JP2013500995A5 - - Google Patents
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- JP2013500995A5 JP2013500995A5 JP2012523084A JP2012523084A JP2013500995A5 JP 2013500995 A5 JP2013500995 A5 JP 2013500995A5 JP 2012523084 A JP2012523084 A JP 2012523084A JP 2012523084 A JP2012523084 A JP 2012523084A JP 2013500995 A5 JP2013500995 A5 JP 2013500995A5
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- zoledronic acid
- acid
- complex
- water
- lysine
- Prior art date
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- XRASPMIURGNCCH-UHFFFAOYSA-N Zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 claims 42
- 229960004276 zoledronic acid Drugs 0.000 claims 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 21
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N DL-lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 8
- 239000004472 Lysine Substances 0.000 claims 8
- 229960003646 lysine Drugs 0.000 claims 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- KVUUQMDVROTSNI-UHFFFAOYSA-N [morpholin-4-yl(phosphono)methyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)N1CCOCC1 KVUUQMDVROTSNI-UHFFFAOYSA-N 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 239000004471 Glycine Substances 0.000 claims 5
- 235000019766 L-Lysine Nutrition 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Natural products NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 4
- 229960000643 Adenine Drugs 0.000 claims 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 229960003966 nicotinamide Drugs 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- 239000011570 nicotinamide Substances 0.000 claims 4
- 206010020583 Hypercalcaemia Diseases 0.000 claims 3
- 208000003393 Mammary Paget's Disease Diseases 0.000 claims 3
- 206010027452 Metastases to bone Diseases 0.000 claims 3
- 208000010191 Osteitis Deformans Diseases 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- 230000000240 adjuvant Effects 0.000 claims 3
- 239000002671 adjuvant Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 230000000148 hypercalcaemia Effects 0.000 claims 3
- 235000018977 lysine Nutrition 0.000 claims 3
- 239000000546 pharmaceutic aid Substances 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 230000036912 Bioavailability Effects 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 150000001413 amino acids Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 230000035514 bioavailability Effects 0.000 claims 2
- 239000006186 oral dosage form Substances 0.000 claims 2
- 230000000069 prophylaxis Effects 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims 1
- 229960004343 Alendronic acid Drugs 0.000 claims 1
- 229960002286 Clodronic Acid Drugs 0.000 claims 1
- ACSIXWWBWUQEHA-UHFFFAOYSA-N Clodronic acid Chemical compound OP(O)(=O)C(Cl)(Cl)P(O)(O)=O ACSIXWWBWUQEHA-UHFFFAOYSA-N 0.000 claims 1
