ZA200603561B - Compositions comprising cyclohexylamines and amino-adamantanes - Google Patents
Compositions comprising cyclohexylamines and amino-adamantanes Download PDFInfo
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- ZA200603561B ZA200603561B ZA200603561A ZA200603561A ZA200603561B ZA 200603561 B ZA200603561 B ZA 200603561B ZA 200603561 A ZA200603561 A ZA 200603561A ZA 200603561 A ZA200603561 A ZA 200603561A ZA 200603561 B ZA200603561 B ZA 200603561B
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- South Africa
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- wiv
- usp
- composition
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- 239000000203 mixture Substances 0.000 title claims description 129
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical class C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 title claims description 37
- 150000003946 cyclohexylamines Chemical class 0.000 title description 13
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 45
- 239000003755 preservative agent Substances 0.000 claims description 41
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 33
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 230000002335 preservative effect Effects 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 16
- OGZQTTHDGQBLBT-UHFFFAOYSA-N neramexane Chemical group CC1(C)CC(C)(C)CC(C)(N)C1 OGZQTTHDGQBLBT-UHFFFAOYSA-N 0.000 claims description 16
- 239000000600 sorbitol Substances 0.000 claims description 16
- 235000010356 sorbitol Nutrition 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 15
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 15
- 229960003415 propylparaben Drugs 0.000 claims description 15
- 235000011187 glycerol Nutrition 0.000 claims description 14
- 229950004543 neramexane Drugs 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 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 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 229960004640 memantine Drugs 0.000 claims description 10
- 235000003599 food sweetener Nutrition 0.000 claims description 9
- 239000003765 sweetening agent Substances 0.000 claims description 9
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical group Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 239000000902 placebo Substances 0.000 claims description 8
- 229940068196 placebo Drugs 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 7
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 7
- 229960002216 methylparaben Drugs 0.000 claims description 7
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 6
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000000796 flavoring agent Substances 0.000 claims description 5
- 235000019634 flavors Nutrition 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 229960000967 memantine hydrochloride Drugs 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 150000003976 azacycloalkanes Chemical class 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 3
- 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 3
- 235000019264 food flavour enhancer Nutrition 0.000 claims description 3
- 235000010241 potassium sorbate Nutrition 0.000 claims description 3
- 239000004302 potassium sorbate Substances 0.000 claims description 3
- 229940069338 potassium sorbate Drugs 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004299 sodium benzoate Substances 0.000 claims description 3
- 235000010234 sodium benzoate Nutrition 0.000 claims description 3
- 239000006068 taste-masking agent Substances 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical group OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000004097 EU approved flavor enhancer Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 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 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229960003885 sodium benzoate Drugs 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 36
- 239000008213 purified water Substances 0.000 claims 14
- 239000001509 sodium citrate Substances 0.000 claims 11
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims 11
- 239000007967 peppermint flavor Substances 0.000 claims 10
- 239000003623 enhancer Substances 0.000 claims 8
