UA79157C2 - Method for the synthesis of thiophenecarboxylic acid esters and the use thereof - Google Patents
Method for the synthesis of thiophenecarboxylic acid esters and the use thereof Download PDFInfo
- Publication number
- UA79157C2 UA79157C2 UAA200503860A UA2005003860A UA79157C2 UA 79157 C2 UA79157 C2 UA 79157C2 UA A200503860 A UAA200503860 A UA A200503860A UA 2005003860 A UA2005003860 A UA 2005003860A UA 79157 C2 UA79157 C2 UA 79157C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- compound
- synthesis
- oxoethyl
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 13
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 13
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 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 claims abstract description 6
- 229950003464 ranelic acid Drugs 0.000 claims abstract description 6
- 150000004677 hydrates Chemical class 0.000 claims abstract description 5
- 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 claims abstract description 4
- 229940079488 strontium ranelate Drugs 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000006184 cosolvent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000001308 synthesis method Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- -1 bis(2-methoxy-2-oxoethyl)amino Chemical group 0.000 description 3
- 239000003344 environmental pollutant Substances 0.000 description 3
- 231100000719 pollutant Toxicity 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000543 intermediate Substances 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
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000256856 Vespidae Species 0.000 description 1
- 230000003262 anti-osteoporosis Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst 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
- 238000009776 industrial production Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052749 magnesium Chemical group 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 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 |
| PCT/FR2003/002775 WO2004029034A1 (fr) | 2002-09-24 | 2003-09-22 | Synthese d’esters d’acide thiophenecarboxyliques pour la fabrication de sels de l’acide ranelique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79157C2 true UA79157C2 (en) | 2007-05-25 |
Family
ID=29415191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200503860A UA79157C2 (en) | 2002-09-24 | 2003-09-22 | Method for the synthesis of thiophenecarboxylic acid esters and the use thereof |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US7091364B2 (pt) |
| EP (1) | EP1403265B1 (pt) |
| JP (1) | JP4136866B2 (pt) |
| KR (1) | KR100551502B1 (pt) |
| CN (1) | CN1280286C (pt) |
| AP (1) | AP1972A (pt) |
| AR (1) | AR041357A1 (pt) |
| AT (1) | ATE449767T1 (pt) |
| AU (2) | AU2003299095A1 (pt) |
| BR (1) | BR0304203A (pt) |
| CA (1) | CA2442881C (pt) |
| CY (1) | CY1109831T1 (pt) |
| DE (1) | DE60330213D1 (pt) |
| DK (1) | DK1403265T3 (pt) |
| EA (1) | EA007108B1 (pt) |
| EC (1) | ECSP055743A (pt) |
| ES (1) | ES2337348T3 (pt) |
| FR (1) | FR2844797B1 (pt) |
| GE (1) | GEP20074139B (pt) |
| HK (1) | HK1061846A1 (pt) |
| HR (1) | HRP20050361B1 (pt) |
| IL (1) | IL167315A (pt) |
| IS (1) | IS2728B (pt) |
| MA (1) | MA26100A1 (pt) |
| ME (1) | ME00453B (pt) |
| MX (1) | MXPA03008647A (pt) |
| MY (1) | MY134924A (pt) |
| NO (1) | NO328626B1 (pt) |
| NZ (1) | NZ528401A (pt) |
| OA (1) | OA12932A (pt) |
| PL (1) | PL215879B1 (pt) |
| PT (1) | PT1403265E (pt) |
| RS (1) | RS51551B (pt) |
| SG (1) | SG110069A1 (pt) |
| SI (1) | SI1403265T1 (pt) |
| TN (1) | TNSN05088A1 (pt) |
| UA (1) | UA79157C2 (pt) |
| WO (1) | WO2004029034A1 (pt) |
| ZA (1) | ZA200307411B (pt) |
