SI20581B - Nove hidratne oblike natrijevega alendronata, postopki za njihovo pridobivanje in ustrezne farmacevtske učinkovine - Google Patents
Nove hidratne oblike natrijevega alendronata, postopki za njihovo pridobivanje in ustrezne farmacevtske učinkovine Download PDFInfo
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- SI20581B SI20581B SI9920070A SI9920070A SI20581B SI 20581 B SI20581 B SI 20581B SI 9920070 A SI9920070 A SI 9920070A SI 9920070 A SI9920070 A SI 9920070A SI 20581 B SI20581 B SI 20581B
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- Prior art keywords
- compound according
- hydroxybutylidene
- amino
- bisphosphonic acid
- equivalents
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 15
- 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 7
- 229960004343 alendronic acid Drugs 0.000 title claims abstract 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 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 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 206010065687 Bone loss Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000004682 monohydrates Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 150000004684 trihydrates Chemical class 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 abstract 1
- 208000020084 Bone disease Diseases 0.000 abstract 1
- 230000024279 bone resorption Effects 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
Classifications
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- 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
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- 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)
Abstract
Predstavljene so nove hidratne oblike natrijevegaalendronata z vsebnostjo vode med približno enimin približno dvanajstimi procenti in postopki zanjihovo pridobivanje. Predstavljene so tudi nove kristaline oblike natrijevega alendronata B, D, E,F, G, in H in postopki za njihovo pridobivanje. Te nove oblike natrijevega alendronata so primerne kot sestavine farmacevtskih učinkovin za zdravljenje pospešene kostne resorpcije pri boleznih kosti.
Claims (18)
1 Sl 20581 NOVE HIDRATNE OBLIKE NATRIJEVEGA ALENDRONATA, POSTOPKI ZA NJIHOVO PRIDOBIVANJE IN NJIHOVI FARMACEVTSKI SESTAVKI PATENTNI ZAHTEVKI 1. Spojina mononatrijeva sol 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline z vsebnostjo vode 5.1% do 7.0%.
2. Kristalen mononatrijev alendronat monohidrat po zahtevku 1.
3. Spojina po patentnem zahtevku 1, značilna po tem, da ima vrhove v rentgenskem difraktogramu praškastega vzorca pri vrednostih dva theta 12.7± 0.2, 16.2±0.2, 17.3±0.2, 17.6±0.2, 24.8+0.2 in 25.5±0.2 stopinj.
4. Metoda za pripravo spojine po kateremkoli patentnem zahtevku od 1 do 3, ki obsega korake: a) obdelavo enega ekvivalenta 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline z enim ekvivalentom natrijeve baze v alkanolu z 1 do 4 atomi ogljika, ki obsega 5 do 200 ekvivalentov vode; in b) izoliranje omenjene spojine po kateremkoli patentnem zahtevku od 1 do 3.
5. Metoda za pripravo spojine po kateremkoli patentnem zahtevku od 1 do 3, ki obsega korake: a) obdelavo mononatrijeve soli 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline v alkanolu z 1 do 4 atomi ogljika z 20-40 ekvivalenti vode; in b) izoliranje omenjene spojine po kateremkoli patentnem zahtevku od 1 do 3.
6. Metoda za pripravo spojine po kateremkoli patentnem zahtevku od 1 do 3, ki obsega korake: 2 a) obdelavo dinatrijeve soli 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline v alkanolu z 1 do 4 atomi ogljika z 20-40 ekvivalenti vode in enim ekvivalentom alendronske kisline; in b) izoliranje omenjene spojine po kateremkoli patentnem zahtevku od 1 do 3.
7. Metoda za pripravo spojine po kateremkoli patentnem zahtevku od 1 do 3, ki obsega korake: a) obdelavo trinatrijeve soli 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline v alkanolu z 1 do 4 atomi ogljika z 20-40 ekvivalenti vode in dvema ekvivalentoma alendronske kisline; in b) izoliranje omenjene spojine po kateremkoli patentnem zahtevku od 1 do 3.
