HRP20000524A2 - Gylcine transport inhibitors - Google Patents
Gylcine transport inhibitors Download PDFInfo
- Publication number
- HRP20000524A2 HRP20000524A2 HR20000524A HRP20000524A HRP20000524A2 HR P20000524 A2 HRP20000524 A2 HR P20000524A2 HR 20000524 A HR20000524 A HR 20000524A HR P20000524 A HRP20000524 A HR P20000524A HR P20000524 A2 HRP20000524 A2 HR P20000524A2
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- alkyl
- represents hydrogen
- radical
- aryl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 60
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 19
- -1 10,11-dihydro-5H-dibenzo[b,f]-azepin-5-yl Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000004471 Glycine Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 13
- 229910052736 halogen Chemical group 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
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- 208000015114 central nervous system disease Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
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- 239000012442 inert solvent Substances 0.000 claims description 2
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-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
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
- 101710083167 Sodium- and chloride-dependent glycine transporter 2 Proteins 0.000 description 3
- 102100028886 Sodium- and chloride-dependent glycine transporter 2 Human genes 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
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- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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EP98200700 | 1998-03-06 | ||
PCT/EP1999/001308 WO1999045011A1 (en) | 1998-03-06 | 1999-02-26 | Glycine transport inhibitors |
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EP (1) | EP1058684A1 (hu) |
JP (1) | JP2002505332A (hu) |
KR (1) | KR20010032967A (hu) |
CN (1) | CN1291984A (hu) |
AU (1) | AU3254499A (hu) |
BG (1) | BG104686A (hu) |
BR (1) | BR9907953A (hu) |
CA (1) | CA2322136A1 (hu) |
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SK (1) | SK13092000A3 (hu) |
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UA73749C2 (en) * | 1999-11-01 | 2005-09-15 | Diarylenines | |
WO2002019967A2 (en) | 2000-09-08 | 2002-03-14 | Gliatech, Inc. | Substituted hydrazine derivatives |
WO2002022581A1 (en) * | 2000-09-14 | 2002-03-21 | Gliatech, Inc. | Nitrogen-containing compounds and their use as glycine transport inhibitors |
KR20030043970A (ko) * | 2000-10-12 | 2003-06-02 | 에스에스 세야쿠 가부시키 가이샤 | 2,2-디페닐부탄아미드 유도체 및 이를 함유하는 의약 |
AR032653A1 (es) | 2001-02-09 | 2003-11-19 | Telik Inc | Inhibidores heterociclicos del trasportador de glicina 2 composiciones farmaceuticas, uso y metodos. |
AU2003220898A1 (en) * | 2002-04-01 | 2003-10-13 | Nippon Chemiphar Co., Ltd. | N-phenyl-n-(4-piperidinyl)amide derivative |
FR2838739B1 (fr) * | 2002-04-19 | 2004-05-28 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl)benzamide, leur preparation et leur application en therapeutique |
US6995168B2 (en) | 2002-05-31 | 2006-02-07 | Euro-Celtique S.A. | Triazaspiro compounds useful for treating or preventing pain |
FR2842804B1 (fr) | 2002-07-29 | 2004-09-03 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
FR2842805A1 (fr) * | 2002-07-29 | 2004-01-30 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide,leur preparation et leur application et therapeutique |
US7202259B2 (en) | 2002-11-18 | 2007-04-10 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
WO2004072034A1 (en) * | 2003-02-17 | 2004-08-26 | F. Hoffmann-La Roche Ag | Piperidine-benzenesulfonamide derivatives |
ME00116B (me) * | 2003-08-11 | 2010-10-10 | Hoffmann La Roche | Piperazin sa ili supstituisanom fenil grupom i njihova upotreba kao inhibitora glyt1 |
FR2861076B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
FR2861070B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique |
FR2861071B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
WO2005058317A1 (en) * | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Glycine transporter-1 inhibirors |
KR100886002B1 (ko) * | 2004-01-30 | 2009-03-03 | 유로-셀띠끄 소시에떼 아노님 | 4-테트라졸릴-4-페닐피페리딘 화합물의 제조방법 |
GB0408774D0 (en) * | 2004-04-20 | 2004-05-26 | Glaxo Group Ltd | Compounds |
