ES8403923A1 - Procedimiento para la preparacion de derivados del acido metilendifosfonico - Google Patents
Procedimiento para la preparacion de derivados del acido metilendifosfonicoInfo
- Publication number
- ES8403923A1 ES8403923A1 ES524495A ES524495A ES8403923A1 ES 8403923 A1 ES8403923 A1 ES 8403923A1 ES 524495 A ES524495 A ES 524495A ES 524495 A ES524495 A ES 524495A ES 8403923 A1 ES8403923 A1 ES 8403923A1
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- products derived
- formula
- image
- methylenediphosphonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract 2
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical compound OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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]
-
- 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
- C07F9/3865—Polyphosphonic acids containing sulfur substituents
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4025—Esters of poly(thio)phosphonic acids
- C07F9/4043—Esters of poly(thio)phosphonic acids containing sulfur substituents
-
- 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
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
- C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8213250A FR2531088B1 (fr) | 1982-07-29 | 1982-07-29 | Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8403923A1 true ES8403923A1 (es) | 1984-04-16 |
| ES524495A0 ES524495A0 (es) | 1984-04-16 |
Family
ID=9276447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES524495A Granted ES524495A0 (es) | 1982-07-29 | 1983-07-28 | Procedimiento para la preparacion de derivados del acido metilendifosfonico |
Country Status (35)
Families Citing this family (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2558837B1 (fr) * | 1984-01-26 | 1986-06-27 | Sanofi Sa | Derives de l'acide methylenediphosphonique, procede d'obtention et medicaments antirhumatismaux les contenant |
| IL77243A (en) * | 1984-12-21 | 1996-11-14 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds |
| PH27078A (en) * | 1984-12-21 | 1993-02-01 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonates |
| US5641762A (en) * | 1985-05-02 | 1997-06-24 | Research Corporation Technologies, Inc. | Bone targeted inhibitors of carbonic anhydrase |
| US4761406A (en) * | 1985-06-06 | 1988-08-02 | The Procter & Gamble Company | Regimen for treating osteoporosis |
| US4902679A (en) * | 1985-12-13 | 1990-02-20 | Norwich Eaton Pharmaceuticals, Inc. | Methods of treating diseases with certain geminal diphosphonates |
| DE3770982D1 (de) * | 1986-04-24 | 1991-08-01 | Fujisawa Pharmaceutical Co | Diphosphonsaeure-verbindungen, verfahren zu deren herstellung und sie enthaltende arzneimittel. |
| IL84731A0 (en) * | 1986-12-19 | 1988-05-31 | Norwich Eaton Pharma | Heterocycle-substituted diphosphonic acids and salts and esters and pharmaceutical compositions containing them |
| KR880011136A (ko) * | 1987-03-11 | 1988-10-26 | 모리오까 시게오 | 아졸- 아미노메틸렌 비스포스폰산 유도체 |
| IL86951A (en) * | 1987-07-06 | 1996-07-23 | Procter & Gamble Pharma | Methylene phosphonoalkylphosphinates and pharmaceutical preparations containing them |
| DE3805663A1 (de) * | 1988-02-24 | 1989-09-07 | Henkel Kgaa | Oxaalkanpolyphosphonsaeuren, ihre verwendung als thresholder sowie diese verbindungen enthaltende, komplexierend wirkende zusammensetzungen |
| CH675422A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-03-31 | 1990-09-28 | Symphar Sa | |
| FR2629716B1 (fr) * | 1988-04-07 | 1991-07-19 | Sanofi Sa | Composition pharmaceutique pour administration orale a base d'un derive d'acide diphosphonique |
| DE3822650A1 (de) * | 1988-07-05 | 1990-02-01 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| JP3021035B2 (ja) * | 1988-11-01 | 2000-03-15 | アーク・デベロップメント・コーポレーション | ホスホン酸及び分離におけるその使用 |
| US5154843A (en) * | 1989-02-08 | 1992-10-13 | The Lubrizol Corporation | Hydroxyalkane phosphonic acids and derivatives thereof and lubricants containing the same |
| PH26923A (en) * | 1989-03-08 | 1992-12-03 | Ciba Geigy | N-substituted amino alkanediphosphonic acids |
