LT4888B - Naujos natrio alendronato hidratinės formos, jų pagaminimo būdai ir jų farmacinės kompozicijos - Google Patents
Naujos natrio alendronato hidratinės formos, jų pagaminimo būdai ir jų farmacinės kompozicijos Download PDFInfo
- Publication number
- LT4888B LT4888B LT2001016A LT2001016A LT4888B LT 4888 B LT4888 B LT 4888B LT 2001016 A LT2001016 A LT 2001016A LT 2001016 A LT2001016 A LT 2001016A LT 4888 B LT4888 B LT 4888B
- Authority
- LT
- Lithuania
- Prior art keywords
- hydroxybutylidene
- amino
- compound according
- compound
- sodium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 94
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229940062527 alendronate Drugs 0.000 title description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 110
- 229960004343 alendronic acid Drugs 0.000 claims abstract description 109
- 238000002360 preparation method Methods 0.000 claims abstract description 59
- 210000000988 bone and bone Anatomy 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 129
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 87
- 239000011734 sodium Substances 0.000 claims description 45
- 229910052708 sodium Inorganic materials 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 41
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 24
- 150000004682 monohydrates Chemical class 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- DUYCFMAOEDAKDN-UHFFFAOYSA-M sodium (4-amino-1-hydroxy-1-phosphonobutyl)-hydroxyphosphinate hydrate Chemical compound O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O DUYCFMAOEDAKDN-UHFFFAOYSA-M 0.000 claims description 16
- 150000005846 sugar alcohols Polymers 0.000 claims description 16
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- CAKRAHQRJGUPIG-UHFFFAOYSA-M sodium;[4-azaniumyl-1-hydroxy-1-[hydroxy(oxido)phosphoryl]butyl]-hydroxyphosphinate Chemical compound [Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O CAKRAHQRJGUPIG-UHFFFAOYSA-M 0.000 claims description 9
- 239000002274 desiccant Substances 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000004683 dihydrates Chemical class 0.000 claims description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 80
- 230000003993 interaction Effects 0.000 claims 25
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 14
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 7
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical group O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 claims 4
- 239000011877 solvent mixture Substances 0.000 claims 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 2
- 230000001174 ascending effect Effects 0.000 claims 1
- KHDOTPVDSFBNMG-UHFFFAOYSA-N ethanol;pyridine Chemical compound CCO.C1=CC=NC=C1 KHDOTPVDSFBNMG-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 abstract description 3
- 238000010348 incorporation Methods 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- DCSBSVSZJRSITC-UHFFFAOYSA-M alendronate sodium trihydrate Chemical compound O.O.O.[Na+].NCCCC(O)(P(O)(O)=O)P(O)([O-])=O DCSBSVSZJRSITC-UHFFFAOYSA-M 0.000 description 88
- AQAZLLYAEFBJMU-UHFFFAOYSA-N (4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid;hydrate Chemical compound O.NCCCC(O)(P(O)(O)=O)P(O)(O)=O AQAZLLYAEFBJMU-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000010992 reflux Methods 0.000 description 18
- 238000001035 drying Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 239000002178 crystalline material Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 9
- 238000002083 X-ray spectrum Methods 0.000 description 8
