LV11471B - Improved process for preparing salts of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (abp) - Google Patents
Improved process for preparing salts of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (abp) Download PDFInfo
- Publication number
- LV11471B LV11471B LVP-96-27A LV960027A LV11471B LV 11471 B LV11471 B LV 11471B LV 960027 A LV960027 A LV 960027A LV 11471 B LV11471 B LV 11471B
- Authority
- LV
- Latvia
- Prior art keywords
- acid
- hydrolysis
- amino
- mixture
- reaction
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 title abstract description 16
- 230000007062 hydrolysis Effects 0.000 claims abstract description 43
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 24
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 12
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 239000008363 phosphate buffer Substances 0.000 claims description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 230000000717 retained effect Effects 0.000 claims 2
- 239000001488 sodium phosphate Substances 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000007853 buffer solution Substances 0.000 claims 1
- 239000001177 diphosphate Substances 0.000 claims 1
- 229910000397 disodium phosphate Inorganic materials 0.000 claims 1
- 235000019800 disodium phosphate Nutrition 0.000 claims 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims 1
- 235000019799 monosodium phosphate Nutrition 0.000 claims 1
- 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 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000010791 quenching Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- 230000000171 quenching effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 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 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000008366 buffered solution Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 208000006386 Bone Resorption Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 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 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 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
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229940124277 aminobutyric acid Drugs 0.000 description 1
- -1 and the like Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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)]
- 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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/540,997 US5019651A (en) | 1990-06-20 | 1990-06-20 | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV11471A LV11471A (lv) | 1996-08-20 |
| LV11471B true LV11471B (en) | 1996-12-20 |
Family
ID=24157769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-96-27A LV11471B (en) | 1990-06-20 | 1996-02-02 | Improved process for preparing salts of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (abp) |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5019651A (sv) |
| EP (1) | EP0462663B1 (sv) |
| JP (1) | JPH07119229B2 (sv) |
| KR (1) | KR0173467B1 (sv) |
| AT (1) | ATE128470T1 (sv) |
| AU (1) | AU642264B2 (sv) |
| CA (1) | CA2044923C (sv) |
| CY (1) | CY1907A (sv) |
| DE (1) | DE69113325T2 (sv) |
| DK (1) | DK0462663T3 (sv) |
| ES (1) | ES2079026T3 (sv) |