- WRUUGTRCQOWXEG-UHFFFAOYSA-N Pamidronic acid Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- DKJJVAGXPKPDRL-UHFFFAOYSA-N Tiludronic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)SC1=CC=C(Cl)C=C1 DKJJVAGXPKPDRL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- MPBVHIBUJCELCL-UHFFFAOYSA-N bondronat Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 claims 1
- 229960005236 ibandronic acid Drugs 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 239000008184 oral solid dosage form Substances 0.000 claims 1
- 229960003978 pamidronic acid Drugs 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229960000759 risedronic acid Drugs 0.000 claims 1
- 229960005324 tiludronic acid Drugs 0.000 claims 1
Claims (26)
- ビスホスホン酸またはその塩と、少なくとも1種の共形成体と、を含む、分子錯体であって、前記分子錯体由来ビスホスホン酸またはその塩の生物学的利用能は、前記共形成体なしでの、前記ビスホスホン酸またはその塩の生物学的利用能を上回る、分子錯体。
- 前記ビスホスホン酸は、ゾレドロン酸、クロドロン酸、チルドロン酸、パミドロン酸、アレンドロン酸、リセドロン酸、およびイバンドロン酸から成る群から選択される、請求項1に記載の分子錯体。
- 少なくとも1種の共形成体は、アミノ酸である、請求項1に記載の分子錯体。
- 前記ビスホスホン酸は、ゾレドロン酸であって、少なくとも1種の共形成体は、アミノ酸である、請求項1に記載の分子錯体。
- 少なくとも1種の共形成体は、リシンである、請求項1−4のいずれかに記載の分子錯体。
- 請求項1−4のいずれかに記載の分子錯体と、過剰量の少なくとも1種の共形成体と、を含む、組成物。
- 前記過剰共形成体は、前記分子錯体の質量の最大100倍の量で存在する、請求項6に記載の組成物。
- 請求項7に記載の組成物と、薬学的に許容される賦形剤と、を含む、医薬組成物。
- 請求項6に記載の組成物と、薬学的に許容される賦形剤と、を含む、医薬組成物。
- 前記医薬組成物は、経口投薬形態である、請求項8に記載の医薬組成物。
- 前記医薬組成物は、経口投薬形態である、請求項9に記載の医薬組成物。
- 前記分子錯体は、結晶性である、請求項1−4のいずれかに記載の分子錯体。
- 骨粗しょう症、高カルシウム血症、癌誘発性骨転移、パジェット病の疾患状態の治療および/または予防、あるいはアジュバントまたはネオアジュバント癌療法のための医薬組成物であって、治療上有効量のビスホスホン酸またはその塩を請求項5に記載の分子錯体の形態で含む医薬組成物。
- 骨粗しょう症、高カルシウム血症、癌誘発性骨転移、パジェット病に関連する疾患状態の治療および/または予防、あるいはアジュバントまたはネオアジュバント癌療法のための医薬組成物であって、治療上有効量のビスホスホン酸またはその塩を請求項6に記載の組成物の形態で含む、医薬組成物。
- ゾレドロン酸と、水と、L−リシン、DL−リシン、ニコチンアミド、アデニン、およびゾレドロン酸塩から選択される化合物と、を含む、ゾレドロン酸の結晶性形態。
- 前記結晶性形態は、
約8.1、13.3、21.5、24.6、および25.6±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、ゾレドロ
ン酸ナトリウム、および水錯体、
約11.0、14.6、15.4、19.9、および29.4±0.2°2θに強いピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸アンモニウムおよび水錯体、
約12.2、13.0、14.1、17.1、および19.3±0.2°2θに強いピークを有する、X線粉末回折パターンを特徴とするゾレドロン酸ジアンモニウム水錯体、
約9.0、14.4、18.1、26.0、および29.6±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、L−リシン、および水錯体、
約9.6、10.7、14.3、21.4、23.5±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、L−リシン、および水錯体、
約8.3、11.8、12.3、15.8、および20.8±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、DL−リシン、および水錯体、
約9.1、14.7、18.0、21.2、および26.0±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、DL−リシン、および水錯体、
約9.7、10.8、14.4、18.9、21.4±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、DL−リシン、および水錯体、
約8.8、9.7、17.6、23.1、および26.5±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、ゾレドロン酸塩、DL−リシン、エタノール、および水錯体、
約13.6、15.9、19.7、27.9、および29.5±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、アデニン、および水錯体、または
約13.1、15.2、21.0、23.9、および26.5±0.2°2θに強いピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸、ニコチンアミド、および水錯体、
である、請求項15に記載のゾレドロン酸の結晶性形態。 - ゾレドロン酸と、グリシンと、を含む、ゾレドロン酸の結晶性形態。
- ゾレドロン酸と、グリシンと、を含む、ゾレドロン酸の分子錯体。