- 238000001757 thermogravimetry curve Methods 0.000 description 8
- 230000004580 weight loss Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- MCWQUGNJOSKXRB-UHFFFAOYSA-N (4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid;trihydrate Chemical compound O.O.O.NCCCC(O)(P(O)(O)=O)P(O)(O)=O MCWQUGNJOSKXRB-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 3
- 239000002106 nanomesh Substances 0.000 description 3
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000010191 Osteitis Deformans Diseases 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 208000027868 Paget disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 208000027202 mammary Paget disease Diseases 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- -1 sodium alkoxide Chemical class 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 208000006386 Bone Resorption Diseases 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000012052 hydrophilic carrier Substances 0.000 description 1
- 239000012051 hydrophobic carrier Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- WZWGGYFEOBVNLA-UHFFFAOYSA-N sodium;dihydrate Chemical compound O.O.[Na] WZWGGYFEOBVNLA-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9831398P | 1998-08-27 | 1998-08-27 | |
| US12974399P | 1999-04-16 | 1999-04-16 | |
| US14446199P | 1999-07-19 | 1999-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT2001016A LT2001016A (en) | 2001-10-25 |
| LT4888B true LT4888B (lt) | 2002-02-25 |
Family
ID=27378576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT2001016A LT4888B (lt) | 1998-08-27 | 2001-02-26 | Naujos natrio alendronato hidratinės formos, jų pagaminimo būdai ir jų farmacinės kompozicijos |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6281381B1 (ja) |
| EP (1) | EP1107974B1 (ja) |
| JP (2) | JP2002523514A (ja) |
| KR (2) | KR20010079701A (ja) |
| AT (1) | ATE334993T1 (ja) |
| AU (1) | AU5698899A (ja) |
| BG (1) | BG65329B1 (ja) |
| BR (1) | BR9913472A (ja) |
| CA (1) | CA2341459A1 (ja) |
| CZ (1) | CZ2001629A3 (ja) |
| DE (1) | DE69932620T2 (ja) |
| DK (1) | DK1107974T3 (ja) |
| EA (1) | EA002739B1 (ja) |
| EE (1) | EE04552B1 (ja) |
| ES (1) | ES2270613T3 (ja) |
| HR (1) | HRP20010129A2 (ja) |
| HU (1) | HUP0203078A3 (ja) |
| IL (1) | IL141423A (ja) |
| IS (1) | IS5864A (ja) |
| LT (1) | LT4888B (ja) |
| LV (1) | LV12720B (ja) |
| NO (1) | NO20010957L (ja) |
| NZ (1) | NZ510682A (ja) |
| PL (1) | PL346347A1 (ja) |
| PT (1) | PT1107974E (ja) |
| RO (1) | RO122854B1 (ja) |
| SI (1) | SI20581B (ja) |
| SK (1) | SK2482001A3 (ja) |
| WO (1) | WO2000012517A1 (ja) |
| YU (1) | YU14701A (ja) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1406910B1 (fr) * | 2001-07-16 | 2010-01-13 | Universite Paris 13 | Procedes de preparation de derives de bisphosphonates |
| GB2383042A (en) | 2001-10-18 | 2003-06-18 | Cipla Ltd | Amorphous alendronate sodium |
| US20040052843A1 (en) * | 2001-12-24 | 2004-03-18 | Lerner E. Itzhak | Controlled release dosage forms |
| KR100897837B1 (ko) * | 2001-12-24 | 2009-05-15 | 테바 파마슈티컬 인더스트리즈 리미티드 | 분말 또는 과립 물질의 압착된 환상체 내에 싸인 활성성분의 코어 정제를 갖는 제형과, 이의 제조 방법 및 툴링 |
| ITMI20020146A1 (it) * | 2002-01-29 | 2003-07-29 | Lyogen Ltd | Alendronato monosodico amorfo e processo per la sua preparazione |
| US20030195171A1 (en) * | 2002-04-05 | 2003-10-16 | Daifotis Anastasia G. | Method for inhibiting bone resorption with an alendronate and vitamin D formulation |
| US20080249068A1 (en) * | 2002-09-05 | 2008-10-09 | Deluca Hector F | Method of Extending the Dose Range of Vitamin D Compounds |