| FI (1) | FI94347C (sv) |
| GR (1) | GR3017544T3 (sv) |
| HK (1) | HK64496A (sv) |
| IE (1) | IE69171B1 (sv) |
| IL (1) | IL98462A (sv) |
| LV (1) | LV11471B (sv) |
| NO (1) | NO180050C (sv) |
| NZ (1) | NZ238493A (sv) |
| PT (1) | PT97963B (sv) |
| ZA (1) | ZA914708B (sv) |
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| IT1246777B (it) * | 1991-04-12 | 1994-11-26 | Boehringer Mannheim Italia | Aminoacil derivati di acidi gem-difosfonici,un processo per la loro preparazione e composizioni farmaceutiche che li contengono |
| US5270365A (en) * | 1991-12-17 | 1993-12-14 | Merck & Co., Inc. | Prevention and treatment of periodontal disease with alendronate |
| US6399592B1 (en) | 1992-12-23 | 2002-06-04 | Merck & Co., Inc. | Bishphosphonate/estrogen synergistic therapy for treating and preventing bone loss |
| US5510517A (en) * | 1993-08-25 | 1996-04-23 | Merck & Co., Inc. | Process for producing N-amino-1-hydroxy-alkylidene-1,1-bisphosphonic acids |
| TW257765B (sv) * | 1993-08-25 | 1995-09-21 | Merck & Co Inc | |
| US5462932A (en) * | 1994-05-17 | 1995-10-31 | Merck & Co., Inc. | Oral liquid alendronate formulations |
| US5449819A (en) * | 1994-06-06 | 1995-09-12 | Merck & Co., Inc. | Process for removing waste pox, alendronate and its by products |
| US5589691A (en) * | 1994-06-06 | 1996-12-31 | Merck & Co., Inc. | Process for recovery and recycle of methanesulfonic acid and phosphorous acid |
| US5780455A (en) * | 1994-08-24 | 1998-07-14 | Merck & Co., Inc. | Intravenous alendronate formulations |
| NZ303022A (en) * | 1995-02-17 | 2000-07-28 | Merck & Co Inc | Treatment of osteoporotic diseases with alendronate |
| TW393488B (en) * | 1995-04-20 | 2000-06-11 | Merck & Co Inc | Process for making 1-hydrox-ybisphosphonates |
| AU713824B2 (en) * | 1995-05-12 | 1999-12-09 | Merck Sharp & Dohme Corp. | Prevention of tooth loss by the administration of alendronate or its salts |
| JP3344726B2 (ja) * | 1995-06-06 | 2002-11-18 | メルク エンド カンパニー インコーポレーテッド | 無水アレンドロネート一ナトリウム塩製剤 |
| AU5973496A (en) | 1995-06-06 | 1996-12-24 | Merck & Co., Inc. | Bisphosphonate cement composition to prevent aseptic loosening of orthopedic implant devices |
| KR100192215B1 (ko) * | 1996-09-03 | 1999-06-15 | 강재헌 | 3-아미노-1-히드록시프로판-1,1-디포스폰산의 제조방법 |
| BR9712197A (pt) * | 1996-10-04 | 1999-08-31 | Merck & Co Inc | Formulação farmacêutica líquida aquosa e processos de preparação da mesma, e, de inibição de reabsorção de osso. |
| CA2197267C (en) * | 1997-02-11 | 2000-02-08 | Yong Tao | Process for the production of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof |
| BR9910074A (pt) | 1998-04-29 | 2000-12-26 | Procter & Gamble | Processo para fabricação de uréias 1,3-di-substituìdas-4-oxocìclicas |
| PL198951B1 (pl) | 1998-04-29 | 2008-08-29 | Procter & Gamble | Sposób wytwarzania 1,3-dipodstawionych-4-oksocyklicznych moczników |
| US20030078211A1 (en) * | 1998-06-24 | 2003-04-24 | Merck & Co., Inc. | Compositions and methods for inhibiting bone resorption |
| WO1999067809A1 (en) | 1998-06-24 | 1999-12-29 | Merck & Co., Inc. | Compositions and methods for inhibiting bone resorption |
| US6008207A (en) * | 1998-08-13 | 1999-12-28 | Merck & Co., Inc. | Anhydrous alendronate monosodium salt formulations |
