AU2003248281B2 - New process for the industrial synthesis of strontium ranelate and its hydrates - Google Patents
New process for the industrial synthesis of strontium ranelate and its hydrates Download PDFInfo
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- AU2003248281B2 AU2003248281B2 AU2003248281A AU2003248281A AU2003248281B2 AU 2003248281 B2 AU2003248281 B2 AU 2003248281B2 AU 2003248281 A AU2003248281 A AU 2003248281A AU 2003248281 A AU2003248281 A AU 2003248281A AU 2003248281 B2 AU2003248281 B2 AU 2003248281B2
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- 238000000034 method Methods 0.000 title claims description 40
- 230000015572 biosynthetic process Effects 0.000 title claims description 37
- 238000003786 synthesis reaction Methods 0.000 title claims description 36
- 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 title claims description 26
- 229940079488 strontium ranelate Drugs 0.000 title claims description 25
- 150000004677 hydrates Chemical class 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 238000010992 reflux Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000005864 Sulphur Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 claims description 8
- 229910001866 strontium hydroxide Inorganic materials 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 6
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 7
- AYCCQDIBOMUCEW-UHFFFAOYSA-N methyl 5-[bis(2-methoxy-2-oxoethyl)amino]-4-cyano-3-(2-methoxy-2-oxoethyl)thiophene-2-carboxylate Chemical compound COC(=O)CN(CC(=O)OC)C=1SC(C(=O)OC)=C(CC(=O)OC)C=1C#N AYCCQDIBOMUCEW-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- BLYLWUDQKYBGJD-UHFFFAOYSA-N methyl 5-amino-4-cyano-3-(2-methoxy-2-oxoethyl)thiophene-2-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)SC(N)=C1C#N BLYLWUDQKYBGJD-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- RNJOKCPFLQMDEC-UHFFFAOYSA-N 4(R),8-dimethyl-trans-2-nonenoyl-CoA Chemical compound COC(=O)CC(=O)CC(=O)OC RNJOKCPFLQMDEC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 2
- 208000020084 Bone disease Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000003262 anti-osteoporosis Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- ZSANYRMTSBBUCA-UHFFFAOYSA-N diethyl 3-oxopentanedioate Chemical compound CCOC(=O)CC(=O)CC(=O)OCC ZSANYRMTSBBUCA-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- YPKDDRKVYUMYEP-UHFFFAOYSA-J distrontium thiophene-2-carboxylate octahydrate Chemical compound O.O.O.O.O.O.O.O.[Sr+2].[Sr+2].S1C(=CC=C1)C(=O)[O-].S1C(=CC=C1)C(=O)[O-].S1C(=CC=C1)C(=O)[O-].S1C(=CC=C1)C(=O)[O-] YPKDDRKVYUMYEP-UHFFFAOYSA-J 0.000 description 1
- QZGJWBFWUITOJD-UHFFFAOYSA-M dodecyl-bis(2-hydroxyethyl)-methylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(CCO)CCO QZGJWBFWUITOJD-UHFFFAOYSA-M 0.000 description 1
- -1 ethyl diester Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- IXLRCPSVPMSMMM-UHFFFAOYSA-N methyl 3-(dicyanomethylidene)-5-hydroxy-5-methoxypent-4-enoate Chemical compound COC(=O)CC(=C(C#N)C#N)C=C(O)OC IXLRCPSVPMSMMM-UHFFFAOYSA-N 0.000 description 1
- YVRHWJWYIONDJT-UHFFFAOYSA-N methyl 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-methoxy-2-oxoethyl)thiophene-2-carboxylate Chemical compound CCOC(=O)CN(CC(=O)OCC)C=1SC(C(=O)OC)=C(CC(=O)OC)C=1C#N YVRHWJWYIONDJT-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Inorganic Insulating Materials (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0211763A FR2844795B1 (fr) | 2002-09-24 | 2002-09-24 | Nouveau procede de synthese industriel du ranelate de strontium et de ses hydrates |
