DE19940740A1 - Pharmazeutische Salze - Google Patents
Pharmazeutische SalzeInfo
- Publication number
- DE19940740A1 DE19940740A1 DE19940740A DE19940740A DE19940740A1 DE 19940740 A1 DE19940740 A1 DE 19940740A1 DE 19940740 A DE19940740 A DE 19940740A DE 19940740 A DE19940740 A DE 19940740A DE 19940740 A1 DE19940740 A1 DE 19940740A1
- Authority
- DE
- Germany
- Prior art keywords
- tramadol
- medicament
- manufacture
- treatment
- salt according
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 31
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims abstract description 61
- 229960004380 tramadol Drugs 0.000 claims abstract description 42
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims abstract description 42
- 239000003814 drug Substances 0.000 claims abstract description 30
- 235000021092 sugar substitutes Nutrition 0.000 claims abstract description 21
- 239000003765 sweetening agent Substances 0.000 claims abstract description 21
- 239000013543 active substance Substances 0.000 claims abstract description 6
- 239000002552 dosage form Substances 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 230000000979 retarding effect Effects 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 11
- 239000011159 matrix material Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 10
- 235000015218 chewing gum Nutrition 0.000 claims description 8
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims description 8
- 239000003826 tablet Substances 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 7
- 229940112822 chewing gum Drugs 0.000 claims description 7
- 206010046543 Urinary incontinence Diseases 0.000 claims description 6
- 239000008188 pellet Substances 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 229940109275 cyclamate Drugs 0.000 claims description 5
- 208000007848 Alcoholism Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 206010011224 Cough Diseases 0.000 claims description 4
- 206010012735 Diarrhoea Diseases 0.000 claims description 4
- 208000007882 Gastritis Diseases 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 229960005164 acesulfame Drugs 0.000 claims description 4
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 4
- 206010001584 alcohol abuse Diseases 0.000 claims description 4
- 208000025746 alcohol use disease Diseases 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 229940081974 saccharin Drugs 0.000 claims description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical group C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019204 saccharin Nutrition 0.000 claims description 4
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 4
- 206010013654 Drug abuse Diseases 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000009505 enteric coating Methods 0.000 claims description 3
- 239000002702 enteric coating Substances 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 210000001124 body fluid Anatomy 0.000 claims description 2
- 239000010839 body fluid Substances 0.000 claims description 2
- 239000007938 effervescent tablet Substances 0.000 claims description 2
- 239000011859 microparticle Substances 0.000 claims description 2
- -1 microtablets Substances 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PPKXEPBICJTCRU-XMZRARIVSA-N (R,R)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-XMZRARIVSA-N 0.000 description 10
- 229960003107 tramadol hydrochloride Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 description 8
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 8
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 5
