HU228820B1 - Process for the preparation of distrontium ranelate - Google Patents

Process for the preparation of distrontium ranelate Download PDF

Info

Publication number: HU228820B1
Authority: HU; Hungary
Prior art keywords: acid; hydrolysis; ranelic; process according; organic solvent
Prior art date: 2010-01-14

Application number

HU1000018A

Other languages

English (en)

Hungarian (hu)

Inventor

Sandor Garadnai

Nikoletta Dr Szalma

Jozsef Neu

Jozsef Toerley

Adam Dr Demeter

Original Assignee

Richter Gedeon Nyrt

Priority date (The priority date 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 date listed.)

2010-01-14

Filing date

2010-01-14

Publication date

2013-05-28

2010-01-14 Application filed by Richter Gedeon Nyrt filed Critical Richter Gedeon Nyrt

2010-01-14 Priority to HU1000018A priority Critical patent/HU228820B1/hu

2010-03-29 Publication of HU1000018D0 publication Critical patent/HU1000018D0/hu

2011-01-14 Priority to EP11703731A priority patent/EP2523947A1/fr

2011-01-14 Priority to PCT/HU2011/000006 priority patent/WO2011086399A1/fr

2011-01-14 Priority to EA201290592A priority patent/EA201290592A1/ru

2011-10-28 Publication of HUP1000018A2 publication Critical patent/HUP1000018A2/hu

2013-05-28 Publication of HU228820B1 publication Critical patent/HU228820B1/hu

Links

238000000034 method Methods 0.000 title claims abstract description 32
238000002360 preparation method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 9
229950003464 ranelic acid Drugs 0.000 claims description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
DJSXNILVACEBLP-UHFFFAOYSA-N ranelic acid Chemical compound OC(=O)CN(CC(O)=O)C=1SC(C(O)=O)=C(CC(O)=O)C=1C#N DJSXNILVACEBLP-UHFFFAOYSA-N 0.000 claims description 44
230000007062 hydrolysis Effects 0.000 claims description 27
238000006460 hydrolysis reaction Methods 0.000 claims description 27
235000019441 ethanol Nutrition 0.000 claims description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
150000003863 ammonium salts Chemical class 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 17
-1 carboxymethylmethyl Chemical group 0.000 claims description 16
239000003960 organic solvent Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
235000011114 ammonium hydroxide Nutrition 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
238000000605 extraction Methods 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
238000001228 spectrum Methods 0.000 claims description 2
239000000178 monomer Substances 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000007516 brønsted-lowry acids Chemical class 0.000 claims 1
239000006185 dispersion Substances 0.000 claims 1
JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims 1
150000003613 toluenes Chemical class 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
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 abstract 2
229940079488 strontium ranelate Drugs 0.000 abstract 1
BGSCYLLQJSFPAG-UHFFFAOYSA-N tetraazanium;5-[bis(carboxylatomethyl)amino]-3-(carboxylatomethyl)-4-cyanothiophene-2-carboxylate Chemical compound N.N.N.N.OC(=O)CN(CC(O)=O)C=1SC(C(O)=O)=C(CC(O)=O)C=1C#N BGSCYLLQJSFPAG-UHFFFAOYSA-N 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
150000002148 esters Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 7
229910001866 strontium hydroxide Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
229910003002 lithium salt Inorganic materials 0.000 description 4
159000000002 lithium salts Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000007790 solid phase Substances 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
210000000988 bone and bone Anatomy 0.000 description 3
239000007857 degradation product Substances 0.000 description 3
238000000634 powder X-ray diffraction Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
229910052712 strontium Inorganic materials 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
UJPLQWOIPCSWCI-UHFFFAOYSA-N ethyl 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate Chemical compound CCOC(=O)CN(CC(=O)OCC)C=1SC(C(=O)OCC)=C(CC(=O)OCC)C=1C#N UJPLQWOIPCSWCI-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000005502 peroxidation Methods 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000000075 primary alcohol group Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
229910001631 strontium chloride Inorganic materials 0.000 description 2
AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
150000003509 tertiary alcohols Chemical class 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 description 1
208000020084 Bone disease Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
LRTOXJSLSJHMNB-UHFFFAOYSA-K [Rh](Cl)(Cl)Cl.[Li] Chemical compound [Rh](Cl)(Cl)Cl.[Li] LRTOXJSLSJHMNB-UHFFFAOYSA-K 0.000 description 1
239000013543 active substance Substances 0.000 description 1
159000000013 aluminium salts Chemical class 0.000 description 1
229910000329 aluminium sulfate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000002491 angiogenic effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
230000037118 bone strength Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000005388 cross polarization Methods 0.000 description 1
238000005384 cross polarization magic-angle spinning Methods 0.000 description 1
238000001160 cross-polarisation magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000011164 ossification Effects 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BSGGVIDZMMSWKM-UHFFFAOYSA-L strontium dichlorite Chemical compound [Sr+2].[O-]Cl=O.[O-]Cl=O BSGGVIDZMMSWKM-UHFFFAOYSA-L 0.000 description 1
ZCCKUOITFYNSQG-UHFFFAOYSA-N styrene;hydrate Chemical compound O.C=CC1=CC=CC=C1 ZCCKUOITFYNSQG-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 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
- C07D333/40—Thiophene-2-carboxylic acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HU1000018A 2010-01-14 2010-01-14 Process for the preparation of distrontium ranelate HU228820B1 (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
HU1000018A HU228820B1 (en)	2010-01-14	2010-01-14	Process for the preparation of distrontium ranelate
EP11703731A EP2523947A1 (fr)	2010-01-14	2011-01-14	Procédé de préparation de ranélate de strontium
PCT/HU2011/000006 WO2011086399A1 (fr)	2010-01-14	2011-01-14	Procédé de préparation de ranélate de strontium
EA201290592A EA201290592A1 (ru)	2010-01-14	2011-01-14	Способ получения ранелата стронция

