ITBO970538A1 - PHARMACEUTICAL COMPOSITIONS CONTAINING CALCITONIN IN A SPRAY DOSER FOR INTRANASAL ADMINISTRATION. - Google Patents
PHARMACEUTICAL COMPOSITIONS CONTAINING CALCITONIN IN A SPRAY DOSER FOR INTRANASAL ADMINISTRATION. Download PDFInfo
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- ITBO970538A1 ITBO970538A1 IT000538A ITBO970538A ITBO970538A1 IT BO970538 A1 ITBO970538 A1 IT BO970538A1 IT 000538 A IT000538 A IT 000538A IT BO970538 A ITBO970538 A IT BO970538A IT BO970538 A1 ITBO970538 A1 IT BO970538A1
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- Prior art keywords
- calcitonin
- solution
- pharmaceutical compositions
- compositions according
- intranasal administration
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- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 title claims description 25
- 102000055006 Calcitonin Human genes 0.000 title claims description 22
- 108060001064 Calcitonin Proteins 0.000 title claims description 22
- 229960004015 calcitonin Drugs 0.000 title claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 16
- 239000007921 spray Substances 0.000 title claims description 10
- 239000000243 solution Substances 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 108010068072 salmon calcitonin Proteins 0.000 claims description 10
- 239000007979 citrate buffer Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960002303 citric acid monohydrate Drugs 0.000 claims description 4
- 239000008213 purified water Substances 0.000 claims description 4
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 4
- 229960000999 sodium citrate dihydrate Drugs 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229960003773 calcitonin (salmon synthetic) Drugs 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- 229940124532 absorption promoter Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 208000030915 hypercalcemia disease Diseases 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 210000004896 polypeptide structure Anatomy 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Description
Descrizione dell'invenjione industriale dal titolo: Description of the industrial invention entitled:
“Composizioni farmaceutiche contenenti calcitonlna in un dosatore spray per somministrazione intranasale “Pharmaceutical compositions containing calcitonin in a spray dispenser for intranasal administration
RIASSUNTO DELL'INVENZIONE SUMMARY OF THE INVENTION
L'oggetto della presente invenzione è costituito da composizioni farmaceutiche per somministrazione intranasale contenenti in un dosatore spray calcitonina sciolta in una soluzione sostanzialmente fisiologica di cloruro sodico regolata a pH compreso tra 3,5 e 4,5 con tampone citrato ed acido cloridrico ed esenti da qualsiasi conservante. The object of the present invention consists of pharmaceutical compositions for intranasal administration containing in a spray dispenser calcitonin dissolved in a substantially physiological solution of sodium chloride adjusted to a pH between 3.5 and 4.5 with citrate buffer and hydrochloric acid and free from any preservatives.
DESCRIZIONE DELL’ INVENZIONE DESCRIPTION OF THE INVENTION
La presente invenzione ha per oggetto composizioni farmaceutiche per somministrazione intranasale contenenti in un dosatore spray calcitonina, preferibilmente calcitonina di salmone nota anche sotto la denominazione di salcatonina, disciolta in una soluzione sostanzialmente fisiologica di cloruro di sodio regolata a pH compreso tra 3,5 e 4,5 con tampone citrato ed acido cloridrico ed esenti da qualsiasi conservante. The present invention relates to pharmaceutical compositions for intranasal administration containing calcitonin in a spray dispenser, preferably salmon calcitonin also known under the name of salcatonin, dissolved in a substantially physiological sodium chloride solution adjusted to pH between 3.5 and 4 , 5 with citrate buffer and hydrochloric acid and free from any preservative.
E' nota l'azione terapeutica esercitata dalla calcitonina nel trattamento dell'osteoporosi, del morbo di Paget e dell'ipercalcemia. The therapeutic action exerted by calcitonin in the treatment of osteoporosis, Paget's disease and hypercalcemia is known.
E' anche noto come le varie calcitonine, a struttura polipeptidica, siano facilmente degradatili e non possano essere somministrate per via orale, mentre la somministrazione per via parenterale presenta vari inconvenienti tra cui anche reazioni dolorose. It is also known that the various calcitonins, having a polypeptide structure, are easily degradable and cannot be administered orally, while parenteral administration has various drawbacks including painful reactions.
Per ovviare ai suddetti inconvenienti, molti farmaci di natura polipeptidica vengono somministrati per via intranasale, come viene descritto, ad esempio, da Felber et al. su Experientia, 1969, pag. 1195, da Gennser et al. su Lancet, 1974, pag. 865 e da Greenberg et al. su Antimicrobial Agents and Chemotherapy, 1978, pag. 596. To overcome the aforementioned drawbacks, many polypeptide drugs are administered intranasally, as described, for example, by Felber et al. on Experientia, 1969, p. 1195, from Gennser et al. in Lancet, 1974, p. 865 and by Greenberg et al. on Antimicrobial Agents and Chemotherapy, 1978, pag. 596.
