SK6282003A3 - Tripeptidyl peptidase inhibitors - Google Patents
Tripeptidyl peptidase inhibitors Download PDFInfo
- Publication number
- SK6282003A3 SK6282003A3 SK628-2003A SK6282003A SK6282003A3 SK 6282003 A3 SK6282003 A3 SK 6282003A3 SK 6282003 A SK6282003 A SK 6282003A SK 6282003 A3 SK6282003 A3 SK 6282003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- alkyl
- amino
- mol
- mixture
- Prior art date
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- 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 title abstract description 5
- 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 title abstract description 5
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 150000001413 amino acids Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- -1 amino, hydroxyl Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000539 amino acid group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001556 benzimidazoles Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 108090000189 Neuropeptides Proteins 0.000 abstract description 4
- 239000012528 membrane Substances 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 230000002779 inactivation Effects 0.000 abstract description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
- 239000000203 mixture Substances 0.000 description 111
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
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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 4
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
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- 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
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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PCT/EP2001/012388 WO2002036116A2 (en) | 2000-10-30 | 2001-10-24 | Tripeptidyl peptidase inhibitors |
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JP (1) | JP2004512365A (da) |
KR (1) | KR100820598B1 (da) |
CN (2) | CN101307046B (da) |
AT (1) | ATE363276T1 (da) |
AU (2) | AU2002224797B2 (da) |
BG (1) | BG107729A (da) |
CA (1) | CA2422617C (da) |
CZ (1) | CZ20031422A3 (da) |
DE (1) | DE60128731T2 (da) |
DK (1) | DK1392291T3 (da) |
EA (1) | EA006443B1 (da) |
EE (1) | EE200300168A (da) |
ES (1) | ES2287185T3 (da) |
HU (1) | HU230376B1 (da) |
IL (2) | IL155604A0 (da) |
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SK (1) | SK6282003A3 (da) |
WO (1) | WO2002036116A2 (da) |
ZA (1) | ZA200303302B (da) |
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CN101307046B (zh) | 2000-10-30 | 2012-08-15 | 詹森药业有限公司 | 三肽酶抑制剂 |
US7041681B2 (en) | 2002-04-29 | 2006-05-09 | Janssen Pharmaceutica N.V. | Compounds as opioid receptor modulators |
AU2012268813B2 (en) * | 2002-04-29 | 2015-04-30 | Janssen Pharmaceutica N.V. | Heterocyclic derivatives as opioid modulators |
AU2003280985A1 (en) * | 2002-07-10 | 2004-02-02 | Bayer Healthcare Ag | Regulation of human tripeptidyl peptidase ii |
EP1581525A2 (en) | 2002-08-09 | 2005-10-05 | AstraZeneca AB | Compounds having an activity at metabotropic glutamate receptors |
JP2007503453A (ja) * | 2003-05-14 | 2007-02-22 | ノボ ノルディスク アクティーゼルスカブ | 肥満症を治療するための新規化合物 |
SI1725537T1 (sl) | 2004-03-15 | 2011-11-30 | Janssen Pharmaceutica Nv | Nove spojine kot modulatorji opioidnih receptorjev |
MX2007011409A (es) * | 2005-03-14 | 2008-02-22 | Johnson & Johnson | Procedimiento de preparacion de moduladores opioides. |
JP4955009B2 (ja) * | 2005-11-11 | 2012-06-20 | エフ.ホフマン−ラ ロシュ アーゲー | 凝固因子Xaの阻害剤としての炭素環式縮合環アミン |
US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