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU1000018A HU228820B1 (en)	2010-01-14	2010-01-14	Process for the preparation of distrontium ranelate

Publications (3)

Publication Number	Publication Date
HU1000018D0 HU1000018D0 (en)	2010-03-29
HUP1000018A2 HUP1000018A2 (en)	2011-10-28
HU228820B1 true HU228820B1 (en)	2013-05-28

Family

ID=89989497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU1000018A HU228820B1 (en)	2010-01-14	2010-01-14	Process for the preparation of distrontium ranelate

Country Status (4)

Country	Link
EP (1)	EP2523947A1 (fr)
EA (1)	EA201290592A1 (fr)
HU (1)	HU228820B1 (fr)
WO (1)	WO2011086399A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1398542B1 (it) *	2010-03-05	2013-03-01	Chemelectiva S R L	Processo per la preparazione di un polimorfo
US8569514B1 (en)	2012-05-17	2013-10-29	Divi's Laboratories, Ltd.	Process for the preparation of strontium ranelate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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.
FR2844795B1 (fr)	2002-09-24	2004-10-22	Servier Lab	Nouveau procede de synthese industriel du ranelate de strontium et de ses hydrates
CA2619720A1 (fr)	2005-08-19	2007-02-22	Glenmark Pharmaceuticals Limited	Procede de preparation de ranelate de strontium
FR2921367B1 (fr)	2007-09-26	2009-10-30	Servier Lab	Nouveau procede de synthese du ranelate de strontium et de ses hydrates

2010
- 2010-01-14 HU HU1000018A patent/HU228820B1/hu unknown
2011
- 2011-01-14 EP EP11703731A patent/EP2523947A1/fr not_active Withdrawn
- 2011-01-14 WO PCT/HU2011/000006 patent/WO2011086399A1/fr not_active Ceased
- 2011-01-14 EA EA201290592A patent/EA201290592A1/ru unknown

Also Published As

Publication number	Publication date
HUP1000018A2 (en)	2011-10-28
EP2523947A1 (fr)	2012-11-21
WO2011086399A1 (fr)	2011-07-21
HU1000018D0 (en)	2010-03-29
EA201290592A1 (ru)	2013-05-30

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