| US5220021A (en) * | 1989-04-03 | 1993-06-15 | The Upjohn Company | Geminal bisphosphonic acids and derivatives as anti-arthritic agents |
| JPH0377894A (ja) * | 1989-08-18 | 1991-04-03 | Toray Ind Inc | メチレンジホスホン酸化合物 |
| EP0416689B1 (en) * | 1989-09-06 | 1995-11-29 | Merck & Co. Inc. | Acyloxymethyl esters of bisphosphonic acids as bone resorption inhibitors |
| EP0438375B1 (de) * | 1990-01-18 | 1995-12-27 | Ciba-Geigy Ag | Phoshponsäure- und Thionophosphonsäure-Derivate |
| IE912115A1 (en) * | 1990-06-25 | 1992-01-01 | Takeda Chemical Industries Ltd | Bisphosphonic acid derivatives, their production and use |
| DE69108733T2 (de) * | 1990-08-21 | 1995-09-14 | Upjohn Co | Bisphosphonsäurederivate als antiarthritische mittel. |
| DK0561948T3 (da) * | 1990-12-07 | 1995-08-21 | Upjohn Co | Phosphonsyrederivater, der kan anvendes som antiinflammatoriske midler |
| ATE133677T1 (de) * | 1990-12-19 | 1996-02-15 | Takeda Chemical Industries Ltd | Bisphosphonsäurederivate, ihre produktion und ihre verwendung |
| IT1244698B (it) * | 1991-02-01 | 1994-08-08 | Gentili Ist Spa | Acidi aril-o arilalchil-acil ammino-alchil-idrossidifosfonici, procedimento per la loro preparazione e loro uso in terapia osteo-articolare e dei tessuti connettori in generale |
| DE69224830D1 (en) * | 1991-06-19 | 1998-04-23 | Upjohn Co | Dialkyl (dialkoxyphosphinyl)methyl phosphate als antientzündungsmittel |
| EP0521622B1 (en) * | 1991-07-03 | 1997-08-13 | PHARMACIA & UPJOHN COMPANY | Pyrazolopyrimidine and pyrimidinyl bisphosphonic esters as anti-inflammatories |
| DE69225325T2 (de) * | 1991-09-05 | 1998-08-27 | Toray Industries | Methandiphosphonsäurederivat, herstellung davon und verwendung davon als arzneimittel |
| JPH06172372A (ja) * | 1991-11-06 | 1994-06-21 | Takeda Chem Ind Ltd | スクアレン合成酵素阻害剤およびその用途 |
| EP0541037A3 (en) * | 1991-11-06 | 1997-02-26 | Takeda Chemical Industries Ltd | Squalene synthetase inhibitory composition and use thereof |
| AU662991B2 (en) * | 1992-05-29 | 1995-09-21 | Procter & Gamble Pharmaceuticals, Inc. | Quaternary nitrogen-containing phosphonates for treating abnormal calcium and phosphate metabolism |
| US5763611A (en) * | 1992-05-29 | 1998-06-09 | The Procter & Gamble Company | Thio-substituted cyclic phosphonate compounds, pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism |
| SG47603A1 (en) * | 1992-05-29 | 1998-04-17 | Procter & Gamble Pharma | Thio-substitute nitrogen containing heterocyclic phosphonate compounds for treating abnormal calcium and phosphate metabolism |
| DE69329199D1 (de) * | 1992-05-29 | 2000-09-14 | Procter & Gamble Pharma | Schwefel-enthaltende phosphonat-verbindungen zur behandlung von abnormalem calzium- und phosphat- metabolismus |
| US5753634A (en) * | 1992-05-29 | 1998-05-19 | The Procter & Gamble Company | Quaternary nitrogen containing phosphonate compounds, pharmaceutical compostions, and methods for treating abnormal calcium and phosphate metabolism |
| US5391743A (en) * | 1992-05-29 | 1995-02-21 | Procter & Gamble Pharmaceuticals, Inc. | Quaternary nitrogen-containing phosphonate compounds, pharmaceutical compositions, and methods of treating abnormal calcium and phosphate metabolism and methods of treating and preventing dental calculus and plaque |
| SK160994A3 (en) * | 1992-06-30 | 1996-01-10 | Procter & Gamble Pharma | Compositions for the treatment of arthritis containing phosphonates and nsaid |
| DE69330114T2 (de) * | 1992-07-10 | 2001-08-02 | Toray Industries, Inc. | Methandiphosphonat-derivat, dessen produktion und dessen verwendung als arzneimittel |
| GB9215433D0 (en) * | 1992-07-21 | 1992-09-02 | Cmb Foodcan Plc | Apparatus for stripping a drawn article from a punch |
| 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. |
| EP0654035B1 (en) * | 1992-08-07 | 1997-08-20 | PHARMACIA & UPJOHN COMPANY | Phosphonoacetic esters and acids as anti-inflammatories |
| US5635495A (en) * | 1992-10-09 | 1997-06-03 | The Upjohn Company | Pyrimidine bisphosphonate esters and (alkoxymethylphosphinyl)alkyl phosphonic acids as anti-inflammatories |
| JPH06135976A (ja) * | 1992-10-30 | 1994-05-17 | Toray Ind Inc | メタンジホスホン酸誘導体、その製造方法およびその医薬用途 |
