HRP20150491T1 - PROCES PRIPREME DERIVATA α-KARBOKSAMIDA - Google Patents
PROCES PRIPREME DERIVATA α-KARBOKSAMIDA Download PDFInfo
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- HRP20150491T1 HRP20150491T1 HRP20150491TT HRP20150491T HRP20150491T1 HR P20150491 T1 HRP20150491 T1 HR P20150491T1 HR P20150491T T HRP20150491T T HR P20150491TT HR P20150491 T HRP20150491 T HR P20150491T HR P20150491 T1 HRP20150491 T1 HR P20150491T1
- Authority
- HR
- Croatia
- Prior art keywords
- bis
- ferrocenyl
- phosphino
- ethyl
- formula
- Prior art date
Links
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 10
- DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 claims 8
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims 8
- 238000000034 method Methods 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- QUIOWIWSMQWLNP-XJVYWJENSA-N 1,4-bis[(s)-(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methyl]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([C@@H](C1N3CCC(C(C3)C=C)C1)C=1C3=CC(OC)=CC=C3N=CC=1)=CC=C2[C@@H](C1N2CCC(C(C2)C=C)C1)C1=CC=NC2=CC=C(OC)C=C21 QUIOWIWSMQWLNP-XJVYWJENSA-N 0.000 claims 1
- FXHUSJFRTDBUIH-UHFFFAOYSA-N 1-[4-[(2-fluorophenyl)methoxy]phenyl]prop-2-en-1-one Chemical compound FC1=CC=CC=C1COC1=CC=C(C(=O)C=C)C=C1 FXHUSJFRTDBUIH-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- -1 halo-C1-3alkyl Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (7)
1. Proces pripreme derivata α-karboksamid pirolidina formule (I):
[image]
naznačen time da
- su R1 i R2 neovisno vodik, C1-6alkil ili C3-6cikloalkil; ili takvi R1 i R2 da zajedno s dušikom, za koji su vezani, mogu formirati nesupstituirani 3-,4-, 5- ili 6-eročlani saturirani prsten;
- X je ugljik ili dušik;
- n je 0, 1 ili 2, pri čemu ako je prisutan onda je svaki R5 neovisno izabran s liste koja se sastoji od C1-3alkila, halogena, cijano skupine, halogen-C1-3alkila, hidroksi skupine, C1-3alkoksi skupine i C1-3halogenalkoksi skupine;
- ili R6 ili R7 je –O-R8, -OCHR9R8, -NCH2R8 ili –(CH2)2R8 pri čemu je drugi ili R6 ili R7 vodik ili R5; i pri čemu je R8 fenilni prsten ili pri čemu je fenilni prsten opcionalno supstituiran s jednom ili više skupina neovisno izabranih s liste koja se sastoji od C1-3alkila, halogena, cijano skupine, halogen-C1-3alkila, hidroksi skupine, C1-3alkoksi skupine i C1-3halogenalkoksi skupine; i R9 je vodik ili C1-3alkil;
koji se sastoji od:
a) reakcije spoja formule (II),
[image]
naznačen time da su X, R5, R6, R7 i n definirani prethodno navedenim,
sa spojem formule (III),
[image]
naznačen time da je R3 C1-4alkil, a R4 i R4' mogu svaki opcionalno biti supstituirani s fenilnim prstenom u prisustvu organskog aprotičnog otapala, aminske baze, kiralnog liganda i odgovarajuće Cu(I) soli, za dobivanje odgovarajućeg spoja formule (IV),
[image]
naznačen time da su X, R5, R6, R7, R3, R4, R4' i n definirani prethodno navedenim, i pri čemu je kiralni ligand izabran iz skupine koja sadrži:
(R)-1-[(S)-2-(difenilfosfino)ferocenil]etildicikloheksilfosfin etanolni adukt;
(S)-1-[(R)-2-(difenilfosfino)ferocenil]etildicikloheksilfosfin etanolni adukt;
(R)-1-[(S)-2-difenilfosfinoferocenil]etildi-tert-butilfosfin;
(S)-1-[(R)-2-difenilfosfinoferocenil]etildi-tert-butilfosfin;
(R)-1-[(S)-2-(dicikloheksilfosfino)ferocenil]etildicikloheksilfosfin;
(S)-1-[(R)-2-(dicikloheksilfosfino)ferocenil]etildicikloheksilfosfin;
(R)-1-[(S)-2-(difenilfosfino)-ferocenil]etil-di-(3,5-ksilil)fosfin;
(S)-1-[(R)-2-(difenilfosfino)-ferocenil]etil-di-(3,5-ksilil)fosfin;
