CA2568445C - Immediate release formulations of memantine oral dosage forms - Google Patents
Immediate release formulations of memantine oral dosage forms Download PDFInfo
- Publication number
- CA2568445C CA2568445C CA2568445A CA2568445A CA2568445C CA 2568445 C CA2568445 C CA 2568445C CA 2568445 A CA2568445 A CA 2568445A CA 2568445 A CA2568445 A CA 2568445A CA 2568445 C CA2568445 C CA 2568445C
- Authority
- CA
- Canada
- Prior art keywords
- dosage form
- oral dosage
- immediate release
- solid oral
- release solid
- 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
- 239000012729 immediate-release (IR) formulation Substances 0.000 title claims abstract description 82
- 239000006186 oral dosage form Substances 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 title abstract description 108
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 title abstract description 98
- 229960004640 memantine Drugs 0.000 title abstract description 92
- 238000009472 formulation Methods 0.000 title abstract description 68
- 239000007787 solid Substances 0.000 claims abstract description 39
- 239000011248 coating agent Substances 0.000 claims abstract description 36
- 238000000576 coating method Methods 0.000 claims abstract description 35
- OGZQTTHDGQBLBT-UHFFFAOYSA-N neramexane Chemical compound CC1(C)CC(C)(C)CC(C)(N)C1 OGZQTTHDGQBLBT-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000004480 active ingredient Substances 0.000 claims abstract description 34
- 239000002552 dosage form Substances 0.000 claims abstract description 33
- 229950004543 neramexane Drugs 0.000 claims abstract description 26
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 48
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 48
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 48
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 48
- 239000003814 drug Substances 0.000 claims description 34
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 34
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 30
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- 150000003839 salts Chemical class 0.000 claims description 25
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 235000019359 magnesium stearate Nutrition 0.000 claims description 17
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 16
- -1 1-aminocyclohexane compound Chemical class 0.000 claims description 14
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 14
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- 229910052623 talc Inorganic materials 0.000 claims description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- CLUKHUGGXSIGRX-UHFFFAOYSA-N methanesulfonic acid;1,3,3,5,5-pentamethylcyclohexan-1-amine Chemical group CS(O)(=O)=O.CC1(C)CC(C)(C)CC(C)(N)C1 CLUKHUGGXSIGRX-UHFFFAOYSA-N 0.000 claims description 11
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 239000000314 lubricant Substances 0.000 claims description 10
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 9
- 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 claims description 9
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- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
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- 238000004090 dissolution Methods 0.000 abstract description 41
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract description 15
