JP2014500235A5 - - Google Patents
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- Publication number
- JP2014500235A5 JP2014500235A5 JP2013530709A JP2013530709A JP2014500235A5 JP 2014500235 A5 JP2014500235 A5 JP 2014500235A5 JP 2013530709 A JP2013530709 A JP 2013530709A JP 2013530709 A JP2013530709 A JP 2013530709A JP 2014500235 A5 JP2014500235 A5 JP 2014500235A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- amino
- substituted
- aminocarbonyl
- 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.)
- Granted
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- -1 C 1 -C 6 -alkyloxy Chemical group 0.000 claims 99
- 229910052739 hydrogen Inorganic materials 0.000 claims 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims 56
- 229910052799 carbon Inorganic materials 0.000 claims 51
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 49
- 239000001257 hydrogen Substances 0.000 claims 49
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 34
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 32
- 150000002431 hydrogen Chemical class 0.000 claims 31
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 27
- 229910052757 nitrogen Inorganic materials 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 25
- 150000002367 halogens Chemical class 0.000 claims 25
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 24
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- HGGNZMUHOHGHBJ-UHFFFAOYSA-N dioxepane Chemical compound C1CCOOCC1 HGGNZMUHOHGHBJ-UHFFFAOYSA-N 0.000 claims 15
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 14
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 12
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 12
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 11
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 8
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 208000030852 Parasitic disease Diseases 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 208000006968 Helminthiasis Diseases 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 1
- PJVQPPHJEYPUDB-UHFFFAOYSA-N 2,3-dihydrofuro[3,2-b]pyridine Chemical compound C1=CC=C2OCCC2=N1 PJVQPPHJEYPUDB-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 claims 1
- 230000006315 carbonylation Effects 0.000 claims 1
- 238000005810 carbonylation reaction Methods 0.000 claims 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 239000000306 component Substances 0.000 claims 1
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims 1
- 229940125670 thienopyridine Drugs 0.000 claims 1
- 239000002175 thienopyridine Substances 0.000 claims 1
- 125000000464 thioxo group Chemical group S=* 0.000 claims 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims 1
- 0 CCCCCCCC=CCC**C(**N)**(*)=*B(*)**C(*)=C(*)* Chemical compound CCCCCCCC=CCC**C(**N)**(*)=*B(*)**C(*)=C(*)* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10181553 | 2010-09-29 | ||
| EP10181553.8 | 2010-09-29 | ||
| US38846610P | 2010-09-30 | 2010-09-30 | |
| US61/388,466 | 2010-09-30 | ||
| PCT/EP2011/066806 WO2012041873A1 (en) | 2010-09-29 | 2011-09-28 | N-heteroaryl compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014500235A JP2014500235A (ja) | 2014-01-09 |
| JP2014500235A5 true JP2014500235A5 (enExample) | 2014-05-29 |
| JP5791725B2 JP5791725B2 (ja) | 2015-10-07 |
Family
ID=44719930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013530709A Expired - Fee Related JP5791725B2 (ja) | 2010-09-29 | 2011-09-28 | Ｎ−ヘテロアリール化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8877934B2 (enExample) |
| EP (1) | EP2621903B1 (enExample) |
| JP (1) | JP5791725B2 (enExample) |
| KR (1) | KR101916481B1 (enExample) |
| CN (2) | CN105294549B (enExample) |
| AR (1) | AR083200A1 (enExample) |
| AU (1) | AU2011310592B2 (enExample) |
| BR (1) | BR112013006030B1 (enExample) |
| CA (1) | CA2811369C (enExample) |
| CO (1) | CO6710926A2 (enExample) |
| ES (1) | ES2622881T3 (enExample) |
| HU (1) | HUE034042T2 (enExample) |
| MX (1) | MX340985B (enExample) |
| NZ (1) | NZ607580A (enExample) |
| PL (1) | PL2621903T3 (enExample) |
| RU (1) | RU2596185C2 (enExample) |
| WO (1) | WO2012041873A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10096073B2 (en) | 2011-05-13 | 2018-10-09 | The Climate Corporation | Systems to prescribe and deliver fertilizer over agricultural fields and related methods |
