NO332936B1 - Faste, farmasoytiske sammensetninger for oral tilforsel av kalsitonin - Google Patents
Faste, farmasoytiske sammensetninger for oral tilforsel av kalsitoninInfo
- Publication number
- NO332936B1 NO332936B1 NO20032511A NO20032511A NO332936B1 NO 332936 B1 NO332936 B1 NO 332936B1 NO 20032511 A NO20032511 A NO 20032511A NO 20032511 A NO20032511 A NO 20032511A NO 332936 B1 NO332936 B1 NO 332936B1
- Authority
- NO
- Norway
- Prior art keywords
- calcitonin
- cnac
- composition according
- pharmacologically active
- crospovidone
- Prior art date
Links
- 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 abstract description 41
- 102000055006 Calcitonin Human genes 0.000 title claims abstract description 25
- 108060001064 Calcitonin Proteins 0.000 title claims abstract description 25
- 229960004015 calcitonin Drugs 0.000 title claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 17
- 239000007787 solid Substances 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 41
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims abstract description 18
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims abstract description 18
- 229960000913 crospovidone Drugs 0.000 claims abstract description 17
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 8
- 229940069328 povidone Drugs 0.000 claims abstract description 5
- XRTHAPZDZPADIL-UHFFFAOYSA-N 8-[(5-chloro-2-hydroxybenzoyl)amino]octanoic acid Chemical compound OC(=O)CCCCCCCNC(=O)C1=CC(Cl)=CC=C1O XRTHAPZDZPADIL-UHFFFAOYSA-N 0.000 claims description 20
- 108010068072 salmon calcitonin Proteins 0.000 claims description 17
- 229960003773 calcitonin (salmon synthetic) Drugs 0.000 claims description 15
- 229940124447 delivery agent Drugs 0.000 claims description 9
- 125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229960002446 octanoic acid Drugs 0.000 claims description 4
- XUHVCHNJCBBXMP-UHFFFAOYSA-M sodium;10-[(2-hydroxybenzoyl)amino]decanoate Chemical compound [Na+].OC1=CC=CC=C1C(=O)NCCCCCCCCCC([O-])=O XUHVCHNJCBBXMP-UHFFFAOYSA-M 0.000 claims description 4
- UOENJXXSKABLJL-UHFFFAOYSA-M sodium;8-[(2-hydroxybenzoyl)amino]octanoate Chemical compound [Na+].OC1=CC=CC=C1C(=O)NCCCCCCCC([O-])=O UOENJXXSKABLJL-UHFFFAOYSA-M 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 2
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 29
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 2
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000002775 capsule Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- XGSDAQOSOKPJML-UHFFFAOYSA-L disodium;8-[(5-chloro-2-oxidobenzoyl)amino]octanoate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCCCCNC(=O)C1=CC(Cl)=CC=C1[O-] XGSDAQOSOKPJML-UHFFFAOYSA-L 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000008215 water for injection Substances 0.000 description 6
- 229920003084 Avicel® PH-102 Polymers 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000008055 phosphate buffer solution Substances 0.000 description 4
- 239000008279 sol Substances 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 3
- 241000288906 Primates Species 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 108010039627 Aprotinin Proteins 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- 208000037147 Hypercalcaemia Diseases 0.000 description 2
- 241000282560 Macaca mulatta Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000010191 Osteitis Deformans Diseases 0.000 description 2