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical group Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 23
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
- 230000036470 plasma concentration Effects 0.000 description 20
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 19
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- 125000003342 alkenyl group Chemical group 0.000 description 8
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- 229910052739 hydrogen Inorganic materials 0.000 description 7
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- 238000012360 testing method Methods 0.000 description 7
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 6
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009506 drug dissolution testing Methods 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 229960000967 memantine hydrochloride Drugs 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 238000012935 Averaging Methods 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 4
- 208000018737 Parkinson disease Diseases 0.000 description 4
- LDDHMLJTFXJGPI-LFPUEVJFSA-N [(3s,5r)-3,5-dimethyl-1-adamantyl]azanium;chloride Chemical compound Cl.C1C(C2)C[C@@]3(C)C[C@]1(C)CC2(N)C3 LDDHMLJTFXJGPI-LFPUEVJFSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- 239000005018 casein Substances 0.000 description 4
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 4
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- 125000003107 substituted aryl group Chemical group 0.000 description 4
- OVDULOGIHPNNKW-UHFFFAOYSA-N 1-(1,3,3,5,5-pentamethylcyclohexyl)pyrrolidine Chemical compound C1C(C)(C)CC(C)(C)CC1(C)N1CCCC1 OVDULOGIHPNNKW-UHFFFAOYSA-N 0.000 description 3
- NBZGMQHFDNUNRQ-UHFFFAOYSA-N 3,3-diethyl-1,5,5-trimethylcyclohexan-1-amine Chemical compound CCC1(CC)CC(C)(C)CC(C)(N)C1 NBZGMQHFDNUNRQ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 125000004450 alkenylene group Chemical group 0.000 description 3
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical class C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexediene Natural products C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000012728 immediate-release (IR) tablet Substances 0.000 description 3
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- JVUYSNBGWFWRLJ-UHFFFAOYSA-N n-ethyl-1,3,3,5,5-pentamethylcyclohexan-1-amine Chemical compound CCNC1(C)CC(C)(C)CC(C)(C)C1 JVUYSNBGWFWRLJ-UHFFFAOYSA-N 0.000 description 3
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
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- PMNUOTQOFZGNNQ-UHFFFAOYSA-N 1,3,5-trimethylcyclohexan-1-amine Chemical compound CC1CC(C)CC(C)(N)C1 PMNUOTQOFZGNNQ-UHFFFAOYSA-N 0.000 description 2
- YKLPCZMZROZLJA-UHFFFAOYSA-N 1-ethyl-3,3,5,5-tetramethylcyclohexan-1-amine Chemical compound CCC1(N)CC(C)(C)CC(C)(C)C1 YKLPCZMZROZLJA-UHFFFAOYSA-N 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- NEVCGYUBKUPZRL-UHFFFAOYSA-N (3,3,5,5-tetramethylcyclohexyl)methanamine Chemical compound CC1(C)CC(CN)CC(C)(C)C1 NEVCGYUBKUPZRL-UHFFFAOYSA-N 0.000 description 1
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- AEWYCWAJLDLBGX-UHFFFAOYSA-N 1-(1,3,3,5-tetramethylcyclohexyl)pyrrolidine Chemical compound C1C(C)CC(C)(C)CC1(C)N1CCCC1 AEWYCWAJLDLBGX-UHFFFAOYSA-N 0.000 description 1