8. Metoda za pripravo spojine po kateremkoli patentnem zahtevku od 1 do 3, ki obsega korake: a) obdelavo tetranatrijeve soli 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline v alkanolu z 1 do 4 atomi ogljika z 20-40 ekvivalenti vode in tremi ekvivalenti alendronske kisline; in b) izoliranje omenjene spojine po kateremkoli patentnem zahtevku od 1 do 3.
9. Metoda po patentnem zahtevku 5, 6, 7 ali 8, pri čemer je nižji alkanol pri stopnji a) etanol.
10. Metoda po patentnem zahtevku 5, pri čemer je natrijeva sol 4-amino-1-hidroksibutiliden-1,1- bisfosfonske kisline mononatrijeva sol trihidrat.
11. Metoda po patentnem zahtevku 4, pri čemer je spojina 4-amino-1-hidroksibutiliden-1,1- bisfosfonska kislina v monohidratni obliki.
12. Metoda po kateremkoli izmed patentnih zahtevkov 4 do 8, pri čemer je nižji alkanol izbran iz skupine, ki sestoji iz metanola, etanola in izopropanola.
13. Metoda po patentnem zahtevku 4, pri čemer je natrijeva baza izbrana iz skupine, ki sestoji iz natrijevega hidroksida, natrijevega metoksida in natrijevega etoksida. 3
14. Metoda po patentnem zahtevku 4, pri čemer je spojina 4-amino-1-hidroksibutiliden-1,1- bisfosfonska kislina v brezvodni obliki.
15. Kristalna oblika mononatrijevega alendronata monohidrata, značilna po tem, da ima vrhove v rentgenskem difraktogramu praškastega vzorca pri vrednostih dva theta 12.7±0.2, 16.2+0.2, 17.3+0.2, 17.6+0.2, 24.8±0.2 in 25.5+0.2.
16. Farmacevtski sestavek, ki obsega farmacevtsko učinkovito množino spojine, definirane v kateremkoli izmed zahtevkov 1 do 3 ali 15, ali je pripravljena po kateremkoli izmed zahtevkov 4 do 14.
17. Uporaba farmacevtskega sestavka po zahtevku 16 za pripravo zdravila za zdravljenje in/ali preventivo izgube kostne mase pri neki osebi.
18. Metoda za pripravo spojine po patentnem zahtevku 1, ki obsega korake: a) reakcijo enega ekvivalenta 4-amino-1-hidroksibutiliden-1,1-bisfosfonske kisline z enim ekvivalentom natrijeve baze v vodni raztopini organskega topila izbranega iz skupine, ki sestoji iz acetona, DMSO, DMF, acetonitrila, alkoholov, polialkoholov, polialkoholnih etrov, piridina, sulfolana, N-metil pirolidinona in dioksana, in b) izoliranje spojine omenjene v patentnem zahtevku 1.