- 前記結晶性形態は、約10.2、17.8、19.9、22.9、および28.1±0.2°2θにピークを有する、X線粉末回折パターンを特徴とする結晶性ゾレドロン酸およびグリシン錯体である、請求項17に記載のゾレドロン酸の結晶性形態。
- ゾレドロン酸と、水と、L−リシン、DL−リシン、ニコチンアミド、アデニン、およびゾレドロン酸塩から選択される、化合物と、を含む、またはゾレドロン酸と、グリシンと、を含む、ゾレドロン酸の分子錯体。
- ゾレドロン酸、ゾレドロン酸ナトリウムおよび水錯体、
ゾレドロン酸アンモニウムおよび水錯体、
ゾレドロン酸ジアンモニア水錯体、
ゾレドロン酸、L−リシン、および水錯体、
ゾレドロン酸、DL−リシン、および水錯体、
ゾレドロン酸、ゾレドロン酸塩、DL−リシン、エタノール、および水錯体、
ゾレドロン酸、アデニン、および水錯体、
ゾレドロン酸、ニコチンアミド、および水錯体、または
ゾレドロン酸グリシン錯体、
から成る群から選択される、請求項20に記載のゾレドロン酸の分子錯体。 - ゾレドロン酸と、リシンと、を含む、分子錯体。
- ゾレドロン酸と、リシンと、を含む、結晶性形態。
- 請求項15−23のいずれかに記載の錯体と、薬学的に許容される賦形剤と、を含む、医薬組成物。
- 前記組成物は、経口固体投薬形態である、請求項24に記載の医薬組成物。
- 骨粗しょう症、高カルシウム血症、癌誘発性骨転移、パジェット病に関連する疾患状態の治療および/または予防、あるいはアジュバントまたはネオアジュバント癌療法のための、請求項24に記載の医薬組成物。
Applications Claiming Priority (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23022209P | 2009-07-31 | 2009-07-31 | |
US61/230,222 | 2009-07-31 | ||
US28803609P | 2009-12-18 | 2009-12-18 | |
US61/288,036 | 2009-12-18 | ||
US30211010P | 2010-02-06 | 2010-02-06 | |
US61/302,110 | 2010-02-06 | ||
US31287910P | 2010-03-11 | 2010-03-11 | |
US61/312,879 | 2010-03-11 | ||
US31850310P | 2010-03-29 | 2010-03-29 | |
US61/318,503 | 2010-03-29 | ||
US35954410P | 2010-06-29 | 2010-06-29 | |
US61/359,544 | 2010-06-29 | ||
PCT/US2010/043892 WO2011014766A2 (en) | 2009-07-31 | 2010-07-30 | Crystallization method and bioavailability |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2013500995A JP2013500995A (ja) | 2013-01-10 |
JP2013500995A5 true JP2013500995A5 (ja) | 2013-09-12 |
JP5852569B2 JP5852569B2 (ja) | 2016-02-03 |
Family
ID=43527595
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012523084A Expired - Fee Related JP5852569B2 (ja) | 2009-07-31 | 2010-07-30 | 結晶化方法および生物学的利用能 |
Country Status (20)
Country | Link |
---|---|
US (5) | US8399023B2 (ja) |
EP (2) | EP2459176B1 (ja) |
JP (1) | JP5852569B2 (ja) |
KR (1) | KR101813728B1 (ja) |
CN (1) | CN102573809B (ja) |
AU (2) | AU2010278860B2 (ja) |
CA (1) | CA2769633C (ja) |
CY (1) | CY1121952T1 (ja) |
DK (1) | DK2459176T3 (ja) |
ES (1) | ES2650665T3 (ja) |
HR (1) | HRP20171755T1 (ja) |
HU (1) | HUE034784T2 (ja) |
IL (1) | IL217828B (ja) |
IN (1) | IN2012DN01216A (ja) |
LT (1) | LT2459176T (ja) |
NO (1) | NO2459176T3 (ja) |
PL (1) | PL2459176T3 (ja) |
PT (1) | PT2459176T (ja) |
SI (1) | SI2459176T1 (ja) |
WO (1) | WO2011014766A2 (ja) |
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DK2459176T3 (en) | 2009-07-31 | 2017-12-04 | Gruenenthal Gmbh | Crystallization process and bioavailability |
EP2458996B1 (en) * | 2009-07-31 | 2016-09-07 | Thar Pharmaceuticals, Inc. | Novel oral forms of a phosphonic acid derivative |
CA2826548A1 (en) * | 2010-02-06 | 2011-08-11 | Thar Pharmaceuticals, Inc. | Crystallization method and bioavailability |
WO2012071517A2 (en) * | 2010-11-24 | 2012-05-31 | Thar Pharmaceuticals, Inc. | Novel crystalline forms |
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-
2010
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