| FR02.11763 | 2002-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003248281A1 AU2003248281A1 (en) | 2004-04-08 |
| AU2003248281B2 true AU2003248281B2 (en) | 2009-08-06 |
Family
ID=29415189
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003248281A Ceased AU2003248281B2 (en) | 2002-09-24 | 2003-09-22 | New process for the industrial synthesis of strontium ranelate and its hydrates |
| AU2003282179A Abandoned AU2003282179A1 (en) | 2002-09-24 | 2003-09-22 | Novel method for the industrial synthesis of strontium ranelate and the hydrates thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003282179A Abandoned AU2003282179A1 (en) | 2002-09-24 | 2003-09-22 | Novel method for the industrial synthesis of strontium ranelate and the hydrates thereof |
Country Status (37)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1745791E (pt) * | 2003-05-07 | 2013-07-23 | Osteologix As | Tratamento de afeções cartilagíneas/ósseas com sais de estrôncio hidrossolúveis |
| DE602004002832T2 (de) * | 2003-05-07 | 2007-06-06 | Osteologix A/S | Behandlung von knorpel/knochen-erkrankungen mit wasserlöslichen strontiumsalzen |
| AU2005216596B2 (en) | 2004-02-26 | 2011-03-24 | Osteologix A/S | Strontium-containing compounds for use in the prevention or treatment of necrotic bone conditions |
| WO2005108339A2 (en) | 2004-05-06 | 2005-11-17 | Osteologix A/S | High yield and rapid syntheses methods for producing metallo-organic salts |
| KR20070034075A (ko) | 2004-06-25 | 2007-03-27 | 스트론틴 에이피에스 | 스트론튬과 비타민 ｄ를 함유하는 조성물 및 그의 용도 |
| 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 |
| CN100538672C (zh) * | 2005-04-18 | 2009-09-09 | 索尼株式会社 | 控制设备和方法 |
| 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 |
| WO2007020527A2 (en) * | 2005-08-19 | 2007-02-22 | Glenmark Pharmaceuticals Limited | Process for the preparation of strontium ranelate |
| US20070292535A1 (en) * | 2006-06-19 | 2007-12-20 | Tabbiner Philip S | Strontium compositions and methods of treating arthritic and or osteoporitic conditions |
| US20070292529A1 (en) * | 2006-06-19 | 2007-12-20 | Tabbiner Philip S | Strontium compositions and methods of treating osteoporotic 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 |
| HU228820B1 (en) | 2010-01-14 | 2013-05-28 | Richter Gedeon Nyrt | Process for the preparation of distrontium ranelate |
| WO2011110597A1 (de) | 2010-03-11 | 2011-09-15 | Azad Pharmaceutical Ingredients Ag | Verfahren zur herstellung von strontiumranelat |
| WO2011124992A1 (en) * | 2010-03-24 | 2011-10-13 | Actavis Group Ptc Ehf | Substantially pure strontium ranelate |
| WO2013013003A1 (en) | 2011-07-21 | 2013-01-24 | Emory University | Methods for treating inflamatory conditions and states, and cancers by antagonizing nf-kb activation |
| CN102321068B (zh) * | 2011-08-01 | 2013-01-23 | 山东铂源药业有限公司 | 一种雷奈酸锶的制备方法 |
| WO2013175270A1 (en) * | 2012-05-25 | 2013-11-28 | Fleming Laboratories Limited | Improved process for the preparation of strontium ranelate hydrates and new polymorphic form of monohydrate |
| ES2505716T3 (es) | 2013-01-21 | 2015-09-04 | Galenicum Health S.L. | Composiciones farmacéuticas que comprenden una sal de ácido |
| CN103319454B (zh) * | 2013-06-14 | 2014-06-18 | 广东众生药业股份有限公司 | 一种高纯度雷尼酸四乙酯及其中间体的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0415850A1 (fr) * | 1989-09-01 | 1991-03-06 | Adir Et Compagnie | Sels de métaux bivalents de l'acide N, N-di(carboxyméthyl)amino-2 cyano-3 carboxyméthyl-4 carboxy-5 thiophène,leur procédé de préparation et les compositions pharmaceutiques les renfermant |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| FR2844797B1 (fr) * | 2002-09-24 | 2004-10-22 | Servier Lab | 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 |
