NO329923B1 - Selektiv krystallisering av natrium 3-pyridyl-1-hydroksyetyliden-1,1-bisfosfonsyre som hemipentahydrat eller monohydrat - Google Patents
Selektiv krystallisering av natrium 3-pyridyl-1-hydroksyetyliden-1,1-bisfosfonsyre som hemipentahydrat eller monohydrat Download PDFInfo
- Publication number
- NO329923B1 NO329923B1 NO20023645A NO20023645A NO329923B1 NO 329923 B1 NO329923 B1 NO 329923B1 NO 20023645 A NO20023645 A NO 20023645A NO 20023645 A NO20023645 A NO 20023645A NO 329923 B1 NO329923 B1 NO 329923B1
- Authority
- NO
- Norway
- Prior art keywords
- monohydrate
- hemipentahydrate
- hydroxyethylidene
- pyridyl
- aqueous solution
- Prior art date
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 125000005644 linolenyl group Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- UEHLXXJAWYWUGI-UHFFFAOYSA-M nitromersol Chemical compound CC1=CC=C([N+]([O-])=O)C2=C1O[Hg]2 UEHLXXJAWYWUGI-UHFFFAOYSA-M 0.000 description 1
- 229940118238 nitromersol Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 235000014786 phosphorus Nutrition 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940026199 risedronate sodium hemi-pentahydrate Drugs 0.000 description 1
- 229940026196 risedronate sodium monohydrate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- KLQNARDFMJRXSF-UHFFFAOYSA-M sodium;hydroxy-(1-hydroxy-1-phosphono-2-pyridin-3-ylethyl)phosphinate;hydrate Chemical compound O.[Na+].OP(=O)(O)C(P(O)([O-])=O)(O)CC1=CC=CN=C1 KLQNARDFMJRXSF-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17950500P | 2000-02-01 | 2000-02-01 | |
| PCT/US2001/003336 WO2001056983A2 (en) | 2000-02-01 | 2001-02-01 | Selective crystallization of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid sodium as the hemipentahydrate or monohydrate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20023645D0 NO20023645D0 (no) | 2002-07-31 |
| NO20023645L NO20023645L (no) | 2002-10-01 |
| NO329923B1 true NO329923B1 (no) | 2011-01-24 |
Family
ID=22656866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023645A NO329923B1 (no) | 2000-02-01 | 2002-07-31 | Selektiv krystallisering av natrium 3-pyridyl-1-hydroksyetyliden-1,1-bisfosfonsyre som hemipentahydrat eller monohydrat |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6410520B2 (he) |
| EP (1) | EP1252170B2 (he) |
| JP (5) | JP2003521532A (he) |
| KR (1) | KR100549038B1 (he) |
| CN (1) | CN1183148C (he) |
| AR (1) | AR030187A1 (he) |
| AT (1) | ATE273984T1 (he) |
| AU (1) | AU784307B2 (he) |
| BR (1) | BRPI0107921B8 (he) |
| CA (1) | CA2399976C (he) |
| CO (1) | CO5271720A1 (he) |
| CZ (1) | CZ303400B6 (he) |
| DE (1) | DE60104978T3 (he) |
| DK (1) | DK1252170T4 (he) |
| ES (1) | ES2225481T5 (he) |
| HK (1) | HK1051046B (he) |
| HU (1) | HU230494B1 (he) |
| IL (2) | IL150511A0 (he) |
| MA (1) | MA25654A1 (he) |
| MX (1) | MXPA02007417A (he) |
| MY (1) | MY119968A (he) |
| NO (1) | NO329923B1 (he) |
| NZ (1) | NZ519966A (he) |
| PE (1) | PE20011061A1 (he) |
| PL (1) | PL207589B1 (he) |
| PT (1) | PT1252170E (he) |
| RU (1) | RU2236415C2 (he) |
| SA (1) | SA01220066B1 (he) |
| SK (1) | SK287884B6 (he) |
| TR (1) | TR200402435T4 (he) |
| TW (1) | TWI310769B (he) |
| WO (1) | WO2001056983A2 (he) |