- 208000027868 Paget disease Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000000148 hypercalcaemia Effects 0.000 description 2
- 208000030915 hypercalcemia disease Diseases 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 208000027202 mammary Paget disease Diseases 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- -1 natural Chemical compound 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000012430 stability testing Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 1
- JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical compound CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 description 1
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- KSIYPKPZIBBUFR-LJNLPFSOSA-N CSCC[C@H](NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=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)C(C)C)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(N)=O Chemical compound CSCC[C@H](NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=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)C(C)C)C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(N)=O KSIYPKPZIBBUFR-LJNLPFSOSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920003085 Kollidon® CL Polymers 0.000 description 1
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 102000015731 Peptide Hormones Human genes 0.000 description 1
- 108010038988 Peptide Hormones Proteins 0.000 description 1
- 229920003075 Plasdone™ K-29/32 polymer Polymers 0.000 description 1
- 229920003072 Plasdone™ povidone Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 101000910302 Sus scrofa Calcitonin Proteins 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960004405 aprotinin Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- VSHJAJRPRRNBEK-LMVCGNDWSA-N eel calcitonin Chemical compound C([C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CS)[C@@H](C)O)C(C)C)CC(C)C)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(O)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C1=CN=CN1 VSHJAJRPRRNBEK-LMVCGNDWSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 208000001685 postmenopausal osteoporosis Diseases 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229940108519 trasylol Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25172900P | 2000-12-06 | 2000-12-06 | |
| PCT/EP2001/014294 WO2002045754A2 (en) | 2000-12-06 | 2001-12-05 | Pharmaceutical compositions for the oral delivery of pharmacologically active agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20032511L NO20032511L (no) | 2003-06-03 |
| NO20032511D0 NO20032511D0 (no) | 2003-06-03 |
| NO332936B1 true NO332936B1 (no) | 2013-02-04 |
Family
ID=22953160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20032511A NO332936B1 (no) | 2000-12-06 | 2003-06-03 | Faste, farmasoytiske sammensetninger for oral tilforsel av kalsitonin |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7049283B2 (xx) |
| EP (1) | EP1341526B1 (xx) |
| JP (2) | JP4898078B2 (xx) |
| KR (1) | KR100847695B1 (xx) |
| CN (1) | CN1304048C (xx) |
| AT (1) | ATE513541T1 (xx) |
| AU (2) | AU2002234547B2 (xx) |
| BR (2) | BR0115965A (xx) |
| CA (1) | CA2436599C (xx) |
| CY (1) | CY1112562T1 (xx) |
| CZ (1) | CZ305418B6 (xx) |
| DK (1) | DK1341526T3 (xx) |
| EC (1) | ECSP034639A (xx) |
| ES (1) | ES2367009T3 (xx) |
| HK (1) | HK1059565A1 (xx) |
| HU (1) | HU230632B1 (xx) |
| IL (2) | IL155992A0 (xx) |
| MX (1) | MXPA03005096A (xx) |