- 235000019658 bitter taste Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000019640 taste Nutrition 0.000 description 5
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 4
- 229960003415 propylparaben Drugs 0.000 description 4
- 239000000811 xylitol Substances 0.000 description 4
- 235000010447 xylitol Nutrition 0.000 description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 4
- 229960002675 xylitol Drugs 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000000230 xanthan gum Substances 0.000 description 3
- 229920001285 xanthan gum Polymers 0.000 description 3
- 235000010493 xanthan gum Nutrition 0.000 description 3
- 229940082509 xanthan gum Drugs 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241001646579 Coryphaenoides cinereus Species 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940041672 oral gel Drugs 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 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
- 238000005453 pelletization Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 229940049703 saccharin sodium dihydrate Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
- A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
- A61K9/2846—Poly(meth)acrylates
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
- A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
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- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Toxicology (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Priority Applications (83)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19940740A DE19940740A1 (de) | 1999-08-31 | 1999-08-31 | Pharmazeutische Salze |
| IL14841100A IL148411A0 (en) | 1999-08-31 | 2000-08-03 | Delayed-action form of administration containing tramadol saccharinate |
| RU2002106741/15A RU2292877C2 (ru) | 1999-08-31 | 2000-08-03 | Лекарственная ретард-форма, содержащая сахаринат трамадола |
| HU0203623A HUP0203623A2 (hu) | 1999-08-31 | 2000-08-03 | Tramadol-szacharinátot tartalmazó, késleltetett hatású adagolási forma és alkalmazása |
| JP2001519896A JP2003508429A (ja) | 1999-08-31 | 2000-08-03 | 医薬用トラマドール塩 |
| JP2001519897A JP2003508430A (ja) | 1999-08-31 | 2000-08-03 | トラマドールサッカリナートを含有する徐放性投薬形 |
| MXPA02002193A MXPA02002193A (es) | 1999-08-31 | 2000-08-03 | Forma de administracion de accion retardada que contiene sacarinato de tramadol. |
| HK02108598.7A HK1047229B (zh) | 1999-08-31 | 2000-08-03 | 药物曲马朵盐 |
| HK02108599.6A HK1047230B (zh) | 1999-08-31 | 2000-08-03 | 含有曲马朵糖精酯的延迟作用给药形式 |
| NZ517366A NZ517366A (en) | 1999-08-31 | 2000-08-03 | Pharmaceutical salts of tramadol and a sugar substitute |
| PCT/EP2000/007527 WO2001015683A1 (de) | 1999-08-31 | 2000-08-03 | Retardierte darreichungsform enthaltend tramadolsaccharinat |
| PL00354264A PL354264A1 (en) | 1999-08-31 | 2000-08-03 | Delayed-action form of administration containing tramadol saccharinate |
| AT00949447T ATE279186T1 (de) | 1999-08-31 | 2000-08-03 | Retardierte darreichungsform enthaltend tramadolsaccharinat |
| ES00958375T ES2284523T3 (es) | 1999-08-31 | 2000-08-03 | Sales farmaceuticas de tramadol. |
| DE2000508261 DE50008261D1 (de) | 1999-08-31 | 2000-08-03 | Retardierte darreichungsform enthaltend tramadolsaccharinat |
| BR0015048-7A BR0015048A (pt) | 1999-08-31 | 2000-08-03 | Sal farmacêutico, medicamento, uso de pelo menos um sal de tramadol e formas de apresentação |
| AT00958375T ATE359064T1 (de) | 1999-08-31 | 2000-08-03 | Pharmazeutische tramadolsalze |
| ES00949447T ES2226886T3 (es) | 1999-08-31 | 2000-08-03 | Forma de administracion de accion retardada que contiene sacarinato de tramadol. |