DE602005014274D1 (de) | 2004-12-09 | 2009-06-10 | Hoffmann La Roche | Phenylpiperazin-methanon-derivate |
JP4709849B2 (ja) * | 2004-12-15 | 2011-06-29 | エフ.ホフマン−ラ ロシュ アーゲー | アルツハイマー病治療のためのグリシントランスポーターi(glyt−1)インヒビターとしての二環式及び三環式置換フェニルメタノン類 |
US7485637B2 (en) | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
BRPI0519794A2 (pt) | 2005-01-07 | 2009-03-17 | Hoffmann La Roche | derivados de [4-(heteroaril)piperazin-1-il]-(fenil 2,5-substituìdo)metanona como inibidores de transportador de glicina 1 (glyt-1) para o tratamento de distúrbios neurológicos e neuropsiquiátricos |
CA2601326A1 (en) | 2005-01-18 | 2006-07-27 | F.Hoffmann-La Roche Ag | 2,5-disubstituted phenyl methanone derivatives as glycine transporter 1(glyt-i) inhibitors for the treatment of neurological and neuropsychiatric disorders |
ES2332529T3 (es) | 2005-01-26 | 2010-02-08 | F. Hoffmann-La Roche Ag | Derivados de fenil-metanona y su empleo como inhibidores del transportador 1 de glicina. |
RS51204B (sr) | 2005-02-07 | 2010-12-31 | F. Hoffmann-La Roche Ag. | Heterociklični supstituisani fenil metanoni kao inhibitori glicin transportera 1 |
CN101189228A (zh) | 2005-04-08 | 2008-05-28 | 辉瑞产品有限公司 | 用作i型甘氨酸转运抑制剂的二环[3.1.0]杂芳酰胺 |
WO2009010479A2 (en) * | 2007-07-13 | 2009-01-22 | Euroscreen S.A. | Heterocyclic methylene piperidine derivatives and their use |
CA2745690A1 (en) * | 2008-12-04 | 2010-06-10 | Evgeny Zlotinikov | Novel polymorphic forms of an azabicyclo-trifluoromethyl benzamide derivative |
CN102766080B (zh) * | 2011-05-06 | 2015-09-23 | 上海医药工业研究院 | 一类吡咯烷衍生物、其制备方法及应用 |
JP5893135B2 (ja) * | 2011-06-28 | 2016-03-23 | ビボゾーン インコーポレイテッド | 多重ターゲッティングの相乗効果を誘発する有効物質の組合せ及びその用途 |
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US3714159A (en) * | 1971-03-30 | 1973-01-30 | Janssen Pharmaceutica Nv | 2,2-diaryl-4-(4'-aryl-4'-hydroxy-piper-idino)-butyramides |
US4695575A (en) * | 1984-11-13 | 1987-09-22 | Janssen Pharmaceutica, N.V. | 4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines |
GB8515934D0 (en) * | 1985-06-24 | 1985-07-24 | Janssen Pharmaceutica Nv | (4-piperidinomethyl and-hetero)purines |
CA1332236C (en) * | 1985-10-11 | 1994-10-04 | Lourens Wals | ,--diaryl-4-aryl-4-hydroxy-1-piperidinebutanamide, n-oxides |
CA2255727A1 (en) * | 1996-05-31 | 1997-12-04 | Trophix Pharmaceuticals, Inc. | Pharmaceutical for treating of neurological and neuropsychiatric disorders |
-
1999
- 1999-02-26 PL PL99342818A patent/PL342818A1/xx unknown
- 1999-02-26 WO PCT/EP1999/001308 patent/WO1999045011A1/en not_active Application Discontinuation
- 1999-02-26 JP JP2000534553A patent/JP2002505332A/ja not_active Withdrawn
- 1999-02-26 TR TR2000/02570T patent/TR200002570T2/xx unknown
- 1999-02-26 AU AU32544/99A patent/AU3254499A/en not_active Abandoned
- 1999-02-26 KR KR1020007006314A patent/KR20010032967A/ko not_active Application Discontinuation
- 1999-02-26 HU HU0101281A patent/HUP0101281A3/hu unknown
- 1999-02-26 EP EP99937930A patent/EP1058684A1/en not_active Withdrawn
- 1999-02-26 CN CN99803530A patent/CN1291984A/zh active Pending
- 1999-02-26 SK SK1309-2000A patent/SK13092000A3/sk unknown
- 1999-02-26 EE EEP200000483A patent/EE200000483A/xx unknown
- 1999-02-26 CA CA002322136A patent/CA2322136A1/en not_active Abandoned
- 1999-02-26 BR BR9907953-4A patent/BR9907953A/pt not_active Application Discontinuation
- 1999-02-26 IL IL138227??A patent/IL138227A0/xx unknown
-
2000
- 2000-08-02 HR HR20000524A patent/HRP20000524A2/hr not_active Application Discontinuation
- 2000-08-11 BG BG104686A patent/BG104686A/xx unknown
- 2000-09-05 NO NO20004432A patent/NO20004432L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
TR200002570T2 (tr) | 2000-12-21 |
NO20004432L (no) | 2000-11-02 |
SK13092000A3 (sk) | 2001-03-12 |
KR20010032967A (ko) | 2001-04-25 |
CA2322136A1 (en) | 1999-09-10 |
BG104686A (en) | 2001-04-30 |
HUP0101281A2 (hu) | 2001-09-28 |
PL342818A1 (en) | 2001-07-02 |
EP1058684A1 (en) | 2000-12-13 |
JP2002505332A (ja) | 2002-02-19 |
NO20004432D0 (no) | 2000-09-05 |
HUP0101281A3 (en) | 2001-11-28 |
AU3254499A (en) | 1999-09-20 |
BR9907953A (pt) | 2000-10-24 |
WO1999045011A1 (en) | 1999-09-10 |
CN1291984A (zh) | 2001-04-18 |
IL138227A0 (en) | 2001-10-31 |
WO1999045011A8 (en) | 1999-10-14 |
EE200000483A (et) | 2002-02-15 |
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