HRP20201687T1 - Postupak pripreme optički čistih i proizvoljno supstituiranih 2-(1-hidroksi-alkil)-kromen-4-on derivata i njihova uporaba u pripremi lijekova - Google Patents
Postupak pripreme optički čistih i proizvoljno supstituiranih 2-(1-hidroksi-alkil)-kromen-4-on derivata i njihova uporaba u pripremi lijekova Download PDFInfo
- Publication number
- HRP20201687T1 HRP20201687T1 HRP20201687TT HRP20201687T HRP20201687T1 HR P20201687 T1 HRP20201687 T1 HR P20201687T1 HR P20201687T T HRP20201687T T HR P20201687TT HR P20201687 T HRP20201687 T HR P20201687T HR P20201687 T1 HRP20201687 T1 HR P20201687T1
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- Croatia
- Prior art keywords
- substituted
- formula
- unsubstituted
- compound
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- 238000000034 method Methods 0.000 title claims 36
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 135
- 150000003839 salts Chemical class 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000004429 atom Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 238000006243 chemical reaction Methods 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 238000010511 deprotection reaction Methods 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 239000012828 PI3K inhibitor Substances 0.000 claims 8
- 239000002585 base Substances 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 229910003813 NRa Inorganic materials 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- KEIVLHIFSZBKGU-UHFFFAOYSA-N CS(=O)=O Chemical compound CS(=O)=O KEIVLHIFSZBKGU-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910004679 ONO2 Inorganic materials 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- RKMUPRSILYQIMJ-LLVKDONJSA-N 2-[(1r)-1-hydroxyethyl]-3-phenylchromen-4-one Chemical compound C[C@@H](O)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 RKMUPRSILYQIMJ-LLVKDONJSA-N 0.000 claims 1
- HJGLKGYUKUOQGN-GFCCVEGCSA-N 2-[(1r)-1-hydroxyethyl]-5-methyl-3-phenylchromen-4-one Chemical compound C[C@@H](O)C=1OC2=CC=CC(C)=C2C(=O)C=1C1=CC=CC=C1 HJGLKGYUKUOQGN-GFCCVEGCSA-N 0.000 claims 1
- OTEKPBYXKUFKKT-SNVBAGLBSA-N 3-(3-fluorophenyl)-2-[(1r)-1-hydroxyethyl]chromen-4-one Chemical compound C[C@@H](O)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 OTEKPBYXKUFKKT-SNVBAGLBSA-N 0.000 claims 1
- SKDLNYCHJKDQEJ-CQSZACIVSA-N 3-(3-fluorophenyl)-2-[(1r)-1-hydroxypropyl]chromen-4-one Chemical compound CC[C@@H](O)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 SKDLNYCHJKDQEJ-CQSZACIVSA-N 0.000 claims 1
- OTEKPBYXKUFKKT-JTQLQIEISA-N 3-(3-fluorophenyl)-2-[(1s)-1-hydroxyethyl]chromen-4-one Chemical compound C[C@H](O)C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC(F)=C1 OTEKPBYXKUFKKT-JTQLQIEISA-N 0.000 claims 1
- XIYIMLNXILXQCS-SNVBAGLBSA-N 6-fluoro-2-[(1r)-1-hydroxyethyl]-3-phenylchromen-4-one Chemical compound C[C@@H](O)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC=C1 XIYIMLNXILXQCS-SNVBAGLBSA-N 0.000 claims 1
- KVWIGTRVURMRQS-SECBINFHSA-N 6-fluoro-3-(3-fluorophenyl)-2-[(1r)-1-hydroxyethyl]chromen-4-one Chemical compound C[C@@H](O)C=1OC2=CC=C(F)C=C2C(=O)C=1C1=CC=CC(F)=C1 KVWIGTRVURMRQS-SECBINFHSA-N 0.000 claims 1
- 239000007821 HATU Substances 0.000 claims 1
- -1 HCTU Chemical compound 0.000 claims 1
- 239000012317 TBTU Substances 0.000 claims 1
- 241000289690 Xenarthra Species 0.000 claims 1
- VORIUEAZEKLUSJ-UHFFFAOYSA-M [(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylidene]-dimethylazanium;trifluoroborane;fluoride Chemical compound [F-].FB(F)F.C1=C(Cl)C=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 VORIUEAZEKLUSJ-UHFFFAOYSA-M 0.000 claims 1
- FPQVGDGSRVMNMR-JCTPKUEWSA-N [[(z)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-(dimethylamino)methylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCOC(=O)C(\C#N)=N/OC(N(C)C)=[N+](C)C FPQVGDGSRVMNMR-JCTPKUEWSA-N 0.000 claims 1
- GPDHNZNLPKYHCN-DZOOLQPHSA-N [[(z)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-morpholin-4-ylmethylidene]-dimethylazanium;hexafluorophosphate Chemical compound F[P-](F)(F)(F)(F)F.CCOC(=O)C(\C#N)=N/OC(=[N+](C)C)N1CCOCC1 GPDHNZNLPKYHCN-DZOOLQPHSA-N 0.000 claims 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1737CH2012 | 2012-05-04 | ||
| US201261671956P | 2012-07-16 | 2012-07-16 | |
| PCT/IB2013/053544 WO2013164801A1 (en) | 2012-05-04 | 2013-05-03 | Process for preparation of optically pure and optionally substituted 2- (1 -hydroxy- alkyl) - chromen - 4 - one derivatives and their use in preparing pharmaceuticals |
| EP13729095.3A EP2844647B1 (en) | 2012-05-04 | 2013-05-03 | Process for preparation of optically pure and optionally substituted 2-(1-hydroxy-alkyl)-chromen-4-one derivatives and their use in preparing pharmaceuticals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20201687T1 true HRP20201687T1 (hr) | 2020-12-25 |
Family
ID=73006467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20201687TT HRP20201687T1 (hr) | 2012-05-04 | 2020-10-19 | Postupak pripreme optički čistih i proizvoljno supstituiranih 2-(1-hidroksi-alkil)-kromen-4-on derivata i njihova uporaba u pripremi lijekova |
Country Status (6)
| Country | Link |
|---|---|
| DK (1) | DK2844647T3 (es) |
| ES (1) | ES2825974T3 (es) |
| HR (1) | HRP20201687T1 (es) |
| HU (1) | HUE051029T2 (es) |
| LT (1) | LT2844647T (es) |
| PT (1) | PT2844647T (es) |
-
2013
- 2013-05-03 PT PT137290953T patent/PT2844647T/pt unknown
- 2013-05-03 ES ES13729095T patent/ES2825974T3/es active Active
- 2013-05-03 LT LTEP13729095.3T patent/LT2844647T/lt unknown
- 2013-05-03 DK DK13729095.3T patent/DK2844647T3/da active
- 2013-05-03 HU HUE13729095A patent/HUE051029T2/hu unknown
-
2020
- 2020-10-19 HR HRP20201687TT patent/HRP20201687T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK2844647T3 (da) | 2020-10-26 |
| LT2844647T (lt) | 2020-11-10 |
| HUE051029T2 (hu) | 2021-01-28 |
| ES2825974T3 (es) | 2021-05-17 |
| PT2844647T (pt) | 2020-10-27 |
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