| IL14840600A IL148406A0 (en) | 1999-08-31 | 2000-08-03 | Pharmaceutical tramadol salts |
| CNB008150931A CN1202815C (zh) | 1999-08-31 | 2000-08-03 | 含有曲马朵糖精盐的持续释放给药剂型 |
| CA002388560A CA2388560A1 (en) | 1999-08-31 | 2000-08-03 | Sustained-release form of administration containing tramadol saccharinate |
| MXPA02002024A MXPA02002024A (es) | 1999-08-31 | 2000-08-03 | Sales farmaceuticas de tramadol. |
| BR0013825-8A BR0013825A (pt) | 1999-08-31 | 2000-08-03 | Formas de apresentação de tramadol |
| SK276-2002A SK2762002A3 (en) | 1999-08-31 | 2000-08-03 | Delayed-action form of administration containing tramadol saccharinate |
| SK235-2002A SK285987B6 (sk) | 1999-08-31 | 2000-08-03 | Farmaceutické soli tramadolu, liečivá obsahujúce tieto látky a ich použitie |
| KR1020027002625A KR20020031419A (ko) | 1999-08-31 | 2000-08-03 | 트라마돌 사카리네이트를 함유하는 지효성 투여형 |
| AU62798/00A AU781058B2 (en) | 1999-08-31 | 2000-08-03 | Delayed-action form of administration containing tramadol saccharinate |
| DK00958375T DK1207868T3 (da) | 1999-08-31 | 2000-08-03 | Farmaceutiske tramadolsalte |
| RU2002106748/15A RU2292876C2 (ru) | 1999-08-31 | 2000-08-03 | Фармацевтические соли трамадола |
| KR1020027002634A KR100730502B1 (ko) | 1999-08-31 | 2000-08-03 | 약제학적 트라마돌 염 및 이를 함유하는 투여 제형 |
| EP00949447A EP1207866B1 (de) | 1999-08-31 | 2000-08-03 | Retardierte darreichungsform enthaltend tramadolsaccharinat |
| CA002386690A CA2386690C (en) | 1999-08-31 | 2000-08-03 | Pharmaceutical tramadol salts |
| SI200030952T SI1207868T1 (sl) | 1999-08-31 | 2000-08-03 | Farmacevtske tramadolne soli |
| SI200030515T SI1207866T1 (en) | 1999-08-31 | 2000-08-03 | Delayed-action form of administration containing tramadol saccharinate |
| MYPI20003557A MY127683A (en) | 1999-08-31 | 2000-08-03 | Pharmaceutical tramadol salts |
| HU0302131A HUP0302131A2 (hu) | 1999-08-31 | 2000-08-03 | Gyógyászati tramadolsók, ezeket tartalmazó gyógyszerkészítmények |
| PCT/EP2000/007526 WO2001015682A1 (de) | 1999-08-31 | 2000-08-03 | Pharmazeutische tramadolsalze |
| NZ517559A NZ517559A (en) | 1999-08-31 | 2000-08-03 | Sustained release pharmaceutical composition containing tramadol saccharinate |
| PT00958375T PT1207868E (pt) | 1999-08-31 | 2000-08-03 | Sais farmacêuticos de tramadol |
| CNB008121591A CN1200700C (zh) | 1999-08-31 | 2000-08-03 | 药用曲马朵盐 |
| PL354238A PL212105B1 (pl) | 1999-08-31 | 2000-08-03 | Farmaceutyczna sól tramadolu, środek leczniczy, zastosowanie soli tramadolu oraz postacie aplikacyjne |
| AU69921/00A AU781852B2 (en) | 1999-08-31 | 2000-08-03 | Pharmaceutical tramadol salts |
| DE50014244T DE50014244D1 (de) | 1999-08-31 | 2000-08-03 | Pharmazeutische tramadolsalze |
| CZ2002671A CZ2002671A3 (cs) | 1999-08-31 | 2000-08-03 | Léková forma se zpoľděným účinkem obsahující tramadolsacharinát |
| CZ20020674A CZ301259B6 (cs) | 1999-08-31 | 2000-08-03 | Farmaceutické soli tramadolu, léciva tyto látky obsahující a jejich použití |
| PT00949447T PT1207866E (pt) | 1999-08-31 | 2000-08-03 | Forma de administracao retardada contendo sacarinato de tramadol |
| EP00958375A EP1207868B1 (de) | 1999-08-31 | 2000-08-03 | Pharmazeutische tramadolsalze |
| PE2000000872A PE20010530A1 (es) | 1999-08-31 | 2000-08-25 | Formas de administracion de tramadol retardadas mediante un revestimiento que contiene la sustancia activa tramadol en forma de sacarinato de tramadol asi como eventualmente otros excipientes |
| PE2000000873A PE20010531A1 (es) | 1999-08-31 | 2000-08-25 | Sales farmaceuticas de la sustancia activa tramadol y al menos un edulcorante y formas de administracion que contienen estas sales |
