ZA200300514B - Novel compounds and their use as glycine transport inhibitors. - Google Patents
Novel compounds and their use as glycine transport inhibitors. Download PDFInfo
- Publication number
- ZA200300514B ZA200300514B ZA200300514A ZA200300514A ZA200300514B ZA 200300514 B ZA200300514 B ZA 200300514B ZA 200300514 A ZA200300514 A ZA 200300514A ZA 200300514 A ZA200300514 A ZA 200300514A ZA 200300514 B ZA200300514 B ZA 200300514B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- propyl
- chloro
- methyl
- dihydro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 26
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims description 24
- 239000004471 Glycine Substances 0.000 title claims description 13
- 239000003112 inhibitor Substances 0.000 title description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N N-methylaminoacetic acid Natural products C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 108010077895 Sarcosine Proteins 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 claims description 10
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- -1 thiophen-1-yl Chemical group 0.000 claims description 6
- 206010012289 Dementia Diseases 0.000 claims description 5
- AQFYBBOVSHVEKK-CPFIQGLUSA-N (2s)-2-[3-[1-(4-chlorophenyl)-3,3-diethyl-2-benzofuran-1-yl]propyl-methylamino]propanoic acid Chemical compound C12=CC=CC=C2C(CC)(CC)OC1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 AQFYBBOVSHVEKK-CPFIQGLUSA-N 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- CDVLPBUKUVKVBA-UEDXYCIISA-N (2s)-2-[3-[5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]propanoic acid Chemical compound C1CC2=CC(Cl)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 CDVLPBUKUVKVBA-UEDXYCIISA-N 0.000 claims description 3
- YERIVNORZKQTBA-UHFFFAOYSA-N 2-[3-[5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]acetic acid Chemical compound C1CC2=CC(Cl)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 YERIVNORZKQTBA-UHFFFAOYSA-N 0.000 claims description 3
- BYEFBPYBYKBWFR-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C=C1 BYEFBPYBYKBWFR-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- RLMHMDMIOFCETG-UBDBMELISA-N (2s)-2-[3-(3,3-diethyl-1-phenyl-2-benzofuran-1-yl)propyl-methylamino]propanoic acid Chemical compound C12=CC=CC=C2C(CC)(CC)OC1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=CC=C1 RLMHMDMIOFCETG-UBDBMELISA-N 0.000 claims description 2
- UAUWLEHSOZBEQW-YXWRBFHGSA-N (2s)-2-[3-[1-(4-fluorophenyl)-5-(trifluoromethyl)-3h-2-benzofuran-1-yl]propyl-methylamino]propanoic acid Chemical compound O1CC2=CC(C(F)(F)F)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(F)C=C1 UAUWLEHSOZBEQW-YXWRBFHGSA-N 0.000 claims description 2
- XKOQVRLECUULHT-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-3,3-dimethyl-2-benzofuran-1-yl]ethyl-methylamino]acetic acid Chemical compound O1C(C)(C)C2=CC=CC=C2C1(CCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 XKOQVRLECUULHT-UHFFFAOYSA-N 0.000 claims description 2
- SHIGDERHWRPXFW-UHFFFAOYSA-N 2-[3-[1,5-bis(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(Cl)C=C1 SHIGDERHWRPXFW-UHFFFAOYSA-N 0.000 claims description 2
- SQWYCLPSDYACTO-UHFFFAOYSA-N 2-[3-[1-(3-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC(Cl)=C1 SQWYCLPSDYACTO-UHFFFAOYSA-N 0.000 claims description 2
- KGPQQENJOWEIII-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-3,3-dimethyl-2h-inden-1-yl]propyl-methylamino]acetic acid Chemical compound C1C(C)(C)C2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 KGPQQENJOWEIII-UHFFFAOYSA-N 0.000 claims description 2
