UA77684C2 - Carboxylic acid amide derivatives - Google Patents
Carboxylic acid amide derivatives Download PDFInfo
- Publication number
- UA77684C2 UA77684C2 UA2004021342A UA2004021342A UA77684C2 UA 77684 C2 UA77684 C2 UA 77684C2 UA 2004021342 A UA2004021342 A UA 2004021342A UA 2004021342 A UA2004021342 A UA 2004021342A UA 77684 C2 UA77684 C2 UA 77684C2
- Authority
- UA
- Ukraine
- Prior art keywords
- oxo
- piperidin
- acid
- dihydro
- acetamide
- Prior art date
Links
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 25
- 150000001875 compounds Chemical class 0.000 abstract description 243
- 238000000034 method Methods 0.000 abstract description 152
- 239000005557 antagonist Substances 0.000 abstract description 19
- 238000011282 treatment Methods 0.000 abstract description 13
- 239000003814 drug Substances 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 6
- 241000124008 Mammalia Species 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 abstract 2
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 abstract 2
- 102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 abstract 1
- 108010038912 Retinoid X Receptors Proteins 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 301
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 118
- 239000000203 mixture Substances 0.000 description 86
- -1 p-tolyloxypiperidin-1-yl Chemical group 0.000 description 78
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 67
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 49
- 239000002253 acid Substances 0.000 description 42
- 239000003480 eluent Substances 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 239000003463 adsorbent Substances 0.000 description 27
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- 208000002193 Pain Diseases 0.000 description 18
- 150000001408 amides Chemical class 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 17
- 239000013078 crystal Substances 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 16
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000011575 calcium Substances 0.000 description 12
- QNNQYQDUKTZSKR-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-2-oxoacetic acid Chemical compound C1CN(C(=O)C(=O)O)CCC1CC1=CC=CC=C1 QNNQYQDUKTZSKR-UHFFFAOYSA-N 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000005605 benzo group Chemical group 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 125000004175 fluorobenzyl group Chemical group 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- LPFCHIMEOSLIGN-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]piperidine Chemical compound C1=CC(OC)=CC=C1CC1CCNCC1 LPFCHIMEOSLIGN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000725303 Human immunodeficiency virus Species 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 6
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- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
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- FJAKCEHATXBFJT-UHFFFAOYSA-N ethyl 2-oxobutanoate Chemical compound CCOC(=O)C(=O)CC FJAKCEHATXBFJT-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000006178 methyl benzyl group Chemical group 0.000 description 4
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- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 3
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Classifications
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- 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
- C07D211/10—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
- 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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- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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HU0103055A HU226978B1 (en) | 2001-07-24 | 2001-07-24 | New carboxylic acid amide compounds, process for their preparation and pharmaceutical compositions containing them and their use |
HU0202213A HU225905B1 (en) | 2002-07-10 | 2002-07-10 | Solid-supported parallel synthesis of new carboxylic acid amide derivatives |
PCT/HU2002/000071 WO2003010159A1 (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as nmda receptor antagonists |
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UA2004021342A UA77684C2 (en) | 2001-07-24 | 2004-01-20 | Carboxylic acid amide derivatives |
