ES2334260T3 - Procedimientos para la preparacion de la forma i cristalina de clorhidrato de cinacalcet. - Google Patents
Procedimientos para la preparacion de la forma i cristalina de clorhidrato de cinacalcet. Download PDFInfo
- Publication number
- ES2334260T3 ES2334260T3 ES06771215T ES06771215T ES2334260T3 ES 2334260 T3 ES2334260 T3 ES 2334260T3 ES 06771215 T ES06771215 T ES 06771215T ES 06771215 T ES06771215 T ES 06771215T ES 2334260 T3 ES2334260 T3 ES 2334260T3
- Authority
- ES
- Spain
- Prior art keywords
- cinacalcet
- hours
- hydrochloride
- solvent
- cinacalcet hydrochloride
- 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.)
- Active
Links
- VDHAWDNDOKGFTD-MRXNPFEDSA-N cinacalcet Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCCC1=CC=CC(C(F)(F)F)=C1 VDHAWDNDOKGFTD-MRXNPFEDSA-N 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 229960003315 cinacalcet Drugs 0.000 title claims description 58
- QANQWUQOEJZMLL-PKLMIRHRSA-N cinacalcet hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCCC1=CC=CC(C(F)(F)F)=C1 QANQWUQOEJZMLL-PKLMIRHRSA-N 0.000 claims description 105
- 229960000478 cinacalcet hydrochloride Drugs 0.000 claims description 91
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 74
- 238000001914 filtration Methods 0.000 claims description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 33
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 30
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002244 precipitate Substances 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 239000002002 slurry Substances 0.000 claims description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012296 anti-solvent Substances 0.000 claims description 12
- 239000011440 grout Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 3
- 238000002441 X-ray diffraction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 3
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical group O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000000428 dust Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- CWUNPFVHATZKFE-MRXNPFEDSA-N cinacalcet carbamate Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)C(=O)OCCCC1=CC=CC(C(F)(F)F)=C1 CWUNPFVHATZKFE-MRXNPFEDSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 34
- 239000013078 crystal Substances 0.000 description 9
- 108090000445 Parathyroid hormone Proteins 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 102100036893 Parathyroid hormone Human genes 0.000 description 5
- 230000002092 calcimimetic effect Effects 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 description 4
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 description 4
- 201000009277 hairy cell leukemia Diseases 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 102000003982 Parathyroid hormone Human genes 0.000 description 2
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000199 parathyroid hormone Substances 0.000 description 2
- 229960001319 parathyroid hormone Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 229940116949 sensipar Drugs 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 206010006002 Bone pain Diseases 0.000 description 1
- 229940124602 FDA-approved drug Drugs 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000849 parathyroid Effects 0.000 description 1
- 210000002990 parathyroid gland Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
- A61P5/20—Drugs for disorders of the endocrine system of the parathyroid hormones for decreasing, blocking or antagonising the activity of PTH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (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)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