| ZA (1) | ZA200205090B (he) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6410520B2 (en) * | 2000-02-01 | 2002-06-25 | The Procter & Gamble Company | Selective crystallization of 3-pyridyl-1-hydroxyethylidene-1, 1-bisphosphonic acid sodium as the hemipentahydrate or monohydrate |
| EP1923052A1 (en) | 2002-04-11 | 2008-05-21 | Teva Pharmaceutical Industries Ltd | Novel polymorphs and pseudopolymorphs of risedronate sodium |
| KR100937184B1 (ko) * | 2002-04-11 | 2010-01-19 | 테바 파마슈티컬 인더스트리즈 리미티드 | 리세드로네이트 나트륨의 신규한 동질이상체 및 유사동질이상체 |
| CZ293349B6 (cs) * | 2002-10-25 | 2004-04-14 | Léčiva, A.S. | Nová krystalická forma sodné soli kyseliny 3-pyridyl-1-hydroxyethyliden-1,1-bisfosfonové |
| DE602004015407D1 (de) * | 2003-01-17 | 2008-09-11 | Teva Pharma | Verfahren zur reduzierung des eisengehalts bei risedronat natrium |
| HUP0300227A2 (hu) * | 2003-01-28 | 2004-09-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás nagy tisztaságú 2-szubsztituált -1-(hidroxi-etilidén)-1,1-biszfoszfonsavak és sóik előállítására |
| BRPI0413067A (pt) * | 2003-07-30 | 2006-10-17 | Procter & Gamble | processo para controlar a estrututra cristalina do risedronato |
| CZ298639B6 (cs) * | 2004-02-05 | 2007-12-05 | Zentiva, A. S. | Krystalická forma risedronátu monosodného |
| US7618953B2 (en) * | 2004-02-26 | 2009-11-17 | Zentiva, A.S. | Amorphous forms of risedronate monosodium |
| WO2005107714A2 (en) * | 2004-05-05 | 2005-11-17 | Alkermes Controlled Therapeutics, Inc. | Method of forming microparticles that include a bisphosphonate and a polymer |
| KR20080083068A (ko) | 2004-05-24 | 2008-09-12 | 더 프록터 앤드 갬블 캄파니 | 킬레이팅제를 함유하는 비스포스포네이트의 고형의 장용 경구 투여 형태 |
| US7358361B2 (en) * | 2004-10-08 | 2008-04-15 | The Board Of Trustees Of The University Of Illinois | Biophosphonate compounds and methods for bone resorption diseases, cancer, bone pain, immune disorders, and infectious diseases |
| US8012949B2 (en) * | 2004-10-08 | 2011-09-06 | The Board Of Trustees Of The University Of Illinois | Bisphosphonate compounds and methods with enhanced potency for multiple targets including FPPS, GGPPS, and DPPS |
| CA2590046A1 (en) * | 2004-11-09 | 2006-05-18 | Jubilant Organosys Limited | Process for preparing a pure polymorphic form of 3-pyridyl-1-hydroxyethylidine-1,1-bisphosphonic acid sodium salt |
| PL199215B1 (pl) * | 2004-12-28 | 2008-08-29 | Politechnika Gdanska | Sposób wytwarzania kwasu [1-hydroksy-2-(3-pirydylo)etylidenobisfosfonowego] oraz jego soli monosodowej dwu i pół wodnej |
| CA2606879A1 (en) * | 2005-05-06 | 2007-03-01 | Medichem, S.A. | Process of making geminal bisphosphonic acids and pharmaceutically acceptable salts and/or hydrates thereof |
| EP1891081B1 (en) * | 2005-06-13 | 2014-08-20 | Jubilant Organosys Limited | Process for producing bisphosphonic acids and forms thereof |
| AR054673A1 (es) * | 2005-07-28 | 2007-07-11 | Gador Sa | Una forma cristalina del acido zoledronico, un proceso para su obtencion y la composicion farmaceutica que la comprende |
| GB0519891D0 (en) * | 2005-09-30 | 2005-11-09 | Pliva Hrvatska D O O | Pharmaceutically acceptable salts and hydrates |
| WO2007042048A2 (en) * | 2005-10-11 | 2007-04-19 | Sandoz A/S | Method for preparing crystalline sodium risedronate |
| EP1775302A1 (en) * | 2005-10-11 | 2007-04-18 | Sandoz A/S | Method for preparing crystalline sodium risedronate |