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EP (1) | EP1409477B1 (zh) |
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HUP0600809A3 (en) * | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New phenylsulfamoyl-benzamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
HUP0600808A3 (en) * | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New benzamide derivatives as bradykinin antagonists, process for their preparation and pharmaceutical compositions containing them |
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WO2008055945A1 (en) | 2006-11-09 | 2008-05-15 | Probiodrug Ag | 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases |
US9126987B2 (en) | 2006-11-30 | 2015-09-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
CN101668525A (zh) | 2007-03-01 | 2010-03-10 | 前体生物药物股份公司 | 谷氨酰胺酰环化酶抑制剂的新用途 |
EP2865670B1 (en) | 2007-04-18 | 2017-01-11 | Probiodrug AG | Thiourea derivatives as glutaminyl cyclase inhibitors |
JPWO2009025265A1 (ja) * | 2007-08-21 | 2010-11-25 | 塩野義製薬株式会社 | ピペラジン誘導体 |
DE102007047737A1 (de) * | 2007-10-05 | 2009-04-30 | Merck Patent Gmbh | Piperidin- und Piperazinderivate |
JP2011500782A (ja) * | 2007-10-27 | 2011-01-06 | リヒター ゲデオン ニルバーノシャン ミーケデーレスベニュタールシャシャーグ | ブラジキニンb1拮抗剤としての新規非ペプチド誘導体 |
JP2011527689A (ja) * | 2008-07-08 | 2011-11-04 | リヒター ゲデオン エヌワイアールティー. | 2−[4−(4−フルオロ−ベンジル)−ピペリジン−1−イル]−2−オキソ−n−(2−オキソ−2,3−ジヒドロ−ベンゾオキサゾール−6−イル)−アセトアミドの結晶形態 |
CN102159210A (zh) * | 2008-08-21 | 2011-08-17 | 吉瑞工厂 | 用于治疗cns障碍的方法 |
CN102159077A (zh) * | 2008-08-21 | 2011-08-17 | 吉瑞工厂 | 用于治疗神经性疼痛的方法 |
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HUP0900130A3 (en) | 2009-03-03 | 2012-02-28 | Richter Gedeon Nyrt | Novel crystalline hydrate, amorphous and polymorphic forms of dihydro-benzoxazole-6-yl-acetamide derivative and processes for their preparation |
EP2475428B1 (en) | 2009-09-11 | 2015-07-01 | Probiodrug AG | Heterocylcic derivatives as inhibitors of glutaminyl cyclase |
JP2013514379A (ja) | 2009-12-15 | 2013-04-25 | ニユーロツプ・インコーポレイテツド | 神経障害の治療のための化合物 |
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US9181233B2 (en) | 2010-03-03 | 2015-11-10 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
AU2011226074B2 (en) | 2010-03-10 | 2015-01-22 | Vivoryon Therapeutics N.V. | Heterocyclic inhibitors of glutaminyl cyclase (QC, EC 2.3.2.5) |
WO2011131748A2 (en) | 2010-04-21 | 2011-10-27 | Probiodrug Ag | Novel inhibitors |
HUP1000424A2 (en) | 2010-08-11 | 2012-05-02 | Richter Gedeon Nyrt | Use of radiprodil in attention deficit hyperactivity disorder |
DK2686313T3 (en) | 2011-03-16 | 2016-05-02 | Probiodrug Ag | Benzimidazole derivatives as inhibitors of glutaminyl cyclase |
EP2921491B1 (de) * | 2011-12-27 | 2017-08-16 | Bayer Intellectual Property GmbH | Zwischenverbindungen zur herstellung von heteroarylpiperidinen und -piperazinderivaten als fungizide |
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WO2014127256A1 (en) * | 2013-02-18 | 2014-08-21 | The Trustees Of Columbia University In The City Of New York | Kappa opioid receptor selective compounds |
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DK3461819T3 (da) | 2017-09-29 | 2020-08-10 | Probiodrug Ag | Inhibitorer af glutaminylcyklase |
CA3083331A1 (en) | 2017-12-08 | 2019-06-13 | Boehringer Ingelheim International Gmbh | Imidazopyridine derivatives and the use thereof as medicament |
WO2019115586A1 (en) * | 2017-12-12 | 2019-06-20 | Phenex Discovery Verwaltungs-GmbH | Oxalamides as modulators of indoleamine 2,3-dioxygenase |
EA202191014A1 (ru) * | 2018-10-17 | 2021-11-09 | Бёрингер Ингельхайм Интернациональ Гмбх | Производные 4-пиразин-2-илметил-морфолина и их применение в качестве лекарственного средства |
TW202035396A (zh) | 2018-10-17 | 2020-10-01 | 德商百靈佳殷格翰國際股份有限公司 | 4-吡啶基甲基-嗎啉衍生物及其作為藥物之用途 |
CN112888684B (zh) * | 2018-10-17 | 2023-10-10 | 勃林格殷格翰国际有限公司 | 4-嘧啶-5-基甲基-吗啉衍生物及其作为药物的用途 |
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CN113234036B (zh) * | 2021-05-12 | 2023-07-14 | 斯莱普泰(上海)生物医药科技有限公司 | Nmda受体拮抗剂及其用途 |
CN118019521A (zh) | 2021-08-06 | 2024-05-10 | 格林治疗股份有限公司 | 雷拉地尔的制剂 |
CN114163388A (zh) * | 2021-12-15 | 2022-03-11 | 陕西汉江药业集团股份有限公司 | 芬苯达唑中的杂质i、杂质ⅱ和杂质ⅲ的制备方法 |
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