ZA200307201B - Glyt-1 inhibitors. - Google Patents
Glyt-1 inhibitors. Download PDFInfo
- Publication number
- ZA200307201B ZA200307201B ZA200307201A ZA200307201A ZA200307201B ZA 200307201 B ZA200307201 B ZA 200307201B ZA 200307201 A ZA200307201 A ZA 200307201A ZA 200307201 A ZA200307201 A ZA 200307201A ZA 200307201 B ZA200307201 B ZA 200307201B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- thienyl
- phenyl
- sarcosine
- prop
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 109
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 74
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 66
- 108010077895 Sarcosine Proteins 0.000 claims description 37
- 229940043230 sarcosine Drugs 0.000 claims description 37
- 239000004471 Glycine Substances 0.000 claims description 33
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 31
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 201000000980 schizophrenia Diseases 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- -1 1-(4-(4-Isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3- yl Chemical group 0.000 claims description 6
- CLNBFFJOAIHNHT-LSCVHKIXSA-N 2-[[(z)-3-[4-(furan-2-yl)phenyl]-3-thiophen-3-ylprop-2-enyl]-methylazaniumyl]acetate Chemical compound C=1C=C(C=2OC=CC=2)C=CC=1C(=C/CN(C)CC(O)=O)/C=1C=CSC=1 CLNBFFJOAIHNHT-LSCVHKIXSA-N 0.000 claims description 3
- 208000036640 Asperger disease Diseases 0.000 claims description 3
- 201000006062 Asperger syndrome Diseases 0.000 claims description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 3
- 208000020706 Autistic disease Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000006289 Rett Syndrome Diseases 0.000 claims description 3
- 208000036353 Rett disease Diseases 0.000 claims description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 3
- 201000007197 atypical autism Diseases 0.000 claims description 3
- 208000024825 childhood disintegrative disease Diseases 0.000 claims description 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 4
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 239000011630 iodine Substances 0.000 claims 4
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 125000003158 alcohol group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- MYKMOIQAHCMLIR-UHFFFAOYSA-N tert-butyl 2-(methylamino)acetate Chemical compound CNCC(=O)OC(C)(C)C MYKMOIQAHCMLIR-UHFFFAOYSA-N 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OWMNRPVXVPPJAE-AFPJDJCSSA-N 2-[[(z)-3-[4-(3-cyanophenyl)phenyl]-3-thiophen-3-ylprop-2-enyl]-methylamino]acetic acid Chemical compound C=1C=C(C=2C=C(C=CC=2)C#N)C=CC=1C(=C/CN(C)CC(O)=O)/C=1C=CSC=1 OWMNRPVXVPPJAE-AFPJDJCSSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 150000001543 aryl boronic acids Chemical class 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 description 19
- 102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 description 18
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 11
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 11
- 239000002858 neurotransmitter agent Substances 0.000 description 9
- 230000001965 increasing effect Effects 0.000 description 7
- 230000001404 mediated effect Effects 0.000 description 7
- 239000003446 ligand Substances 0.000 description 6
- 108010078791 Carrier Proteins Proteins 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 210000000225 synapse Anatomy 0.000 description 5
- 102000011714 Glycine Receptors Human genes 0.000 description 4
- 108010076533 Glycine Receptors Proteins 0.000 description 4
- 102100028886 Sodium- and chloride-dependent glycine transporter 2 Human genes 0.000 description 4
- 101710083167 Sodium- and chloride-dependent glycine transporter 2 Proteins 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
- HWZCEKFYJQGDBJ-JJFYIABZSA-N 2-[methyl-[(z)-3-(2-methylphenyl)-3-(4-thiophen-3-ylphenyl)prop-2-enyl]amino]acetic acid Chemical compound C=1C=CC=C(C)C=1C(=C/CN(C)CC(O)=O)\C(C=C1)=CC=C1C=1C=CSC=1 HWZCEKFYJQGDBJ-JJFYIABZSA-N 0.000 description 3
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 3
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000002964 excitative effect Effects 0.000 description 3