| WO2007083243A2 (en) * | 2006-01-20 | 2007-07-26 | Aurobindo Pharma Limited | An improved process for the preparation of risedronate sodium hemi-pentahydrate |
| CA2646334A1 (en) * | 2006-03-17 | 2007-09-27 | The Board Of Trustees Of The University Of Illinois | Bisphosphonate compounds and methods |
| JP5354858B2 (ja) * | 2006-05-09 | 2013-11-27 | 株式会社Ａｄｅｋａ | スルホンアミド化合物の金属塩を含有するポリエステル樹脂組成物 |
| KR20090005206A (ko) | 2006-05-11 | 2009-01-12 | 인드-스위프트 래버러토리즈 리미티드 | 순수한 리세드론산 또는 염의 제조 방법 |
| CA2656053A1 (en) * | 2006-07-03 | 2008-01-10 | Generics [Uk] Limited | Novel process for the preparation of bisphosphonic acids |
| WO2008065542A2 (en) * | 2006-09-22 | 2008-06-05 | Orchid Chemicals & Pharmaceuticals Ltd. | An improved process for the preparation of risedronate sodium |
| WO2008044245A2 (en) * | 2006-10-10 | 2008-04-17 | Matrix Laboratories Ltd | A process for the preparation of risedronate sodium hemipentahydrate |
| KR100828705B1 (ko) | 2006-12-04 | 2008-05-09 | 씨제이제일제당 (주) | 리세드론산 나트륨 수화물의 제조방법 |
| KR100775440B1 (ko) | 2006-12-20 | 2007-11-12 | 동우신테크 주식회사 | 리세드로네이트 나트륨 헤미펜타히드레이트의 제조방법 |
| KR100798855B1 (ko) * | 2007-02-14 | 2008-01-28 | 주식회사 엔지켐 | 리세드론산 나트륨 헤미펜타하이드레이트의 제조방법 |
| KR100812528B1 (ko) * | 2007-04-12 | 2008-03-12 | 보령제약 주식회사 | 리세드로네이트 나트륨염의 헤미펜타히드레이트의 선택적결정화방법 |
| WO2008152518A2 (en) * | 2007-05-16 | 2008-12-18 | Actavis Group Ptc Ehf | Process for the preparation of risedronic acid or risedronate sodium |
| WO2009050731A2 (en) * | 2007-06-20 | 2009-04-23 | Alkem Laboratories Ltd | Novel process for preparing risedronic acid |
| DE102007030370A1 (de) | 2007-06-29 | 2009-01-02 | Ratiopharm Gmbh | Essigsäure-Solvate von Risedronat, Polymorph hiervon, deren Herstellung und Verwendung sowie pharmazeutische Zusammensetzung, enthaltend diese |
| KR100925835B1 (ko) * | 2007-12-07 | 2009-11-06 | 동우신테크 주식회사 | 리세드로네이트 나트륨 무수물 및 수화물의 제조방법 |
| KR101010062B1 (ko) | 2008-04-11 | 2011-01-21 | 주식회사 대희화학 | 증발 결정화를 이용한 결정상 리세드로네이트 모노소듐모노하이드레이트의 제조방법 |
| US8629178B2 (en) * | 2009-11-03 | 2014-01-14 | Li Liu | Sodium tanshinone IIA sulfonate hydrate and preparation method and use thereof |
| SI3319970T1 (sl) * | 2015-07-08 | 2019-12-31 | Daiichi Sankyo Company | Pirido-oksazinon derivati kot TNAP inhibitorji |
| EP3901190B1 (en) | 2017-06-06 | 2023-08-30 | Mitsubishi Chemical Corporation | Polyorganosiloxane-containing graft copolymer, thermoplastic resin composition, and molded article |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2534391C2 (de) | 1975-08-01 | 1983-01-13 | Henkel KGaA, 4000 Düsseldorf | 1-Hydroxy-3-aminoalkan-1,1-diphosphonsäuren |
| US4447256A (en) | 1977-07-20 | 1984-05-08 | Nissan Chemical Industries, Ltd. | N-(Unsubstituted or substituted pyridyl)aminomethylene-diphosphonic acids, herbicidal compositions containing same, their use for herbicides, and process for preparing same |
| DE2745083C2 (de) | 1977-10-07 | 1985-05-02 | Henkel KGaA, 4000 Düsseldorf | Hydroxydiphosphonsäuren und Verfahren zu deren Herstellung |
| US4330537A (en) | 1977-12-07 | 1982-05-18 | The Procter & Gamble Company | Compositions for inhibiting mobilization of calcium phosphate in animal tissue |
| JPS5598193A (en) | 1979-01-22 | 1980-07-25 | Nissan Chem Ind Ltd | Methylenediphosphonic acid derivative and herbicide comprising it as active constituent |