- 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 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 235000009754 Vitis X bourquina Nutrition 0.000 claims 2
- 235000012333 Vitis X labruscana Nutrition 0.000 claims 2
- 240000006365 Vitis vinifera Species 0.000 claims 2
- 235000014787 Vitis vinifera Nutrition 0.000 claims 2
- 239000008135 aqueous vehicle Substances 0.000 claims 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 claims 1
- 108010011485 Aspartame Proteins 0.000 claims 1
- 241000167854 Bourreria succulenta Species 0.000 claims 1
- 101000801619 Homo sapiens Long-chain-fatty-acid-CoA ligase ACSBG1 Proteins 0.000 claims 1
- 102100033564 Long-chain-fatty-acid-CoA ligase ACSBG1 Human genes 0.000 claims 1
- 244000246386 Mentha pulegium Species 0.000 claims 1
- 235000016257 Mentha pulegium Nutrition 0.000 claims 1
- 235000004357 Mentha x piperita Nutrition 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000000605 aspartame Substances 0.000 claims 1
- 235000010357 aspartame Nutrition 0.000 claims 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims 1
- 229960003438 aspartame Drugs 0.000 claims 1
- 235000010634 bubble gum Nutrition 0.000 claims 1
- 235000019693 cherries Nutrition 0.000 claims 1
- 235000001050 hortel pimenta Nutrition 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229940085605 saccharin sodium Drugs 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001488 sodium phosphate Substances 0.000 claims 1
- 229910000162 sodium phosphate Inorganic materials 0.000 claims 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 claims 1
- 229960002920 sorbitol Drugs 0.000 claims 1
- 229960004793 sucrose Drugs 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- 239000004480 active ingredient Substances 0.000 description 19
- 239000007788 liquid Substances 0.000 description 18
- 238000009472 formulation Methods 0.000 description 16
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 15
- 230000000845 anti-microbial effect Effects 0.000 description 10
- -1 Aminoadamantane compound Chemical class 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 8
- 208000024827 Alzheimer disease Diseases 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000019640 taste Nutrition 0.000 description 5
- 206010012289 Dementia Diseases 0.000 description 4
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000002906 microbiologic effect Effects 0.000 description 4
- 238000004321 preservation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000010199 sorbic acid Nutrition 0.000 description 4
- 239000004334 sorbic acid Substances 0.000 description 4
- 229940075582 sorbic acid Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000006193 liquid solution Substances 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 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
- 239000007787 solid Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UXQDWARBDDDTKG-UHFFFAOYSA-N tromantadine Chemical compound C1C(C2)CC3CC2CC1(NC(=O)COCCN(C)C)C3 UXQDWARBDDDTKG-UHFFFAOYSA-N 0.000 description 3
- PMNUOTQOFZGNNQ-UHFFFAOYSA-N 1,3,5-trimethylcyclohexan-1-amine Chemical compound CC1CC(C)CC(C)(N)C1 PMNUOTQOFZGNNQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- JINZKAFNDLFUEW-UHFFFAOYSA-N 3-ethyl-1,3,5,5-tetramethylcyclohexan-1-amine Chemical compound CCC1(C)CC(C)(C)CC(C)(N)C1 JINZKAFNDLFUEW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 208000010412 Glaucoma Diseases 0.000 description 2
- 208000005176 Hepatitis C Diseases 0.000 description 2
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
- 239000000006 Nitroglycerin Substances 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- YEESUBCSWGVPCE-UHFFFAOYSA-N azanylidyneoxidanium iron(2+) pentacyanide Chemical compound [Fe++].[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.N#[O+] YEESUBCSWGVPCE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 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 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229960003711 glyceryl trinitrate Drugs 0.000 description 2
- 208000007386 hepatic encephalopathy Diseases 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 201000004792 malaria Diseases 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 208000021722 neuropathic pain Diseases 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009747 swallowing Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229960000832 tromantadine Drugs 0.000 description 2
- 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
- WCYNWVWYGZJUFX-UHFFFAOYSA-N 1,3,3,5-tetramethylcyclohexan-1-amine Chemical compound CC1CC(C)(C)CC(C)(N)C1 WCYNWVWYGZJUFX-UHFFFAOYSA-N 0.000 description 1
- WCBGLHDVUJFUDO-UHFFFAOYSA-N 1,3,3-trimethyl-5,5-dipropylcyclohexan-1-amine Chemical compound CCCC1(CCC)CC(C)(C)CC(C)(N)C1 WCBGLHDVUJFUDO-UHFFFAOYSA-N 0.000 description 1
- BADMBUCXLGEWNJ-UHFFFAOYSA-N 1,3-dimethyl-3-propylcyclohexan-1-amine Chemical compound CCCC1(C)CCCC(C)(N)C1 BADMBUCXLGEWNJ-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
- 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 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- OIHULWBOFIEYPQ-UHFFFAOYSA-N 2-(3,3,5,5-tetramethylcyclohexyl)ethanamine Chemical compound CC1(C)CC(CCN)CC(C)(C)C1 OIHULWBOFIEYPQ-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- OMYKWZGACJRFAJ-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-propylcyclohexan-1-amine Chemical compound CCCC1(N)CC(C)(C)CC(C)(C)C1 OMYKWZGACJRFAJ-UHFFFAOYSA-N 0.000 description 1
- XOEUSMBMGXZZJL-UHFFFAOYSA-N 3,5,7-trimethyladamantan-1-amine Chemical compound C1C(C2)(C)CC3(C)CC1(C)CC2(N)C3 XOEUSMBMGXZZJL-UHFFFAOYSA-N 0.000 description 1
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- 229960002675 xylitol Drugs 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
- A61K31/13—Amines
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0063—Periodont
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nutrition Science (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51798103P | 2003-11-05 | 2003-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603561B true ZA200603561B (en) | 2007-07-25 |
Family
ID=34572981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603561A ZA200603561B (en) | 2003-11-05 | 2006-05-04 | Compositions comprising cyclohexylamines and amino-adamantanes |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US20070270500A1 (pl) |
| EP (2) | EP2289489B1 (pl) |
| AR (1) | AR046314A1 (pl) |
| AT (1) | ATE504290T1 (pl) |
| AU (1) | AU2004287489B9 (pl) |
| CA (1) | CA2543865C (pl) |
| CL (1) | CL2008000125A1 (pl) |
| CY (1) | CY1111456T1 (pl) |
| DE (1) | DE602004032164D1 (pl) |
| DK (1) | DK1684715T3 (pl) |
| ES (2) | ES2362581T3 (pl) |
| HR (1) | HRP20110482T1 (pl) |
| IL (1) | IL175623A (pl) |
| PL (1) | PL1684715T3 (pl) |
| PT (1) | PT1684715E (pl) |
| SI (1) | SI1684715T1 (pl) |
| TW (1) | TWI350750B (pl) |
| WO (1) | WO2005044228A2 (pl) |
| ZA (1) | ZA200603561B (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060002999A1 (en) | 2004-06-17 | 2006-01-05 | Forest Laboratories, Inc. | Immediate release formulations of 1-aminocyclohexane compounds, memantine and neramexane |
| EP1765287A2 (en) * | 2004-06-17 | 2007-03-28 | Merz Pharma GmbH & Co. KGaA | Immediate release formulations of memantine oral dosage forms |
| US20070060887A1 (en) * | 2005-08-22 | 2007-03-15 | Marsh David A | Ophthalmic injector |
| TW200916091A (en) * | 2007-06-08 | 2009-04-16 | Merz Pharma Gmbh & Amp Co Kgaa | Neramexane for the treatment of nystagmus |
| ES2377253T3 (es) | 2007-09-12 | 2012-03-23 | Merz Pharma Gmbh & Co. Kgaa | Neramexano para uso en el tratamiento de tinitus subagudo |
| TW201006463A (en) * | 2008-06-26 | 2010-02-16 | Merz Pharma Gmbh & Co Kgaa | Pharmaceutical compositions comprising aminocyclohexane derivatives |
| TWI432188B (zh) | 2008-12-19 | 2014-04-01 | Merz Pharma Gmbh & Co Kgaa | 供治療發炎性皮膚疾病之１－胺基－烷基環己烷衍生物類 |
| AU2009328497A1 (en) | 2008-12-19 | 2010-06-24 | Merz Pharma Gmbh & Co. Kgaa | 1-amino-alkylcyclohexane derivatives for the treatment of mast cell mediated diseases |
| EP2582356A1 (en) | 2010-06-18 | 2013-04-24 | Merz Pharma GmbH & Co. KGaA | Gel formulations for the topical use of 1-amino-alkylcyclohexane derivatives |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH603545A5 (pl) | 1972-04-20 | 1978-08-31 | Merz & Co | |
| DE2856393C2 (de) | 1978-12-27 | 1983-04-28 | Merz + Co GmbH & Co, 6000 Frankfurt | Arzneimittel zur Behandlung von Morbus Parkinson |
| 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 |
| 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 |
| WO1992018112A1 (en) | 1991-04-19 | 1992-10-29 | The Children's Medical Center Corporation | Method of preventing nmda receptor complex-mediated neuronal damage |
| US6071966A (en) * | 1997-06-30 | 2000-06-06 | Merz + Co. Gmbh & Co. | 1-amino-alkylcyclohexane NMDA receptor antagonists |
| CZ293248B6 (cs) | 1997-06-30 | 2004-03-17 | Merz Pharma Gmbh & Co. Kgaa | 1-Aminocyklohexanový derivát a farmaceutická kompozice na jeho bázi |
| 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 |
| MXPA03005130A (es) * | 2000-12-07 | 2004-12-06 | Neuromolecular Inc | Metodos para tratar trastornos neurosiquiatricos con antagonistas del receptor del nmda. |
| US6828462B2 (en) * | 2001-11-07 | 2004-12-07 | Merz Pharma Gmbh & Co. Kgaa | Unsaturated 1-amino-alkylcyclohexane NMDA, 5HT3, and neuronal nicotinic receptor antagonists |
| TW200410672A (en) * | 2002-07-19 | 2004-07-01 | Merz Pharma Gmbh & Co Kgaa | NMDA receptor antagonists and their use in inhibiting abnormal hyperphosphorylation of microtubule associated protein tau |
| UA80055C2 (en) * | 2003-05-27 | 2007-08-10 | Forest Laboratories | Combination of nmda-receptor antagonist and selective inhibitor of serotonin reuptake for a depression and other pscihiatric disorders treatment |
-
2004
- 2004-11-01 AR ARP040104007A patent/AR046314A1/es not_active Application Discontinuation
- 2004-11-05 ES ES04810445T patent/ES2362581T3/es active Active
- 2004-11-05 PL PL04810445T patent/PL1684715T3/pl unknown
- 2004-11-05 EP EP10184394.4A patent/EP2289489B1/en active Active
- 2004-11-05 DE DE602004032164T patent/DE602004032164D1/de active Active
- 2004-11-05 AT AT04810445T patent/ATE504290T1/de active
- 2004-11-05 DK DK04810445.9T patent/DK1684715T3/da active
- 2004-11-05 CA CA2543865A patent/CA2543865C/en not_active Expired - Fee Related
- 2004-11-05 US US10/578,765 patent/US20070270500A1/en not_active Abandoned
- 2004-11-05 TW TW093133869A patent/TWI350750B/zh not_active IP Right Cessation
- 2004-11-05 EP EP04810445A patent/EP1684715B1/en active Active
- 2004-11-05 PT PT04810445T patent/PT1684715E/pt unknown
- 2004-11-05 SI SI200431683T patent/SI1684715T1/sl unknown
- 2004-11-05 ES ES10184394.4T patent/ES2507500T3/es active Active
- 2004-11-05 WO PCT/US2004/037026 patent/WO2005044228A2/en active Application Filing
- 2004-11-05 AU AU2004287489A patent/AU2004287489B9/en not_active Ceased
-
2006
- 2006-05-04 ZA ZA200603561A patent/ZA200603561B/en unknown
- 2006-05-14 IL IL175623A patent/IL175623A/en not_active IP Right Cessation
-
2008
- 2008-01-16 CL CL200800125A patent/CL2008000125A1/es unknown
-
2009
- 2009-10-14 US US12/587,885 patent/US20100035995A1/en not_active Abandoned
-
2011
- 2011-05-09 CY CY20111100444T patent/CY1111456T1/el unknown
- 2011-06-29 HR HR20110482T patent/HRP20110482T1/hr unknown
-
2012
- 2012-04-26 US US13/456,751 patent/US20120238631A1/en not_active Abandoned
-
2014
- 2014-08-07 US US14/453,807 patent/US20140350114A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2543865A1 (en) | 2005-05-19 |
| WO2005044228A2 (en) | 2005-05-19 |
| IL175623A (en) | 2012-10-31 |
| US20070270500A1 (en) | 2007-11-22 |
| EP2289489B1 (en) | 2014-07-16 |
| ATE504290T1 (de) | 2011-04-15 |
| EP1684715A2 (en) | 2006-08-02 |
| PL1684715T3 (pl) | 2011-09-30 |
| US20140350114A1 (en) | 2014-11-27 |
| TW200526195A (en) | 2005-08-16 |
| SI1684715T1 (sl) | 2011-07-29 |
| AU2004287489A1 (en) | 2005-05-19 |
| ES2362581T3 (es) | 2011-07-07 |
| WO2005044228A3 (en) | 2006-06-22 |
| US20120238631A1 (en) | 2012-09-20 |
| AU2004287489B2 (en) | 2008-08-28 |
| CL2008000125A1 (es) | 2008-03-14 |
| CY1111456T1 (el) | 2015-08-05 |
| EP1684715B1 (en) | 2011-04-06 |
| ES2507500T3 (es) | 2014-10-15 |
| HRP20110482T1 (hr) | 2011-07-31 |
| TWI350750B (en) | 2011-10-21 |
| DE602004032164D1 (de) | 2011-05-19 |
| CA2543865C (en) | 2012-09-04 |
| AU2004287489B9 (en) | 2008-10-09 |
| PT1684715E (pt) | 2011-05-02 |
| AR046314A1 (es) | 2005-11-30 |
| EP2289489A3 (en) | 2012-06-06 |
| US20100035995A1 (en) | 2010-02-11 |
| EP2289489A2 (en) | 2011-03-02 |
| DK1684715T3 (da) | 2011-07-11 |
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