CA2704780C - Method of treating vitamin b12 deficiency - Google Patents
Method of treating vitamin b12 deficiency Download PDFInfo
- Publication number
- CA2704780C CA2704780C CA2704780A CA2704780A CA2704780C CA 2704780 C CA2704780 C CA 2704780C CA 2704780 A CA2704780 A CA 2704780A CA 2704780 A CA2704780 A CA 2704780A CA 2704780 C CA2704780 C CA 2704780C
- Authority
- CA
- Canada
- Prior art keywords
- vitamin
- pharmaceutical composition
- tablet
- snac
- hydroxybenzoyl
- 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 - Fee Related
Links
- 208000002670 vitamin B12 deficiency Diseases 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title abstract description 10
- 229930003779 Vitamin B12 Natural products 0.000 claims abstract description 52
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 claims abstract description 52
- 235000019163 vitamin B12 Nutrition 0.000 claims abstract description 52
- 239000011715 vitamin B12 Substances 0.000 claims abstract description 52
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims abstract 3
- 229960002446 octanoic acid Drugs 0.000 claims abstract 3
- 238000011282 treatment Methods 0.000 claims description 18
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000003086 colorant Substances 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 239000000796 flavoring agent Substances 0.000 claims description 9
- 235000013355 food flavoring agent Nutrition 0.000 claims description 9
- 235000003599 food sweetener Nutrition 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 9
- 239000003765 sweetening agent Substances 0.000 claims description 9
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 8
- 230000003247 decreasing effect Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 5
- 241000124008 Mammalia Species 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 239000003826 tablet Substances 0.000 description 45
- 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 description 41
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 description 38
- 235000000639 cyanocobalamin Nutrition 0.000 description 19
- 239000011666 cyanocobalamin Substances 0.000 description 19
- 229960002104 cyanocobalamin Drugs 0.000 description 19
- 229940088594 vitamin Drugs 0.000 description 19
- 229930003231 vitamin Natural products 0.000 description 19
- 235000013343 vitamin Nutrition 0.000 description 19
- 239000011782 vitamin Substances 0.000 description 19
- 150000003722 vitamin derivatives Chemical class 0.000 description 19
- 239000002253 acid Substances 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- OAYRYNVEFFWSHK-UHFFFAOYSA-N carsalam Chemical compound C1=CC=C2OC(=O)NC(=O)C2=C1 OAYRYNVEFFWSHK-UHFFFAOYSA-N 0.000 description 6
- 229950004289 carsalam Drugs 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 4
- 238000012369 In process control Methods 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102000011409 Transcobalamins Human genes 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010965 in-process control Methods 0.000 description 3
- 229940029329 intrinsic factor Drugs 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- -1 phenoxybenzoyl Chemical group 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 2
- 108010023603 Transcobalamins Proteins 0.000 description 2
- 229930003270 Vitamin B Natural products 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 210000000133 brain stem Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- YOZNUFWCRFCGIH-BYFNXCQMSA-L hydroxocobalamin Chemical compound O[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O YOZNUFWCRFCGIH-BYFNXCQMSA-L 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 229960000581 salicylamide Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 235000019156 vitamin B Nutrition 0.000 description 2
- 239000011720 vitamin B Substances 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 229920003082 Povidone K 90 Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940010007 cobalamins Drugs 0.000 description 1
- 150000001867 cobalamins Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000004136 fatty acid synthesis Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001914 gastric parietal cell Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000004867 hydroxocobalamin Nutrition 0.000 description 1
- 239000011704 hydroxocobalamin Substances 0.000 description 1
- 229960001103 hydroxocobalamin Drugs 0.000 description 1
- 238000013095 identification testing Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 235000007672 methylcobalamin Nutrition 0.000 description 1
- 239000011585 methylcobalamin Substances 0.000 description 1