EP2034998A1 (en) | 2006-05-11 | 2009-03-18 | Janssen Pharmaceutica, N.V. | 1,2,3,4-tetrahydro-quinoline derivatives as cetp inhibitors |
JP2009536954A (ja) | 2006-05-11 | 2009-10-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Cetp阻害剤としての3,4−ジヒドロ−2h−ベンゾ[1,4]オキサジンおよびチアジン誘導体 |
US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
GB0709031D0 (en) * | 2007-05-10 | 2007-06-20 | Sareum Ltd | Pharmaceutical compounds |
GB201202027D0 (en) | 2012-02-06 | 2012-03-21 | Sareum Ltd | Pharmaceutical compounds |
DK3040336T3 (da) | 2012-03-02 | 2020-06-22 | Sareum Ltd | Forbindelser til brug i behandling af TYK2 Kinase-medierede tilstande |
EP2708535A1 (en) | 2012-05-11 | 2014-03-19 | Les Laboratoires Servier | Agents for treating disorders involving modulation of ryanodine receptors |
US10208023B2 (en) | 2013-03-01 | 2019-02-19 | Mark G. DeGiacomo | Heterocyclic inhibitors of the sodium channel |
US9675587B2 (en) | 2013-03-14 | 2017-06-13 | Allergan Holdings Unlimited Company | Opioid receptor modulator dosage formulations |
GB201617871D0 (en) | 2016-10-21 | 2016-12-07 | Sareum Limited | Pharmaceutical compounds |
JP6717968B2 (ja) * | 2016-11-01 | 2020-07-08 | 日本農薬株式会社 | N‐アルキルスルホニルインドリン化合物及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
CN114555594A (zh) * | 2019-10-17 | 2022-05-27 | 奇华顿股份有限公司 | 作为trmp8调节剂的取代的氮杂环 |
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CH543479A (de) | 1970-05-06 | 1973-10-31 | Hoffmann La Roche | Verfahren zur Herstellung von Phenyläthylaminderivaten |
GB2146026A (en) | 1983-09-07 | 1985-04-11 | Tanabe Seiyaku Co | Peptides and process for preparing the same |
JPS61227506A (ja) | 1985-04-01 | 1986-10-09 | Nippon Tokushu Noyaku Seizo Kk | カルバモイルイミダゾ−ル類、その中間体、それらの製法並びに除草剤又は農園芸用殺菌剤 |
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FR2678938B1 (fr) | 1991-07-10 | 1993-10-08 | Rhone Poulenc Rorer Sa | Derives de pyrrolidine, leur preparation et les medicaments les contenant. |
JPH05339240A (ja) | 1992-06-04 | 1993-12-21 | Yamanouchi Pharmaceut Co Ltd | テトラヒドロイソキノリンアミド誘導体 |
SE9402880D0 (sv) | 1994-08-30 | 1994-08-30 | Astra Ab | New peptide derivatives |
FR2733995B1 (fr) | 1995-05-09 | 1997-07-25 | Inst Nat Sante Rech Med | Inhibiteurs de l'inactivation de neuropeptides endogenes notamment la cholecystokinine, leurs procedes de preparation leur utilisation comme medicaments et procede de criblage de medicaments |
FR2735776B1 (fr) | 1995-06-22 | 1997-07-18 | Synthelabo | Derives de 2,3-dihydro-1h-indole, leur preparation et leur application en therapeutique |
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US6335360B1 (en) | 1997-12-23 | 2002-01-01 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Tripeptidyl peptidase inhibitors |
AU3768799A (en) * | 1998-04-28 | 1999-11-16 | Trega Biosciences, Inc. | Isoquinoline compound melanocortin receptor ligands and methods of using same |
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US6916905B2 (en) | 2000-03-24 | 2005-07-12 | The United States Of America As Represented By The Department Of Health And Human Services | Dmt-Tic di-and tri-peptidic derivatives and related compositions and methods of use |
CN101307046B (zh) * | 2000-10-30 | 2012-08-15 | 詹森药业有限公司 | 三肽酶抑制剂 |
FR2816207B1 (fr) | 2000-11-08 | 2003-01-03 | Oreal | Composition de teinture d'oxydation pour fibres keratiniques comprenant un polyurethane associatif cationique |
US6755387B2 (en) | 2001-02-08 | 2004-06-29 | Symons Corporation | Transition strip for disparate concrete forms |
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