(R)-1-[(S)-2-di-(3,5-bis(trifluorometil)fenil)fosfino-ferocenil]etildicikloheksilfosfin;
(S)-1-[(R)-2-di-(3,5-bis(trifluorometil)fenil)fosfino-ferocenil]etildicikloheksilfosfin;
(R)-1-[(S)-2-di-(4-metoksi-3,5-dimetilfenil)fosfino-ferocenil]etildicikloheksilfosfin;
(S)-1-[(R)-2-di-(4-metoksi-3,5-dimetilfenil)fosfino-ferocenil]etildicikloheksilfosfin;
(R)-1-[(S)-2-di-(3,5-bis(trifluorometil)fenil)fosfino-ferocenil]etil-di-(3,5-ksilil)fosfin;
(S)-1-[(R)-2-di-(3,5-bis(trifluorometil)fenil)fosfino-ferocenil]etil-di-(3,5-ksilil)fosfin;
(R)-1-[(S)-2-(dicikloheksilfosfino)ferocenil]etildi-tert-butilfosfin;
(S)-1-[(R)-2-(dicikloheksilfosfino)ferocenil]etildi-tert-butilfosfin;
(R)-1-[(S)-2-di-(4-trifluorometilfenil)fosfino-ferocenil]etildi-tert-butilfosfin;
(S)-1-[(R)-2-di-(4-trifluorometilfenil)fosfino-ferocenil]etildi-tert-butilfosfin;
(R)-1-[(S)-2-(di-2-furilfosfino)ferocenil]etil-di-(3,5-ksilil)fosfin;
(S)-1-[(R)-2-(di-2-furilfosfino)ferocenil]etil-di-(3,5-ksilil)fosfin;
(R)-4-izopropil-2-[(R)-2-(difenilfosfino)ferocen-1-il]oksazolin;
(S)-4-izopropil-2-[(S)-2-(difenilfosfino)ferocen-1-il]oksazolin;
(S)-1-difenilfosfino-2-[(R)-α-(N,N-dimetilamino)-o-difenilfosfinofenil-metil]ferocen;
(R)-1-difenilfosfino-2-[(S)-α-(N,N-dimetilamino)-o-difenilfosfinofenil-metil]ferocen;
(R)-1-[(R)-2-(2'-difenilfosfinofenil)ferocenil]etildi-(bis-3,5-trifluorometilfenil)fosfin;
(S)-1-[(S)-2-(2'-difenilfosfinofenil)ferocenil]etildi-(bis-3,5-trifluorometilfenil)fosfin;
(R)-1-[(R)-2-(2'-difenilfosfinofenil)ferocenil]etildifenilfosfin;
(S)-1-[(S)-2-(2'-difenilfosfinofenil)ferocenil]etildifenilfosfin;
(S)-1-[(S)-2-{2'-di(3,5-dimetil-4-metoksifenil)fosfinofenil}-ferocenil]etildi-(bis-3,5-trifluorometilfenil)fosfin;
(R)-1-[(R)-2-{2'-di(3,5-dimetil-4-metoksifenil)fosfinofenil}-ferocenil]etildi-(bis-3,5-trifluorometilfenil)fosfin;
(αR,αR)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(S,S)-1,1'-bis(difenilfosfino)ferocen;
(αS,αS)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(R,R)-1,1'-bis(difenilfosfino)ferocen;
(αR,αR)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(S,S)-1,1'-bis(dicikloheksilfosfino)ferocen;
(αS,αS)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(R,R)-1,1'-bis(dicikloheksilfosfino)ferocen;
(αR,αR)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(S,S)-1,1'-bis[di(bis(3,5-trifluorometil)fenil)-fosfino]ferocen;
(αS,αS)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(R,R)-1,1'-bis[di(bis(3,5-trifluorometil)fenil)-fosfino]ferocen;
(αR,αR)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(S,S)-1,1'-bis[di(3,5-dimetil-4-metoksifenil)fosfino]ferocen;
(αS,αS)-2,2'-bis(α-N,N-dimetilaminofenilmetil)-(R,R)-1,1'-bis[di(3,5-dimetil-4-metoksifenil)fosfino]ferocen;
hidrokinidin(antrakinon-1,4-diil) dieter;
hidrokinidin-2,5-difenil-4,6-pirimidindiil dieter;
(S)-(-)-2,2'-bis(di-p-tolilfosfino)-1,1'-binaftil i
(R)-(+)-2,2'-bis(di-p-tolilfosfino)-1,1'-binaftil;
b) reakcije spoja formule (IV) u kiselom vodenom mediju za dobivanje spoja formule (V) nakon neutralizacije bazom,
[image]
naznačen time da su X, R5, R6, R7, R3, R4, R4' i n definirani prethodno navedenim;
c) reakcije spoja formule (V) s Pt/C pod atmosferskim uvjetima ili vodikom i pod povišenim tlakom, u protičnom otapalu, na sobnoj temperaturi, za dobivanje spoja formule (VI),
[image]
naznačen time da su X, R5, R6, R7, R3, R4, R4' i n definirani prethodno navedenim;
i
d) reakcije spoja formule (VI) s otopinom amina NR1R2 u protičnom otapalu za dobivanje spoja formule (I).