| ARP000104480A AR025426A1 (es) | 1999-08-31 | 2000-08-28 | Sales farmaceuticas de la sustancia activa tramadol y al menos un edulcorante, medicamentos que contienen estas sales, el uso de estas sales para lapreparacion de medicamentos y formas de administracion que contienen esas sales |
| CO00064193A CO5190687A1 (es) | 1999-08-31 | 2000-08-28 | Formas de administracion de tramadol retardadas mediante un revestimiento que contiene la sustancia activa tramadol en forma de sacarinato de tramadol asi como eventualmente otros excipientes |
| CO00064190A CO5190689A1 (es) | 1999-08-31 | 2000-08-28 | Sales de tramadol formadas por tramadol y un edulcorante y formas farmaceuticas que contienen dichas sales |
| CZ2002673A CZ2002673A3 (cs) | 1999-08-31 | 2000-08-29 | Lékové formy pro orální podávání |
| SK237-2002A SK2372002A3 (en) | 1999-08-31 | 2000-08-29 | Oral dosage forms |
| HU0203204A HUP0203204A3 (en) | 1999-08-31 | 2000-08-29 | Oral dosage forms |
| JP2001519881A JP2003511351A (ja) | 1999-08-31 | 2000-08-29 | 経口投薬形 |
| PL00354362A PL354362A1 (en) | 1999-08-31 | 2000-08-29 | Oral dosage forms |
| PE2000000883A PE20010521A1 (es) | 1999-08-31 | 2000-08-29 | Formas de administracion oral con liberacion total controlada de sustancia activa, encontrandose una misma sustancia activa en forma de al menos dos sales distintas que en la forma de administracion se encuentran en estado solido y que presentan dife |
| CN00815085A CN1384735A (zh) | 1999-08-31 | 2000-08-29 | 口服剂型 |
| MXPA02002189A MXPA02002189A (es) | 1999-08-31 | 2000-08-29 | Formas de dosificacion oral. |
| BR0013826-6A BR0013826A (pt) | 1999-08-31 | 2000-08-29 | Formas orais de apresentação |
| CA2391832A CA2391832C (en) | 1999-08-31 | 2000-08-29 | Oral dosage forms |
| EP00964052A EP1207858A1 (de) | 1999-08-31 | 2000-08-29 | Orale darreichungsformen |
| ARP000104500A AR025437A1 (es) | 1999-08-31 | 2000-08-29 | Formas de administracion oral con liberacion total controlada de sustancia activa, encontrandose una misma sustancia activaen forma de al menos dos sales distintas que en la forma de administracion se encuentran en estado solido y que presentan diferente liberacionin vitro de la sustancia activa. |
| HK02108601.2A HK1047232A1 (zh) | 1999-08-31 | 2000-08-29 | 口服剂型 |
| CO00064447A CO5190691A1 (es) | 1999-08-31 | 2000-08-29 | Formas de administracion oral con la liberacion total controlada de sustancia activa, encontrandose una misma sustancia activa en forma de al menos dos sales distintas que en la forma de administracion se encuentran en estado solido y que presenta di |
| KR1020027002783A KR20020031421A (ko) | 1999-08-31 | 2000-08-29 | 경구 투여 형태 |
| AU75116/00A AU782943B2 (en) | 1999-08-31 | 2000-08-29 | Oral dosage forms |
| IL14842200A IL148422A0 (en) | 1999-08-31 | 2000-08-29 | Oral dosage forms |
| PCT/EP2000/008402 WO2001015667A1 (de) | 1999-08-31 | 2000-08-29 | Orale darreichungsformen |
| NZ517683A NZ517683A (en) | 1999-08-31 | 2000-08-29 | A controlled release oral dosage form containing at least two different salts of the active ingredient |
| UY26318A UY26318A1 (es) | 1999-08-31 | 2000-08-31 | Formas de administracion oral con liberacion total controlada de sustancia activa, encontrandose una misma sustancia activa en forma de al menos dos sales distintas que en la forma de administracion se encuentran en estado solido y que presentan dife |
| UY26320A UY26320A1 (es) | 1999-08-31 | 2000-08-31 | Sales farmaceuticas de la sustancia activa tramadol y al menos un edulcorante, medicamentos que contienen estas sales, el uso de estas sales para la preparacion de medicamentos y formas de administracion que contienen esas sales. ley 17164 |
