DK168754B1 - Farmaceutiske kompositioner indeholdende geminale diphosphonsyreforbindelser samt specifikke sådanne forbindelser - Google Patents

Farmaceutiske kompositioner indeholdende geminale diphosphonsyreforbindelser samt specifikke sådanne forbindelser Download PDF

Info

Publication number: DK168754B1
Authority: DK; Denmark
Prior art keywords: diphosphonic acid; amino; hydrocarbon chain; pyridyl; hydroxy
Prior art date: 1984-12-21

Application number

DK599685A

Other languages

Danish (da)

English (en)

Other versions

DK599685A (da

DK599685D0 (da

Inventor

James John Benedict

Christhopher Mark Perkins

Original Assignee

Procter & Gamble

Priority date (The priority date 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 date listed.)

1984-12-21

Filing date

1985-12-20

Publication date

1994-06-06

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24748488&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DK168754(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1985-12-20 Application filed by Procter & Gamble filed Critical Procter & Gamble

1985-12-20 Publication of DK599685D0 publication Critical patent/DK599685D0/da

1986-06-22 Publication of DK599685A publication Critical patent/DK599685A/da

1994-06-06 Application granted granted Critical

1994-06-06 Publication of DK168754B1 publication Critical patent/DK168754B1/da

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 33
150000001875 compounds Chemical class 0.000 title claims description 34
XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical group OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 title claims description 11
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 37
239000011575 calcium Substances 0.000 claims abstract description 37
229910052791 calcium Inorganic materials 0.000 claims abstract description 37
229910019142 PO4 Inorganic materials 0.000 claims abstract description 18
230000002159 abnormal effect Effects 0.000 claims abstract description 18
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 18
239000010452 phosphate Substances 0.000 claims abstract description 18
230000004060 metabolic process Effects 0.000 claims abstract description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
201000010099 disease Diseases 0.000 claims abstract description 4
-1 diphosphonic acid compound Chemical group 0.000 claims description 84
229910052739 hydrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 42
FRCICXIVPRNPLM-UHFFFAOYSA-N [amino(phosphono)methyl]phosphonic acid Chemical compound OP(=O)(O)C(N)P(O)(O)=O FRCICXIVPRNPLM-UHFFFAOYSA-N 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 34
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 30
150000002148 esters Chemical class 0.000 claims description 29
150000002431 hydrogen Chemical class 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
229920006395 saturated elastomer Polymers 0.000 claims description 20
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims description 19
239000003937 drug carrier Substances 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 18
230000000144 pharmacologic effect Effects 0.000 claims description 15
229930195734 saturated hydrocarbon Natural products 0.000 claims description 15
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 15
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000003368 amide group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims 21
KZMOFWIRXNQJET-UHFFFAOYSA-N (1-phosphono-2-pyridin-3-ylethyl)phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)CC1=CC=CN=C1 KZMOFWIRXNQJET-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
238000000034 method Methods 0.000 abstract description 7
DCCMANRPEHXGDK-UHFFFAOYSA-L azane;hydroxy-[[[hydroxy(oxido)phosphoryl]methyl-(phosphonomethyl)amino]methyl]phosphinate;platinum(2+) Chemical compound N.N.[Pt+2].OP(O)(=O)CN(CP(O)(O)=O)CP([O-])([O-])=O DCCMANRPEHXGDK-UHFFFAOYSA-L 0.000 description 35
229960005069 calcium Drugs 0.000 description 34
239000000243 solution Substances 0.000 description 18
241001465754 Metazoa Species 0.000 description 17
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 16
150000002430 hydrocarbons Chemical group 0.000 description 16
235000021317 phosphate Nutrition 0.000 description 15
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical class [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
125000004433 nitrogen atom Chemical group N* 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
208000037147 Hypercalcaemia Diseases 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000008021 deposition Effects 0.000 description 6
229940079593 drug Drugs 0.000 description 6
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229910052500 inorganic mineral Inorganic materials 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011707 mineral Substances 0.000 description 6
238000005303 weighing Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
208000010191 Osteitis Deformans Diseases 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
239000002775 capsule Substances 0.000 description 5
210000004349 growth plate Anatomy 0.000 description 5
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229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
NGMZSXZBZNXBGX-UHFFFAOYSA-N (1-phosphono-2-pyridin-2-ylethyl)phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)CC1=CC=CC=N1 NGMZSXZBZNXBGX-UHFFFAOYSA-N 0.000 description 4
208000004434 Calcinosis Diseases 0.000 description 4
WWNZQFVHLBNMDJ-UHFFFAOYSA-N OP(OP(O)=O)=O.O Chemical compound OP(OP(O)=O)=O.O WWNZQFVHLBNMDJ-UHFFFAOYSA-N 0.000 description 4
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208000035475 disorder Diseases 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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239000011541 reaction mixture Substances 0.000 description 4
210000002303 tibia Anatomy 0.000 description 4
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 4
ZWHKKFUMEGWCKH-UHFFFAOYSA-N (1-hydroxy-1-phosphono-2-pyridin-4-ylethyl)phosphonic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=NC=C1 ZWHKKFUMEGWCKH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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SEEGPWYJEBDACP-UHFFFAOYSA-N P(=O)(O)OP(=O)O.N1=C(N=CC=C1)NC Chemical compound P(=O)(O)OP(=O)O.N1=C(N=CC=C1)NC SEEGPWYJEBDACP-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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MXYOPVWZZKEAGX-UHFFFAOYSA-N 1-phosphonoethylphosphonic acid Chemical compound OP(=O)(O)C(C)P(O)(O)=O MXYOPVWZZKEAGX-UHFFFAOYSA-N 0.000 description 2
ROPQINLWRARCTM-UHFFFAOYSA-N 2-phosphonopropan-2-ylphosphonic acid Chemical compound OP(=O)(O)C(C)(C)P(O)(O)=O ROPQINLWRARCTM-UHFFFAOYSA-N 0.000 description 2
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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)
- 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
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
- 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
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- 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