Applications Claiming Priority (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68415205P | 2005-05-23 | 2005-05-23 | |
| US684152P | 2005-05-23 | ||
| US69698105P | 2005-07-05 | 2005-07-05 | |
| US696981P | 2005-07-05 | ||
| US69711105P | 2005-07-06 | 2005-07-06 | |
| US697111P | 2005-07-06 | ||
| US69861305P | 2005-07-11 | 2005-07-11 | |
| US698613P | 2005-07-11 | ||
| US70123205P | 2005-07-20 | 2005-07-20 | |
| US701232P | 2005-07-20 | ||
| US70291805P | 2005-07-26 | 2005-07-26 | |
| US702918P | 2005-07-26 | ||
| US70691005P | 2005-08-09 | 2005-08-09 | |
| US706910P | 2005-08-09 | ||
| US73005005P | 2005-10-24 | 2005-10-24 | |
| US730050P | 2005-10-24 | ||
| US73208305P | 2005-10-31 | 2005-10-31 | |
| US732083P | 2005-10-31 | ||
| US73300805P | 2005-11-02 | 2005-11-02 | |
| US733008P | 2005-11-02 | ||
| US73466905P | 2005-11-07 | 2005-11-07 | |
| US734669P | 2005-11-07 | ||
| US73512605P | 2005-11-08 | 2005-11-08 | |
| US735126P | 2005-11-08 | ||
| US73882705P | 2005-11-21 | 2005-11-21 | |
| US738827P | 2005-11-21 | ||
| US74178705P | 2005-12-01 | 2005-12-01 | |
| US741787P | 2005-12-01 | ||
| US75091005P | 2005-12-15 | 2005-12-15 | |
| US750910P | 2005-12-15 | ||
| US79480406P | 2006-04-24 | 2006-04-24 | |
| US794804P | 2006-04-24 | ||
| PCT/US2006/020304 WO2006127933A1 (en) | 2005-05-23 | 2006-05-23 | Processes for preparing cinacalcet hydrochloride crystal form i |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2334260T3 true ES2334260T3 (es) | 2010-03-08 |
Family
ID=37101358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06771215T Active ES2334260T3 (es) | 2005-05-23 | 2006-05-23 | Procedimientos para la preparacion de la forma i cristalina de clorhidrato de cinacalcet. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7294735B2 (enExample) |
| EP (3) | EP1883618B1 (enExample) |
| JP (3) | JP4638491B2 (enExample) |
| KR (2) | KR20070088485A (enExample) |
| CN (1) | CN101180261A (enExample) |
| AT (1) | ATE445587T1 (enExample) |
| CA (2) | CA2605736A1 (enExample) |
| ES (1) | ES2334260T3 (enExample) |
| IL (2) | IL185108A0 (enExample) |
| MX (1) | MX2007000983A (enExample) |
| TW (1) | TW200716512A (enExample) |
| WO (2) | WO2006127932A2 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2645494C (en) * | 2006-03-23 | 2016-01-12 | Amgen Inc. | Methods and compositions for making and using polymorphs of cinacalcet |
| EP1913941A1 (en) * | 2006-10-19 | 2008-04-23 | Sandoz AG | Polymorphic forms and solvates of Cinacalcet hydrochloride |
| US20090258949A1 (en) * | 2006-06-27 | 2009-10-15 | Johannes Ludescher | Amorphous form of cinacalcet |
| WO2008000423A1 (en) * | 2006-06-27 | 2008-01-03 | Sandoz Ag | Crystalline form of cinacalcet |
| US20080181959A1 (en) * | 2006-09-01 | 2008-07-31 | Ilan Zalit | Solid composites of a calcium receptor-active compound |
| WO2008058236A2 (en) * | 2006-11-08 | 2008-05-15 | Dr. Reddy's Labortories, Ltd. | Methods for preparing cinacalcet hydrochloride |
| WO2008063645A1 (en) * | 2006-11-20 | 2008-05-29 | Teva Pharmaceutical Industries Ltd. | Process for preparing cinacalcet |
| CA2691196C (en) * | 2007-06-21 | 2016-05-24 | Amgen Inc. | Methods of synthesizing cinacalcet and salts thereof |
| ITMI20071261A1 (it) | 2007-06-22 | 2008-12-23 | Dipharma Francis Srl | Procedimento per la preparazione di cinacalcet |
| US20090093652A1 (en) * | 2007-08-16 | 2009-04-09 | Michal Rafilovich | Crystalline forms cinacalcet fumarate and cinacalcet succinate and processes for preparation thereof |