- 230000027928 long-term synaptic potentiation Effects 0.000 description 3
- 210000000653 nervous system Anatomy 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 230000005062 synaptic transmission Effects 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- 208000012202 Pervasive developmental disease Diseases 0.000 description 2
- 230000036982 action potential Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 208000029560 autism spectrum disease Diseases 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 210000000133 brain stem Anatomy 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 150000002332 glycine derivatives Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010369 molecular cloning Methods 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 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
- 230000000946 synaptic effect Effects 0.000 description 2
- 238000011830 transgenic mouse model Methods 0.000 description 2
- FTQWYMOYJRLUFC-LSCVHKIXSA-N 2-[methyl-[(z)-3-thiophen-2-yl-3-(4-thiophen-3-ylphenyl)prop-2-enyl]amino]acetic acid Chemical compound C=1C=C(C2=CSC=C2)C=CC=1C(=C/CN(C)CC(O)=O)/C1=CC=CS1 FTQWYMOYJRLUFC-LSCVHKIXSA-N 0.000 description 1
- SRUROZLXEFMFKB-SWNXQHNESA-N 2-[methyl-[(z)-3-thiophen-3-yl-3-(4-thiophen-3-ylphenyl)prop-2-enyl]azaniumyl]acetate Chemical compound C=1C=C(C2=CSC=C2)C=CC=1C(=C/CN(C)CC(O)=O)/C=1C=CSC=1 SRUROZLXEFMFKB-SWNXQHNESA-N 0.000 description 1
- OHYZEWIWDWQNHJ-NKVSQWTQSA-N 2-[methyl-[(z)-3-thiophen-3-yl-3-[4-[3-(trifluoromethoxy)phenyl]phenyl]prop-2-enyl]amino]acetic acid Chemical compound C=1C=C(C=2C=C(OC(F)(F)F)C=CC=2)C=CC=1C(=C/CN(C)CC(O)=O)/C=1C=CSC=1 OHYZEWIWDWQNHJ-NKVSQWTQSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CEEIJOOHMCRBMH-UHFFFAOYSA-N 4-methylthiophene Chemical compound CC1=[C]SC=C1 CEEIJOOHMCRBMH-UHFFFAOYSA-N 0.000 description 1
- HWZCEKFYJQGDBJ-UHFFFAOYSA-N C=1C=CC=C(C)C=1C(=CCN(C)CC(O)=O)C(C=C1)=CC=C1C=1C=CSC=1 Chemical compound C=1C=CC=C(C)C=1C(=CCN(C)CC(O)=O)C(C=C1)=CC=C1C=1C=CSC=1 HWZCEKFYJQGDBJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010062745 Chloride Channels Proteins 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 102000005665 Neurotransmitter Transport Proteins Human genes 0.000 description 1
- 108010084810 Neurotransmitter Transport Proteins Proteins 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 206010042008 Stereotypy Diseases 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 230000000848 glutamatergic effect Effects 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000009539 inhibitory neurotransmission Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000035992 intercellular communication Effects 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004897 n-terminal region Anatomy 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 230000008062 neuronal firing Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 210000000063 presynaptic terminal Anatomy 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 108020001572 subunits Proteins 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000003956 synaptic plasticity Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26924101P | 2001-02-16 | 2001-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200307201B true ZA200307201B (en) | 2004-07-28 |
Family
ID=23026417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200307201A ZA200307201B (en) | 2001-02-16 | 2003-09-15 | Glyt-1 inhibitors. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6667336B2 (sk) |
| EP (1) | EP1368336B9 (sk) |
| JP (2) | JP2004523548A (sk) |
| KR (1) | KR100900020B1 (sk) |
| CN (1) | CN1219776C (sk) |
| AT (1) | ATE327986T1 (sk) |
| AU (1) | AU2002235682C1 (sk) |
| BG (1) | BG108164A (sk) |
| BR (1) | BR0207307A (sk) |
| CA (1) | CA2438367A1 (sk) |
| CY (1) | CY1105529T1 (sk) |
| CZ (1) | CZ20032503A3 (sk) |
| DE (1) | DE60211866T2 (sk) |
| DK (1) | DK1368336T3 (sk) |
| EA (1) | EA006636B1 (sk) |
| EE (1) | EE05329B1 (sk) |
| ES (1) | ES2266446T3 (sk) |
| HK (1) | HK1061025A1 (sk) |
| HR (1) | HRP20030696A2 (sk) |
| HU (1) | HUP0303185A3 (sk) |
| IL (1) | IL157194A (sk) |
| MX (1) | MXPA03007309A (sk) |
| NO (1) | NO329038B1 (sk) |
| NZ (1) | NZ527695A (sk) |