- PIUPRVAVNBKRAQ-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(2-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=CC=C1C PIUPRVAVNBKRAQ-UHFFFAOYSA-N 0.000 claims description 2
- JUWVFZAPYCYAKO-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(C(F)(F)F)C=C1 JUWVFZAPYCYAKO-UHFFFAOYSA-N 0.000 claims description 2
- RTWGCBZBZKLFHN-UHFFFAOYSA-N 2-[3-[4-chloro-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC(C(=CC=C2)Cl)=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 RTWGCBZBZKLFHN-UHFFFAOYSA-N 0.000 claims description 2
- KDETUNZZDAVRHR-UHFFFAOYSA-N 2-[3-[4-chloro-1-(4-fluoro-3-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC(C(=CC=C2)Cl)=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C(C)=C1 KDETUNZZDAVRHR-UHFFFAOYSA-N 0.000 claims description 2
- PFUNWACYBDHFAL-UHFFFAOYSA-N 2-[3-[5-bromo-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(Br)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 PFUNWACYBDHFAL-UHFFFAOYSA-N 0.000 claims description 2
- CYKZSTVLKQCCOE-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluoro-3-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C(C)=C1 CYKZSTVLKQCCOE-UHFFFAOYSA-N 0.000 claims description 2
- FQMHYNZGTKQLBE-UHFFFAOYSA-N 2-[3-[6-chloro-1-(4-methoxyphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1(CCCN(C)CC(O)=O)C2=CC(Cl)=CC=C2CO1 FQMHYNZGTKQLBE-UHFFFAOYSA-N 0.000 claims description 2
- FPZVLWDUJCYRDE-UHFFFAOYSA-N 2-[3-[6-chloro-1-(4-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC=C(Cl)C=C2C1(CCCN(C)CC(O)=O)C1=CC=C(C)C=C1 FPZVLWDUJCYRDE-UHFFFAOYSA-N 0.000 claims description 2
- GXOOUMOOGHJCHS-UHFFFAOYSA-N 2-[methyl-[3-(3-methyl-1-phenylinden-1-yl)propyl]amino]acetic acid Chemical compound C1=C(C)C2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC=C1 GXOOUMOOGHJCHS-UHFFFAOYSA-N 0.000 claims description 2
- HYHCUOXXBRKVIT-UHFFFAOYSA-N 2-[methyl-[3-[1-(4-methylphenyl)-3h-2-benzofuran-1-yl]propyl]amino]acetic acid Chemical compound O1CC2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(C)C=C1 HYHCUOXXBRKVIT-UHFFFAOYSA-N 0.000 claims description 2
- FWMFQNAGGJQHLP-UHFFFAOYSA-N 2-[methyl-[3-[1-[3-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl]amino]acetic acid Chemical compound O1CC2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC(C(F)(F)F)=C1 FWMFQNAGGJQHLP-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000008733 trauma Effects 0.000 claims description 2
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- TUKYQPWIBZTOSR-BJQOMGFOSA-N (2s)-2-[methyl-[3-(1-phenyl-3h-2-benzothiophen-1-yl)propyl]amino]propanoic acid Chemical compound S1CC2=CC=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=CC=C1 TUKYQPWIBZTOSR-BJQOMGFOSA-N 0.000 claims 1
- SCTGAEHVEUYYGU-UHFFFAOYSA-N 2-[2-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]ethyl-methylamino]acetic acid Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCN(C)CC(O)=O)C1=CC=C(F)C=C1 SCTGAEHVEUYYGU-UHFFFAOYSA-N 0.000 claims 1
- SPHUZYRFLZYOHP-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(2,5-dichlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC(Cl)=CC=C1Cl SPHUZYRFLZYOHP-UHFFFAOYSA-N 0.000 claims 1
- RBAQCYGDDPOWCE-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(4-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(C)C=C1 RBAQCYGDDPOWCE-UHFFFAOYSA-N 0.000 claims 1
- TXGJKJXYOREALM-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-[3-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=CC(C(F)(F)F)=C1 TXGJKJXYOREALM-UHFFFAOYSA-N 0.000 claims 1