Applications Claiming Priority (4)
| 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 | |
| PCT/US1999/019838 WO2000012517A1 (en) | 1998-08-27 | 1999-08-27 | Novel hydrate forms of alendronate sodium, processes for manufacture thereof, and pharmaceutical compositions thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI20581A SI20581A (sl) | 2001-12-31 |
| SI20581B true SI20581B (sl) | 2008-06-30 |
Family
ID=27378576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9920070A SI20581B (sl) | 1998-08-27 | 1999-08-27 | Nove hidratne oblike natrijevega alendronata, postopki za njihovo pridobivanje in ustrezne farmacevtske učinkovine |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6281381B1 (sl) |
| EP (1) | EP1107974B1 (sl) |
| JP (2) | JP2002523514A (sl) |
| KR (2) | KR20070034132A (sl) |
| AT (1) | ATE334993T1 (sl) |
| AU (1) | AU5698899A (sl) |
| BG (1) | BG65329B1 (sl) |
| BR (1) | BR9913472A (sl) |
| CA (1) | CA2341459A1 (sl) |
| CZ (1) | CZ2001629A3 (sl) |
| DE (1) | DE69932620T2 (sl) |
| DK (1) | DK1107974T3 (sl) |
| EA (1) | EA002739B1 (sl) |
| EE (1) | EE04552B1 (sl) |
| ES (1) | ES2270613T3 (sl) |
| HR (1) | HRP20010129A2 (sl) |
| HU (1) | HUP0203078A3 (sl) |
| IL (1) | IL141423A (sl) |
| IS (1) | IS5864A (sl) |
| LT (1) | LT4888B (sl) |
| LV (1) | LV12720B (sl) |
| NO (1) | NO20010957L (sl) |
| NZ (1) | NZ510682A (sl) |
| PL (1) | PL346347A1 (sl) |
| PT (1) | PT1107974E (sl) |
| RO (1) | RO122854B1 (sl) |
| SI (1) | SI20581B (sl) |
| SK (1) | SK2482001A3 (sl) |
| WO (1) | WO2000012517A1 (sl) |
| YU (1) | YU14701A (sl) |
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 |
| HUP0600680A3 (en) * | 2001-12-24 | 2008-04-28 | Teva Pharma | Dosage form with a core tablet of active ingredient sheathed in a compressed annular body of powder or granular material, and process and tooling for producing it |
| ITMI20020146A1 (it) * | 2002-01-29 | 2003-07-29 | Lyogen Ltd | Alendronato monosodico amorfo e processo per la sua preparazione |
| JP2005531532A (ja) * | 2002-04-05 | 2005-10-20 | メルク エンド カムパニー インコーポレーテッド | アレンドロナートおよびビタミンｄ製剤を用いる骨吸収阻害法 |
| 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 |
| DK1753395T3 (da) | 2004-05-24 | 2010-11-08 | Warner Chilcott Co Llc | Enterisk, fast, oral doseringsform af et bisphosphonat, der indeholder et chelateringsmiddel |
| CZ296937B6 (cs) * | 2004-09-02 | 2006-07-12 | Zentiva, A. S | Trisodná sul kyseliny 4-amino-1-hydroxybutyliden-1,1-bisfosfonové |
| ES2331015T3 (es) * | 2004-10-29 | 2009-12-18 | Sandoz Ag | Proceso para la preparacion de un glatiramero. |
| 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 |
| NZ589053A (en) * | 2006-10-27 | 2012-03-30 | Signal Pharm Llc | Process of preparing 4-[9-(tetrahydro-furan-3-yl)-8-(2,4,6-trifluoro-phenylamino)-9h-purin-2-ylamino]-cyclohexan-1-ol compounds |
| JP5244608B2 (ja) * | 2006-11-22 | 2013-07-24 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 二糖類化合物のナトリウム塩及びその製造方法並びにその使用 |
| 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 |
| US8629178B2 (en) * | 2009-11-03 | 2014-01-14 | Li Liu | Sodium tanshinone IIA sulfonate hydrate and preparation method and use thereof |
| SG10202012791TA (en) | 2013-11-15 | 2021-01-28 | Akebia Therapeutics Inc | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3016289A1 (de) | 1980-04-28 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren |
| IT1201087B (it) | 1982-04-15 | 1989-01-27 | Gentili Ist Spa | Bifosfonati farmacologicamente attivi,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| US4639338A (en) * | 1984-08-06 | 1987-01-27 | Ciba-Geigy Corporation | Preparation of crystalline disodium 3-amino-1-hydroxypropane-1,1-diphosphonate pentahydrate |
