JP2015528013A5 - - Google Patents
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- Publication number
- JP2015528013A5 JP2015528013A5 JP2015524222A JP2015524222A JP2015528013A5 JP 2015528013 A5 JP2015528013 A5 JP 2015528013A5 JP 2015524222 A JP2015524222 A JP 2015524222A JP 2015524222 A JP2015524222 A JP 2015524222A JP 2015528013 A5 JP2015528013 A5 JP 2015528013A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- heterocyclyl
- heteroaryl
- aryl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000623 heterocyclic group Chemical group 0.000 claims 126
- 125000001072 heteroaryl group Chemical group 0.000 claims 94
- 125000003118 aryl group Chemical group 0.000 claims 83
- -1 urea compound Chemical class 0.000 claims 57
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 125000005842 heteroatom Chemical group 0.000 claims 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 28
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 26
- 125000004104 aryloxy group Chemical group 0.000 claims 22
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 22
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 22
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 21
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 125000000565 sulfonamide group Chemical group 0.000 claims 18
- 238000000034 method Methods 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 239000000543 intermediate Substances 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 230000021235 carbamoylation Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 3
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 2
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 claims 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001542 azirines Chemical class 0.000 claims 2
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261676554P | 2012-07-27 | 2012-07-27 | |
| US61/676,554 | 2012-07-27 | ||
| PCT/PT2013/000050 WO2014017938A2 (en) | 2012-07-27 | 2013-07-26 | Process for the synthesis of substituted urea compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015528013A JP2015528013A (ja) | 2015-09-24 |
| JP2015528013A5 true JP2015528013A5 (enExample) | 2016-09-15 |
Family
ID=49003969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015524222A Pending JP2015528013A (ja) | 2012-07-27 | 2013-07-26 | 置換ウレア化合物の合成方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20150197503A1 (enExample) |
| EP (1) | EP2882712A2 (enExample) |
| JP (1) | JP2015528013A (enExample) |
| CN (1) | CN104662002A (enExample) |
| BR (1) | BR112015001769A2 (enExample) |
| CA (1) | CA2880299A1 (enExample) |
| RU (1) | RU2015104103A (enExample) |
| WO (1) | WO2014017938A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201401198D0 (en) | 2014-01-24 | 2014-03-12 | Bial Portela & Ca Sa | Process for the syntheis of substituted urea compounds |
| US10774064B2 (en) | 2016-06-02 | 2020-09-15 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| JP6997197B2 (ja) | 2017-01-23 | 2022-01-17 | カデント セラピューティクス，インコーポレーテッド | カリウムチャネルモジュレーター |
| MA52422A (fr) | 2018-02-27 | 2021-01-06 | Incyte Corp | Imidazopyrimidines et triazolopyrimidines en tant qu'inhibiteurs a2a/a2b |
| MX2020012376A (es) | 2018-05-18 | 2021-03-09 | Incyte Corp | Derivados de pirimidina fusionados como inhibidores de los receptores de adenosina a2a/a2b. |
| MA53097A (fr) | 2018-07-05 | 2021-05-12 | Incyte Corp | Dérivés de pyrazine fusionnés en tant qu'inhibiteurs d'a2a/a2b |
| MX2021004647A (es) | 2018-10-22 | 2021-08-16 | Novartis Ag | Formas cristalinas de moduladores de los canales de potasio. |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1238971A (enExample) * | 1968-03-02 | 1971-07-14 | ||
| DE2458965C3 (de) * | 1974-12-13 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | 3-Amino-indazol-N-carbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
| EP0014810A3 (en) * | 1979-01-18 | 1980-11-26 | Fbc Limited | Pesticidal pyrazoles, their production, compositions and uses, as well as intermediates and their preparation |
| GB8516573D0 (en) * | 1985-07-01 | 1985-08-07 | Janssen Pharmaceuticaa Nv | Controlling weeds |
| JPH01203366A (ja) * | 1988-02-10 | 1989-08-16 | Mitsui Petrochem Ind Ltd | Ｎ−置換イミダゾール誘導体 |
| JPH01203368A (ja) * | 1988-02-10 | 1989-08-16 | Mitsui Petrochem Ind Ltd | チオイミダゾール誘導体 |
| FR2674855B1 (fr) * | 1991-04-03 | 1994-01-14 | Synthelabo | Derives de piperidine, leur preparation et leur application en therapeutique. |
| EP0665226A1 (en) * | 1992-10-28 | 1995-08-02 | Toyama Chemical Co., Ltd. | Novel 1,2-benzisoxazole derivative or salt thereof, and brain protective agent comprising the same |
| US20030203862A1 (en) * | 1998-03-26 | 2003-10-30 | Miraglia Loren J. | Antisense modulation of MDM2 expression |
| JP2004512810A (ja) * | 1999-08-31 | 2004-04-30 | サーナ・セラピューティクス・インコーポレイテッド | 核酸に基づく遺伝子発現の調節剤 |
| NZ529043A (en) * | 2001-04-16 | 2006-11-30 | Tanabe Seiyaku Co | Large conductance calcium-activated K channel opener |
| US7329662B2 (en) * | 2003-10-03 | 2008-02-12 | Hoffmann-La Roche Inc. | Pyrazolo-pyridine |
| DE102004005172A1 (de) * | 2004-02-02 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Indazolderivate als Inhibitoren der Hormon Sensitiven Lipase |
| CN100424089C (zh) * | 2006-01-18 | 2008-10-08 | 中国药科大学 | 一种制备大环内酯类半合成抗生素泰利霉素的方法 |
| CN105399731A (zh) * | 2008-12-24 | 2016-03-16 | 比亚尔-珀特拉和Ca股份公司 | 药物化合物 |
| CA2806701A1 (en) * | 2010-07-29 | 2012-02-02 | Bial - Portela & Ca, S.A. | Process for the synthesis of substituted urea compounds |
-
2013
- 2013-07-26 US US14/417,354 patent/US20150197503A1/en not_active Abandoned
- 2013-07-26 WO PCT/PT2013/000050 patent/WO2014017938A2/en not_active Ceased
- 2013-07-26 RU RU2015104103A patent/RU2015104103A/ru not_active Application Discontinuation
- 2013-07-26 BR BR112015001769A patent/BR112015001769A2/pt not_active IP Right Cessation
- 2013-07-26 CN CN201380050477.4A patent/CN104662002A/zh active Pending
- 2013-07-26 CA CA2880299A patent/CA2880299A1/en not_active Abandoned
- 2013-07-26 JP JP2015524222A patent/JP2015528013A/ja active Pending
- 2013-07-26 EP EP13750964.2A patent/EP2882712A2/en not_active Withdrawn