- JEWJRMKHSMTXPP-BYFNXCQMSA-M methylcobalamin Chemical compound C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O JEWJRMKHSMTXPP-BYFNXCQMSA-M 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001711 oxyntic cell Anatomy 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7135—Compounds containing heavy metals
- A61K31/714—Cobalamins, e.g. cyanocobalamin, i.e. vitamin B12
-
- 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
- A61K9/2009—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Nutrition Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98489807P | 2007-11-02 | 2007-11-02 | |
| US60/984,898 | 2007-11-02 | ||
| US2010808P | 2008-01-09 | 2008-01-09 | |
| US61/020,108 | 2008-01-09 | ||
| US8356608P | 2008-07-25 | 2008-07-25 | |
| US61/083,566 | 2008-07-25 | ||
| PCT/US2008/082064 WO2009059188A1 (en) | 2007-11-02 | 2008-10-31 | Method of treating vitamin b12 deficiency |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2704780A1 CA2704780A1 (en) | 2009-05-07 |
| CA2704780C true CA2704780C (en) | 2014-06-10 |
Family
ID=40591491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2704780A Expired - Fee Related CA2704780C (en) | 2007-11-02 | 2008-10-31 | Method of treating vitamin b12 deficiency |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US8022048B2 (enExample) |
| EP (1) | EP2215047B1 (enExample) |
| JP (1) | JP5555634B2 (enExample) |
| KR (1) | KR101344369B1 (enExample) |
| CN (1) | CN101952241B (enExample) |
| AU (1) | AU2008318423B2 (enExample) |
| BR (1) | BRPI0817396C8 (enExample) |
| CA (1) | CA2704780C (enExample) |
| CL (1) | CL2010000434A1 (enExample) |
| CO (1) | CO6280475A2 (enExample) |
| DK (1) | DK2215047T3 (enExample) |
| ES (1) | ES2443817T3 (enExample) |
| MX (1) | MX2010004716A (enExample) |
| NZ (1) | NZ585080A (enExample) |
| PL (1) | PL2215047T3 (enExample) |
| PT (1) | PT2215047E (enExample) |
| RU (1) | RU2469728C2 (enExample) |
| WO (1) | WO2009059188A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110039930A1 (en) * | 2009-08-03 | 2011-02-17 | Emisphere Technologies, Inc. | Fast-acting naproxen composition with reduced gastrointestinal effects |
| KR20130026429A (ko) * | 2010-02-24 | 2013-03-13 | 에미스페어 테크놀로지스, 인코포레이티드 | 경구 ｂ12 치료요법 |
| 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. |
| KR101972836B1 (ko) | 2011-04-12 | 2019-04-29 | 노보 노르디스크 에이/에스 | 이중 아실화된 ｇｌｐ-1 유도체 |
| US8805208B2 (en) * | 2012-02-03 | 2014-08-12 | Tyco Electronics Subsea Communications Llc | System and method for polarization de-multiplexing in a coherent optical receiver |
| EP2827885B1 (en) | 2012-03-22 | 2018-08-15 | Novo Nordisk A/S | Compositions of glp-1 peptides and preparation thereof |
| WO2013139695A1 (en) | 2012-03-22 | 2013-09-26 | Novo Nordisk A/S | Compositions comprising a delivery agent and preparation thereof |
| HRP20190489T1 (hr) | 2012-03-22 | 2019-05-03 | Novo Nordisk A/S | Pripravci koji sadrže sredstvo za unošenje i njihova priprava |
| US9993430B2 (en) | 2012-06-20 | 2018-06-12 | Novo Nordisk A/S | Tablet formulation comprising semaglutide and a delivery agent |
| US9603812B2 (en) | 2013-04-11 | 2017-03-28 | Richard Louis Price | Treatment of autistic spectrum disorder |
| US20170348417A1 (en) | 2013-04-11 | 2017-12-07 | Richard Louis Price | Treatment of attention deficit disorders and associated symptoms |
| US9211284B2 (en) | 2013-04-11 | 2015-12-15 | Richard Louis Price | Diagnosis and treatment of P.R.I.C.E. syndrome |
| US10098848B2 (en) | 2013-04-11 | 2018-10-16 | Richard Louis Price | Inositol-containing comestible units and methods of treatment using the same |
| US20140309270A1 (en) | 2013-04-11 | 2014-10-16 | Richard Louis Price | Diagnosis and treatment of a form of autistic spectrum disorder |
| SMT201800492T1 (it) | 2013-05-02 | 2018-11-09 | Novo Nordisk As | Dosaggio orale di composti di glp-1 |
| KR102393596B1 (ko) | 2016-04-22 | 2022-05-04 | 리셉터 홀딩스, 인크. | 속효성 식물-계 의약 화합물 및 영양 보충제 |
| EA201892396A1 (ru) | 2016-12-02 | 2019-04-30 | Ресептор Лайф Сайенсиз, Инк. | Быстродействующие растительные лекарственные соединения и биологически активные добавки |
| AR113749A1 (es) * | 2017-10-05 | 2020-06-10 | Receptor Holdings Inc | Formulaciones cannabinoides sintéticas y a base de plantas de inicio rápido y acción prolongada |
| BR112020006690A2 (pt) * | 2017-10-05 | 2020-10-06 | Receptor Holdings, Inc. | composições à base de plantas com biodisponibilidade aprimorada |
| EP4299118A3 (en) | 2018-02-02 | 2024-04-10 | Novo Nordisk A/S | Solid compositions comprising a glp-1 agonist, a salt of n-(8-(2-hydroxybenzoyl)amino)caprylic acid and a lubricant |