Numerosi documenti brevettuali descrivono e rivendicano composizioni farmaceutiche per la somministrazione intranasale di calcitonina. Numerous patent documents describe and claim pharmaceutical compositions for the intranasal administration of calcitonin.
Il brevetto italiano 1172324 rivendica composizioni farmaceutiche contenenti calcitonina, cloruro di benzalconio e/o un tensioattivo. Questi additivi vengono definiti necessari per assicurare una buona biodisponibilità della calcitonina, cioè per garantirne un assorbimento efficace da parte della mucosa nasale, ed il cloruro di benzalconio viene definito necessario come preservante nei confronti dei microorganismi patogeni. Il brevetto europeo EP 193372 rivendica composizioni analoghe contenenti un sale ammonico quaternario come il cloruro di benzalconio ed il bromuro di cetiltrimetilammonio con funzione sia preservante che di acceleratori di assorbimento. The Italian patent 1172324 claims pharmaceutical compositions containing calcitonin, benzalkonium chloride and / or a surfactant. These additives are defined as necessary to ensure a good bioavailability of calcitonin, that is to guarantee its effective absorption by the nasal mucosa, and benzalkonium chloride is defined as necessary as a preservative against pathogenic microorganisms. The European patent EP 193372 claims similar compositions containing a quaternary ammonium salt such as benzalkonium chloride and cetyltrimethylammonium bromide with both preservative and absorption accelerator functions.
Numerosi altri documenti brevettuali rivendicano formulazioni nasali di calcitonina contenenti agenti adiuvanti di assorbimento: la domanda di brevetto giapponese 61126034 rivendica l'uso di glucosio e/o glucosamina, la domanda di brevetto giapponese 61118325 rivendica l'uso di aminoacidi, infine il brevetto europeo EP 0183525 rivendica l'uso come promotori di assorbimento di alcool benzilico, alcool etilico, acido salicilico e polietilenglicole. Numerous other patent documents claim nasal formulations of calcitonin containing adjuvant absorption agents: the Japanese patent application 61126034 claims the use of glucose and / or glucosamine, the Japanese patent application 61118325 claims the use of amino acids, finally the European patent EP 0183525 claims the use as absorption promoters of benzyl alcohol, ethyl alcohol, salicylic acid and polyethylene glycol.
La letteratura brevettuale è pertanto concorde nel sottolineare la necessità di aggiungere alle composizioni intranasali di calcitonina additivi di vario genere con lo scopo di mantenerne la conservabilità e di aumentarne la biodisponibilità. The patent literature therefore agrees in underlining the need to add additives of various kinds to the intranasal compositions of calcitonin in order to maintain their shelf life and increase their bioavailability.
E' pertanto decisamente sorprendente l'aver trovato che composizioni farmaceutiche per somministrazione intranasale contenenti in un dosatore spray calcitonina in una soluzione acquosa sostanzialmente fisiologica di cloruro sodico regolata a pH compreso tra 3,5 e 4,5 con tampone citrato ed acido cloridrico posseggono la stessa biodisponibilità e conservabilità delle composizioni farmaceutiche di calcitonina contenenti agenti conservanti e/o adiuvanti dell'assorbimento . It is therefore quite surprising to have found that pharmaceutical compositions for intranasal administration containing in a spray dispenser calcitonin in a substantially physiological aqueous solution of sodium chloride adjusted to pH between 3.5 and 4.5 with citrate buffer and hydrochloric acid possess the same bioavailability and shelf life as pharmaceutical compositions of calcitonin containing preservative agents and / or absorption adjuvants.
Composizioni farmaceutiche per somministrazione intranasale contenenti in un dosatore spray quantità terapeuticamente efficaci di calcitonina sciolta in una soluzione sostanzialmente fisiologica di cloruro sodico in acqua depurata regolata· ad un pH compreso tra 3,5 e 4,5 con tampone citrato ed acido cloridrico costituiscono l'oggetto della presente invenzione. Pharmaceutical compositions for intranasal administration containing in a spray dispenser therapeutically effective quantities of calcitonin dissolved in a substantially physiological solution of sodium chloride in purified water adjusted to a pH between 3.5 and 4.5 with citrate buffer and hydrochloric acid constitute the object of the present invention.
Il tampone citrato viene usato per conferire una maggiore stabilità del pH della soluzione nel corso della validità del prodotto. Citrate buffer is used to impart greater stability to the pH of the solution over the life of the product.