| NO (1) | NO332936B1 (xx) |
| NZ (1) | NZ526196A (xx) |
| PL (1) | PL209703B1 (xx) |
| PT (1) | PT1341526E (xx) |
| RU (1) | RU2287999C2 (xx) |
| SI (1) | SI1341526T1 (xx) |
| SK (1) | SK287613B6 (xx) |
| WO (1) | WO2002045754A2 (xx) |
| ZA (1) | ZA200304295B (xx) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2369591C (en) | 1999-04-05 | 2011-06-14 | Emisphere Technologies, Inc. | Disodium salts, monohydrate, and ethanol solvates |
| KR101320817B1 (ko) * | 2001-06-01 | 2013-10-21 | 노파르티스 아게 | 부갑상선 호르몬 및 칼시토닌의 경구 투여 |
| US20050054557A1 (en) * | 2002-05-09 | 2005-03-10 | Goldberg Michael M. | Compositions for delivering parathyroid hormone and calcitonin |
| TW200403052A (en) * | 2002-07-17 | 2004-03-01 | Novartis Ag | Use of organic compounds |
| TWI307279B (en) * | 2002-08-01 | 2009-03-11 | Novartis Ag | Oral administration of calcitonin |
| JP5546715B2 (ja) * | 2003-03-17 | 2014-07-09 | 日本たばこ産業株式会社 | Ｃｅｔｐ阻害剤の医薬組成物 |
| TWI393560B (zh) * | 2003-05-02 | 2013-04-21 | Japan Tobacco Inc | 包含ｓ-〔２（〔〔１-（２-乙基丁基）環己基〕羰基〕胺基）苯基〕２-甲基丙烷硫酯及ｈｍｇ輔酶ａ還原酶抑制劑之組合 |
| EP1651248B1 (en) * | 2003-07-11 | 2009-09-09 | Novartis AG | Orally dosed pharmaceutical compositions comprising a delivery agent in micronized form |
| TR201910177T4 (tr) * | 2003-09-12 | 2019-08-21 | Amgen Inc | Bir sinakalset HCl içeren hızlı çözünme formülasyonu. |
| NZ551597A (en) * | 2004-05-19 | 2010-11-26 | Emisphere Tech Inc | Topical cromolyn formulations |
| GB0422644D0 (en) * | 2004-10-12 | 2004-11-10 | Novartis Ag | Organic compounds |
| GB0427603D0 (en) | 2004-12-16 | 2005-01-19 | Novartis Ag | Organic compounds |
| JP5175553B2 (ja) * | 2005-02-01 | 2013-04-03 | エミスフェアー・テクノロジーズ・インク | 胃内滞留および制御放出型送達系 |
| WO2007005995A2 (en) * | 2005-07-05 | 2007-01-11 | Emisphere Technologies, Inc. | Compositions for buccal delivery of human growth hormone |
| CN105641686A (zh) | 2005-09-19 | 2016-06-08 | 爱密斯菲尔科技公司 | N-(5-氯水杨酰基)-8-氨基辛酸的二钠盐的晶形 |
| GB0522566D0 (en) | 2005-11-04 | 2005-12-14 | Novartis Ag | Organic compounds |
| KR101432313B1 (ko) * | 2005-11-17 | 2014-08-20 | 노파르티스 아게 | 약제학적 조성물 |
| JP2009527504A (ja) * | 2006-02-23 | 2009-07-30 | イオメディックス スリープ インターナショナル エスアールエル | 良質な睡眠の誘導および維持のための組成物および方法 |
| CA2659655A1 (en) * | 2006-08-08 | 2008-02-21 | Alan M. Fogelman | Salicylanilides enhance oral delivery of therapeutic peptides |
| PT2059260E (pt) * | 2006-08-31 | 2013-09-03 | Novartis Ag | Composições farmacêuticas compreendendo hgh para distribuição oral |
| CA2572004A1 (en) * | 2006-12-08 | 2008-06-08 | Bernard Charles Sherman | Tablets comprising entacapone and crospovidone |
| CN101621991A (zh) * | 2007-03-02 | 2010-01-06 | 诺瓦提斯公司 | 降钙素的口服施用 |
| AU2008318423B2 (en) | 2007-11-02 | 2013-12-05 | Emisphere Technologies, Inc. | Method of treating vitamin B12 deficiency |
| NZ591497A (en) | 2008-08-18 | 2012-11-30 | Entera Bio Ltd | A compositions comprising a protein, a protease inhibitor and N-(8-[2-hydroxybenzoyl]amino)caprylate (SNAC) or N-(10[2-hydroxybenzoyl]amino)decanoate (SNAD) for diabetes mellitus treatment |
| JP5993147B2 (ja) * | 2009-03-12 | 2016-09-14 | キーバイオサイエンス・アクチエンゲゼルシャフト | 糖尿病およびメタボリックシンドロームの治療 |
| JP5865903B2 (ja) * | 2010-06-09 | 2016-02-17 | エミスフェアー・テクノロジーズ・インク | 経口鉄欠乏療法 |
| MX345501B (es) | 2010-12-16 | 2017-02-02 | Novo Nordisk As | Composiciones solidas que comprenden agonista de glp-1 y sal del acido n-(8-(2-hidroxibenzoil)amino)caprilico. |