| US5332728A (en) * | 1992-11-23 | 1994-07-26 | Bristol-Myers Squibb Company | Method for treating a fungal infection |
| AU670337B2 (en) | 1992-11-30 | 1996-07-11 | Novartis Ag | Use of certain methanebisphosphonic acid derivatives in fracture healing |
| US6399592B1 (en) | 1992-12-23 | 2002-06-04 | Merck & Co., Inc. | Bishphosphonate/estrogen synergistic therapy for treating and preventing bone loss |
| JP2546067B2 (ja) * | 1993-02-25 | 1996-10-23 | 東レ株式会社 | メタンジホスホン酸化合物の製造方法 |
| FR2703590B1 (fr) * | 1993-04-05 | 1995-06-30 | Sanofi Elf | Utilisation de derives d'acide bisphosphonique pour la preparation de medicaments destines a favoriser la reparation osseuse . |
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| WO2003061566A2 (en) * | 2002-01-24 | 2003-07-31 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Anti-cancer combination and use thereof |
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| AU2003233731A1 (en) * | 2002-06-06 | 2003-12-22 | Xavier Billot | 1,5-disubstituted imidazolidin-2-one derivatives for use as ep4 receptor agonists in the treatment of eye and bone diseases |
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| EP1673336B1 (en) | 2003-08-21 | 2014-06-04 | Merck Canada Inc. | Cathepsin cysteine protease inhibitors |
| AU2004273672A1 (en) * | 2003-09-19 | 2005-03-31 | Wisconsin Alumni Research Foundation | Pharmaceutical compositions and methods comprising combinations of 2-alkylidene-19-nor-vitamin D derivatives and a bisphosphonate |
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| US8697139B2 (en) | 2004-09-21 | 2014-04-15 | Frank M. Phillips | Method of intervertebral disc treatment using articular chondrocyte cells |
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| DE1302557B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-04-09 | 1971-08-26 | ||
| US3957858A (en) * | 1970-04-13 | 1976-05-18 | Monsanto Company | Substituted ethane diphosphonic acids and salts and esters thereof |
| US3654151A (en) * | 1970-04-13 | 1972-04-04 | Monsanto Co | Deflocculation of solid materials in aqueous medium |
| US3705191A (en) * | 1970-04-13 | 1972-12-05 | Monsanto Co | Substituted ethane diphosphonic acids and salts and esters thereof |
| US3683080A (en) * | 1970-08-28 | 1972-08-08 | Procter & Gamble | Compositions for inhibiting anomalous deposition and mobilization of calcium phosphate in animal tissue |
| US4171373A (en) * | 1974-01-07 | 1979-10-16 | William H. Rorer, Inc. | Ethynylbenzene compounds and derivatives thereof to treat pain, fever and inflammation |
| US4071584A (en) * | 1977-01-03 | 1978-01-31 | Monsanto Company | Hydroxyphenylthiophosphoranylidene organophosphorus compounds |
| US4264582A (en) * | 1978-07-31 | 1981-04-28 | The Procter & Gamble Company | Isobutylphenylacetate anti-inflammatory composition |
| JPS5598193A (en) * | 1979-01-22 | 1980-07-25 | Nissan Chem Ind Ltd | Methylenediphosphonic acid derivative and herbicide comprising it as active constituent |
| GB2043072B (en) * | 1979-02-13 | 1983-11-23 | Symphar Sa | Diphosphonate compounds |
| US4330530A (en) * | 1980-12-22 | 1982-05-18 | The Procter & Gamble Company | Anti-arthritic compositions and method using gold salts and organophosphonates |
| DE3365492D1 (en) * | 1982-01-27 | 1986-10-02 | Schering Ag | Diphosphonic acid derivatives and pharmaceutical preparations containing them |
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1982
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1983
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- 1983-07-25 EP EP83401520A patent/EP0100718B1/fr not_active Expired
- 1983-07-25 LU LU88723C patent/LU88723I2/fr unknown
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1984
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1985
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1986
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1988
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1991
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1996
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20040218 |