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Chemical & Material Sciences (AREA)
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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)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Output Control And Ontrol Of Special Type Engine (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

DK599685A 1984-12-21 1985-12-20 Farmaceutiske kompositioner indeholdende geminale diphosphonsyreforbindelser samt specifikke sådanne forbindelser DK168754B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68454384A	1984-12-21	1984-12-21
US68454384		1984-12-21

Publications (3)

Publication Number	Publication Date
DK599685D0 DK599685D0 (da)	1985-12-20
DK599685A DK599685A (da)	1986-06-22
DK168754B1 true DK168754B1 (da)	1994-06-06

Family

ID=24748488

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Application Number	Title	Priority Date	Filing Date
DK599685A DK168754B1 (da)	1984-12-21	1985-12-20	Farmaceutiske kompositioner indeholdende geminale diphosphonsyreforbindelser samt specifikke sådanne forbindelser

Country Status (11)

Country	Link
US (1)	US5583122A (fr)
EP (1)	EP0186405B1 (fr)
AT (1)	ATE61370T1 (fr)
DE (2)	DE3582033D1 (fr)
DK (1)	DK168754B1 (fr)
ES (4)	ES8707543A1 (fr)
IE (1)	IE58749B1 (fr)
IL (1)	IL77243A (fr)
LU (1)	LU90669I2 (fr)
NL (1)	NL300031I2 (fr)
ZA (1)	ZA859694B (fr)

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DE2755940C2 (de) *	1977-12-15	1986-01-02	Basf Ag, 6700 Ludwigshafen	Mittel zur Regulierung des Pflanzenwachstums
JPS54135724A (en) *	1978-04-11	1979-10-22	Nissan Chem Ind Ltd	Preparation of amino-methylenedisulfonic acid derivative
JPS5598193A (en) *	1979-01-22	1980-07-25	Nissan Chem Ind Ltd	Methylenediphosphonic acid derivative and herbicide comprising it as active constituent
DE3016289A1 (de) *	1980-04-28	1981-10-29	Henkel KGaA, 4000 Düsseldorf	Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren
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DE3365492D1 (en) *	1982-01-27	1986-10-02	Schering Ag	Diphosphonic acid derivatives and pharmaceutical preparations containing them
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IT1201087B (it) *	1982-04-15	1989-01-27	Gentili Ist Spa	Bifosfonati farmacologicamente attivi,procedimento per la loro preparazione e relative composizioni farmaceutiche
FR2531088B1 (fr) *	1982-07-29	1987-08-28	Sanofi Sa	Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation
DE3425812A1 (de) *	1984-07-13	1986-01-16	Deutsches Krebsforschungszentrum, 6900 Heidelberg	Neue 1-hydroxy-1,1-diphosphonsaeureverbindungen, verfahren zu ihrer herstellung und pharmakologische zubereitungen, insbesondere zur behandlung von knochentumoren
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1985
- 1985-12-05 IL IL7724385A patent/IL77243A/en not_active IP Right Cessation
- 1985-12-06 US US06/806,155 patent/US5583122A/en not_active Expired - Lifetime
- 1985-12-16 DE DE8585309140T patent/DE3582033D1/de not_active Expired - Lifetime
- 1985-12-16 DE DE2000175030 patent/DE10075030I2/de active Active
- 1985-12-16 EP EP85309140A patent/EP0186405B1/fr not_active Expired - Lifetime
- 1985-12-16 AT AT85309140T patent/ATE61370T1/de active
- 1985-12-19 ZA ZA859694A patent/ZA859694B/xx unknown
- 1985-12-20 ES ES550302A patent/ES8707543A1/es not_active Expired
- 1985-12-20 ES ES000550302D patent/ES8707543B9/es not_active Expired - Lifetime
- 1985-12-20 DK DK599685A patent/DK168754B1/da not_active IP Right Cessation
- 1985-12-21 IE IE328685A patent/IE58749B1/en not_active IP Right Cessation
1987
- 1987-01-16 ES ES557322D patent/ES8802428B9/es not_active Expired - Lifetime
- 1987-01-16 ES ES557322A patent/ES8802428A1/es not_active Expired
2000
- 2000-11-10 LU LU90669C patent/LU90669I2/fr unknown
- 2000-12-01 NL NL300031C patent/NL300031I2/nl unknown