| PL (1) | PL365024A1 (sk) |
| PT (1) | PT1368336E (sk) |
| SI (1) | SI1368336T1 (sk) |
| SK (1) | SK287304B6 (sk) |
| UA (1) | UA75114C2 (sk) |
| WO (1) | WO2002066456A2 (sk) |
| ZA (1) | ZA200307201B (sk) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6191165B1 (en) * | 1996-05-31 | 2001-02-20 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| PL1830833T3 (pl) * | 2004-12-16 | 2010-06-30 | Janssen Pharmaceutica Nv | Połączenie inhibitora transportera glicyny (GLYT1) i środka przeciwpsychotycznego do leczenia objawów schizofrenii jak również sposoby jego wytwarzania oraz zastosowanie |
| WO2008040669A2 (en) * | 2006-10-02 | 2008-04-10 | Janssen Pharmaceutica N.V. | Novel intermediates for the preparation of a glyt1 inhibitor |
| WO2008065500A2 (en) * | 2006-11-30 | 2008-06-05 | Pfizer Products Inc. | Heteroaryl amides as type i glycine transport inhibitors |
| CN103374057B (zh) * | 2012-04-16 | 2015-08-19 | 中国医药集团总公司四川抗菌素工业研究所 | 一种对甘氨酸转运子具有抑制活性的化合物 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3050800C2 (sk) | 1979-03-22 | 1989-06-22 | Continental Pharma Inc., Bruessel/Bruxelles, Be | |
| BE885303A (fr) | 1980-09-19 | 1981-03-19 | Continental Pharma | Glycinamides |
| US4383999A (en) | 1981-05-26 | 1983-05-17 | Smithkline Beckman Corporation | Inhibition of GABA uptake by N-substituted azaheterocyclic carboxylic acids and their esters |
| AU552050B2 (en) | 1981-05-26 | 1986-05-22 | Smithkline Beckman Corporation | N-substituted azeheterocyclic carboxylic acids and their esters |
| US4514414A (en) | 1982-10-25 | 1985-04-30 | Smithkline Beckman Corporation | N-Substituted pyrrolidineacetic acids and their esters |
| DK288385D0 (da) | 1985-06-26 | 1985-06-26 | Novo Industri As | Aminosyrederivater |
| US4772615A (en) | 1985-11-08 | 1988-09-20 | Warner-Lambert Company | Various N-substituted 3-piperidine carboxylic acids or N-substituted 3-pyridinecarboxylic acids and derivatives thereof |
| FI864246A (fi) | 1985-11-08 | 1987-05-09 | Warner Lambert Co | N-substituerade 3-piperidin- eller 3-pyridinkarboxylsyror samt deras derivat. |
| DE3787657T2 (de) | 1986-01-07 | 1994-02-03 | Novo Ind A S Bagsvaerd | Aminosäure-Derivate. |
| JPH02129158A (ja) | 1988-11-07 | 1990-05-17 | Nippon Steel Corp | 光学活性なグリシン誘導体及びその製造方法 |
| IE913279A1 (en) * | 1990-09-26 | 1992-04-08 | Astra Ab | (2-Thienyl)alkylamine Derivatives Having Neuroprotective¹Properties |
| ES2036926B1 (es) | 1991-08-08 | 1994-01-16 | Uriach & Cia Sa J | "procedimiento para la obtencion de derivados de la (2-alquil-3-piridil)metilpiperazina". |
| DE69635959T2 (de) | 1995-12-07 | 2006-12-07 | Javitt, Daniel C. | Behandlung negativer und kognitiver symptome der schizophrenie mit antagonisten der glycinaufnahme |
| US6191165B1 (en) | 1996-05-31 | 2001-02-20 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| CZ294348B6 (cs) * | 1996-05-31 | 2004-12-15 | Allelix Neuroscience Inc. | Substituovaný derivát glycinu a farmaceutický prostředek s jeho obsahem |
| AU3434697A (en) * | 1996-07-22 | 1998-02-10 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| ES2209244T3 (es) * | 1998-01-09 | 2004-06-16 | Pfizer Inc. | Inhibidores de las metaloproteasas de la matriz. |
| US6103743A (en) * | 1999-08-06 | 2000-08-15 | Allelix Neuroscience, Inc. | Unsaturated amino acid derivatives |
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- 2002-02-15 AT AT02702186T patent/ATE327986T1/de not_active IP Right Cessation
- 2002-02-15 AU AU2002235682A patent/AU2002235682C1/en not_active Ceased
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- 2002-02-15 JP JP2002565971A patent/JP2004523548A/ja active Pending
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- 2002-02-15 US US10/077,579 patent/US6667336B2/en not_active Expired - Fee Related
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- 2002-02-15 DE DE60211866T patent/DE60211866T2/de not_active Expired - Lifetime
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- 2003-08-15 NO NO20033634A patent/NO329038B1/no not_active IP Right Cessation
- 2003-09-01 HR HR20030696A patent/HRP20030696A2/xx not_active Application Discontinuation
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