HRP20100260T1 - Postupak za proizvodnju stroncij ranelata i njegovih hidrata - Google Patents
Postupak za proizvodnju stroncij ranelata i njegovih hidrata Download PDFInfo
- Publication number
- HRP20100260T1 HRP20100260T1 HR20100260T HRP20100260T HRP20100260T1 HR P20100260 T1 HRP20100260 T1 HR P20100260T1 HR 20100260 T HR20100260 T HR 20100260T HR P20100260 T HRP20100260 T HR P20100260T HR P20100260 T1 HRP20100260 T1 HR P20100260T1
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- HR
- Croatia
- Prior art keywords
- formula
- process according
- synthesis process
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- reaction
- Prior art date
Links
- 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 abstract 6
- 229940079488 strontium ranelate Drugs 0.000 title claims abstract 6
- 150000004677 hydrates Chemical class 0.000 title claims abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 11
- 238000003786 synthesis reaction Methods 0.000 claims abstract 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims abstract 8
- 229910001631 strontium chloride Inorganic materials 0.000 claims abstract 8
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims abstract 4
- 239000003960 organic solvent Substances 0.000 claims abstract 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims abstract 2
- 229910052700 potassium Inorganic materials 0.000 claims abstract 2
- 229910052708 sodium Inorganic materials 0.000 claims abstract 2
- 239000011734 sodium Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims 6
- 238000001914 filtration Methods 0.000 claims 2
- 239000012266 salt solution Substances 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 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
- C07D333/42—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 with nitro or nitroso radicals directly attached to ring carbon atoms
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Abstract
Postupak za sintezu stroncij ranelata formule (I): i njegovih hidrata reakcijom spoja formule (II): pri čemu R i R1, koji mogu biti isti ili različiti, svaki predstavlja ravnu ili razgrananu (C1-C6)alkilnu skupinu, s natrijevim hidroksidom ili kalijevim hidroksidom, u vodi ili u smjesi vode i organskog otapala odabranog od tetrahidrofurana, acetona, 2-metil-tetrahidrodurana, dimetil sulfoksida, acetonitrila, N-metilpirolidona, etanola, izopropanola i izobutanola na temperaturi od 0 do 100 °C, kako bi se dobila sol formule (III): pri čemu A predstavlja Na ili K, koji su reagirali sa stroncij kloridom pri temperaturi od 0 do 100 °C, kako bi se nakon izolacije dobio stroncij ranelat ili jedan od njegovih hidrata, naznačeno time, da je korak reakcije soli formule (III) sa stroncij kloridom izvođen u smjesi vode i organskog otapala odabranog od tetrahidrofurana, acetona, 2-metil-tetrahidrofurana, dimetil sulfoksida, acetonitrila, N-metilpirolidona, metanola, izopropanola i izobutanola. Patent sadrži još 11 patentnih zahtjeva.
Claims (12)
1. Postupak za sintezu stroncij ranelata formule (I):
[image]
i njegovih hidrata reakcijom spoja formule (II):
[image]
pri čemu R i R1, koji mogu biti isti ili različiti, svaki predstavlja ravnu ili razgrananu (C1-C6)alkilnu skupinu, s natrijevim hidroksidom ili kalijevim hidroksidom,
u vodi ili u smjesi vode i organskog otapala odabranog od tetrahidrofurana, acetona, 2-metil-tetrahidrodurana, dimetil sulfoksida, acetonitrila, N-metilpirolidona, etanola, izopropanola i izobutanola na temperaturi od 0 do 100 °C, kako bi se dobila sol formule (III):
[image]
pri čemu A predstavlja Na ili K,
koji su reagirali sa stroncij kloridom pri temperaturi od 0 do 100 °C,
kako bi se nakon izolacije dobio stroncij ranelat ili jedan od njegovih hidrata, naznačeno time, da je korak reakcije soli formule (III) sa stroncij kloridom izvođen u smjesi vode i organskog otapala odabranog od tetrahidrofurana, acetona, 2-metil-tetrahidrofurana, dimetil sulfoksida, acetonitrila, N-metilpirolidona, metanola, izopropanola i izobutanola.
2. Postupak sinteze u skladu s patentnim zahtjevom 1, naznačen time, da je količina natrijevog hidroksida ili kalijevog hidroksida veća od ili jednaka 4 mola po molu spoja formule (II).