Also Published As

Publication number	Publication date
IE58749B1 (en)	1993-11-03
DE10075030I2 (de)	2004-01-29
ES8802428B9 (en)	2011-08-25
DE10075030I1 (de)	2000-12-21
IE853286L (en)	1986-06-21
LU90669I2 (fr)	2001-01-10
DK599685A (da)	1986-06-22
US5583122A (en)	1996-12-10
NL300031I2 (nl)	2001-03-01
ES557322A0 (es)	1988-06-01
DE3582033D1 (de)	1991-04-11
ES8707543A1 (es)	1987-08-01
ZA859694B (en)	1986-08-27
ATE61370T1 (de)	1991-03-15
EP0186405A2 (fr)	1986-07-02
IL77243A (en)	1996-11-14
ES8707543B9 (es)	2013-05-08
ES8802428A1 (es)	1988-06-01
EP0186405A3 (en)	1987-10-28
EP0186405B1 (fr)	1991-03-06
NL300031I1 (nl)	2001-02-01
ES550302A0 (es)	1987-08-01
DK599685D0 (da)	1985-12-20

Legal Events

Date	Code	Title	Description
1994-06-06	B1	Patent granted (law 1993)
2006-01-09	PUP	Patent expired

Publication	Publication Date	Title
DK168754B1 (da)	1994-06-06	Farmaceutiske kompositioner indeholdende geminale diphosphonsyreforbindelser samt specifikke sådanne forbindelser
DK173943B1 (da)	2002-03-04	Eventuelt substituerede indan- og hexahydroindan-2.2-diphosphonsyrer og farmaceutisk acceptable salte deraf samt farmaceutisk komposition omfattende samme
JP2859271B2 (ja)	1999-02-17	メチレンホスホノアルキルホスフィネート類、医薬組成物、及び異常カルシウム及びホスフェート代謝の治療方法
EP0230068B1 (fr)	1992-07-15	Utilisation de diphosphonates geminaux pour la preparation d'un medicament
CA1321198C (fr)	1993-08-10	Composes diphosphonate a substituant heterocyclique, compositions pharmaceutiques et methode pour traiter le metabolisme anormal du calcium et du phosphate
DK171068B1 (da)	1996-05-20	Nitrogenholdige, mættede, bicykliske cyclopentanringholdige diphosphonsyrer og farmaceutiske sammensætninger omfattende disse
JP2568999B2 (ja)	1997-01-08	ｇｅｍ−ジホスホネ−トを含有する薬学的組成物
US5071840A (en)	1991-12-10	Certain heterocyclic substituted diphosphonate compounds pharmaceutical compositions, and methods of treating abnormal calcium and phosphate metabolism
RO119433B1 (ro)	2004-11-30	Tetraesteri ai acidului piridinil-aminometilidenbisfosfonic, compoziţie farmaceutică pentru tratamentul afecţiunilor osoase şi utilizarea acestora
DK174685B1 (da)	2003-09-08	Monocykliske geminale diphosphonsyrer og farmaceutisk acceptable salte heraf samt farmaceutisk sammensætning omfattende disse