-
2002
- 2002-09-24 FR FR0211763A patent/FR2844795B1/fr not_active Expired - Fee Related
-
2003
- 2003-09-17 MY MYPI20033542A patent/MY134921A/en unknown
- 2003-09-22 PT PT3292319T patent/PT1403266E/pt unknown
- 2003-09-22 AU AU2003248281A patent/AU2003248281B2/en not_active Ceased
- 2003-09-22 UA UAA200503858A patent/UA79156C2/uk unknown
- 2003-09-22 ES ES03292319.5T patent/ES2478620T3/es not_active Expired - Lifetime
- 2003-09-22 JP JP2003330440A patent/JP4136867B2/ja not_active Expired - Fee Related
- 2003-09-22 SI SI200332352T patent/SI1403266T1/sl unknown
- 2003-09-22 ME MEP-2008-689A patent/ME00455B/me unknown
- 2003-09-22 OA OA1200500083A patent/OA12934A/en unknown
- 2003-09-22 RS YUP-2005/0240A patent/RS20050240A/sr unknown
- 2003-09-22 WO PCT/FR2003/002777 patent/WO2004029036A1/fr not_active Ceased
- 2003-09-22 AU AU2003282179A patent/AU2003282179A1/en not_active Abandoned
- 2003-09-22 EP EP03292319.5A patent/EP1403266B1/fr not_active Expired - Lifetime
- 2003-09-22 HR HRP20050359AA patent/HRP20050359B1/hr not_active IP Right Cessation
- 2003-09-22 AP AP2005003256A patent/AP1910A/xx active
- 2003-09-22 DK DK03292319.5T patent/DK1403266T3/da active
- 2003-09-22 GE GEAP20048761A patent/GEP20074215B/en unknown
- 2003-09-22 RS RSP20050240 patent/RS53509B1/sr unknown
- 2003-09-23 EA EA200300925A patent/EA007489B1/ru not_active IP Right Cessation
- 2003-09-23 PL PL362365A patent/PL214400B1/pl unknown
- 2003-09-23 AR ARP030103453A patent/AR041355A1/es not_active Application Discontinuation
- 2003-09-23 ZA ZA200307409A patent/ZA200307409B/xx unknown
- 2003-09-23 NZ NZ528402A patent/NZ528402A/en not_active IP Right Cessation
- 2003-09-23 CA CA002442878A patent/CA2442878C/fr not_active Expired - Fee Related
- 2003-09-23 BR BR0304213-8A patent/BR0304213A/pt not_active Application Discontinuation
- 2003-09-23 KR KR1020030065783A patent/KR100551501B1/ko not_active Expired - Fee Related
- 2003-09-23 MX MXPA03008643A patent/MXPA03008643A/es active IP Right Grant
- 2003-09-23 NO NO20034235A patent/NO328638B1/no not_active IP Right Cessation
- 2003-09-24 CN CNB031348130A patent/CN1212321C/zh not_active Expired - Fee Related
- 2003-09-24 MA MA27321A patent/MA26102A1/fr unknown
- 2003-09-24 SG SG200305555A patent/SG110071A1/en unknown
- 2003-09-24 US US10/669,301 patent/US7214805B2/en not_active Expired - Fee Related
-
2005
- 2005-03-08 IL IL167316A patent/IL167316A/en not_active IP Right Cessation
- 2005-03-18 CR CR7764A patent/CR7764A/es unknown
- 2005-03-23 TN TNP2005000087A patent/TNSN05087A1/fr unknown
- 2005-04-19 IS IS7807A patent/IS7807A/is unknown
- 2005-04-22 EC EC2005005741A patent/ECSP055741A/es unknown
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2014
- 2014-06-05 CY CY20141100397T patent/CY1115162T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0415850A1 (fr) * | 1989-09-01 | 1991-03-06 | Adir Et Compagnie | Sels de métaux bivalents de l'acide N, N-di(carboxyméthyl)amino-2 cyano-3 carboxyméthyl-4 carboxy-5 thiophène,leur procédé de préparation et les compositions pharmaceutiques les renfermant |
Non-Patent Citations (1)
| Title |
|---|
| Bull Soc Chim France 1975, pp 1786-1792 * |
Also Published As
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| Publication | Publication Date | Title |
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