2. Proces u skladu sa zahtjevom 1, pri čemu je u koraku a) ligand (S)-4-izopropil-2-[(S)-2-(difenilfosfino)ferocen-1-il]oksazolin, a Cu(I) kompleks je Cu(MeCN)4PF6.
3. Proces u skladu sa zahtjevom 1 ili 2, pri čemu je dobiveni spoj formule (I) (5R)-5-(4-{[(2-fluorofenil)metil]oksi}fenil)-1-prolinamid, a spoj formule (II) iz koraka a) je 1-(4-[2-fluorobenziloksi]fenil)-2-propen-1-on.
4. Proces u skladu s bilo kojim od zahtjeva 1-3, pri čemu je povišeni tlak iz koraka c) 2atm.
5. Proces u skladu s bilo kojim od zahtjeva 1-4, pri čemu je amin iz koraka d) otopina koncentracije 7N ili 11,2 M.
6. Proces u skladu s bilo kojim od zahtjeva 1-5, pri čemu je protično otapalo iz koraka d) metanol.
7. Proces u skladu s bilo kojim od zahtjeva 1-5, pri čemu je korak d) izvođen na sobnoj temperaturi.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24200309P | 2009-09-14 | 2009-09-14 | |
| EP10749642.4A EP2477964B1 (en) | 2009-09-14 | 2010-09-01 | Process for preparing alpha-carboxamide derivatives |
| PCT/EP2010/062826 WO2011029762A1 (en) | 2009-09-14 | 2010-09-01 | Process for preparing alpha-carboxamide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150491T1 true HRP20150491T1 (hr) | 2015-08-14 |
Family
ID=43014091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150491TT HRP20150491T1 (hr) | 2009-09-14 | 2015-05-08 | PROCES PRIPREME DERIVATA α-KARBOKSAMIDA |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8759542B2 (hr) |
| EP (1) | EP2477964B1 (hr) |
| JP (1) | JP5855000B2 (hr) |
| DK (1) | DK2477964T5 (hr) |
| ES (1) | ES2536694T3 (hr) |
| HR (1) | HRP20150491T1 (hr) |
| PL (1) | PL2477964T3 (hr) |
| PT (1) | PT2477964E (hr) |
| SI (1) | SI2477964T1 (hr) |
| SM (1) | SMT201500113B (hr) |
| WO (1) | WO2011029762A1 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201122113D0 (en) | 2011-12-22 | 2012-02-01 | Convergence Pharmaceuticals | Novel compounds |
| GB201209015D0 (en) | 2012-05-22 | 2012-07-04 | Convergence Pharmaceuticals | Novel compounds |
| ES2912881T3 (es) | 2014-12-23 | 2022-05-30 | Convergence Pharmaceuticals | Procedimiento para preparar derivados de alfa-carboxamida pirrolidina |
| US20200062705A1 (en) * | 2017-05-19 | 2020-02-27 | Biogen Ma Inc. | Novel crystalline forms |
| WO2019071162A2 (en) | 2017-10-05 | 2019-04-11 | Biogen Inc. | PROCESS FOR THE PREPARATION OF PYRROLIDINE ALPHA-CARBOXAMIDE DERIVATIVES |
| MA50371A (fr) | 2017-10-10 | 2021-03-31 | Biogen Inc | Procédé de préparation de dérivés spiro |
| WO2022072184A1 (en) * | 2020-09-30 | 2022-04-07 | Eastman Chemical Company | Use of highly isoselective, thermally stable ferrocene catalysts for propylene hydroformylation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005110982A2 (en) | 2004-04-07 | 2005-11-24 | Neurogen Corporation | Substituted 1-benzyl-4-substituted piperazine analogues |
| TW200730494A (en) * | 2005-10-10 | 2007-08-16 | Glaxo Group Ltd | Novel compounds |
| DE602006015215D1 (de) | 2005-10-10 | 2010-08-12 | Glaxo Group Ltd | Prolinamidderivate als natriumkanalmodulatoren |
| TW200728258A (en) * | 2005-10-10 | 2007-08-01 | Glaxo Group Ltd | Novel compounds |
| GB0701365D0 (en) * | 2007-01-24 | 2007-03-07 | Glaxo Group Ltd | Novel pharmaceutical compositions |
