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
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- 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
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- 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
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- 239000012453 solvate Substances 0.000 claims description 2
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- 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
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- 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
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- 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
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- 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
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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
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Epoxy Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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 (pt) |
| EP (1) | EP1368336B9 (pt) |
| JP (2) | JP2004523548A (pt) |
| KR (1) | KR100900020B1 (pt) |
| CN (1) | CN1219776C (pt) |
| AT (1) | ATE327986T1 (pt) |
| AU (1) | AU2002235682C1 (pt) |
| BG (1) | BG108164A (pt) |
| BR (1) | BR0207307A (pt) |
| CA (1) | CA2438367A1 (pt) |
| CY (1) | CY1105529T1 (pt) |
| CZ (1) | CZ20032503A3 (pt) |
| DE (1) | DE60211866T2 (pt) |
| DK (1) | DK1368336T3 (pt) |
| EA (1) | EA006636B1 (pt) |
| EE (1) | EE05329B1 (pt) |
| ES (1) | ES2266446T3 (pt) |
| HK (1) | HK1061025A1 (pt) |
| HR (1) | HRP20030696A2 (pt) |
| HU (1) | HUP0303185A3 (pt) |
| IL (1) | IL157194A (pt) |
| MX (1) | MXPA03007309A (pt) |
| NO (1) | NO329038B1 (pt) |
| NZ (1) | NZ527695A (pt) |
| PL (1) | PL365024A1 (pt) |
| PT (1) | PT1368336E (pt) |
| SI (1) | SI1368336T1 (pt) |
| SK (1) | SK287304B6 (pt) |
| UA (1) | UA75114C2 (pt) |
| WO (1) | WO2002066456A2 (pt) |
| ZA (1) | ZA200307201B (pt) |
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 |
| PT1830833E (pt) * | 2004-12-16 | 2010-03-12 | Janssen Pharmaceutica Nv | Combinação de um inibidor do transportador da glicina (glyt1) e um antipsicótico para o tratamento de sintomas de esquizofrenia, bem como a sua preparação e sua utilização |
| 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 (pt) | 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 |
| FI864246A (fi) | 1985-11-08 | 1987-05-09 | Warner Lambert Co | N-substituerade 3-piperidin- eller 3-pyridinkarboxylsyror samt deras derivat. |
| 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 |
| IL81179A (en) | 1986-01-07 | 1992-02-16 | Novo Nordisk As | N-phenylbutenyl substituted azaheterocyclic carboxylic acids,their preparation and pharmaceutical compositions comprising them |
| 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". |
| WO1997020553A1 (en) | 1995-12-07 | 1997-06-12 | Javitt Daniel C | Treatment of negative and cognitive symptoms of schizophrenia with glycine uptake antagonists |
| US6191165B1 (en) | 1996-05-31 | 2001-02-20 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| SK285854B6 (sk) * | 1996-05-31 | 2007-09-06 | Allelix Neuroscience Inc. | Substituovaný amín, spôsoby jeho prípravy a použitie, farmaceutický prostriedok a jeho použitie |
| DE69734215T2 (de) * | 1996-07-22 | 2006-06-29 | Novo Nordisk A/S | Verbindungen mit Wachstumshormon-freisetzenden Eigenschaften |
| HUP0101300A3 (en) * | 1998-01-09 | 2002-11-28 | Pfizer | Matrix metalloprotease inhibitors |
| US6103743A (en) * | 1999-08-06 | 2000-08-15 | Allelix Neuroscience, Inc. | Unsaturated amino acid derivatives |
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2002
- 2002-02-15 AT AT02702186T patent/ATE327986T1/de not_active IP Right Cessation
- 2002-02-15 SI SI200230381T patent/SI1368336T1/sl unknown
- 2002-02-15 WO PCT/CA2002/000176 patent/WO2002066456A2/en active IP Right Grant
- 2002-02-15 DE DE60211866T patent/DE60211866T2/de not_active Expired - Lifetime
- 2002-02-15 US US10/077,579 patent/US6667336B2/en not_active Expired - Fee Related
- 2002-02-15 CN CNB028050819A patent/CN1219776C/zh not_active Expired - Fee Related
- 2002-02-15 CZ CZ20032503A patent/CZ20032503A3/cs unknown
- 2002-02-15 NZ NZ527695A patent/NZ527695A/en unknown
- 2002-02-15 BR BR0207307-2A patent/BR0207307A/pt not_active IP Right Cessation
- 2002-02-15 UA UA2003087630A patent/UA75114C2/uk unknown
- 2002-02-15 EP EP02702186A patent/EP1368336B9/en not_active Expired - Lifetime
- 2002-02-15 CA CA002438367A patent/CA2438367A1/en not_active Abandoned
- 2002-02-15 EA EA200300900A patent/EA006636B1/ru not_active IP Right Cessation
- 2002-02-15 HU HU0303185A patent/HUP0303185A3/hu unknown
- 2002-02-15 ES ES02702186T patent/ES2266446T3/es not_active Expired - Lifetime
- 2002-02-15 KR KR1020037010609A patent/KR100900020B1/ko not_active IP Right Cessation
- 2002-02-15 PT PT02702186T patent/PT1368336E/pt unknown
- 2002-02-15 DK DK02702186T patent/DK1368336T3/da active
- 2002-02-15 EE EEP200300394A patent/EE05329B1/xx not_active IP Right Cessation
- 2002-02-15 SK SK1144-2003A patent/SK287304B6/sk not_active IP Right Cessation
- 2002-02-15 JP JP2002565971A patent/JP2004523548A/ja active Pending
- 2002-02-15 MX MXPA03007309A patent/MXPA03007309A/es active IP Right Grant
- 2002-02-15 AU AU2002235682A patent/AU2002235682C1/en not_active Ceased
- 2002-02-15 PL PL02365024A patent/PL365024A1/xx unknown
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2003
- 2003-07-31 IL IL157194A patent/IL157194A/en not_active IP Right Cessation
- 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
- 2003-09-09 BG BG108164A patent/BG108164A/xx unknown
- 2003-09-15 ZA ZA200307201A patent/ZA200307201B/en unknown
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2004
- 2004-06-08 HK HK04104072A patent/HK1061025A1/xx not_active IP Right Cessation
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2006
- 2006-08-22 CY CY20061101160T patent/CY1105529T1/el unknown
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2009
- 2009-11-09 JP JP2009255663A patent/JP2010059182A/ja active Pending
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