| UY26321A UY26321A1 (es) | 1999-08-31 | 2000-08-31 | Formas de administracion de tramadol retardadas mediante un revestimiento que contiene la sustancia activa tramadol en forma de sacarinato de tramadol asi como eventualmente otros excipientes |
| NO20020939A NO20020939L (no) | 1999-08-31 | 2002-02-26 | Oral administreringsform |
| IL148406A IL148406A (en) | 1999-08-31 | 2002-02-27 | Tramadol salts for pharmaceutical use |
| NO20020975A NO20020975L (no) | 1999-08-31 | 2002-02-27 | Retardierte administreringsformer inneholdende tramadolsakkarinat |
| NO20020974A NO329625B1 (no) | 1999-08-31 | 2002-02-27 | Farmasoytisk tramadolsalt, legemiddel inneholdende dette, administrasjonsform samt anvendelse av tramadolsaltet. |
| US10/084,248 US6576260B2 (en) | 1999-08-31 | 2002-02-28 | Sustained-release form of administration containing tramadol saccharinate |
| US10/084,674 US7572463B2 (en) | 1999-08-31 | 2002-02-28 | Oral dosage forms |
| US10/084,682 US6723343B2 (en) | 1999-08-31 | 2002-02-28 | Pharmaceutical tramadol salts |
| ZA200202536A ZA200202536B (en) | 1999-08-31 | 2002-03-28 | Pharmaceutical tramadol salts. |
| CY20071100802T CY1107675T1 (el) | 1999-08-31 | 2007-06-18 | Φαρμακευτικα αλατα τραμαδολης |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19940740A DE19940740A1 (de) | 1999-08-31 | 1999-08-31 | Pharmazeutische Salze |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19940740A1 true DE19940740A1 (de) | 2001-03-01 |
Family
ID=7919846
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19940740A Withdrawn DE19940740A1 (de) | 1999-08-31 | 1999-08-31 | Pharmazeutische Salze |
| DE50014244T Expired - Lifetime DE50014244D1 (de) | 1999-08-31 | 2000-08-03 | Pharmazeutische tramadolsalze |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50014244T Expired - Lifetime DE50014244D1 (de) | 1999-08-31 | 2000-08-03 | Pharmazeutische tramadolsalze |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6723343B2 (https=) |
| EP (1) | EP1207868B1 (https=) |
| JP (1) | JP2003508429A (https=) |
| KR (1) | KR100730502B1 (https=) |
| CN (1) | CN1200700C (https=) |
| AR (1) | AR025426A1 (https=) |
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| US6909017B2 (en) | 2001-02-21 | 2005-06-21 | Grunenthal Gmbh | Method for isolating and purifying (1RS,2RS)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol |
| WO2002066414A1 (de) * | 2001-02-21 | 2002-08-29 | Grünenthal GmbH | Verfahren zur isolierung und reinigung von (1rs,2rs)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-cyclohexanol |
| US20170137370A1 (en) * | 2001-02-28 | 2017-05-18 | Grünenthal GmbH | Pharmaceutical salts |
| US10160719B2 (en) * | 2001-02-28 | 2018-12-25 | Grunenthal Gmbh | Pharmaceutical salts |
| US20120059066A1 (en) * | 2001-02-28 | 2012-03-08 | Grunenthal Gmbh | Pharmaceutical salts |
| EP1364649A1 (en) * | 2002-05-23 | 2003-11-26 | Cilag AG | Adduct of topiramate and tramadol hydrochioride and uses thereof |
| WO2003099273A1 (en) * | 2002-05-23 | 2003-12-04 | Cilag Ag | Adduct of topiramate and tramadol hydrochloride and uses thereof |
| US7378519B2 (en) | 2002-05-23 | 2008-05-27 | Cilag Gmbh International | Adduct of topiramate and tramadol hydrochloride and uses thereof |
| US10369109B2 (en) | 2002-06-17 | 2019-08-06 | Grünenthal GmbH | Abuse-proofed dosage form |
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| US8192722B2 (en) | 2003-08-06 | 2012-06-05 | Grunenthal Gmbh | Abuse-proof dosage form |
