCNVIE-UHFFFAOYSA-N 5-amino-3-(carboxymethyl)-4-cyanothiophene-2-carboxylic acid Chemical compound NC=1SC(C(O)=O)=C(CC(O)=O)C=1C#N KNPBNTMMZCNVIE-UHFFFAOYSA-N 0.000 title 1
- -1 methyl diester Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229940079488 strontium ranelate Drugs 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- XXUZFRDUEGQHOV-UHFFFAOYSA-J strontium ranelate Chemical compound [Sr+2].[Sr+2].[O-]C(=O)CN(CC([O-])=O)C=1SC(C([O-])=O)=C(CC([O-])=O)C=1C#N XXUZFRDUEGQHOV-UHFFFAOYSA-J 0.000 claims description 4
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 159000000008 strontium salts Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- DJSXNILVACEBLP-UHFFFAOYSA-N ranelic acid Chemical class OC(=O)CN(CC(O)=O)C=1SC(C(O)=O)=C(CC(O)=O)C=1C#N DJSXNILVACEBLP-UHFFFAOYSA-N 0.000 abstract description 2
- 229950003464 ranelic acid Drugs 0.000 abstract description 2
- ZHEZAQJNZMLYBA-UHFFFAOYSA-J distrontium;5-[bis(carboxylatomethyl)amino]-3-(carboxylatomethyl)-4-cyanothiophene-2-carboxylate;octahydrate Chemical compound O.O.O.O.O.O.O.O.[Sr+2].[Sr+2].[O-]C(=O)CN(CC([O-])=O)C=1SC(C([O-])=O)=C(CC([O-])=O)C=1C#N ZHEZAQJNZMLYBA-UHFFFAOYSA-J 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052749 magnesium Chemical group 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical group [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0211765A FR2844797B1 (fr) | 2002-09-24 | 2002-09-24 | Nouveau procede de synthese industriel des tetraesters de l'acide 5-[bis (carboxymethyl)]-3-carboxymethyl-4-cyano-2- thiophenecarboxylique, et application a la synthese des sels bivalents de l'acide ranelique et de leurs hydrates |
| FR0211765 | 2002-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1500784A CN1500784A (zh) | 2004-06-02 |
| CN1280286C true CN1280286C (zh) | 2006-10-18 |
Family
ID=29415191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031348122A Expired - Fee Related CN1280286C (zh) | 2002-09-24 | 2003-09-24 | 工业合成取代的噻吩甲酸酯的新方法和该化合物的应用 |
Country Status (38)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2844796A1 (fr) * | 2002-09-24 | 2004-03-26 | Servier Lab | Nouveau procede de synthese industrielle du diester methylique de l'acide 5-amino-3-carboxymethyl-4-cyano-2- thiophenecarboxylique, et application a la synthese des sels bivalents de l'acide ranelique et de leurs hydrates |
| FR2844795B1 (fr) * | 2002-09-24 | 2004-10-22 | Servier Lab | Nouveau procede de synthese industriel du ranelate de strontium et de ses hydrates |
| ES2275218T3 (es) * | 2003-05-07 | 2007-06-01 | Osteologix A/S | Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos. |
| WO2004098618A2 (en) * | 2003-05-07 | 2004-11-18 | Osteologix A/S | Strontium combinations for prophylaxis/treatment of cartilage and/or bone conditions |
| US20050085531A1 (en) * | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| PL1732575T3 (pl) | 2004-02-26 | 2011-05-31 | Osteologix As | Związki zawierające stron do stosowania w zapobieganiu lub leczeniu stanów nekrotycznych kości |
| CA2571449C (en) | 2004-06-25 | 2015-12-08 | John Nikolaj Hvarre Christensen | Compositions comprising strontium and vitamin d and uses thereof |
| FR2875807B1 (fr) * | 2004-09-30 | 2006-11-17 | Servier Lab | Forme cristalline alpha du ranelate de strontium, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| CN100391955C (zh) * | 2005-04-30 | 2008-06-04 | 河北医科大学 | 一种雷尼酸锶中间体的合成方法 |
| US20070292529A1 (en) * | 2006-06-19 | 2007-12-20 | Tabbiner Philip S | Strontium compositions and methods of treating osteoporotic conditions |
| US20070292535A1 (en) * | 2006-06-19 | 2007-12-20 | Tabbiner Philip S | Strontium compositions and methods of treating arthritic and or osteoporitic conditions |
| US20120123131A1 (en) * | 2008-08-22 | 2012-05-17 | Koilpillai Joseph Prabahar | Process for the preparation of strontium ranelate |
| CN101665483B (zh) * | 2008-09-01 | 2013-01-23 | 河北医科大学 | 一种雷尼酸锶中间体化合物ⅱ的合成方法 |
| WO2011124992A1 (en) * | 2010-03-24 | 2011-10-13 | Actavis Group Ptc Ehf | Substantially pure strontium ranelate |
| CN101812048B (zh) * | 2010-04-06 | 2012-11-14 | 浙江东亚药业有限公司 | 雷尼酸锶及其水合物的合成方法 |
| EP2602248A1 (en) | 2011-12-05 | 2013-06-12 | University Of Leicester | Novel pyrrole compounds |