- QVEQDLBYFRYKKW-UHFFFAOYSA-N 1-(1,3,5-trimethylcyclohexyl)pyrrolidine Chemical compound C1C(C)CC(C)CC1(C)N1CCCC1 QVEQDLBYFRYKKW-UHFFFAOYSA-N 0.000 description 1
- LODZBBPOQRJCTJ-UHFFFAOYSA-N 1-(3,3,5,5-tetramethyl-1-propylcyclohexyl)pyrrolidine Chemical compound C1CCCN1C1(CCC)CC(C)(C)CC(C)(C)C1 LODZBBPOQRJCTJ-UHFFFAOYSA-N 0.000 description 1
- JURFVVKQIRIWBJ-UHFFFAOYSA-N 1-(3,3-diethyl-1,5,5-trimethylcyclohexyl)pyrrolidine Chemical compound C1C(CC)(CC)CC(C)(C)CC1(C)N1CCCC1 JURFVVKQIRIWBJ-UHFFFAOYSA-N 0.000 description 1
- VZMMNFHWJMVOSI-UHFFFAOYSA-N 1-(3-ethyl-1,3,5,5-tetramethylcyclohexyl)pyrrolidine Chemical compound C1C(CC)(C)CC(C)(C)CC1(C)N1CCCC1 VZMMNFHWJMVOSI-UHFFFAOYSA-N 0.000 description 1
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 1
- OZNXTQSXSHODFR-UHFFFAOYSA-N 1-chloroadamantane Chemical class C1C(C2)CC3CC2CC1(Cl)C3 OZNXTQSXSHODFR-UHFFFAOYSA-N 0.000 description 1
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- 125000000914 phenoxymethylpenicillanyl group Chemical group CC1(S[C@H]2N([C@H]1C(=O)*)C([C@H]2NC(COC2=CC=CC=C2)=O)=O)C 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 230000000391 smoking effect Effects 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
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- 208000011117 substance-related disease Diseases 0.000 description 1
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
-
- 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
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58124404P | 2004-06-17 | 2004-06-17 | |
| US60/581,244 | 2004-06-17 | ||
| PCT/US2005/021284 WO2006096194A2 (en) | 2004-06-17 | 2005-06-16 | Drinkable immediate release tablet made with direct compression of memantine or neramexane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2568445A1 CA2568445A1 (en) | 2006-09-14 |
| CA2568445C true CA2568445C (en) | 2011-05-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2568445A Expired - Fee Related CA2568445C (en) | 2004-06-17 | 2005-06-16 | Immediate release formulations of memantine oral dosage forms |
Country Status (11)
| Country | Link |
|---|---|
| EP (3) | EP1765287A2 (enExample) |
| JP (1) | JP5025468B2 (enExample) |
| KR (1) | KR20090033410A (enExample) |
| CN (1) | CN101389315A (enExample) |
| AU (1) | AU2005328701B2 (enExample) |
| BR (1) | BRPI0512263A (enExample) |
| CA (1) | CA2568445C (enExample) |
| EA (1) | EA011290B1 (enExample) |
| ES (1) | ES2483126T3 (enExample) |
| IL (1) | IL179992A (enExample) |
| WO (1) | WO2006096194A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2386299B1 (en) * | 2007-09-12 | 2016-07-13 | Merz Pharma GmbH & Co. KGaA | 1-Amino-Alkylcyclohexane derivatives for use in the treatment of tinnitus associated with hearing loss |
| SI2448910T1 (sl) * | 2009-06-29 | 2013-07-31 | Merz Pharma Gmbh & Co. Kgaa | Postopek za pripravo nerameksana |
| CA2765611A1 (en) * | 2009-06-29 | 2011-01-06 | Merz Pharma Gmbh & Co. Kgaa | Method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane |
| ES2446365T3 (es) * | 2009-06-29 | 2014-03-07 | Merz Pharma Gmbh & Co. Kgaa | Procedimiento de preparación de neramexane |
| EP2316434A1 (en) * | 2009-10-22 | 2011-05-04 | Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi | Orally disintegrating tablets of memantine |
| US20110294890A1 (en) * | 2010-05-28 | 2011-12-01 | Merz Pharma Gmbh & Co. Kgaa | Neramexane for the treatment or prevention of inner ear disorders |