| MX355361B (es) | 2011-04-12 | 2018-04-17 | Novo Nordisk As | Derivados de peptido 1 tipo glucagon (glp-1) doblemente acilados. |
| EP4331667A3 (en) | 2012-03-22 | 2024-05-08 | Novo Nordisk A/S | Compositions comprising a delivery agent and preparation thereof |
| MY171146A (en) | 2012-03-22 | 2019-09-27 | Novo Nordisk As | Compositions of glp-1 peptides and preparation thereof |
| HUE042757T2 (hu) | 2012-03-22 | 2019-07-29 | Novo Nordisk As | Szállító szert tartalmazó készítmények és elõállításuk |
| EP2863895B1 (en) | 2012-06-20 | 2021-04-14 | Novo Nordisk A/S | Tablet formulation comprising a peptide and a delivery agent |
| CN104961687B (zh) * | 2015-06-03 | 2017-07-25 | 苏州维泰生物技术有限公司 | 1,2‑二嗪衍生物及其制剂、用途 |
| US20170008924A1 (en) * | 2015-07-08 | 2017-01-12 | Research & Business Foundation Sungkyunkwan University | Pyrrolidine carboxamido derivatives and methods for preparing and using the same |
| EA036204B1 (ru) * | 2015-10-16 | 2020-10-14 | Нобел Илач Санайи Ве Тиджарет А.Ш. | Фармацевтические композиции нилотиниба гидрохлорида |
| CN107080739A (zh) * | 2017-04-17 | 2017-08-22 | 深圳市泛谷药业股份有限公司 | 一种用于口服给药的固体快速释放布南色林片及其制备方法 |
| KR102647171B1 (ko) | 2018-02-02 | 2024-03-15 | 노보 노르디스크 에이/에스 | Glp-1 작용제 및 n-(8-(2-하이드록시벤조일)아미노)카프릴산의 염을 포함하는 고형 조성물 |
| JP2021054781A (ja) * | 2019-09-26 | 2021-04-08 | デボン エルエス，リミテッド | 共結晶形エフィナコナゾール、及びその製造方法 |
| KR102301743B1 (ko) * | 2020-12-29 | 2021-09-13 | 대봉엘에스 주식회사 | 에피나코나졸 경구용 조성물 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015633A (en) | 1987-04-27 | 1991-05-14 | E. R. Squibb & Sons, Inc. | Method for inhibiting loss of cognitive functions employing an ace inhibitor |
| US5756450A (en) | 1987-09-15 | 1998-05-26 | Novartis Corporation | Water soluble monoesters as solubilisers for pharmacologically active compounds and pharmaceutical excipients and novel cyclosporin galenic forms |
| US5002771A (en) | 1989-02-06 | 1991-03-26 | Rorer Pharmaceutical Corp. | Calcitonin suppository formulations |
| IT1238072B (it) | 1990-01-19 | 1993-07-03 | Sclavo Spa | Composizioni farmaceutiche e forme di dosaggio per la somministrazione orale di calcitonina |
| JPH052771A (ja) * | 1991-06-25 | 1993-01-08 | Pioneer Electron Corp | 光記録媒体 |
| US5681811A (en) * | 1993-05-10 | 1997-10-28 | Protein Delivery, Inc. | Conjugation-stabilized therapeutic agent compositions, delivery and diagnostic formulations comprising same, and method of making and using the same |
| PT800384E (pt) | 1994-12-14 | 2001-06-29 | Enbalt Trading Ltd | Metodo para a preparacao de um comprimido farmaceutico |
| US5866536A (en) | 1995-03-31 | 1999-02-02 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| BR9604880A (pt) * | 1995-03-31 | 1998-05-19 | Emisphere Tech Inc | Composto composição forma de unidade de dosagem métodos para administração de um agente biologicamente ativo para preparar uma composição para administração de um agente ativo e para preparar um composto e composição farmacológica |
| US5912014A (en) * | 1996-03-15 | 1999-06-15 | Unigene Laboratories, Inc. | Oral salmon calcitonin pharmaceutical products |
| US5972381A (en) | 1996-06-28 | 1999-10-26 | Schering Corporation | Solid solution of an antifungal agent with enhanced bioavailability |
| US5958453A (en) | 1996-10-31 | 1999-09-28 | Takeda Chemical Industries, Ltd. | Solid pharmaceutical preparation with improved buccal disintegrability and/or dissolubility |