| AR117118A1 (es) | 2018-11-19 | 2021-07-14 | Receptor Holdings Inc | Aminoácidos grasos n-acilados para reducir la variabilidad de absorción en composiciones a base de cannabinoides |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5665379A (en) | 1990-09-28 | 1997-09-09 | Pharmacia & Upjohn Aktiebolag | Lipid particle forming matrix, preparation and use thereof |
| US5474978A (en) | 1994-06-16 | 1995-12-12 | Eli Lilly And Company | Insulin analog formulations |
| US5650386A (en) | 1995-03-31 | 1997-07-22 | Emisphere Technologies, Inc. | Compositions for oral delivery of active agents |
| US6274564B1 (en) * | 1996-09-18 | 2001-08-14 | William J. Sarill | Compositions of cobalamin and related corrinoids, and uses thereof |
| US5773647A (en) | 1997-02-07 | 1998-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6255294B1 (en) * | 1998-12-28 | 2001-07-03 | Allergy Limited | Cyanocobalamin (vitamin B12) treatment in allergic disease |
| NZ534409A (en) | 1999-04-05 | 2006-03-31 | Emisphere Tech Inc | Disodium salts, monohydrates, and ethanol solvates for delivering active agents |
| EP1535625B1 (en) | 1999-04-05 | 2014-01-08 | Novartis AG | Composition containing n-(5-chlorosalicyloyl)-8-aminocaprylic acid and salmon calcitonin |
| CA2402719C (en) | 2000-03-21 | 2012-03-20 | Emisphere Technologies, Inc. | Method of preparing alkylated salicylamides via a dicarboxylate intermediate |
| US7049283B2 (en) | 2000-12-06 | 2006-05-23 | Novartis Ag | Pharmaceutical compositions for the oral delivery of pharmacologically active agents |
| CA2446929C (en) | 2001-06-01 | 2013-04-09 | Novartis Ag | Orally administering parathyroid hormone and calcitonin |
| WO2003015822A1 (en) | 2001-08-17 | 2003-02-27 | Novartis Ag | 5-cnac as oral delivery agent for parathyroid hormone fragments |
| 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 |
| PE20040724A1 (es) | 2002-08-01 | 2004-12-06 | Novartis Ag | Composicion para la administracion oral de calcitonina |
| RU2359698C2 (ru) * | 2002-09-13 | 2009-06-27 | Сайдекс, Инк. | Капсулы, содержащие водные наполняющие композиции, стабилизированные производным циклодекстрина |
| WO2004087640A1 (en) | 2003-04-04 | 2004-10-14 | Dsm Ip Assets B.V. | Process for the manufacture of n-alkoxalyl-alaninates |
| US6938439B2 (en) | 2003-05-22 | 2005-09-06 | Cool Clean Technologies, Inc. | System for use of land fills and recyclable materials |
| JP3924616B2 (ja) | 2003-06-30 | 2007-06-06 | 独立行政法人物質・材料研究機構 | 微小サイズの温度感知素子を用いる温度計測方法 |
| EP1643978A1 (en) | 2003-07-04 | 2006-04-12 | Nycomed Danmark A/S | Parathyroid hormone (pth) containing pharmaceutical compositions for oral use |
| PT1651248E (pt) | 2003-07-11 | 2009-11-10 | Novartis Ag | Composições farmacêuticas para dose oral compreendendo um agente de administração na forma micronizada |
| PL1651249T3 (pl) | 2003-07-23 | 2013-04-30 | Novartis Ag | Zastosowanie kalcytoniny w zapaleniu kości i stawów |
| SG153039A1 (en) | 2004-05-06 | 2009-06-29 | Emisphere Tech Inc | Crystalline polymorphic forms of monosodium n-[8- (2hydroxybenzoyl)amino]caprylate |
| WO2006020291A2 (en) * | 2004-08-02 | 2006-02-23 | Bebaas, Inc. | Vitamin b12 compositions |
| JP2008509933A (ja) | 2004-08-13 | 2008-04-03 | エミスフェアー・テクノロジーズ・インク | 送達剤のマイクロ粒子またはナノ粒子を含む医薬製剤 |
| US20060116334A1 (en) | 2004-12-01 | 2006-06-01 | Curt Hendrix | Folate based composition for treatment of the cardiovascular system |
| GB0427600D0 (en) | 2004-12-16 | 2005-01-19 | Novartis Ag | Organic compounds |
| GB0427603D0 (en) | 2004-12-16 | 2005-01-19 | Novartis Ag | Organic compounds |
| CA2626029A1 (en) | 2005-11-04 | 2007-05-18 | Genta Incorporated | Pharmaceutical gallium compositions and methods |
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2008
- 2008-10-31 WO PCT/US2008/082064 patent/WO2009059188A1/en not_active Ceased
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- 2008-10-31 CN CN200880119724.0A patent/CN101952241B/zh not_active Expired - Fee Related
- 2008-10-31 JP JP2010532292A patent/JP5555634B2/ja not_active Expired - Fee Related
- 2008-10-31 KR KR1020107010771A patent/KR101344369B1/ko not_active Expired - Fee Related
- 2008-10-31 EP EP08844673.7A patent/EP2215047B1/en not_active Not-in-force
- 2008-10-31 ES ES08844673.7T patent/ES2443817T3/es active Active
- 2008-10-31 DK DK08844673.7T patent/DK2215047T3/da active
- 2008-10-31 PL PL08844673T patent/PL2215047T3/pl unknown
- 2008-10-31 RU RU2010118423/15A patent/RU2469728C2/ru active
- 2008-10-31 PT PT88446737T patent/PT2215047E/pt unknown
- 2008-10-31 CA CA2704780A patent/CA2704780C/en not_active Expired - Fee Related
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- 2010-06-02 CO CO10066425A patent/CO6280475A2/es active IP Right Grant
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2011
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