- LTSWUMKWZXTGOB-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-fluoro-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(F)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 LTSWUMKWZXTGOB-UHFFFAOYSA-N 0.000 claims 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
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- 150000001450 anions Chemical class 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
- 230000002461 excitatory amino acid Effects 0.000 description 1
- 239000003257 excitatory amino acid Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001057 ionotropic effect Effects 0.000 description 1
- VLSMHEGGTFMBBZ-OOZYFLPDSA-N kainic acid Chemical compound CC(=C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VLSMHEGGTFMBBZ-OOZYFLPDSA-N 0.000 description 1
- 229950006874 kainic acid Drugs 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200001124 | 2000-07-21 |
Publications (1)
Publication Number | Publication Date |
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ZA200300514B true ZA200300514B (en) | 2004-08-20 |
Family
ID=8159626
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200300514A ZA200300514B (en) | 2000-07-21 | 2003-01-20 | Novel compounds and their use as glycine transport inhibitors. |
Country Status (28)
Country | Link |
---|---|
US (1) | US6921774B2 (ja) |
EP (1) | EP1301502B1 (ja) |
JP (1) | JP2004504393A (ja) |
KR (1) | KR20030015889A (ja) |
CN (1) | CN100509791C (ja) |
AR (1) | AR032358A1 (ja) |
AT (1) | ATE295844T1 (ja) |
AU (2) | AU2001281740B2 (ja) |
BG (1) | BG107530A (ja) |
BR (1) | BR0113011A (ja) |
CA (1) | CA2416447A1 (ja) |
CZ (1) | CZ2003396A3 (ja) |
DE (1) | DE60110914T2 (ja) |
EA (1) | EA005621B1 (ja) |
ES (1) | ES2238466T3 (ja) |
HR (1) | HRP20030053A2 (ja) |
HU (1) | HUP0302778A3 (ja) |
IL (2) | IL153988A0 (ja) |
IS (1) | IS6693A (ja) |
MX (1) | MXPA03000642A (ja) |
NO (1) | NO20030243L (ja) |
NZ (1) | NZ523720A (ja) |
PL (1) | PL364439A1 (ja) |
PT (1) | PT1301502E (ja) |
SK (1) | SK2022003A3 (ja) |
UA (1) | UA75081C2 (ja) |
WO (1) | WO2002008216A1 (ja) |
ZA (1) | ZA200300514B (ja) |
Families Citing this family (12)
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CN100439330C (zh) * | 2003-04-30 | 2008-12-03 | H.隆德贝克有限公司 | 芳族羟苯基和芳族硫基苯基衍生物 |
MXPA06002002A (es) * | 2003-08-21 | 2006-05-17 | Lundbeck & Co As H | La combinacion de un inhibidor de reabsorcion de serotonina y un inhibidor de transportador de glicina tipo 1 para el tratamiento de depresion. |
US7163954B2 (en) * | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
WO2005087708A1 (en) * | 2004-03-12 | 2005-09-22 | H. Lundbeck A/S | Phenyl indan derivatives |
WO2005100301A1 (en) * | 2004-03-31 | 2005-10-27 | Eli Lilly And Company | 2-aryloxyethyl glycine derivatives and their use as glycine transport inhibitors |
WO2006000222A2 (en) * | 2004-06-24 | 2006-01-05 | H. Lundbeck A/S | The combination of an antipsychotic and a glycine transporter type i inhibitor for the treatment of schizophrenia |
KR101389209B1 (ko) * | 2006-07-18 | 2014-04-24 | 아스텔라스세이야쿠 가부시키가이샤 | 아미노인단 유도체 또는 그의 염 |
BRPI0715729A2 (pt) * | 2006-08-30 | 2013-09-24 | Hoffmann La Roche | inibidores para glyt-1 |
US20100083581A1 (en) * | 2007-06-18 | 2010-04-08 | Mattice Douglas A | Environmental brush seal |
EP3006023B1 (en) | 2009-01-20 | 2019-06-26 | Los Angeles Biomedical Research Institute at Harbor-UCLA Medical Center | Sorbic acid and derivatives thereof to enhance the activity of a neuropharmaceutical |
EP2380595A1 (en) | 2010-04-19 | 2011-10-26 | Nlife Therapeutics S.L. | Compositions and methods for selective delivery of oligonucleotide molecules to specific neuron types |