| DE2943498C2 (de) | 1979-10-27 | 1983-01-27 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur Herstellung von 3-Amino-1-hydroxypropan-1,1-diphosphonsäure |
| DE3016289A1 (de) | 1980-04-28 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren |
| US4304734A (en) | 1980-10-16 | 1981-12-08 | Vysoka Skola Chemicko-Technologicka | 6-Amino-1-hydroxyhexylidene diphosphonic acid, salts and a process for production thereof |
| DE3151038A1 (de) | 1981-12-23 | 1983-07-28 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von 3-amino-1-hydroxypropan-1,1-diphosphonsaeure |
| IT1201087B (it) | 1982-04-15 | 1989-01-27 | Gentili Ist Spa | Bifosfonati farmacologicamente attivi,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| DE3428524A1 (de) * | 1984-08-02 | 1986-02-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| IT1196315B (it) | 1984-10-29 | 1988-11-16 | Gentili Ist Spa | Procedimento per la preparazione di acidi difosfonici |
| PH27078A (en) * | 1984-12-21 | 1993-02-01 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonates |
| IL77243A (en) | 1984-12-21 | 1996-11-14 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds |
| IT1187750B (it) | 1985-10-15 | 1987-12-23 | Eurand Spa | Procedimento per la preparazione di compresse,anche a rilascio prolungato,di iscsorbide-5-mononitrato stabilizzato e formulazioni cosi' ottenute |
| DE3540150A1 (de) | 1985-11-13 | 1987-05-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| GB8531071D0 (en) | 1985-12-17 | 1986-01-29 | Boots Co Plc | Therapeutic compound |
| EP0239015B1 (en) | 1986-03-24 | 1991-10-16 | Nippon Kayaku Kabushiki Kaisha | Process for producing 1-beta-d-arabinofuranosylcytosine-5'-stearylphosphate monosodium salt and monohydrate thereof, and pharmaceutical composition containing the latter |
| DE3623397A1 (de) | 1986-07-11 | 1988-01-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3626058A1 (de) | 1986-08-01 | 1988-02-11 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| EP0275821B1 (de) | 1986-11-21 | 1992-02-26 | Ciba-Geigy Ag | Neue substituierte Alkandiphosphonsäuren |
| DE3700772A1 (de) | 1987-01-13 | 1988-07-21 | Inst Khim Kinetiki I Gorenija | Verfahren zur herstellung von i-funktionellsubstituierten alkyliden-i,i-diphosphonsaeuren und deren gemischen |
| US5091525A (en) | 1987-10-07 | 1992-02-25 | Eli Lilly And Company | Monohydrate and DMF solvates of a new carbacephem antibiotic |
| US5035898A (en) | 1987-11-27 | 1991-07-30 | Schering Corporation | Potassium/magnesium supplement |
| US5110807A (en) | 1988-12-01 | 1992-05-05 | Ciba-Geigy Corporation | Araliphatylaminoalkanediphosphonic acids |
| DE3822650A1 (de) | 1988-07-05 | 1990-02-01 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3917153A1 (de) | 1989-05-26 | 1990-11-29 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| MX21452A (es) | 1989-07-07 | 1994-01-31 | Ciba Geigy Ag | Preparaciones farmaceuticas que se administran en forma topica. |
| MX21453A (es) | 1989-07-07 | 1994-01-31 | Ciba Geigy Ag | Preparaciones farmaceuticas que se administran en forma topica. |
| TW208013B (he) | 1990-03-01 | 1993-06-21 | Daiichi Co Ltd | |
| AU8495091A (en) | 1990-08-21 | 1992-03-17 | Upjohn Company, The | Bisphosphonic acid derivatives as anti-arthritic agents |