| US5773647A (en) | 1997-02-07 | 1998-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| WO1998034632A1 (en) | 1997-02-07 | 1998-08-13 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| PL343276A1 (en) | 1998-03-16 | 2001-08-13 | Inhale Therapeutic Syst | Aerosolized active agent delivery |
| AU3574500A (en) | 1999-03-25 | 2000-10-16 | Yuhan Corporation | Rapidly disintegrable tablet for oral administration |
| CA2369591C (en) | 1999-04-05 | 2011-06-14 | Emisphere Technologies, Inc. | Disodium salts, monohydrate, and ethanol solvates |
| AU4218400A (en) * | 1999-04-05 | 2000-10-23 | Emisphere Technologies, Inc. | Lyophilized solid dosage forms and methods of making |
-
2001
- 2001-12-04 US US10/006,311 patent/US7049283B2/en not_active Expired - Fee Related
- 2001-12-05 JP JP2002547536A patent/JP4898078B2/ja not_active Expired - Fee Related
- 2001-12-05 AT AT01985368T patent/ATE513541T1/de active
- 2001-12-05 CZ CZ2003-1566A patent/CZ305418B6/cs not_active IP Right Cessation
- 2001-12-05 CA CA2436599A patent/CA2436599C/en not_active Expired - Fee Related
- 2001-12-05 SI SI200130999T patent/SI1341526T1/sl unknown
- 2001-12-05 AU AU2002234547A patent/AU2002234547B2/en not_active Ceased
- 2001-12-05 IL IL15599201A patent/IL155992A0/xx active IP Right Grant
- 2001-12-05 BR BR0115965-8A patent/BR0115965A/pt not_active IP Right Cessation
- 2001-12-05 WO PCT/EP2001/014294 patent/WO2002045754A2/en active IP Right Grant
- 2001-12-05 CN CNB018201423A patent/CN1304048C/zh not_active Expired - Fee Related
- 2001-12-05 PT PT01985368T patent/PT1341526E/pt unknown
- 2001-12-05 KR KR1020037007098A patent/KR100847695B1/ko not_active IP Right Cessation
- 2001-12-05 SK SK688-2003A patent/SK287613B6/sk not_active IP Right Cessation
- 2001-12-05 HU HU0302319A patent/HU230632B1/hu not_active IP Right Cessation
- 2001-12-05 DK DK01985368.8T patent/DK1341526T3/da active
- 2001-12-05 RU RU2003119545/15A patent/RU2287999C2/ru not_active IP Right Cessation
- 2001-12-05 NZ NZ526196A patent/NZ526196A/en not_active IP Right Cessation
- 2001-12-05 ES ES01985368T patent/ES2367009T3/es not_active Expired - Lifetime
- 2001-12-05 EP EP01985368A patent/EP1341526B1/en not_active Expired - Lifetime
- 2001-12-05 PL PL362247A patent/PL209703B1/pl unknown
- 2001-12-05 BR BRPI0115965-8A patent/BRPI0115965B1/pt unknown
- 2001-12-05 MX MXPA03005096A patent/MXPA03005096A/es active IP Right Grant
- 2001-12-05 AU AU3454702A patent/AU3454702A/xx active Pending
-
2003
- 2003-05-19 IL IL155992A patent/IL155992A/en not_active IP Right Cessation
- 2003-06-02 ZA ZA200304295A patent/ZA200304295B/en unknown
- 2003-06-03 NO NO20032511A patent/NO332936B1/no not_active IP Right Cessation
- 2003-06-04 EC EC2003004639A patent/ECSP034639A/es unknown
-
2004
- 2004-02-11 HK HK04100920.1A patent/HK1059565A1/xx not_active IP Right Cessation
-
2009
- 2009-04-13 JP JP2009097262A patent/JP2009185052A/ja not_active Withdrawn
-
2011
- 2011-08-09 CY CY20111100759T patent/CY1112562T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO332936B1 (no) | Faste, farmasoytiske sammensetninger for oral tilforsel av kalsitonin | |
| AU2002234547A1 (en) | Pharmaceutical compositions for the oral delivery of pharmacologically active agents | |
| US7569539B2 (en) | Oral administration of calcitonin | |
| US8410052B2 (en) | Oral administration of a calcitonin | |
| AU2005202705B2 (en) | Pharmaceutical compositions for the oral delivery of pharmacologically active agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |