DK173589B1 - Anvendelse af D-cycloserin og dets forstadier eller farmaceutisk acceptable salte deraf til fremstilling af præparater til - Google Patents
Anvendelse af D-cycloserin og dets forstadier eller farmaceutisk acceptable salte deraf til fremstilling af præparater til Download PDFInfo
- Publication number
- DK173589B1 DK173589B1 DK198806690A DK669088A DK173589B1 DK 173589 B1 DK173589 B1 DK 173589B1 DK 198806690 A DK198806690 A DK 198806690A DK 669088 A DK669088 A DK 669088A DK 173589 B1 DK173589 B1 DK 173589B1
- Authority
- DK
- Denmark
- Prior art keywords
- alkyl
- atoms
- hydrido
- dosage form
- pharmaceutically acceptable
- Prior art date
Links
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 title claims abstract description 16
- 150000003839 salts Chemical class 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 title abstract description 14
- 239000002243 precursor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000002552 dosage form Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002262 Schiff base Substances 0.000 claims description 8
- 150000004753 Schiff bases Chemical class 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000008366 benzophenones Chemical class 0.000 claims description 2
- 230000006870 function Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 230000027928 long-term synaptic potentiation Effects 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 230000001149 cognitive effect Effects 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- FERCDDZJYIRSMF-UHFFFAOYSA-N 2-amino-1,2-oxazolidin-3-one Chemical compound NN1OCCC1=O FERCDDZJYIRSMF-UHFFFAOYSA-N 0.000 claims 1
- 208000023584 Alzheimer disease 10 Diseases 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000037411 cognitive enhancing Effects 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 19
- 241000700159 Rattus Species 0.000 description 11
- 239000004471 Glycine Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- -1 phenalkyl Chemical group 0.000 description 8
- 230000035939 shock Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 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 5
- 238000007792 addition Methods 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- GJNNXIYZWIZFRH-UHFFFAOYSA-N 2-(pentylamino)acetamide Chemical compound CCCCCNCC(N)=O GJNNXIYZWIZFRH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 230000008499 blood brain barrier function Effects 0.000 description 3
- 210000001218 blood-brain barrier Anatomy 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000006883 memory enhancing effect Effects 0.000 description 3
- 229950000928 milacemide Drugs 0.000 description 3
- 125000006684 polyhaloalkyl group Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- MYDMWESTDPJANS-UHFFFAOYSA-N 2-amino-7-phosphonoheptanoic acid Chemical compound OC(=O)C(N)CCCCCP(O)(O)=O MYDMWESTDPJANS-UHFFFAOYSA-N 0.000 description 2
- 102000011714 Glycine Receptors Human genes 0.000 description 2
- 108010076533 Glycine Receptors Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 2
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920005372 Plexiglas® Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229960003077 cycloserine Drugs 0.000 description 2
- 125000004982 dihaloalkyl group Chemical group 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000006993 memory improvement Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000006682 monohaloalkyl group Chemical group 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 102000015404 Amino Acid Receptors Human genes 0.000 description 1
- 108010025177 Amino Acid Receptors Proteins 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229940127427 Glycine Agonists Drugs 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 241000282412 Homo Species 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
- DYDCUQKUCUHJBH-REOHCLBHSA-N L-Cycloserine Chemical compound N[C@H]1CONC1=O DYDCUQKUCUHJBH-REOHCLBHSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007087 memory ability Effects 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000004800 psychological effect Effects 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/33—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
- A61K31/42—Oxazoles
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12712187 | 1987-12-01 | ||
| US07/127,121 US4904681A (en) | 1987-12-01 | 1987-12-01 | D-cycloserine and its prodrugs as cognitive enhancers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK669088D0 DK669088D0 (da) | 1988-11-30 |
| DK669088A DK669088A (da) | 1989-06-02 |
| DK173589B1 true DK173589B1 (da) | 2001-04-02 |
Family
ID=22428413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198806690A DK173589B1 (da) | 1987-12-01 | 1988-11-30 | Anvendelse af D-cycloserin og dets forstadier eller farmaceutisk acceptable salte deraf til fremstilling af præparater til |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4904681A (enExample) |
| EP (2) | EP0319824B1 (enExample) |
| JP (2) | JPH0621065B2 (enExample) |
| KR (1) | KR0134198B1 (enExample) |
| AT (1) | ATE68698T1 (enExample) |
| AU (4) | AU622630B2 (enExample) |
| CA (1) | CA1328617C (enExample) |
| DE (1) | DE3865817D1 (enExample) |
| DK (1) | DK173589B1 (enExample) |
| ES (1) | ES2040314T3 (enExample) |
| FI (1) | FI885559A0 (enExample) |
| GR (1) | GR3003571T3 (enExample) |
| IE (1) | IE61825B1 (enExample) |
| IL (1) | IL88531A (enExample) |
| NO (1) | NO885337D0 (enExample) |
| NZ (1) | NZ227131A (enExample) |
| PH (1) | PH26467A (enExample) |
| PT (1) | PT89109B (enExample) |
| WO (1) | WO1989005144A1 (enExample) |
| ZA (1) | ZA888981B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187171A (en) * | 1989-01-09 | 1993-02-16 | G. D. Searle & Co. | Use of a glycine b partial agonist as an antipsychotic |
| US5061721A (en) * | 1989-03-15 | 1991-10-29 | G. D. Searle & Co. | Composition containing d-cycloserine and d-alanine for memory and learning enhancement or treatment of a cognitive or psychotic disorder |
| US5260324A (en) * | 1990-02-06 | 1993-11-09 | G. D. Searle & Company | Composition containing D-cycloserine and D-alanine for memory and learning enhancement or treatment of a cognitive or psychotic disorder |
| US5066665A (en) * | 1990-05-21 | 1991-11-19 | Warner-Lambert Co. | Substituted isoxazolidin-3-ones and derivatives thereof acting at muscarinic receptors |
| JPH07505908A (ja) * | 1992-09-28 | 1995-06-29 | マックセチーニ、マリア ルイザ | Ｎｍｄａ受容体のアロステリックモジュレーター |
| US5428069A (en) * | 1993-01-11 | 1995-06-27 | The United States Of America As Represented By The Department Of Health & Human Services | Treating cognition with, aminocyclopropanecarboxylic derivatives |
| US5523323A (en) * | 1993-09-14 | 1996-06-04 | Maccecchini; Maria-Luisa | Use of partial agonists of the NMDA receptor to reduce opiate induced tolerance and dependence |
| NZ260302A (en) * | 1994-04-13 | 1996-05-28 | New Zealand Meat Ind Res Inst | Treating bait aversion by including substances which disrupt the associative learning process into bait compositions |
| AU4128896A (en) * | 1994-11-23 | 1996-06-17 | G.D. Searle & Co. | Use of amino-isoxazolidone compounds for treatment of memory impairment following traumatic brain injury |
| AU4019395A (en) * | 1994-11-23 | 1996-06-17 | G.D. Searle & Co. | Use of amino-isoxazolidone compounds for improvement of implicit memory |
| ATE204852T1 (de) * | 1995-02-15 | 2001-09-15 | Bearsden Bio Inc | Alkylcarboxy-aminosäure modulatoren für den kainat-rezeptor |
| PT871440E (pt) * | 1995-12-07 | 2006-07-31 | Daniel C Javitt | Tratamento de sintomas negativos e cognitivos de esquizofrenia com antagonistas da captacao de glicina |
| US6355681B2 (en) * | 1995-12-07 | 2002-03-12 | Glytech, Inc. | Glycine substitutes and precursors for treating a psychosis |
| US6361957B1 (en) | 1999-08-03 | 2002-03-26 | Glytech, Inc. | Assay for D-serine transport antagonist and use for treating psychosis |
| FR2742748B1 (fr) * | 1995-12-21 | 1998-01-30 | Adir | Nouveau derive de 4-imidazolidinone, son procede de preparation et les compositions pharmaceutiques qui le contiennent |
| KR100396114B1 (ko) * | 1996-10-31 | 2003-11-20 | 동아제약 주식회사 | D-시클로세린의 제조방법 |
| AU765603C (en) * | 1998-04-14 | 2004-08-05 | General Hospital Corporation, The | Methods for treating neuropsychiatric disorders |
| EP1084704B1 (en) * | 1998-06-10 | 2006-03-29 | Meiji Seika Kaisha Ltd. | Remedies for spinocerebellar ataxia and compositions for treating spinocerebellar ataxia |
| US20040122090A1 (en) * | 2001-12-07 | 2004-06-24 | Lipton Stuart A. | Methods for treating neuropsychiatric disorders with nmda receptor antagonists |
| US20060252761A1 (en) * | 2001-03-29 | 2006-11-09 | Michael Davis | Augmentation of extinction via administration of sub-antimicrobial doses of D-cycloserine |
| ATE519485T1 (de) * | 2001-03-29 | 2011-08-15 | Michael Davis | Akute pharmakologische verstärkung einer psychotherapie mit d-cycloserine |
| CN1527813A (zh) | 2001-04-02 | 2004-09-08 | О | 作为治疗剂的抗氧化剂硝基氧和亚硝氮碳基 |
| US7160913B2 (en) * | 2002-09-13 | 2007-01-09 | Thomas Jefferson University | Methods and kit for treating Parkinson's disease |
| 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 |
| EP1660634A4 (en) * | 2003-08-08 | 2009-02-18 | Burnham Inst | P16-mediated regulation of NMDA receptors |
| US8058291B2 (en) | 2005-04-06 | 2011-11-15 | Adamas Pharmaceuticals, Inc. | Methods and compositions for the treatment of CNS-related conditions |
| US7619007B2 (en) * | 2004-11-23 | 2009-11-17 | Adamas Pharmaceuticals, Inc. | Method and composition for administering an NMDA receptor antagonist to a subject |
| MX2011003015A (es) | 2008-09-18 | 2011-11-18 | Univ Northwestern | Moduladores del receptor de n-metil-d-aspartato, y usos de los mismos. |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US8951968B2 (en) | 2009-10-05 | 2015-02-10 | Northwestern University | Methods of treating depression and other related diseases |
| SG10201501050RA (en) | 2010-02-11 | 2015-04-29 | Univ Northwestern | Secondary Structure Stabilized NMDA Receptor Modulators And Uses Thereof |
| KR101692275B1 (ko) | 2010-02-11 | 2017-01-04 | 노오쓰웨스턴 유니버시티 | ２차 구조 안정화된 ｎｍｄａ 수용체 조절제 및 그의 용도 |
| JP6419087B2 (ja) | 2013-01-29 | 2018-11-07 | アプティニックス インコーポレイテッド | スピロラクタム系ｎｍｄａ受容体モジュレーターおよびその使用 |
| CA2898861C (en) | 2013-01-29 | 2021-07-20 | Naurex, Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| WO2014120784A1 (en) | 2013-01-29 | 2014-08-07 | Naurex, Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| SG11201505937SA (en) | 2013-01-29 | 2015-09-29 | Naurex Inc | Spiro-lactam nmda receptor modulators and uses thereof |
| CN105308049A (zh) | 2013-01-29 | 2016-02-03 | 阿普廷伊克斯股份有限公司 | 螺-内酰胺nmda受体调节剂及其用途 |
| PE20190174A1 (es) | 2016-05-19 | 2019-02-01 | Aptinyx Inc | Moduladores del receptor espiro-lactama n-metil-d-aspartato y usos de los mismos |
| WO2017201285A1 (en) | 2016-05-19 | 2017-11-23 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| JP2019527235A (ja) | 2016-08-01 | 2019-09-26 | アプティニックス インコーポレイテッド | スピロ−ラクタム及びビス−スピロ−ラクタムｎｍｄａ受容体修飾因子及びその使用 |
| PE20190501A1 (es) | 2016-08-01 | 2019-04-10 | Aptinyx Inc | Moduladores nmda espiro-lactam y metodos de uso de los mismos |
| EP3490992B1 (en) | 2016-08-01 | 2023-03-22 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| CA3031534C (en) | 2016-08-01 | 2023-10-17 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| CN109890825B (zh) | 2016-08-01 | 2022-03-11 | 阿普廷伊克斯股份有限公司 | 螺-内酰胺nmda受体调节剂及其用途 |
| EP3427729A1 (en) | 2017-07-13 | 2019-01-16 | Paris Sciences et Lettres - Quartier Latin | Probenecid for use in treating epileptic diseases, disorders or conditions |
| PE20210455A1 (es) | 2018-01-31 | 2021-03-08 | Aptinyx Inc | Moduladores del receptor nmda espiro-lactama y usos de los mismos |
| US12012413B2 (en) | 2019-11-11 | 2024-06-18 | Tenacia Biotechnology (Hong Kong) Co., Limited | Methods of treating painful diabetic peripheral neuropathy |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3010599A1 (de) * | 1979-03-22 | 1980-10-09 | Continental Pharma | Derivate von glycinamid, deren herstellung und verwendung |
-
1987
- 1987-12-01 US US07/127,121 patent/US4904681A/en not_active Expired - Lifetime
-
1988
- 1988-11-28 PH PH37866A patent/PH26467A/en unknown
- 1988-11-29 PT PT89109A patent/PT89109B/pt not_active IP Right Cessation
- 1988-11-29 IE IE356788A patent/IE61825B1/en not_active IP Right Cessation
- 1988-11-29 ES ES88119863T patent/ES2040314T3/es not_active Expired - Lifetime
- 1988-11-29 AU AU26319/88A patent/AU622630B2/en not_active Ceased
- 1988-11-29 IL IL88531A patent/IL88531A/xx not_active IP Right Cessation
- 1988-11-29 DE DE88119863T patent/DE3865817D1/de not_active Expired - Fee Related
- 1988-11-29 AT AT88119863T patent/ATE68698T1/de not_active IP Right Cessation
- 1988-11-29 EP EP88119863A patent/EP0319824B1/en not_active Expired - Lifetime
- 1988-11-29 NZ NZ227131A patent/NZ227131A/xx unknown
- 1988-11-30 JP JP63303873A patent/JPH0621065B2/ja not_active Expired - Lifetime
- 1988-11-30 KR KR1019880015895A patent/KR0134198B1/ko not_active Expired - Fee Related
- 1988-11-30 DK DK198806690A patent/DK173589B1/da not_active IP Right Cessation
- 1988-11-30 NO NO885337A patent/NO885337D0/no unknown
- 1988-11-30 ZA ZA888981A patent/ZA888981B/xx unknown
- 1988-11-30 CA CA000584621A patent/CA1328617C/en not_active Expired - Fee Related
- 1988-11-30 FI FI885559A patent/FI885559A0/fi not_active Application Discontinuation
- 1988-12-01 EP EP89900543A patent/EP0421997A1/en not_active Withdrawn
- 1988-12-01 WO PCT/US1988/004244 patent/WO1989005144A1/en not_active Ceased
- 1988-12-01 AU AU28130/89A patent/AU2813089A/en not_active Abandoned
-
1992
- 1992-01-15 GR GR910401170T patent/GR3003571T3/el unknown
- 1992-02-10 AU AU10839/92A patent/AU1083992A/en not_active Abandoned
- 1992-07-03 JP JP4177094A patent/JPH05201859A/ja active Pending
-
1994
- 1994-10-26 AU AU77467/94A patent/AU7746794A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0621065B2 (ja) | 1994-03-23 |
| DK669088D0 (da) | 1988-11-30 |
| IL88531A0 (en) | 1989-06-30 |
| IE883567L (en) | 1989-06-01 |
| PT89109B (pt) | 1993-07-30 |
| ES2040314T3 (es) | 1995-04-01 |
| EP0319824B1 (en) | 1991-10-23 |
| EP0421997A1 (en) | 1991-04-17 |
| WO1989005144A1 (en) | 1989-06-15 |
| AU2631988A (en) | 1989-06-01 |
| FI885559A0 (fi) | 1988-11-30 |
| JPH05201859A (ja) | 1993-08-10 |
| KR890009392A (ko) | 1989-08-01 |
| DE3865817D1 (enExample) | 1991-11-28 |
| IE61825B1 (en) | 1994-11-30 |
| ATE68698T1 (de) | 1991-11-15 |
| ZA888981B (en) | 1990-01-31 |
| AU7746794A (en) | 1995-01-05 |
| KR0134198B1 (ko) | 1998-04-21 |
| DK669088A (da) | 1989-06-02 |
| PH26467A (en) | 1992-07-27 |
| NZ227131A (en) | 1991-09-25 |
| CA1328617C (en) | 1994-04-19 |
| AU1083992A (en) | 1992-05-07 |
| US4904681A (en) | 1990-02-27 |
| JPH01193220A (ja) | 1989-08-03 |
| AU622630B2 (en) | 1992-04-16 |
| PT89109A (pt) | 1989-12-29 |
| IL88531A (en) | 1993-02-21 |
| GR3003571T3 (enExample) | 1993-03-16 |
| NO885337D0 (no) | 1988-11-30 |
| AU2813089A (en) | 1989-07-05 |
| EP0319824A1 (en) | 1989-06-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0319824B1 (en) | D-cycloserine and its prodrugs as cognitive enhancers | |
| RU2566821C2 (ru) | Модулятор nmda-рецептора со стабилизированной вторичной структурой и его применение | |
| US8822462B2 (en) | Subunit selective NMDA receptor potentiators for the treatment of neurological conditions | |
| EA031746B1 (ru) | СТИМУЛЯТОРЫ sGC | |
| JP2007534657A (ja) | ベンゾ［ｄ］イソオキサゾール阻害剤 | |
| US4874780A (en) | Anticancer compounds | |
| JPH08510990A (ja) | グリシンｎｍｄａレセプター複合体の機能的アンタゴニストによる認識の改良方法 | |
| US20240207265A1 (en) | TREATMENT OF CNS DISEASES WITH sGC STIMULATORS | |
| US5187171A (en) | Use of a glycine b partial agonist as an antipsychotic | |
| SU1545941A3 (ru) | Способ получени оксотиазолидиновых соединений | |
| JP2004535398A (ja) | ＮＡＡＬＡＤａｓｅ阻害剤としてのヒドロキサム酸およびアシルヒドロキサミン | |
| US10259827B2 (en) | BMP potentiators | |
| US5087633A (en) | Use of a glycine B partial agonist for memory and learning enhancement or treatment of a cognitive disorder | |
| US5468763A (en) | Use of a glycine B partial agonist for memory and learning enhancement or treatment of a cognitive disorder | |
| US20040019200A1 (en) | Mixed steroidal 1, 2, 4, 5- tetraoxane compounds and methods of making and using thereof | |
| US5476867A (en) | Pharmaceutical compositions | |
| JPWO2017131097A1 (ja) | アダマンタン誘導体およびその使用 | |
| US20010027204A1 (en) | Use of amino-isoxazolidone compounds for improvement of implicit memory | |
| WO2018181986A1 (ja) | アダマンチルメチルアミン誘導体およびその医薬としての使用 | |
| JP2026515016A (ja) | Ｎｏｄ２アゴニストとしてのデスムラミルペプチド二酸及びその使用 | |
| CN116554166A (zh) | 一种哒嗪并吡啶酮类化合物、其药物组合物及应用 | |
| HK1230171B (en) | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment | |
| HK1230171A1 (en) | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |
Country of ref document: DK |