| DE69932620T2 (de) * | 1998-08-27 | 2006-12-14 | Teva Pharmaceutical Industries Ltd. | Hydratformen des natriumsalzes von alendronat, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese enthalten |
| EP1702924A3 (en) * | 1998-08-27 | 2007-07-18 | Teva Pharmaceutical Industries Ltd | Novel hydrate forms of alendronate sodium, processes for manufacture thereof, and pharmaceutical compositions thereof |
| US6331533B1 (en) | 1998-11-16 | 2001-12-18 | Merck & Co., Inc. | Method for inhibiting dental resorptive lesions |
| KR100327786B1 (ko) * | 1999-03-25 | 2002-03-14 | 유승필 | 4-아미노-1-하이드록시부틸리덴-1,1-비스포스폰산 또는 이의 염의 제조방법 |
| US6315566B1 (en) | 1999-05-18 | 2001-11-13 | 3M Innovative Properties Company | Dental materials |
| US6143919A (en) * | 1999-05-18 | 2000-11-07 | 3M Innovative Properties Company | Polymerizable acidic compounds and methods of preparation |
| US6963008B2 (en) * | 1999-07-19 | 2005-11-08 | Teva Pharmaceutical Industries Ltd. | Hydrate forms of alendronate sodium, processes for manufacture thereof, and pharmaceutical compositions thereof |
| ES2153794B1 (es) * | 1999-08-06 | 2001-10-16 | Medichem Sa | Procedimiento para la obtencion del acido 4-amino-1-hidroxibutiliden-1,1-bisfosfonico y de su sal monosodica trihidratada. |
| US6677320B2 (en) | 2000-01-20 | 2004-01-13 | Hoffmann-La Roches Inc. | Parenteral bisphosphonate composition with improved local tolerance |
| US6476006B2 (en) | 2000-06-23 | 2002-11-05 | Teva Pharmaceutical Industries, Ltd. | Composition and dosage form for delayed gastric release of alendronate and/or other bis-phosphonates |
| KR100327787B1 (ko) * | 2001-02-27 | 2002-03-15 | 유승필 | 4-아미노-1-하이드록시부틸리덴-1,1-비스포스폰산 일나트륨 삼수화물의 제조방법 |
| US6558702B2 (en) * | 2001-04-13 | 2003-05-06 | Alkermes Controlled Therapeutics, Inc. | Method of modifying the release profile of sustained release compositions |
| US20060269602A1 (en) * | 2001-04-13 | 2006-11-30 | Dasch James R | Method of modifying the release profile of sustained release compositions |
| TR200101250A2 (tr) * | 2001-05-10 | 2003-04-21 | E�S Eczaciba�I �Zg�N K�Myasal �R�Nler Sanay� A.�. | 4-amino-1-hidroksibutiliden-1,1-bifosfonik asit veya tuzlarının hazırlanmasına ilişkin proses |
| GB0115824D0 (en) * | 2001-06-28 | 2001-08-22 | Rhodia Cons Spec Ltd | Improved solvent systems |
| MXPA04006027A (es) * | 2001-12-21 | 2004-09-27 | Procter & Gamble | Metodo para el tratamiento de trastornos de los huesos. |
| CA2472578A1 (en) * | 2002-01-24 | 2003-07-31 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Anti-cancer combination and use thereof |
| ITMI20020908A1 (it) * | 2002-04-29 | 2003-10-29 | Chemi Spa | Processo di preparazione di sodio alendronato |
| JP2005522526A (ja) | 2002-05-10 | 2005-07-28 | エフ．ホフマン−ラ ロシュ アーゲー | 骨粗鬆症の治療および予防用のビスホスホン酸 |
| CN1665825A (zh) * | 2002-05-17 | 2005-09-07 | 特瓦制药工业有限公司 | 用一定的稀释剂制备双膦酸 |
| CA2487977A1 (en) * | 2002-06-06 | 2003-12-18 | Merck Frosst Canada & Co./Merck Frosst Canada & Cie | 1,5-disubstituted imidazolidin-2-one derivatives for use as ep4 receptor agonists in the treatment of eye and bone diseases |
| JP4485117B2 (ja) * | 2002-06-27 | 2010-06-16 | 日東電工株式会社 | 保護剥離用フィルム |
| AU2003258433A1 (en) * | 2002-08-28 | 2004-03-19 | Merck Frosst Canada Ltd | Oxazolidin-2-one and thiazolidin-2-one derivatives for use as ep4 receptor agonists in the treatment of glaucoma |
