ES2365919T3 - Procedimiento para la preparación de ácidos alquil y arildifosfónicos y las sales de los mismos. - Google Patents

Procedimiento para la preparación de ácidos alquil y arildifosfónicos y las sales de los mismos. Download PDF

Info

Publication number: ES2365919T3
Authority: ES; Spain
Prior art keywords: acid; preparation; acids; salt; salts
Prior art date: 2003-12-23
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.): Expired - Lifetime

Application number

ES04804152T

Other languages

English (en)

Spanish (es)

Inventor

Simona Grassi

Anna Volante

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ALCHYMARS SpA

TRIFARMA SpA

Original Assignee

ALCHYMARS SpA

TRIFARMA SpA

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.)

2003-12-23

Filing date

2004-12-22

Publication date

2011-10-13

2004-12-22 Application filed by ALCHYMARS SpA, TRIFARMA SpA filed Critical ALCHYMARS SpA

2011-10-13 Application granted granted Critical

2011-10-13 Publication of ES2365919T3 publication Critical patent/ES2365919T3/es

2024-12-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 10
239000002253 acid Substances 0.000 title description 8
150000007513 acids Chemical class 0.000 title description 7
MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 claims abstract description 23
229960005236 ibandronic acid Drugs 0.000 claims abstract description 15
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 3
238000004108 freeze drying Methods 0.000 claims description 3
239000007921 spray Substances 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
238000009938 salting Methods 0.000 claims 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
229910000029 sodium carbonate Inorganic materials 0.000 claims 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 9
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229940015872 ibandronate Drugs 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 7
229960000759 risedronic acid Drugs 0.000 description 6
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
229960004276 zoledronic acid Drugs 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 3
238000010908 decantation Methods 0.000 description 3
239000012530 fluid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
UQXNEWQGGVUVQA-UHFFFAOYSA-N 8-aminooctanoic acid Chemical compound NCCCCCCCC(O)=O UQXNEWQGGVUVQA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
-1 N-methyl-N-pentylamino Chemical group 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000007711 solidification Methods 0.000 description 2
230000008023 solidification Effects 0.000 description 2
XXNASZAYANFLID-UHFFFAOYSA-N (1-hydroxy-1-phosphono-2-pyridin-2-ylethyl)phosphonic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CC=N1 XXNASZAYANFLID-UHFFFAOYSA-N 0.000 description 1
LEWJCGSLUNRPMZ-UHFFFAOYSA-N (8-amino-1-hydroxy-1-phosphonooctyl)phosphonic acid Chemical compound NCCCCCCCC(O)(P(O)(O)=O)P(O)(O)=O LEWJCGSLUNRPMZ-UHFFFAOYSA-N 0.000 description 1
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
JKZJSYXGKHQHRA-UHFFFAOYSA-N 2-imidazol-1-ylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CN1C=CN=C1 JKZJSYXGKHQHRA-UHFFFAOYSA-N 0.000 description 1
XVCCOEWNFXXUEV-UHFFFAOYSA-N 2-pyridin-3-ylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CN=C1 XVCCOEWNFXXUEV-UHFFFAOYSA-N 0.000 description 1
BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 1
YWSCUVIPKSJBRU-UHFFFAOYSA-N 3-[methyl(pentyl)azaniumyl]propanoate Chemical compound CCCCCN(C)CCC(O)=O YWSCUVIPKSJBRU-UHFFFAOYSA-N 0.000 description 1
208000006386 Bone Resorption Diseases 0.000 description 1
208000037147 Hypercalcaemia Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
208000010191 Osteitis Deformans Diseases 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
208000027868 Paget disease Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000024279 bone resorption Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000000148 hypercalcaemia Effects 0.000 description 1
208000030915 hypercalcemia disease Diseases 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
208000027202 mammary Paget disease Diseases 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
239000008183 oral pharmaceutical preparation Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VBDRTGFACFYFCT-UHFFFAOYSA-M sodium;hydroxy-[(1r)-1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl]phosphinate;hydrate Chemical compound O.[Na+].CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)([O-])=O VBDRTGFACFYFCT-UHFFFAOYSA-M 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1

ES04804152T 2003-12-23 2004-12-22 Procedimiento para la preparación de ácidos alquil y arildifosfónicos y las sales de los mismos. Expired - Lifetime ES2365919T3 (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ITMI03A2582		2003-12-23
ITMI20032582 ITMI20032582A1 (it)	2003-12-23	2003-12-23	Ibandronato monosodico amorfo
ITMI04A0080		2004-01-22

Publications (1)

Publication Number	Publication Date
ES2365919T3 true ES2365919T3 (es)	2011-10-13

Family

ID=43722040

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES04804152T Expired - Lifetime ES2365919T3 (es)	2003-12-23	2004-12-22	Procedimiento para la preparación de ácidos alquil y arildifosfónicos y las sales de los mismos.

Country Status (2)

Country	Link
ES (1)	ES2365919T3 (it)
IT (1)	ITMI20032582A1 (it)

2003
- 2003-12-23 IT ITMI20032582 patent/ITMI20032582A1/it unknown
2004
- 2004-12-22 ES ES04804152T patent/ES2365919T3/es not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ITMI20032582A1 (it)	2005-06-24

Publication	Publication Date	Title
EP1716161B1 (en)	2011-05-04	Ibandronic acid monosodium salt in the amorphous form
JP4642762B2 (ja)	2011-03-02	ビスホスホン酸化合物の製造方法
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