Esso è costituito da una miscela di acido citrico monoidrato e di sodio citrato diidrato, in preferenza la miscela è formata da 0,40 a 0,70 g di acido citrico monoidrato e da 0,40 a 0,70 g di sodio citrato diidrato per ciascun litro di soluzione contenente la calcitonina. Il pH della soluzione viene, regolato ad un valore compreso tra 3,5 e 4,5 per aggiunta di una soluzione acquosa IN di acido cloridrico, preferibilmente compresa tra 0,08 g e 0,25 g per ogni litro di soluzione. It consists of a mixture of citric acid monohydrate and sodium citrate dihydrate, preferably the mixture is formed from 0.40 to 0.70 g of citric acid monohydrate and from 0.40 to 0.70 g of sodium citrate dihydrate for each liter of solution containing calcitonin. The pH of the solution is adjusted to a value between 3.5 and 4.5 by adding an 1N aqueous solution of hydrochloric acid, preferably between 0.08 g and 0.25 g for each liter of solution.
In un aspetto preferito dell'invenzione, la calcitonina usata è costituita da calcitonina di salmone, nota anche sotto la denominazione di salcatonina, e le quantità terapeuticamente efficaci sono comprese tra 500 e 2500 U.I. di calcitonina per millilitro di soluzione. In a preferred aspect of the invention, the calcitonin used is constituted by salmon calcitonin, also known under the name of salcatonin, and the therapeutically effective quantities are comprised between 500 and 2500 I.U. of calcitonin per milliliter of solution.
In un ulteriore aspetto preferito dell'invenzione, il dosatore spray per la somministrazione intranasale della calcitonina è costituito da un flacone che contiene la soluzione di calcitonina ed azoto ad una pressione compresa tra 0,2 e 0,3 bar ed alla cui imboccatura è posta una pompa dosatrice priva di valvola di aspirazione e mandata e dotata di una guarnizione a collare che aderisce all'imboccatura del flacone costituendo una chiusura ermetica che impedisce qualsiasi scambio di gas con l'esterno. In a further preferred aspect of the invention, the spray dispenser for the intranasal administration of calcitonin consists of a bottle containing the calcitonin and nitrogen solution at a pressure between 0.2 and 0.3 bar and at the mouth of which it is placed a metering pump without a suction and delivery valve and equipped with a collar gasket that adheres to the mouth of the bottle, forming a hermetic seal that prevents any exchange of gas with the outside.
Detto flacone può avere una capacità compresa tra 5 e 10 mi e la pompa dosatrice eroga circa 100 microlitri di soluzione ad ogni azionamento. Said bottle can have a capacity of between 5 and 10 ml and the metering pump delivers about 100 microliters of solution at each actuation.
Le composizioni farmaceutiche secondo l'invenzione presentano il vantaggio, rispetto a quelle note dalla tecnica precedente, di essere prive sia dei sali ammonici quaternari di cui sono noti gli effetti indesiderati sulle mucose [Am. J. Opthalmol., 105, (6), 670-3, (1988); Contact Dermatitis, 17, (1), 41-2, (1987); Cutis, 39, (5), 381-3, (1987)] che degli altri adiuvanti dell'assorbimento che, anche a prescindere da possibili effetti indesiderati, comportano comunque un aumento dei costi di produzione. The pharmaceutical compositions according to the invention have the advantage, with respect to those known from the prior art, of being free both of the quaternary ammonium salts of which the undesirable effects on the mucous membranes are known [Am. J. Opthalmol., 105, (6), 670-3, (1988); Contact Dermatitis, 17, (1), 41-2, (1987); Cutis, 39, (5), 381-3, (1987)] and other absorption adjuvants which, even apart from possible undesirable effects, still involve an increase in production costs.
Gli esempi di seguito riportati servono ad illustrare ulteriormente le composizioni farmaceutiche oggetto della presente invenzione e non debbono essere considerate come una sua limitazione. The examples reported below serve to further illustrate the pharmaceutical compositions object of the present invention and should not be considered as a limitation thereof.
ESEMPIO 1 EXAMPLE 1
Una quantità di salcatonina equivalente a 1.000.000 U.I. viene disciolta in una soluzione contenente 8,7 g di cloruro sodico analiticamente puro in 800 mi di acqua depurata. La risultante soluzione viene quindi addizionata di 0,58 g di acido citrico monoidrato, 0,58 g di sodio citrato diidrato e 0,18 g di una soluzione acquosa IN di acido cloridrico analiticamente puro. An amount of salcatonin equivalent to 1,000,000 I.U. it is dissolved in a solution containing 8.7 g of analytically pure sodium chloride in 800 ml of purified water. The resulting solution is then added with 0.58 g of citric acid monohydrate, 0.58 g of sodium citrate dihydrate and 0.18 g of an aqueous 1N solution of analytically pure hydrochloric acid.