Families Citing this family (20)
| 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 |
| EP2266584B1 (en) * | 2003-05-07 | 2012-09-05 | Osteologix A/S | Composition with strontium and vitamin D for the prophylaxis and/or treatment of cartilage and/or bone conditions |
| PL1745791T3 (pl) * | 2003-05-07 | 2013-11-29 | Osteologix As | Leczenie chorób chrząstki/kości za pomocą rozpuszczalnych w wodzie soli strontu |
| 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 |
| EP1732575B1 (en) | 2004-02-26 | 2010-12-29 | Osteologix A/S | Strontium-containing compounds for use in the prevention or treatment of necrotic bone conditions |
| ATE443541T1 (de) | 2004-06-25 | 2009-10-15 | Strontin Aps | Zusammensetzungen mit strontium und vitamin d und ihre verwendungen |
| 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 |
| FR2921367B1 (fr) | 2007-09-26 | 2009-10-30 | Servier Lab | Nouveau procede de synthese du ranelate de strontium et de ses hydrates |
| 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 |
-
2002
- 2002-09-24 FR FR0211765A patent/FR2844797B1/fr not_active Expired - Fee Related
-
2003
- 2003-09-17 MY MYPI20033533A patent/MY134924A/en unknown
- 2003-09-22 WO PCT/FR2003/002775 patent/WO2004029034A1/fr not_active Application Discontinuation
- 2003-09-22 JP JP2003330439A patent/JP4136866B2/ja not_active Expired - Fee Related
- 2003-09-22 AU AU2003299095A patent/AU2003299095A1/en not_active Abandoned
- 2003-09-22 EP EP03292318A patent/EP1403265B1/fr not_active Expired - Lifetime
- 2003-09-22 DE DE60330213T patent/DE60330213D1/de not_active Expired - Lifetime
- 2003-09-22 DK DK03292318.7T patent/DK1403265T3/da active
- 2003-09-22 UA UAA200503860A patent/UA79157C2/uk unknown
- 2003-09-22 ME MEP-2008-687A patent/ME00453B/me unknown
- 2003-09-22 PT PT03292318T patent/PT1403265E/pt unknown
- 2003-09-22 OA OA1200500081A patent/OA12932A/en unknown
- 2003-09-22 AT AT03292318T patent/ATE449767T1/de active
- 2003-09-22 ES ES03292318T patent/ES2337348T3/es not_active Expired - Lifetime
- 2003-09-22 GE GEAP20038759A patent/GEP20074139B/en unknown
- 2003-09-22 RS YUP-2005/0241A patent/RS51551B/en unknown
- 2003-09-22 AU AU2003248280A patent/AU2003248280B2/en not_active Ceased
- 2003-09-22 AP AP2005003255A patent/AP1972A/xx active
- 2003-09-22 SI SI200331715T patent/SI1403265T1/sl unknown
- 2003-09-23 ZA ZA200307411A patent/ZA200307411B/xx unknown
- 2003-09-23 MX MXPA03008647A patent/MXPA03008647A/es active IP Right Grant
- 2003-09-23 KR KR1020030065784A patent/KR100551502B1/ko not_active IP Right Cessation
- 2003-09-23 CA CA2442881A patent/CA2442881C/fr not_active Expired - Fee Related
- 2003-09-23 PL PL362366A patent/PL215879B1/pl unknown
- 2003-09-23 NO NO20034236A patent/NO328626B1/no not_active IP Right Cessation
- 2003-09-23 NZ NZ528401A patent/NZ528401A/en not_active IP Right Cessation
- 2003-09-23 BR BR0304203-0A patent/BR0304203A/pt not_active Application Discontinuation
- 2003-09-23 EA EA200300927A patent/EA007108B1/ru not_active IP Right Cessation
- 2003-09-23 AR ARP030103455A patent/AR041357A1/es not_active Application Discontinuation
- 2003-09-24 SG SG200305553A patent/SG110069A1/en unknown
- 2003-09-24 MA MA27319A patent/MA26100A1/fr unknown
- 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
-
2004
- 2004-07-05 HK HK04104809A patent/HK1061846A1/xx not_active IP Right Cessation
-
2005
- 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
- 2005-04-21 HR HRP20050361AA patent/HRP20050361B1/hr not_active IP Right Cessation
- 2005-04-22 EC EC2005005743A patent/ECSP055743A/es unknown
-
2010
- 2010-01-19 CY CY20101100055T patent/CY1109831T1/el unknown
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