US9700563B2 (en) * | 2012-09-06 | 2017-07-11 | MediSynergies, LLC | Kappa opioid receptor compounds |
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GB1166711A (en) * | 1966-03-28 | 1969-10-08 | Kefalas As | Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives |
US3549656A (en) | 1967-12-28 | 1970-12-22 | Kefalas As | Antidepressant 1 - aminoalkyl - thiophthalanes and acid addition salts thereof |
GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
US5225323A (en) | 1988-11-21 | 1993-07-06 | Baylor College Of Medicine | Human high-affinity neurotransmitter uptake system |
EP0614487A4 (en) | 1991-11-12 | 1995-04-19 | Synaptic Pharma Corp | AND CODING A GLYCINE CONVEYOR AND ITS USES. |
US5824486A (en) | 1996-05-31 | 1998-10-20 | Allelix Neuroscience Inc. | Glycine transporter-transfected cells and uses thereof |
US6008015A (en) | 1997-04-11 | 1999-12-28 | Allelix Neuroscience Inc. | Glycine transporter |
AR021509A1 (es) * | 1998-12-08 | 2002-07-24 | Lundbeck & Co As H | Derivados de benzofurano, su preparacion y uso |
AR021155A1 (es) * | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
US6566550B2 (en) * | 2001-06-21 | 2003-05-20 | Pfizer Inc | Substituted aromatic ethers as inhibitors of glycine transport |
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2001
- 2001-07-19 PL PL01364439A patent/PL364439A1/xx not_active Application Discontinuation
- 2001-07-19 EP EP01960184A patent/EP1301502B1/en not_active Expired - Lifetime
- 2001-07-19 CZ CZ2003396A patent/CZ2003396A3/cs unknown
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- 2001-07-19 DE DE60110914T patent/DE60110914T2/de not_active Expired - Fee Related
- 2001-07-19 EA EA200300180A patent/EA005621B1/ru not_active IP Right Cessation
- 2001-07-19 JP JP2002514122A patent/JP2004504393A/ja not_active Withdrawn
- 2001-07-19 CA CA002416447A patent/CA2416447A1/en not_active Abandoned
- 2001-07-19 HU HU0302778A patent/HUP0302778A3/hu unknown
- 2001-07-19 AT AT01960184T patent/ATE295844T1/de not_active IP Right Cessation
- 2001-07-19 IL IL15398801A patent/IL153988A0/xx not_active IP Right Cessation
- 2001-07-19 AU AU2001281740A patent/AU2001281740B2/en not_active Ceased
- 2001-07-19 SK SK202-2003A patent/SK2022003A3/sk unknown
- 2001-07-19 MX MXPA03000642A patent/MXPA03000642A/es not_active Application Discontinuation
- 2001-07-19 NZ NZ523720A patent/NZ523720A/en unknown
- 2001-07-19 KR KR10-2003-7000851A patent/KR20030015889A/ko not_active Application Discontinuation
- 2001-07-19 UA UA2003010452A patent/UA75081C2/uk unknown
- 2001-07-19 ES ES01960184T patent/ES2238466T3/es not_active Expired - Lifetime
- 2001-07-19 AU AU8174001A patent/AU8174001A/xx active Pending
- 2001-07-19 PT PT01960184T patent/PT1301502E/pt unknown
- 2001-07-19 CN CNB018158579A patent/CN100509791C/zh not_active Expired - Fee Related
- 2001-07-19 WO PCT/DK2001/000510 patent/WO2002008216A1/en not_active Application Discontinuation
- 2001-07-20 AR ARP010103460A patent/AR032358A1/es not_active Application Discontinuation
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2003
- 2003-01-16 IL IL153988A patent/IL153988A/en unknown
- 2003-01-17 US US10/348,490 patent/US6921774B2/en not_active Expired - Fee Related
- 2003-01-17 NO NO20030243A patent/NO20030243L/no not_active Application Discontinuation
- 2003-01-20 IS IS6693A patent/IS6693A/is unknown
- 2003-01-20 ZA ZA200300514A patent/ZA200300514B/en unknown
- 2003-01-27 HR HR20030053A patent/HRP20030053A2/hr not_active Application Discontinuation
- 2003-02-05 BG BG107530A patent/BG107530A/bg unknown
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