| WO2009039241A2 (en) * | 2007-09-18 | 2009-03-26 | Medichem, S.A. | Improved process for preparing cinacalcet hydrochloride |
| US7696372B2 (en) * | 2007-10-01 | 2010-04-13 | Ascenta Therapeutics, Inc. | Process for preparing R-gossypol L-phenylalaninol dienamine |
| US20110189241A1 (en) * | 2008-05-05 | 2011-08-04 | Medichem, S.A. | Process For Controlling The Particle Size of A [3-(Trifluoromethyl)Phenyl]-1-Aminopropane Derivative |
| EP2321256B1 (en) * | 2008-06-18 | 2014-11-12 | ERREGIERRE S.p.A. | Process for the synthesis of cinacalcet hydrochloride |
| EP2328860A2 (en) * | 2008-08-06 | 2011-06-08 | Actavis Group PTC EHF | Unsaturated cinacalcet salts and processes for preparing cinacalcet hydrochloride |
| US20110318417A1 (en) * | 2008-12-08 | 2011-12-29 | Actavis Group Ptc Ehf | Highly pure cinacalcet or a pharmaceutically acceptable salt thereof |
| EP2398763A2 (en) | 2009-02-19 | 2011-12-28 | ZaCh System S.p.A. | Process for preparing cinacalcet hydrochloride |
| US8575393B2 (en) | 2009-03-05 | 2013-11-05 | Cipla Limited | Process for the preparation of cinacalcet and salts thereof, and intermediates for use in the process |
| WO2010128388A2 (en) | 2009-05-08 | 2010-11-11 | Aurobindo Pharma Limited | An improved process for the preparation of intermediate compounds useful for the preparation of cinacalcet |
| CN102548955B (zh) | 2009-09-10 | 2014-06-04 | Zach系统股份公司 | 用于制备西那卡塞特的方法 |
| US8722732B2 (en) | 2009-09-29 | 2014-05-13 | Nektar Therapeutics | Oligomer-calcimimetic conjugates and related compounds |
| IT1396623B1 (it) | 2009-11-26 | 2012-12-14 | Dipharma Francis Srl | Procedimento per la preparazione di cinacalcet e suoi intermedi |
| CZ2011770A3 (cs) * | 2011-11-25 | 2013-01-16 | Zentiva, K.S. | Zpusob výroby Cinacalcetu |
| CN103450027B (zh) | 2012-05-29 | 2015-07-29 | 上海京新生物医药有限公司 | 盐酸西那卡塞的制备方法 |
| FR2995307A1 (fr) | 2012-09-07 | 2014-03-14 | Prod Chim Auxiliaires Et De Synthese | Procede de preparation du cinacalcet et de ses sels pharmaceutiquement acceptables |
| CN103739500B (zh) * | 2012-12-27 | 2016-03-23 | 国药一心制药有限公司 | 一种盐酸西那卡塞的合成与精制方法 |
| CN103193655B (zh) * | 2013-04-15 | 2015-06-24 | 山东新华制药股份有限公司 | 盐酸西那卡塞晶型ⅰ的制备方法 |
| CN104512864B (zh) * | 2013-09-30 | 2017-08-22 | 中国石油化工股份有限公司 | 一种低温脱除微量碳氧化物的方法 |
| AU2014348523B2 (en) | 2013-11-15 | 2019-01-03 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
| BR102015025502B1 (pt) * | 2015-04-30 | 2022-06-21 | Aegerion Pharmaceuticals, Inc | Composição de lomitapida, tablete, produto de lomitapida, métodos para analisar uma composição de amostra de lomitapida e para determinar uma quantidade de uma impureza em uma amostra da composição |
| CN104892428A (zh) * | 2015-06-05 | 2015-09-09 | 南京辰逸生物科技有限公司 | 一种盐酸西那卡塞的制备方法 |
| CN106610404B (zh) * | 2015-10-21 | 2019-01-15 | 华仁药业股份有限公司 | 采用hplc法检测盐酸西那卡塞同分异构体的方法 |
| CN105439818B (zh) * | 2015-12-31 | 2017-11-28 | 苏州汇和药业有限公司 | 一种西那卡塞中间体3‑(3‑三氟甲基苯基)丙醇的合成方法 |
| CN107879939A (zh) * | 2016-09-30 | 2018-04-06 | 上海天慈生物谷生物工程有限公司 | 一种制备 n‑((1r)‑1‑(1‑萘基)乙基)‑3‑(3‑(三氟甲基)苯基)丙‑1‑胺盐酸盐的方法 |
| KR20200022712A (ko) | 2018-08-23 | 2020-03-04 | 주식회사 오스코텍 | 8-브로모-2-(1-메틸피페리딘-4-일아미노)-4-(4-페녹시페닐아미노)피리도[4,3-d]피리미딘-5(6H)-온 염산염의 결정다형체 및 그 제조방법 |
| CN109096119B (zh) * | 2018-10-29 | 2019-10-25 | 江苏永安制药有限公司 | 一种制备盐酸西那卡塞的方法 |
| CN110041206B (zh) * | 2019-04-29 | 2021-10-19 | 梯尔希（南京）药物研发有限公司 | 一种西那卡塞杂质的制备方法 |
| CN111153832B (zh) * | 2020-01-20 | 2022-02-25 | 广州九植医药科技有限公司 | 一种西那卡塞杂质的制备方法 |
| KR20250003360A (ko) * | 2023-06-30 | 2025-01-07 | 주식회사 종근당 | 화합물의 신규한 제조방법 및 신규한 결정형 |