| US8980318B2 (en) * | 2010-06-24 | 2015-03-17 | Merz Pharma Gmbh & Co. Kgaa | Neramexane multiple unit dosage form |
| WO2012048871A1 (en) | 2010-10-12 | 2012-04-19 | Merz Pharma Gmbh & Co. Kgaa | Memantine for improving cognitive performance in subjects |
| MX2013004123A (es) | 2010-10-12 | 2013-12-16 | Univ Johns Hopkins | Composiciones antitusigenas que comprenden memantina. |
| EP2526925A1 (en) | 2011-05-23 | 2012-11-28 | Deva Holding Anonim Sirketi | A dose adjustable oral pump spray or aerosol spray containing memantine |
| CN107334744B (zh) * | 2017-07-24 | 2020-09-04 | 湖南洞庭药业股份有限公司 | 盐酸美金刚药物组合物和制法 |
| HRP20231200T1 (hr) * | 2019-05-31 | 2024-01-19 | Tecnimede, Sociedade Técnico-Medicinal, Sa | Kombinacija fiksne doze memantina i donepezila s trenutnim otpuštanjem |
| CN114199812A (zh) * | 2021-12-28 | 2022-03-18 | 南通联亚药业有限公司 | 一种盐酸美金刚缓释制剂中盐酸美金刚的检测方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7305644A (enExample) | 1972-04-20 | 1973-10-23 | ||
| DE2856393C2 (de) | 1978-12-27 | 1983-04-28 | Merz + Co GmbH & Co, 6000 Frankfurt | Arzneimittel zur Behandlung von Morbus Parkinson |
| US4346112A (en) * | 1981-06-29 | 1982-08-24 | University Patents Inc. | Composition and method for treating patients having Parkinson's Disease |
| JPS6216413A (ja) * | 1985-07-12 | 1987-01-24 | Teijin Ltd | キチン類誘導体を用いた徐放性医薬品組成物 |
| US5506231A (en) | 1989-03-31 | 1996-04-09 | The Children's Medical Center Corporation | Treatment of aids dementia, myelopathy and blindness |
| US5334618A (en) | 1991-04-04 | 1994-08-02 | The Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| DE10299048I2 (de) | 1989-04-14 | 2006-07-13 | Merz Pharma Gmbh & Co Kgaa | Verwendung von Adamantan-Derivaten zur Pr{vention und Behandlung der cerebralen Isch{mie |
| DE4014672A1 (de) * | 1990-05-08 | 1991-11-14 | Werner E G Prof Dr Mueller | Verwendung von adamantan-derivaten zur zytoprotektion von nicht-infizierten und virus-infizierten lymphozyten als auch anderen zelltypen |
| US5614560A (en) | 1991-04-04 | 1997-03-25 | Children's Medical Center Corporation | Method of preventing NMDA receptor-mediated neuronal damage |
| US5455279A (en) | 1991-04-19 | 1995-10-03 | The Children's Medical Center Corporation | Regimen method of mediating neuronal damage using nitroglycerine |
| EP0581856B1 (en) | 1991-04-19 | 1999-07-14 | The Children's Medical Center Corporation | Method of preventing nmda receptor complex-mediated neuronal damage |
| DE4225730C2 (de) | 1992-08-04 | 2003-04-30 | Merz Pharma Gmbh & Co Kgaa | Verfahren zur Herstellung von festen Arzneiformkörpern mit protrahierter 2-Stufen-Freisetzung |
| GB9517062D0 (en) * | 1995-08-18 | 1995-10-25 | Scherer Ltd R P | Pharmaceutical compositions |
| JPH0971523A (ja) * | 1995-09-07 | 1997-03-18 | Riyuukakusan:Kk | 口腔内で崩壊性の速い錠剤 |
| AUPN605795A0 (en) * | 1995-10-19 | 1995-11-09 | F.H. Faulding & Co. Limited | Analgesic pharmaceutical composition |
| ES2200358T3 (es) * | 1997-06-30 | 2004-03-01 | MERZ PHARMA GMBH & CO. KGAA | 1-amino-alquilciclohexanos antagonistas del receptor de nmda. |
| US6071966A (en) | 1997-06-30 | 2000-06-06 | Merz + Co. Gmbh & Co. | 1-amino-alkylcyclohexane NMDA receptor antagonists |
| US6413556B1 (en) | 1999-01-08 | 2002-07-02 | Sky High, Llc | Aqueous anti-apoptotic compositions |
| SE9901077D0 (sv) | 1999-03-23 | 1999-03-23 | Astra Ab | Novel use |