| JP2008253987A (ja) * | 2007-03-09 | 2008-10-23 | Japan Science & Technology Agency | 金属触媒、及び光学活性α−アミノ酸誘導体の製造方法 |
| GB0706630D0 (en) * | 2007-04-04 | 2007-05-16 | Glaxo Group Ltd | Novel compounds |
-
2010
- 2010-09-01 SI SI201030931T patent/SI2477964T1/sl unknown
- 2010-09-01 PL PL10749642T patent/PL2477964T3/pl unknown
- 2010-09-01 US US13/393,174 patent/US8759542B2/en active Active
- 2010-09-01 EP EP10749642.4A patent/EP2477964B1/en active Active
- 2010-09-01 WO PCT/EP2010/062826 patent/WO2011029762A1/en active Application Filing
- 2010-09-01 DK DK10749642.4T patent/DK2477964T5/en active
- 2010-09-01 JP JP2012528321A patent/JP5855000B2/ja active Active
- 2010-09-01 PT PT107496424T patent/PT2477964E/pt unknown
- 2010-09-01 ES ES10749642.4T patent/ES2536694T3/es active Active
-
2015
- 2015-05-08 HR HRP20150491TT patent/HRP20150491T1/hr unknown
- 2015-05-11 SM SM201500113T patent/SMT201500113B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2477964A1 (en) | 2012-07-25 |
| US20120226053A1 (en) | 2012-09-06 |
| DK2477964T3 (en) | 2015-05-18 |
| PT2477964E (pt) | 2015-06-04 |
| SI2477964T1 (sl) | 2015-10-30 |
| DK2477964T5 (en) | 2015-05-26 |
| ES2536694T3 (es) | 2015-05-27 |
| JP5855000B2 (ja) | 2016-02-09 |
| SMT201500113B (it) | 2015-07-09 |
| JP2013504529A (ja) | 2013-02-07 |
| US8759542B2 (en) | 2014-06-24 |
| EP2477964B1 (en) | 2015-02-11 |
| PL2477964T3 (pl) | 2015-08-31 |
| WO2011029762A1 (en) | 2011-03-17 |
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|---|---|---|
| HRP20150491T1 (hr) | PROCES PRIPREME DERIVATA α-KARBOKSAMIDA | |
| Zhang et al. | Asymmetric hydrogenation of nonaromatic cyclic substrates | |
| Jiao et al. | Catalytic methods for aromatic C–H amination: an ideal strategy for nitrogen-based functional molecules | |
| Urgaonkar et al. | P (i-BuNCH2CH2) 3N: an effective ligand in the palladium-catalyzed amination of aryl bromides and iodides | |
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| EP0301457B1 (de) | Verfahren zur Herstellung von optisch aktiven sekundären Aminen | |
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| Huang et al. | Intermolecular dehydrative [4+ 2] aza-annulation of N-arylamides with alkenes: a direct and divergent entrance to aza-heterocycles | |
| Xu et al. | Visible Light Photoredox-Catalyzed α-Alkylation of Cyclic Tertiary Arylamines | |
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| Mi et al. | Iridium (III)-catalyzed C–H amidation of nitrones with dioxazolones | |
| Xu et al. | Organocatalytic, enantioselective reductive bis-functionalization of secondary amides: one-pot construction of chiral 2, 2-disubstituted 3-iminoindoline | |
| Chen et al. | Double Addition of Alkynyllithium Reagents to Amides/Lactams: A Direct and Flexible Synthesis of 3-Amino-1, 4-diynes Bearing an Aza-Quaternary Carbon Center | |
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| Liu et al. | Palladium-catalyzed hiyama cross-couplings of arylsilanes with 3-iodoazetidine: synthesis of 3-arylazetidines | |
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| Xie et al. | 1, 2-Diamines as the amine sources in amidation and rhodium-catalyzed asymmetric reductive amination cascade reactions |