JP2014511387A5 - - Google Patents
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- JP2014511387A5 JP2014511387A5 JP2013555878A JP2013555878A JP2014511387A5 JP 2014511387 A5 JP2014511387 A5 JP 2014511387A5 JP 2013555878 A JP2013555878 A JP 2013555878A JP 2013555878 A JP2013555878 A JP 2013555878A JP 2014511387 A5 JP2014511387 A5 JP 2014511387A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 78
- 239000002904 solvent Substances 0.000 claims description 59
- 238000004519 manufacturing process Methods 0.000 claims description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 4
- -1 chloro, dimethylamino Chemical group 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000003871 sulfonates Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000004210 ether based solvent Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000005456 alcohol based solvent Substances 0.000 claims 1
- 0 *c1c(-c2cc(*)ncc2)[s]c(NC(N(CCC2)C2C(N)=O)=O)n1 Chemical compound *c1c(-c2cc(*)ncc2)[s]c(NC(N(CCC2)C2C(N)=O)=O)n1 0.000 description 4
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161448774P | 2011-03-03 | 2011-03-03 | |
| US61/448,774 | 2011-03-03 | ||
| PCT/EP2012/053559 WO2012117071A1 (en) | 2011-03-03 | 2012-03-01 | Synthesis of 2-carboxamide cycloamino urea derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014511387A JP2014511387A (ja) | 2014-05-15 |
| JP2014511387A5 true JP2014511387A5 (enExample) | 2015-04-09 |
| JP6022485B2 JP6022485B2 (ja) | 2016-11-09 |
Family
ID=45787206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013555878A Active JP6022485B2 (ja) | 2011-03-03 | 2012-03-01 | ２−カルボキサミドシクロアミノ尿素誘導体の合成 |
Country Status (33)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA112539C2 (uk) * | 2011-03-03 | 2016-09-26 | Новартіс Аг | Спосіб одержання похідних 2-карбоксамідциклоаміносечовини |
| AU2015346037A1 (en) * | 2014-11-14 | 2017-07-06 | Gemphire Therapeutics Inc. | Processes and intermediates for preparing alpha,omega-dicarboxylic acid-terminated dialkane ethers |
| IL269884B2 (en) | 2017-04-18 | 2023-09-01 | Gemphire Therapeutics Inc | Gamkaban its accepted pharmaceutical salts, their compositions and methods of their use |
| CN112961090A (zh) * | 2019-12-13 | 2021-06-15 | 武汉九州钰民医药科技有限公司 | 合成Alpelisib的关键中间体及其制备方法 |
| CN111057051A (zh) * | 2019-12-16 | 2020-04-24 | 武汉九州钰民医药科技有限公司 | PI3K抑制剂Alpelisib的新合成方法 |
| CN110964005A (zh) * | 2019-12-16 | 2020-04-07 | 武汉九州钰民医药科技有限公司 | 一种Alpelisib的制备工艺 |
| KR20220125753A (ko) | 2021-03-05 | 2022-09-14 | 배성륭 | 기능성 풍력 발전시스템 |
| CN119462487A (zh) * | 2023-08-08 | 2025-02-18 | 重庆博腾制药科技股份有限公司 | 一种阿培利司中间体4-甲基吡啶类化合物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534056A (en) * | 1967-03-02 | 1970-10-13 | Pennwalt Corp | Fluoro-alkyl pyridines and their preparation |
| UA60365C2 (uk) | 1998-06-04 | 2003-10-15 | Пфайзер Продактс Інк. | Похідні ізотіазолу, спосіб їх одержання, фармацевтична композиція та спосіб лікування гіперпроліферативного захворювання у ссавця |
| IL148385A0 (en) | 1999-09-10 | 2002-09-12 | Merck & Co Inc | Tyrosine kinase inhibitors |
| TW200519106A (en) * | 2003-05-02 | 2005-06-16 | Novartis Ag | Organic compounds |
| WO2007087427A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| TWI428091B (zh) | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
| BRPI0820722A2 (pt) | 2007-12-20 | 2015-06-16 | Novartis Ag | Derivados de tiazol usados como inibidores de pi 3 cinases |