| US6444702B1 (en) | 2000-02-22 | 2002-09-03 | Neuromolecular, Inc. | Aminoadamantane derivatives as therapeutic agents |
| TW593223B (en) * | 2000-06-20 | 2004-06-21 | Merz Pharma Gmbh & Co Kgaa | 1-amino-alkylcyclohexanes as 5-HT3 and neuronal nicotinic receptor antagonists |
| US6828462B2 (en) * | 2001-11-07 | 2004-12-07 | Merz Pharma Gmbh & Co. Kgaa | Unsaturated 1-amino-alkylcyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists |
| JP2005518411A (ja) * | 2002-01-16 | 2005-06-23 | エンド ファーマシューティカルズ インコーポレーテッド | 中枢神経系の障害を治療する製薬組成物及び方法 |
| TW200306189A (en) | 2002-03-21 | 2003-11-16 | Merz Pharma Gmbh & Co Kgaa | Azabicyclic, azatricyclic and azaspirocyclic derivatives of aminocyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists |
| FR2841138B1 (fr) * | 2002-06-25 | 2005-02-25 | Cll Pharma | Composition pharmaceutique solide contenant un principe actif lipophile, son procede de preparation |
| US20040127541A1 (en) * | 2002-07-31 | 2004-07-01 | Janet Codd | Bicifadine formulation |
| PL378902A1 (pl) * | 2003-06-16 | 2006-05-29 | Allergan, Inc. | Doustne postaci użytkowe memantyny |
| AR046314A1 (es) * | 2003-11-05 | 2005-11-30 | Merz Pharma Gmbh & Co Kgaa | Composiciones que comprenden ciclohexilaminas y aminoadamantanos |
| ES2899417T3 (es) * | 2004-01-20 | 2022-03-11 | Novartis Ag | Formulación y proceso de compresión directa |
| KR20060124731A (ko) * | 2004-01-29 | 2006-12-05 | 뉴로몰레큘라 파마슈티칼스, 인코포레이티드 | 중추신경계-관련 질환 치료용 ｎｍｄａ 수용체 길항제 및ｍａｏ-억제제 또는 ｇａｄｐｈ-억제제의 배합물 |
| GT200600008A (es) * | 2005-01-18 | 2006-08-09 | Formulacion de compresion directa y proceso |
-
2005
- 2005-06-16 BR BRPI0512263-5A patent/BRPI0512263A/pt not_active IP Right Cessation
- 2005-06-16 CN CNA2005800198789A patent/CN101389315A/zh active Pending
- 2005-06-16 AU AU2005328701A patent/AU2005328701B2/en not_active Ceased
- 2005-06-16 WO PCT/US2005/021284 patent/WO2006096194A2/en not_active Ceased
- 2005-06-16 JP JP2007516731A patent/JP5025468B2/ja not_active Expired - Lifetime
- 2005-06-16 CA CA2568445A patent/CA2568445C/en not_active Expired - Fee Related
- 2005-06-16 EA EA200700055A patent/EA011290B1/ru not_active IP Right Cessation
- 2005-06-16 EP EP05857458A patent/EP1765287A2/en not_active Withdrawn
- 2005-06-16 EP EP13153135.2A patent/EP2601937A1/en not_active Withdrawn
- 2005-06-16 KR KR1020097005872A patent/KR20090033410A/ko not_active Withdrawn
- 2005-06-16 EP EP11179637.1A patent/EP2397122B1/en not_active Expired - Lifetime
- 2005-06-16 ES ES11179637.1T patent/ES2483126T3/es not_active Expired - Lifetime
-
2006
- 2006-12-11 IL IL179992A patent/IL179992A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2397122A2 (en) | 2011-12-21 |
| WO2006096194A8 (en) | 2007-01-11 |
| EP2397122A3 (en) | 2012-01-25 |
| CN101389315A (zh) | 2009-03-18 |
| WO2006096194A2 (en) | 2006-09-14 |
| IL179992A0 (en) | 2007-05-15 |
| AU2005328701A1 (en) | 2006-09-14 |
| JP5025468B2 (ja) | 2012-09-12 |
| EA200700055A1 (ru) | 2007-10-26 |
| ES2483126T3 (es) | 2014-08-05 |
| AU2005328701B2 (en) | 2009-08-13 |
| BRPI0512263A (pt) | 2008-02-26 |
| EP2601937A1 (en) | 2013-06-12 |
| JP2008509089A (ja) | 2008-03-27 |
| CA2568445A1 (en) | 2006-09-14 |
| EA011290B1 (ru) | 2009-02-27 |
| WO2006096194A3 (en) | 2007-11-22 |
| KR20090033410A (ko) | 2009-04-02 |
| EP1765287A2 (en) | 2007-03-28 |
| IL179992A (en) | 2012-02-29 |
| EP2397122B1 (en) | 2014-05-14 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130618 |