| WO2013113319A1 (en) | 2012-01-31 | 2013-08-08 | Pharmathen S.A. | Process for the preparation of strontium ranelate, intermediate or hydrates thereof |
| ES2505716T3 (es) | 2013-01-21 | 2015-09-04 | Galenicum Health S.L. | Composiciones farmacéuticas que comprenden una sal de ácido |
| GB201310126D0 (en) * | 2013-06-06 | 2013-07-24 | Univ Leicester | Novel pyrrole derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3624304A1 (de) | 1986-07-18 | 1988-01-28 | Bayer Ag | Fungizide verwendung von substituierten thienylaminen |
| GB8715925D0 (en) * | 1987-07-07 | 1987-08-12 | Shell Int Research | Thiapentanamide derivatives |
| FR2651497B1 (fr) | 1989-09-01 | 1991-10-25 | Adir | Nouveaux sels de metaux bivalents de l'acide n, n-di (carboxymethyl)amino-2 cyano-3 carboxymethyl-4 carboxy-5 thiophene, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| DE19528380A1 (de) * | 1995-08-02 | 1997-02-06 | Hoechst Ag | Heterogene Vinylacetat/Ethylen-Dispersion |
| FR2749759B1 (fr) * | 1996-06-17 | 1999-11-26 | Adir | Utilisation de sels de strontium pour l'obtention de compositions pharmaceutiques destinees au traitement de l'arthrose |
| DE19650196A1 (de) * | 1996-12-04 | 1998-06-10 | Bayer Ag | Thienylsulfonylamino(thio)carbonylverbindungen |
| US6835745B2 (en) * | 2002-01-15 | 2004-12-28 | Wyeth | Phenyl substituted thiophenes as estrogenic agents |
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2002
- 2002-09-24 FR FR0211765A patent/FR2844797B1/fr not_active Expired - Fee Related
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- 2003-09-17 MY MYPI20033533A patent/MY134924A/en unknown
- 2003-09-22 UA UAA200503860A patent/UA79157C2/uk unknown
- 2003-09-22 RS YUP-2005/0241A patent/RS51551B/sr unknown
- 2003-09-22 ME MEP-2008-687A patent/ME00453B/me unknown
- 2003-09-22 WO PCT/FR2003/002775 patent/WO2004029034A1/fr not_active Ceased
- 2003-09-22 JP JP2003330439A patent/JP4136866B2/ja not_active Expired - Fee Related
- 2003-09-22 ES ES03292318T patent/ES2337348T3/es not_active Expired - Lifetime
- 2003-09-22 DK DK03292318.7T patent/DK1403265T3/da active
- 2003-09-22 AU AU2003299095A patent/AU2003299095A1/en not_active Abandoned
- 2003-09-22 SI SI200331715T patent/SI1403265T1/sl unknown
- 2003-09-22 OA OA1200500081A patent/OA12932A/en unknown
- 2003-09-22 AU AU2003248280A patent/AU2003248280B2/en not_active Ceased
- 2003-09-22 DE DE60330213T patent/DE60330213D1/de not_active Expired - Lifetime
- 2003-09-22 PT PT03292318T patent/PT1403265E/pt unknown
- 2003-09-22 EP EP03292318A patent/EP1403265B1/fr not_active Expired - Lifetime
- 2003-09-22 GE GEAP20038759A patent/GEP20074139B/en unknown
- 2003-09-22 AP AP2005003255A patent/AP1972A/xx active
- 2003-09-22 AT AT03292318T patent/ATE449767T1/de active
- 2003-09-22 HR HRP20050361AA patent/HRP20050361B1/hr not_active IP Right Cessation
- 2003-09-23 ZA ZA200307411A patent/ZA200307411B/xx unknown
- 2003-09-23 NZ NZ528401A patent/NZ528401A/en not_active IP Right Cessation
- 2003-09-23 PL PL362366A patent/PL215879B1/pl unknown
- 2003-09-23 EA EA200300927A patent/EA007108B1/ru not_active IP Right Cessation
- 2003-09-23 CA CA2442881A patent/CA2442881C/fr not_active Expired - Fee Related
- 2003-09-23 AR ARP030103455A patent/AR041357A1/es not_active Application Discontinuation
- 2003-09-23 BR BR0304203-0A patent/BR0304203A/pt not_active Application Discontinuation
- 2003-09-23 NO NO20034236A patent/NO328626B1/no not_active IP Right Cessation
- 2003-09-23 KR KR1020030065784A patent/KR100551502B1/ko not_active Expired - Fee Related
- 2003-09-23 MX MXPA03008647A patent/MXPA03008647A/es active IP Right Grant
- 2003-09-24 US US10/669,302 patent/US7091364B2/en not_active Expired - Fee Related
- 2003-09-24 CN CNB031348122A patent/CN1280286C/zh not_active Expired - Fee Related
- 2003-09-24 MA MA27319A patent/MA26100A1/fr unknown
- 2003-09-24 SG SG200305553A patent/SG110069A1/en unknown
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- 2005-03-08 IL IL167315A patent/IL167315A/en not_active IP Right Cessation
- 2005-03-23 TN TNP2005000088A patent/TNSN05088A1/fr unknown
- 2005-04-18 IS IS7803A patent/IS2728B/is unknown
- 2005-04-22 EC EC2005005743A patent/ECSP055743A/es unknown
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2010
- 2010-01-19 CY CY20101100055T patent/CY1109831T1/el unknown
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