| US20100296486A1 (en) * | 2007-12-21 | 2010-11-25 | Carlo Sansone | Method, Apparatus and Computer Program for Handover From A First Access Point To A Second Access Point |
| UA104147C2 (uk) * | 2008-09-10 | 2014-01-10 | Новартис Аг | Похідна піролідиндикарбонової кислоти та її застосування у лікуванні проліферативних захворювань |
| UA112539C2 (uk) * | 2011-03-03 | 2016-09-26 | Новартіс Аг | Спосіб одержання похідних 2-карбоксамідциклоаміносечовини |
-
2012
- 2012-01-03 UA UAA201310018A patent/UA112539C2/uk unknown
- 2012-03-01 EA EA201691331A patent/EA201691331A1/ru unknown
- 2012-03-01 DK DK12706843.5T patent/DK2681192T3/en active
- 2012-03-01 KR KR1020137025764A patent/KR101851421B1/ko active Active
- 2012-03-01 CN CN201610412757.0A patent/CN106083840B/zh active Active
- 2012-03-01 EA EA201892052A patent/EA201892052A1/ru unknown
- 2012-03-01 EP EP12706843.5A patent/EP2681192B1/en active Active
- 2012-03-01 AU AU2012222346A patent/AU2012222346B2/en active Active
- 2012-03-01 PH PH1/2013/501796A patent/PH12013501796A1/en unknown
- 2012-03-01 EA EA201391267A patent/EA025381B1/ru not_active IP Right Cessation
- 2012-03-01 HU HUE12706843A patent/HUE036319T2/hu unknown
- 2012-03-01 ES ES12706843.5T patent/ES2663717T3/es active Active
- 2012-03-01 SG SG2013062153A patent/SG192793A1/en unknown
- 2012-03-01 PE PE2013002003A patent/PE20140917A1/es not_active Application Discontinuation
- 2012-03-01 MY MYPI2013002966A patent/MY163214A/en unknown
- 2012-03-01 AR ARP120100665A patent/AR088714A1/es active IP Right Grant
- 2012-03-01 SI SI201231240T patent/SI2681192T1/en unknown
- 2012-03-01 BR BR112013021882A patent/BR112013021882A2/pt not_active Application Discontinuation
- 2012-03-01 MX MX2017005292A patent/MX351740B/es unknown
- 2012-03-01 US US13/985,069 patent/US9650373B2/en active Active
- 2012-03-01 CN CN201280011348.XA patent/CN103402982B/zh active Active
- 2012-03-01 PT PT127068435T patent/PT2681192T/pt unknown
- 2012-03-01 EA EA201792068A patent/EA032802B1/ru not_active IP Right Cessation
- 2012-03-01 MX MX2013010132A patent/MX347348B/es active IP Right Grant
- 2012-03-01 NO NO12706843A patent/NO2681192T3/no unknown
- 2012-03-01 MA MA36278A patent/MA34982B1/fr unknown
- 2012-03-01 PL PL12706843T patent/PL2681192T3/pl unknown
- 2012-03-01 CA CA2828509A patent/CA2828509C/en active Active
- 2012-03-01 WO PCT/EP2012/053559 patent/WO2012117071A1/en not_active Ceased
- 2012-03-01 JP JP2013555878A patent/JP6022485B2/ja active Active
- 2012-03-02 TW TW106106845A patent/TWI607994B/zh not_active IP Right Cessation
- 2012-03-02 TW TW101107070A patent/TWI597279B/zh not_active IP Right Cessation
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2013
- 2013-08-16 ZA ZA2013/06174A patent/ZA201306174B/en unknown
- 2013-08-19 IL IL228023A patent/IL228023A/en active IP Right Grant
- 2013-08-28 GT GT201300211A patent/GT201300211A/es unknown
- 2013-08-28 TN TNP2013000354A patent/TN2013000354A1/fr unknown
- 2013-08-30 CO CO13206319A patent/CO6751286A2/es unknown
- 2013-09-02 CL CL2013002521A patent/CL2013002521A1/es unknown
- 2013-10-02 EC ECSP13012914 patent/ECSP13012914A/es unknown
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2017
- 2017-04-06 US US15/480,835 patent/US9776966B2/en active Active
- 2017-08-23 US US15/684,419 patent/US10059670B2/en active Active
-
2021
- 2021-09-23 AR ARP210102644A patent/AR123584A2/es unknown
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