La soluzione viene portata al volume di 1000 mi con acqua depurata, filtrata su filtro da 0,2 μιη e ripartita nei dosatori spray tarati per la somministrazione di 0,1 mi di soluzione, pari a 100 U.I. di salcatonina, ad ogni azionamento. The solution is brought to the volume of 1000 ml with purified water, filtered on a 0.2 μιη filter and distributed in the calibrated spray dispensers for the administration of 0.1 ml of solution, equal to 100 I.U. of salcatonin, at each actuation.
ESEMPIO 2 EXAMPLE 2
L'esempio 1 viene ripetuto con le varianti di utilizzare una quantità doppia di salcatonina (2.000.000 U.I.). . Ciascuna dose da 0,1 mi equivale a 200 U.I. di salcatonina. Example 1 is repeated with the variants of using a double quantity of salcatonin (2,000,000 I.U.). . Each 0.1 ml dose is equivalent to 200 I.U. of salcatonin.
Claims (5)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT97BO000538 IT1294191B1 (en) | 1997-09-05 | 1997-09-05 | Composition for treating osteoporosis, Paget's disease or hypercalcemia, comprises calcitonin dissolved in acidic sodium chloride solution |
| TR1998/01018A TR199801018A2 (en) | 1997-09-05 | 1998-06-04 | Pharmaceutical compositions containing calcitonin in a spray feeder for intranasal administration. |
| ES9801849A ES2151838B1 (en) | 1997-09-05 | 1998-09-02 | PHARMACEUTICAL COMPOSITIONS CONTAINING CALCITONIN IN A SPRAY DOSER FOR INTRANASAL ADMINISTRATION. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT97BO000538 IT1294191B1 (en) | 1997-09-05 | 1997-09-05 | Composition for treating osteoporosis, Paget's disease or hypercalcemia, comprises calcitonin dissolved in acidic sodium chloride solution |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ITBO970538A0 ITBO970538A0 (en) | 1997-09-05 |
| ITBO970538A1 true ITBO970538A1 (en) | 1999-03-05 |
| IT1294191B1 IT1294191B1 (en) | 1999-03-22 |
Family
ID=11342512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT97BO000538 IT1294191B1 (en) | 1997-09-05 | 1997-09-05 | Composition for treating osteoporosis, Paget's disease or hypercalcemia, comprises calcitonin dissolved in acidic sodium chloride solution |
Country Status (3)
| Country | Link |
|---|---|
| ES (1) | ES2151838B1 (en) |
| IT (1) | IT1294191B1 (en) |
| TR (1) | TR199801018A2 (en) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61267528A (en) * | 1984-11-26 | 1986-11-27 | Yamanouchi Pharmaceut Co Ltd | Transnasal calcitonin agent containing absorbefacient |
| DE3726324A1 (en) * | 1987-08-07 | 1989-02-16 | Hoechst Ag | CYCLOPEPTIDE AS RESORPTION FOLDER IN APPLICATION TO THE MEAT |
| HU206367B (en) * | 1988-04-30 | 1992-10-28 | Sandoz Ag | Process for producing acid addition salts of steroid carboxylic acid-amidated taurine and glycine, as well as pharmaceutical compositions comprising such salts |
| IL91856A0 (en) * | 1988-10-11 | 1990-06-10 | Schiapparelli Salute Spa | Pharmaceutical compositions comprising calcitonin for intranasal administration and a spray unit for the administration of the same |
| EP0489217A1 (en) * | 1990-12-05 | 1992-06-10 | Dr. A. Tosi Farmaceutici S.R.L. | Calcitonin compositions for intranasal administration |
| IT1251685B (en) * | 1991-10-11 | 1995-05-19 | Isf Spa | PHARMACEUTICAL COMPOSITIONS CONTAINING A CALCITONIN |
-
1997
- 1997-09-05 IT IT97BO000538 patent/IT1294191B1/en active IP Right Grant
-
1998
- 1998-06-04 TR TR1998/01018A patent/TR199801018A2/en unknown
- 1998-09-02 ES ES9801849A patent/ES2151838B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TR199801018A3 (en) | 1999-11-22 |
| ES2151838A1 (en) | 2001-01-01 |
| TR199801018A2 (en) | 1999-11-22 |
| IT1294191B1 (en) | 1999-03-22 |
| ITBO970538A0 (en) | 1997-09-05 |
| ES2151838B1 (en) | 2001-08-16 |
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