3. Postupak sinteze u skladu s patentnim zahtjevom 1 ili 2, naznačen time, da je temperatura reakcije saponifikacije na spoju formule (II) od 20 do 70 °C.
4. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da je sol formule (III) izolirana prije reakcije sa stroncij kloridom.
5. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da je otopina soli formule (III) izbistrena prije uporabe u reakciji sa stroncij kloridom.
6. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da je otopina soli formule (III) korištena kao takva u reakciji sa stroncij kloridom.
7. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time, da je količina stroncij klorida veća od ili jednaka 2 mola po molu spoja formule (II).
8. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time, da je temperatura reakcije pretvaranja soli u spoj formule (III) od 20 do 50 °C.
9. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time, da je stroncij ranelat izoliran filtracijom.
10. Postupak sinteze u skladu s patentnim zahtjevom 9, naznačen time, da je korak filtracije popraćen s jednim ili više koraka pranja i sušenja.
11. Spoj formule (IIIb):
[image]
12. Postupak sinteze u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time, da R i R1 svaki predstavlja metilnu skupinu.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0706731A FR2921367B1 (fr) | 2007-09-26 | 2007-09-26 | Nouveau procede de synthese du ranelate de strontium et de ses hydrates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100260T1 true HRP20100260T1 (hr) | 2010-06-30 |
Family
ID=39431194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100260T HRP20100260T1 (hr) | 2007-09-26 | 2010-05-11 | Postupak za proizvodnju stroncij ranelata i njegovih hidrata |
Country Status (47)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2921367B1 (fr) * | 2007-09-26 | 2009-10-30 | Servier Lab | Nouveau procede de synthese du ranelate de strontium et de ses hydrates |
| EP2346846A1 (en) * | 2008-09-29 | 2011-07-27 | Ratiopharm GmbH | Anhydrate and hydrate forms of strontium ranelate |
| HU228820B1 (en) | 2010-01-14 | 2013-05-28 | Richter Gedeon Nyrt | Process for the preparation of distrontium ranelate |
| IT1398542B1 (it) | 2010-03-05 | 2013-03-01 | Chemelectiva S R L | Processo per la preparazione di un polimorfo |
| 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 |
| US20110275834A1 (en) * | 2010-05-06 | 2011-11-10 | Divi's Laboratories, Limited | Polymorph of strontium ranelate and a process for its preparation |
| WO2012046251A2 (en) * | 2010-10-08 | 2012-04-12 | Glenmark Generics Limited | Novel form of ranelic acid |
| CZ2011320A3 (cs) * | 2011-05-30 | 2012-12-12 | Zentiva, K.S. | Stabilní krystalická forma X stroncium ranelátu |
| CN102391247B (zh) * | 2011-09-20 | 2016-12-28 | 浙江华海药业股份有限公司 | 一种雷尼酸锶水合物晶形k及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| GB2235691A (en) * | 1989-09-04 | 1991-03-13 | Du Pont Canada | Concentrates of modifying agents in polymers |
| JP3880262B2 (ja) * | 1998-11-02 | 2007-02-14 | 株式会社カネカ | 水不溶化再生コラーゲン繊維の製造方法 |
| 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 |
| FR2844795B1 (fr) * | 2002-09-24 | 2004-10-22 | Servier Lab | Nouveau procede de synthese industriel du ranelate de strontium et de ses hydrates |
| US7138529B2 (en) * | 2003-04-16 | 2006-11-21 | Hoffmann-La Roche Inc. | Substituted 3-cyanothiophene acetamides as glucagon receptor antagonists |
| WO2007020527A2 (en) * | 2005-08-19 | 2007-02-22 | Glenmark Pharmaceuticals Limited | Process for the preparation of strontium ranelate |