| US20040138180A1 (en) * | 2002-10-03 | 2004-07-15 | Barr Laboratories, Inc. | Bisphosphonate composition and process for the preparation thereof |
| EP1790347B1 (en) * | 2002-12-20 | 2014-12-24 | F. Hoffmann-La Roche AG | High dose ibandronate formulation |
| US20040206932A1 (en) * | 2002-12-30 | 2004-10-21 | Abuelyaman Ahmed S. | Compositions including polymerizable bisphosphonic acids and methods |
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-
1990
- 1990-06-20 US US07/540,997 patent/US5019651A/en not_active Expired - Lifetime
-
1991
- 1991-06-11 NZ NZ238493A patent/NZ238493A/en not_active IP Right Cessation
- 1991-06-12 IL IL9846291A patent/IL98462A/en not_active IP Right Cessation
- 1991-06-14 ES ES91201490T patent/ES2079026T3/es not_active Expired - Lifetime
- 1991-06-14 DE DE69113325T patent/DE69113325T2/de not_active Expired - Lifetime
- 1991-06-14 EP EP91201490A patent/EP0462663B1/en not_active Expired - Lifetime
- 1991-06-14 DK DK91201490.9T patent/DK0462663T3/da active
- 1991-06-14 CY CY190791A patent/CY1907A/xx unknown
- 1991-06-14 PT PT97963A patent/PT97963B/pt not_active IP Right Cessation
- 1991-06-14 AT AT91201490T patent/ATE128470T1/de not_active IP Right Cessation
- 1991-06-18 AU AU78498/91A patent/AU642264B2/en not_active Expired
- 1991-06-18 CA CA002044923A patent/CA2044923C/en not_active Expired - Lifetime
- 1991-06-19 KR KR1019910010131A patent/KR0173467B1/ko not_active IP Right Cessation
- 1991-06-19 JP JP3147090A patent/JPH07119229B2/ja not_active Expired - Lifetime
- 1991-06-19 IE IE211291A patent/IE69171B1/en not_active IP Right Cessation
- 1991-06-19 ZA ZA914708A patent/ZA914708B/xx unknown
- 1991-06-19 NO NO912395A patent/NO180050C/no not_active IP Right Cessation
- 1991-06-19 FI FI913008A patent/FI94347C/sv not_active IP Right Cessation
-
1995
- 1995-09-28 GR GR950402510T patent/GR3017544T3/el unknown
-
1996
- 1996-02-02 LV LVP-96-27A patent/LV11471B/en unknown
- 1996-04-11 HK HK64496A patent/HK64496A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CY1907A (en) | 1991-06-14 |
| AU7849891A (en) | 1992-01-02 |
| JPH07119229B2 (ja) | 1995-12-20 |
| FI94347C (sv) | 1995-08-25 |
| NO912395L (no) | 1991-12-23 |
| IE912112A1 (en) | 1992-01-01 |
| FI94347B (sv) | 1995-05-15 |
| EP0462663B1 (en) | 1995-09-27 |
| NO180050B (no) | 1996-10-28 |
| KR0173467B1 (en) | 1999-04-01 |
| DK0462663T3 (da) | 1996-01-29 |
| US5019651A (en) | 1991-05-28 |
| GR3017544T3 (en) | 1995-12-31 |
| HK64496A (en) | 1996-04-19 |
| IL98462A0 (en) | 1992-07-15 |
| CA2044923C (en) | 1996-06-18 |
| CA2044923A1 (en) | 1991-12-21 |
| AU642264B2 (en) | 1993-10-14 |
| IL98462A (en) | 1995-12-08 |
| JPH05132492A (ja) | 1993-05-28 |
| EP0462663A1 (en) | 1991-12-27 |
| NZ238493A (en) | 1992-09-25 |
| NO912395D0 (no) | 1991-06-19 |
| IE69171B1 (en) | 1996-08-07 |
| ZA914708B (en) | 1992-03-25 |
| DE69113325D1 (de) | 1995-11-02 |
| DE69113325T2 (de) | 1996-05-02 |
| LV11471A (lv) | 1996-08-20 |
| FI913008A (sv) | 1991-12-21 |
| PT97963A (pt) | 1992-03-31 |
| ES2079026T3 (es) | 1996-01-01 |
| PT97963B (pt) | 1998-11-30 |
| ATE128470T1 (de) | 1995-10-15 |
| FI913008A0 (sv) | 1991-06-19 |
| NO180050C (no) | 1997-02-05 |
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