| US10842144B2 (en) * | 2011-05-13 | 2020-11-24 | The Climate Corporation | Method and system to map biological pests in agricultural fields using remotely-sensed data for field scouting and targeted chemical application |
| WO2013144179A1 (en) * | 2012-03-28 | 2013-10-03 | Intervet International B.V. | Heteroaryl compounds with a-cyclic bridging unit |
| PL2931044T3 (pl) * | 2012-12-13 | 2017-12-29 | Dow Agrosciences Llc | Sposoby wytwarzania 4-amino-3-halogeno-6-(podstawionych)pikolinianów i 4-amino-5-fluoro-3- halogeno-6-(podstawionych)pikolinianów |
| JP6310939B2 (ja) * | 2012-12-13 | 2018-04-11 | ダウ アグロサイエンシィズ エルエルシー | ４−アミノ−５−フルオロ−３−クロロ−６−（置換）ピコリネートの調製方法 |
| CN106458803A (zh) | 2014-05-21 | 2017-02-22 | 英特维特国际股份有限公司 | 改进的制备取代的丁烯酸的方法 |
| CR20170076A (es) | 2014-08-04 | 2017-06-26 | Nuevolution As | Derivados de pirimidima sustituidos con heterociclilo opcionalmente condensados útiles para el tratamiento de enfermedades inflamatorias, metabólicas, oncológicas y autoinmunitarias |
| AU2016378477A1 (en) * | 2015-12-23 | 2018-06-14 | Intervet International B.V. | Improved process for making crotonylaminopyridines |
| AR111260A1 (es) | 2017-03-31 | 2019-06-19 | Intervet Int Bv | Formulación farmacéutica de la sal de crotonil amino piridina |
| JP7292394B2 (ja) * | 2018-12-21 | 2023-06-16 | サルティゴ・ゲーエムベーハー | ２－アルコキシ－４－アミノ－５－メチル－ピリジン及び／又は２－アルコキシ－４－アルキルアミノ－５－メチル－ピリジンを調製するためのプロセス |
| EP4077322A1 (en) | 2019-12-18 | 2022-10-26 | Intervet International B.V. | Anthelmintic compounds comprising azaindoles structure |
| AU2020405446A1 (en) | 2019-12-20 | 2022-05-26 | Nuevolution A/S | Compounds active towards nuclear receptors |
| AU2020408107B2 (en) | 2019-12-20 | 2026-04-23 | Nuevolution A/S | Compounds active towards nuclear receptors |
| CN110960485B (zh) * | 2020-01-06 | 2021-02-02 | 安丘市人民医院 | 一种用于治疗角膜炎的药物及其制备方法 |
| US11613532B2 (en) | 2020-03-31 | 2023-03-28 | Nuevolution A/S | Compounds active towards nuclear receptors |
| EP4126874A1 (en) | 2020-03-31 | 2023-02-08 | Nuevolution A/S | Compounds active towards nuclear receptors |
| WO2025152919A1 (en) * | 2024-01-15 | 2025-07-24 | Impact Therapeutics (Shanghai) , Inc. | Crystal forms of a weel inhibitor and preparation method thereof |
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| WO2009051956A2 (en) | 2007-10-16 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Pyrazole-substituted isoxazoline insecticides |
| CN101284812A (zh) * | 2008-06-05 | 2008-10-15 | 中山大学 | 他克林-阿魏酸杂联体,其制备方法及其药物组合物 |
| WO2010053517A2 (en) | 2008-10-29 | 2010-05-14 | Aroian Raffi V | Combination therapy to combat helminth resistance |
| US8007761B2 (en) | 2008-12-24 | 2011-08-30 | Praxair Technology, Inc. | Carbon dioxide emission reduction method |
-
2011
- 2011-09-28 US US13/876,724 patent/US8877934B2/en active Active
- 2011-09-28 KR KR1020137007888A patent/KR101916481B1/ko not_active Expired - Fee Related
- 2011-09-28 CN CN201510648665.8A patent/CN105294549B/zh not_active Expired - Fee Related
- 2011-09-28 AU AU2011310592A patent/AU2011310592B2/en not_active Ceased
- 2011-09-28 WO PCT/EP2011/066806 patent/WO2012041873A1/en not_active Ceased
- 2011-09-28 CN CN201180052605.XA patent/CN103189356B/zh not_active Expired - Fee Related
- 2011-09-28 MX MX2013003635A patent/MX340985B/es active IP Right Grant
- 2011-09-28 ES ES11761595.5T patent/ES2622881T3/es active Active
- 2011-09-28 HU HUE11761595A patent/HUE034042T2/en unknown
- 2011-09-28 CA CA2811369A patent/CA2811369C/en not_active Expired - Fee Related
- 2011-09-28 BR BR112013006030-1A patent/BR112013006030B1/pt not_active IP Right Cessation
- 2011-09-28 AR ARP110103573A patent/AR083200A1/es not_active Application Discontinuation
- 2011-09-28 RU RU2013119681/04A patent/RU2596185C2/ru active
- 2011-09-28 NZ NZ607580A patent/NZ607580A/en not_active IP Right Cessation
- 2011-09-28 EP EP11761595.5A patent/EP2621903B1/en active Active
- 2011-09-28 JP JP2013530709A patent/JP5791725B2/ja not_active Expired - Fee Related
- 2011-09-28 PL PL11761595T patent/PL2621903T3/pl unknown
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2013
- 2013-04-17 CO CO13099093A patent/CO6710926A2/es unknown
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