| WO2005035542A1 (en) * | 2003-10-14 | 2005-04-21 | Pliva-Istrazivanje I Razvoj D.O.O. | Solid-state form of alendronate sodium and preparation thereof |
| US20050181043A1 (en) * | 2004-02-12 | 2005-08-18 | Indranil Nandi | Alendronate salt tablet compositions |
| US20050261250A1 (en) * | 2004-05-19 | 2005-11-24 | Merck & Co., Inc., | Compositions and methods for inhibiting bone resorption |
| SMAP200600038A (it) | 2004-05-24 | 2006-12-27 | Procter & Gamble | Forme di dosaggio di bisfosfonati |
| CZ296937B6 (cs) * | 2004-09-02 | 2006-07-12 | Zentiva, A. S | Trisodná sul kyseliny 4-amino-1-hydroxybutyliden-1,1-bisfosfonové |
| JP5297653B2 (ja) * | 2004-10-29 | 2013-09-25 | サンド・アクチエンゲゼルシヤフト | グラチラマーの製造法 |
| US20060134190A1 (en) * | 2004-12-16 | 2006-06-22 | Banner Pharmacaps Inc. | Formulations of bisphosphonate drugs with improved bioavailability |
| CZ297262B6 (cs) * | 2004-12-28 | 2006-10-11 | Zentiva, A. S. | Trisodná sul kyseliny 4-amino-1-hydroxybutyliden-1,1-bisfosfonové |
| US8003820B2 (en) * | 2005-10-20 | 2011-08-23 | Dr. Reddy's Laboratories Limited | Process for preparing bisphosphonic acids |
| AR058168A1 (es) * | 2005-11-07 | 2008-01-23 | Merck & Co Inc | Sintesis del alendronato de sodio trihidratado |
| NZ576347A (en) * | 2006-10-27 | 2011-10-28 | Signal Pharm Llc | Solid forms comprising 4-[9-(tetrahydro-furan-3-yl)-8-(2,4,6-trifluoro-phenylamino)-9h-purin-2-ylamino]-cyclohexan-1-ol, compositions thereof, and use therewith |
| ES2392890T3 (es) * | 2006-11-22 | 2012-12-14 | Eisai R&D Management Co., Ltd. | Sal sódica de un compuesto disacarídico, procedimiento para la producción de la misma y uso de la misma |
| US20090118238A1 (en) * | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090076144A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched bazedoxifene |
| US20090170815A1 (en) * | 2007-12-28 | 2009-07-02 | Roxane Laboratories Incorporated. | Alendronate oral liquid formulations |
| WO2011054182A1 (zh) * | 2009-11-03 | 2011-05-12 | Liu Li | 丹参酮ⅱa磺酸钠水合物及其制备方法和用途 |
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| US4407761A (en) | 1980-04-28 | 1983-10-04 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of ω-amino-1-hydroxyalkylidene-1,1-bisphosphonic acid |
| US4621077A (en) | 1982-04-15 | 1986-11-04 | Istituto Gentili S.P.A. | Pharmacologically active biphosphonates, process for the preparation thereof and pharmaceutical compositions therefrom |
| US4705651A (en) | 1984-10-29 | 1987-11-10 | Istituto Gentili S.P.A. | Process for the preparation of diphosphonic acids |
| US4922007A (en) | 1989-06-09 | 1990-05-01 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof |
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- 1999-08-27 EP EP99944004A patent/EP1107974B1/en not_active Expired - Lifetime
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- 1999-08-27 CA CA002341459A patent/CA2341459A1/en not_active Abandoned
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- 1999-08-27 HU HU0203078A patent/HUP0203078A3/hu unknown
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- 1999-08-27 EE EEP200100126A patent/EE04552B1/xx not_active IP Right Cessation
- 1999-08-27 KR KR1020017002535A patent/KR20010079701A/ko active Search and Examination
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- 1999-08-27 SK SK248-2001A patent/SK2482001A3/sk unknown
- 1999-08-27 BR BR9913472-1A patent/BR9913472A/pt not_active Application Discontinuation
- 1999-08-27 SI SI9920070A patent/SI20581B/sl not_active IP Right Cessation
- 1999-08-27 JP JP2000567539A patent/JP2002523514A/ja not_active Withdrawn
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