| US10058548B2 (en) | 2003-08-06 | 2018-08-28 | Grünenthal GmbH | Abuse-proofed dosage form |
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| US8420056B2 (en) | 2003-08-06 | 2013-04-16 | Grunenthal Gmbh | Abuse-proofed dosage form |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| US8114383B2 (en) | 2003-08-06 | 2012-02-14 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| US8309060B2 (en) | 2003-08-06 | 2012-11-13 | Grunenthal Gmbh | Abuse-proofed dosage form |
| US11224576B2 (en) | 2003-12-24 | 2022-01-18 | Grünenthal GmbH | Process for the production of an abuse-proofed dosage form |
| US8114384B2 (en) | 2004-07-01 | 2012-02-14 | Gruenenthal Gmbh | Process for the production of an abuse-proofed solid dosage form |
| US11844865B2 (en) | 2004-07-01 | 2023-12-19 | Grünenthal GmbH | Abuse-proofed oral dosage form |
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| US8722086B2 (en) | 2007-03-07 | 2014-05-13 | Gruenenthal Gmbh | Dosage form with impeded abuse |
| US9750701B2 (en) | 2008-01-25 | 2017-09-05 | Grünenthal GmbH | Pharmaceutical dosage form |
| US8383152B2 (en) | 2008-01-25 | 2013-02-26 | Gruenenthal Gmbh | Pharmaceutical dosage form |
| US9161917B2 (en) | 2008-05-09 | 2015-10-20 | Grünenthal GmbH | Process for the preparation of a solid dosage form, in particular a tablet, for pharmaceutical use and process for the preparation of a precursor for a solid dosage form, in particular a tablet |
| WO2010004256A1 (en) * | 2008-06-17 | 2010-01-14 | E-Therapeutics Plc | Controlled release treatment of depression |
| US9925146B2 (en) | 2009-07-22 | 2018-03-27 | Grünenthal GmbH | Oxidation-stabilized tamper-resistant dosage form |
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| US9636303B2 (en) | 2010-09-02 | 2017-05-02 | Gruenenthal Gmbh | Tamper resistant dosage form comprising an anionic polymer |
| US10300141B2 (en) | 2010-09-02 | 2019-05-28 | Grünenthal GmbH | Tamper resistant dosage form comprising inorganic salt |
| US10201502B2 (en) | 2011-07-29 | 2019-02-12 | Gruenenthal Gmbh | Tamper-resistant tablet providing immediate drug release |
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| US10335373B2 (en) | 2012-04-18 | 2019-07-02 | Grunenthal Gmbh | Tamper resistant and dose-dumping resistant pharmaceutical dosage form |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| US10154966B2 (en) | 2013-05-29 | 2018-12-18 | Grünenthal GmbH | Tamper-resistant dosage form containing one or more particles |
| US9737490B2 (en) | 2013-05-29 | 2017-08-22 | Grünenthal GmbH | Tamper resistant dosage form with bimodal release profile |
| US10624862B2 (en) | 2013-07-12 | 2020-04-21 | Grünenthal GmbH | Tamper-resistant dosage form containing ethylene-vinyl acetate polymer |
| US10449547B2 (en) | 2013-11-26 | 2019-10-22 | Grünenthal GmbH | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
| US9913814B2 (en) | 2014-05-12 | 2018-03-13 | Grünenthal GmbH | Tamper resistant immediate release capsule formulation comprising tapentadol |
| US9872835B2 (en) | 2014-05-26 | 2018-01-23 | Grünenthal GmbH | Multiparticles safeguarded against ethanolic dose-dumping |
| EP3009134A1 (en) * | 2014-10-14 | 2016-04-20 | Sapere IP, LLC | A treatment method for primary premature ejaculation |
| US9855263B2 (en) | 2015-04-24 | 2018-01-02 | Grünenthal GmbH | Tamper-resistant dosage form with immediate release and resistance against solvent extraction |
| US10842750B2 (en) | 2015-09-10 | 2020-11-24 | Grünenthal GmbH | Protecting oral overdose with abuse deterrent immediate release formulations |
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