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| US4966988A (en) * | 1989-02-17 | 1990-10-30 | Chevron Research Company | Process for preparing acetonitrile 3-trifluoromethyl benzene |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) * | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| HU228150B1 (en) * | 1994-10-21 | 2012-12-28 | Nps Pharma Inc | Calcium receptor-active compounds, medicaments comprising them, and the use of said medicaments |
| US5648541A (en) * | 1995-09-28 | 1997-07-15 | Nps Pharmaceuticals, Inc. | Chiral reductions of imines leading to the syntheses of optically active amines |
| EP0907631B1 (en) * | 1996-05-01 | 2003-06-18 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| US7829595B2 (en) * | 2003-09-12 | 2010-11-09 | Amgen Inc. | Rapid dissolution formulation of a calcium receptor-active compound |
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2006
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- 2006-05-23 ES ES06771215T patent/ES2334260T3/es active Active
- 2006-05-23 US US11/440,246 patent/US7294735B2/en not_active Expired - Fee Related
- 2006-05-23 CA CA002605736A patent/CA2605736A1/en not_active Abandoned
- 2006-05-23 AT AT06771215T patent/ATE445587T1/de not_active IP Right Cessation
- 2006-05-23 EP EP06771214A patent/EP1805135A2/en not_active Withdrawn
- 2006-05-23 JP JP2007522852A patent/JP4638491B2/ja not_active Expired - Fee Related
- 2006-05-23 CA CA002606099A patent/CA2606099A1/en not_active Abandoned
- 2006-05-23 US US11/439,570 patent/US7247751B2/en not_active Expired - Fee Related
- 2006-05-23 EP EP08012814A patent/EP1975150A1/en not_active Withdrawn
- 2006-05-23 KR KR1020077004036A patent/KR20070088485A/ko not_active Ceased
- 2006-05-23 WO PCT/US2006/020303 patent/WO2006127932A2/en not_active Ceased
- 2006-05-23 KR KR1020077001966A patent/KR20070083471A/ko not_active Ceased
- 2006-05-23 WO PCT/US2006/020304 patent/WO2006127933A1/en not_active Ceased
- 2006-05-23 MX MX2007000983A patent/MX2007000983A/es not_active Application Discontinuation
- 2006-05-23 JP JP2007522851A patent/JP2008507565A/ja active Pending
- 2006-05-23 TW TW095118275A patent/TW200716512A/zh unknown
- 2006-05-23 CN CNA2006800179392A patent/CN101180261A/zh active Pending
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2007
- 2007-08-07 IL IL185108A patent/IL185108A0/en unknown
- 2007-08-23 IL IL185494A patent/IL185494A0/en unknown
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2010
- 2010-09-02 JP JP2010197123A patent/JP2010280715A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008507566A (ja) | 2008-03-13 |
| EP1805135A2 (en) | 2007-07-11 |
| US7294735B2 (en) | 2007-11-13 |
| CN101180261A (zh) | 2008-05-14 |
| WO2006127933A1 (en) | 2006-11-30 |
| EP1883618B1 (en) | 2009-10-14 |
| US20070060645A1 (en) | 2007-03-15 |
| JP2010280715A (ja) | 2010-12-16 |
| KR20070088485A (ko) | 2007-08-29 |
| IL185108A0 (en) | 2007-12-03 |
| MX2007000983A (es) | 2007-04-16 |
| ATE445587T1 (de) | 2009-10-15 |
| IL185494A0 (en) | 2008-01-06 |
| JP4638491B2 (ja) | 2011-02-23 |
| US20070099998A1 (en) | 2007-05-03 |
| US7247751B2 (en) | 2007-07-24 |
| CA2606099A1 (en) | 2006-11-30 |
| WO2006127932A2 (en) | 2006-11-30 |
| WO2006127932A3 (en) | 2007-02-01 |
| EP1975150A1 (en) | 2008-10-01 |
| JP2008507565A (ja) | 2008-03-13 |
| KR20070083471A (ko) | 2007-08-24 |
| CA2605736A1 (en) | 2006-11-30 |
| EP1883618A1 (en) | 2008-02-06 |
| WO2006127933A8 (en) | 2007-08-30 |
| TW200716512A (en) | 2007-05-01 |
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