| US5039819A (en) | 1990-09-18 | 1991-08-13 | Merck & Co., Inc. | Diphosphonate intermediate for preparing an antihypercalcemic agent |
| IT1246992B (it) | 1991-01-08 | 1994-12-12 | Gentili Ist Spa | Procedimento per la preparazione di acidi difosfonici e loro sali |
| DK58291D0 (da) | 1991-04-02 | 1991-04-02 | Novo Nordisk As | Krystalinsk stof og dets fremstilling |
| KR100274734B1 (ko) * | 1991-11-22 | 2000-12-15 | 제이코버스 코넬리스 레이서 | 리제드로네이트 지연-방출성 조성물 |
| SE501389C2 (sv) | 1992-04-24 | 1995-01-30 | Leiras Oy | Farmaceutiskt preparat och förfarande för dess framställning |
| US5317015A (en) | 1992-05-01 | 1994-05-31 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Azacyclic bisphosphonates as anticholesterolemic agents |
| DK0647649T3 (da) | 1992-06-23 | 1999-07-26 | Yamanouchi Pharma Co Ltd | Ny krystal af heterocyklisk bis(phosphonsyre)monohydratderivat |
| FR2694558B1 (fr) * | 1992-08-05 | 1994-10-28 | Sanofi Elf | Monohydrate du sel disodique de l'acide 4-chlorophénylthiométhylène bisphosphonique, sa préparation, les compositions pharmaceutiques en contenant. |
| US5312925A (en) | 1992-09-01 | 1994-05-17 | Pfizer Inc. | Monohydrate of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one-hydrochloride |
| PL311278A1 (en) | 1993-04-28 | 1996-02-05 | Pfizer | Crystalline glycosidal spirostantil monohydrate |
| TW257765B (he) * | 1993-08-25 | 1995-09-21 | Merck & Co Inc | |
| US5510517A (en) | 1993-08-25 | 1996-04-23 | Merck & Co., Inc. | Process for producing N-amino-1-hydroxy-alkylidene-1,1-bisphosphonic acids |
| US5580977A (en) | 1995-03-01 | 1996-12-03 | Eli Lilly And Company | Process for preparing loracarbef monohydrate |
| TW393488B (en) | 1995-04-20 | 2000-06-11 | Merck & Co Inc | Process for making 1-hydrox-ybisphosphonates |
| US5656288A (en) * | 1995-06-08 | 1997-08-12 | Sanofi Winthrop, Inc. | Stable pharmaceutical compositions containing tiludronate hydrates and process for producing the pharmaceutical compositions |
| JP2000504718A (ja) | 1996-02-14 | 2000-04-18 | バインダーマン，イザク | 骨吸収を予防するための局所用ビスホスホネート |
| AU712710B2 (en) | 1996-05-17 | 1999-11-11 | Merck Sharp & Dohme Corp. | Effervescent bisphosphonate formulation |
| US5730715A (en) | 1996-06-14 | 1998-03-24 | Becton Dickinson And Company | Method for the iontophoretic administration of bisphosphonates |
| KR100192215B1 (ko) | 1996-09-03 | 1999-06-15 | 강재헌 | 3-아미노-1-히드록시프로판-1,1-디포스폰산의 제조방법 |
| IL133405A0 (en) * | 1997-06-11 | 2001-04-30 | Procter & Gamble | Film-coated tablet for improved upper gastrointestinal tract safety |
| DE69827079T2 (de) * | 1997-07-15 | 2005-09-08 | Gador S.A. | Kristalline Form von N,N-dimethyl-3-amino-1-hydroxypropan-1,1-Diphosphonsäure Mononatriumsalz Monohydrat und ein Verfahren zu ihrer Herstellung |
| US6432932B1 (en) * | 1997-07-22 | 2002-08-13 | Merck & Co., Inc. | Method for inhibiting bone resorption |
| EP1089750A4 (en) * | 1998-06-24 | 2001-10-04 | Merck & Co Inc | COMPOSITIONS AND METHODS FOR INHIBITING BONE RESORPTION. |
| WO2001045636A1 (en) * | 1999-12-20 | 2001-06-28 | Merck & Co., Inc. | Pharmaceutical kit |
| US6410520B2 (en) * | 2000-02-01 | 2002-06-25 | The Procter & Gamble Company | Selective crystallization of 3-pyridyl-1-hydroxyethylidene-1, 1-bisphosphonic acid sodium as the hemipentahydrate or monohydrate |
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