| US20070292529A1 (en) * | 2006-06-19 | 2007-12-20 | Tabbiner Philip S | Strontium compositions and methods of treating osteoporotic conditions |
| CN100554263C (zh) * | 2006-07-19 | 2009-10-28 | 天津药物研究院 | 雷奈酸锶七水合物的制备方法 |
| FR2921367B1 (fr) * | 2007-09-26 | 2009-10-30 | Servier Lab | Nouveau procede de synthese du ranelate de strontium et de ses hydrates |
-
2007
- 2007-09-26 FR FR0706731A patent/FR2921367B1/fr not_active Expired - Fee Related
-
2008
- 2008-09-15 AP AP2008004617A patent/AP2400A/xx active
- 2008-09-15 SG SG200806787-8A patent/SG151207A1/en unknown
- 2008-09-15 IL IL194089A patent/IL194089A/en not_active IP Right Cessation
- 2008-09-15 PE PE2008001612A patent/PE20090703A1/es not_active Application Discontinuation
- 2008-09-15 UY UY31341A patent/UY31341A1/es unknown
- 2008-09-16 MA MA31243A patent/MA30319B1/fr unknown
- 2008-09-16 MY MYPI20083603A patent/MY144180A/en unknown
- 2008-09-17 CR CR10292A patent/CR10292A/es unknown
- 2008-09-17 CN CNA2008101489170A patent/CN101397292A/zh active Pending
- 2008-09-19 AU AU2008221618A patent/AU2008221618B2/en not_active Ceased
- 2008-09-19 SV SV2008003033A patent/SV2008003033A/es active IP Right Grant
- 2008-09-19 UA UAA200811373A patent/UA97638C2/ru unknown
- 2008-09-19 CO CO08099515A patent/CO6110143A1/es active IP Right Grant
- 2008-09-19 GT GT200800190A patent/GT200800190A/es unknown
- 2008-09-20 SA SA08290594A patent/SA08290594B1/ar unknown
- 2008-09-22 GE GEAP200810919A patent/GEP20115191B/en unknown
- 2008-09-23 MX MX2008012119A patent/MX2008012119A/es active IP Right Grant
- 2008-09-24 PA PA20088797001A patent/PA8797001A1/es unknown
- 2008-09-24 CL CL2008002833A patent/CL2008002833A1/es unknown
- 2008-09-24 US US12/284,695 patent/US8063100B2/en not_active Expired - Fee Related
- 2008-09-24 TW TW097136693A patent/TWI358408B/zh not_active IP Right Cessation
- 2008-09-24 AR ARP080104129A patent/AR068535A1/es not_active Application Discontinuation
- 2008-09-25 ZA ZA200808176A patent/ZA200808176B/en unknown
- 2008-09-25 ES ES08290906T patent/ES2342233T3/es active Active
- 2008-09-25 NI NI200800257A patent/NI200800257A/es unknown
- 2008-09-25 NZ NZ571511A patent/NZ571511A/en not_active IP Right Cessation
- 2008-09-25 PL PL08290906T patent/PL2042497T3/pl unknown
- 2008-09-25 WO PCT/FR2008/001329 patent/WO2009074741A2/fr active Application Filing
- 2008-09-25 DK DK08290906.0T patent/DK2042497T3/da active
- 2008-09-25 KR KR1020080094125A patent/KR101099995B1/ko not_active IP Right Cessation
- 2008-09-25 EC EC2008008771A patent/ECSP088771A/es unknown
- 2008-09-25 JP JP2008245193A patent/JP5016575B2/ja not_active Expired - Fee Related
- 2008-09-25 SI SI200830031T patent/SI2042497T1/sl unknown
- 2008-09-25 EP EP08290906A patent/EP2042497B1/fr active Active
- 2008-09-25 JO JO2008427A patent/JO2964B1/en active
- 2008-09-25 CA CA2640041A patent/CA2640041C/fr not_active Expired - Fee Related
- 2008-09-25 RS RSP-2010/0252A patent/RS51356B/en unknown
- 2008-09-25 PT PT08290906T patent/PT2042497E/pt unknown
- 2008-09-25 DE DE602008000790T patent/DE602008000790D1/de active Active
- 2008-09-25 AT AT08290906T patent/ATE460408T1/de active
- 2008-09-25 ME MEP-2010-252A patent/ME01849B/me unknown
- 2008-09-25 BR BRPI0803636-5A patent/BRPI0803636A2/pt not_active IP Right Cessation
- 2008-09-25 EA EA200801884A patent/EA014247B1/ru not_active IP Right Cessation
- 2008-09-26 HN HN2008001490A patent/HN2008001490A/es unknown
-
2010
- 2010-05-11 HR HR20100260T patent/HRP20100260T1/hr unknown
- 2010-05-17 CY CY20101100439T patent/CY1110036T1/el unknown
-
2011
- 2011-10-11 US US13/317,114 patent/US20120029210A1/en not_active Abandoned
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