| DE3434667A1 (de) | 1984-09-21 | 1986-04-03 | Henkel KGaA, 4000 Düsseldorf | 4-dimethylamino-1-hydroxybutan-1,1-diphosphonsaeure, deren wasserloesliche salze, verfahren zu ihrer herstellung sowie ihre verwendung |
| IT1196315B (it) * | 1984-10-29 | 1988-11-16 | Gentili Ist Spa | Procedimento per la preparazione di acidi difosfonici |
| US4711800A (en) * | 1985-06-06 | 1987-12-08 | Divincenzo Maureen | Needlecraft with metallic substrate |
| 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 |
| US5019651A (en) * | 1990-06-20 | 1991-05-28 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
| US5039819A (en) | 1990-09-18 | 1991-08-13 | Merck & Co., Inc. | Diphosphonate intermediate for preparing an antihypercalcemic agent |
| US5159108A (en) | 1990-09-18 | 1992-10-27 | Merck & Co., Inc. | Process for preparing an antihypercalcemic agent |
| CA2221844A1 (en) | 1995-06-06 | 1996-12-12 | Merck & Co., Inc. | Disodium alendronate formulations |
| DK0833643T3 (da) * | 1995-06-06 | 2005-05-30 | Merck & Co Inc | Formuleringer af vandfrit mononatriumsalt af alendronat og deres anvendelse til behandling af knoglesygdomme |
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1999
- 1999-08-27 EP EP99944004A patent/EP1107974B1/en not_active Expired - Lifetime
- 1999-08-27 US US09/384,145 patent/US6281381B1/en not_active Expired - Fee Related
- 1999-08-27 JP JP2000567539A patent/JP2002523514A/ja not_active Withdrawn
- 1999-08-27 SI SI9920070A patent/SI20581B/sl not_active IP Right Cessation
- 1999-08-27 KR KR1020077004456A patent/KR20070034132A/ko not_active Ceased
- 1999-08-27 AU AU56988/99A patent/AU5698899A/en not_active Abandoned
- 1999-08-27 AT AT99944004T patent/ATE334993T1/de not_active IP Right Cessation
- 1999-08-27 IL IL14142399A patent/IL141423A/xx not_active IP Right Cessation
- 1999-08-27 PT PT99944004T patent/PT1107974E/pt unknown
- 1999-08-27 RO ROA200100219A patent/RO122854B1/ro unknown
- 1999-08-27 HR HR20010129A patent/HRP20010129A2/hr not_active Application Discontinuation
- 1999-08-27 PL PL99346347A patent/PL346347A1/xx not_active Application Discontinuation
- 1999-08-27 WO PCT/US1999/019838 patent/WO2000012517A1/en not_active Ceased
- 1999-08-27 ES ES99944004T patent/ES2270613T3/es not_active Expired - Lifetime
- 1999-08-27 BR BR9913472-1A patent/BR9913472A/pt not_active Application Discontinuation
- 1999-08-27 CZ CZ2001629A patent/CZ2001629A3/cs unknown
- 1999-08-27 EA EA200100184A patent/EA002739B1/ru not_active IP Right Cessation
- 1999-08-27 YU YU14701A patent/YU14701A/sh unknown
- 1999-08-27 SK SK248-2001A patent/SK2482001A3/sk unknown
- 1999-08-27 EE EEP200100126A patent/EE04552B1/xx not_active IP Right Cessation
- 1999-08-27 CA CA002341459A patent/CA2341459A1/en not_active Abandoned
- 1999-08-27 DK DK99944004T patent/DK1107974T3/da active
- 1999-08-27 NZ NZ510682A patent/NZ510682A/en not_active IP Right Cessation
- 1999-08-27 DE DE69932620T patent/DE69932620T2/de not_active Expired - Fee Related
- 1999-08-27 HU HU0203078A patent/HUP0203078A3/hu unknown
- 1999-08-27 KR KR1020017002535A patent/KR20010079701A/ko not_active Ceased
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2001
- 2001-02-26 BG BG105292A patent/BG65329B1/bg unknown
- 2001-02-26 IS IS5864A patent/IS5864A/is unknown
- 2001-02-26 LT LT2001016A patent/LT4888B/lt not_active IP Right Cessation
- 2001-02-26 NO NO20010957A patent/NO20010957L/no not_active Application Discontinuation
- 2001-04-05 LV LVP-01-26A patent/LV12720B/en unknown
- 2001-07-03 US US09/898,756 patent/US6696601B2/en not_active Expired - Fee Related
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2009
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