HRP20120460T1 - Novi 5-supstituirani hidantoini - Google Patents
Novi 5-supstituirani hidantoini Download PDFInfo
- Publication number
- HRP20120460T1 HRP20120460T1 HRP20120460AT HRP20120460T HRP20120460T1 HR P20120460 T1 HRP20120460 T1 HR P20120460T1 HR P20120460A T HRP20120460A T HR P20120460AT HR P20120460 T HRP20120460 T HR P20120460T HR P20120460 T1 HRP20120460 T1 HR P20120460T1
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- Prior art keywords
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- general formula
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- aryl
- branched
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- 150000001469 hydantoins Chemical class 0.000 title abstract 5
- 238000000034 method Methods 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 102100036238 Dihydropyrimidinase Human genes 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 108091022884 dihydropyrimidinase Proteins 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002081 enamines Chemical class 0.000 claims 1
- 108010088443 hydantoin racemase Proteins 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000001371 alpha-amino acids Chemical class 0.000 abstract 1
- 235000008206 alpha-amino acids Nutrition 0.000 abstract 1
- 229960002582 perindopril Drugs 0.000 abstract 1
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 abstract 1
- 229960003401 ramipril Drugs 0.000 abstract 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Spoj formule (1) naznačen time da R1 je -Z-R11, gdje Z je O ili S ili S(O) ili S(O)2 i R11 je -C(O)R111 ili -S(O)R111 ili -S(O)2R111 ilipri čemu R1 je ; tepri čemu p ima vrijednost 1, 2, 3, 4, 5 ili 6 i pri čemu R4 i R5 su nezavisno odabrani sa popisa koji sadrži -CH3,
Claims (11)
1. Spoj formule (1)
[image]
naznačen time da R1 je -Z-R11, gdje Z je O ili S ili S(O) ili S(O)2 i R11 je -C(O)R111 ili -S(O)R111 ili -S(O)2R111 ili
pri čemu R1 je
[image]
; te
pri čemu p ima vrijednost 1, 2, 3, 4, 5 ili 6 i pri čemu R4 i R5 su nezavisno odabrani sa popisa koji sadrži -CH3, -CH2CH3, -CH2CH2CH3, -C6H6, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika, aril ili pri čemu R4 i R5 su vezani jedan na drugoga da formiraju prsten koji je odabran sa popisa koji sadrži -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- i -CH2ACH2- pri čemu A je -(CH2)qO-, -(CH2)qS-, -(CH2)qS(O)-, -(CH2)qS(O)2- gdje q je 0, 1, 2, 3 ili 4; i
R2 je -H ili -C(O)R22 ili -S(O)R22 ili -S(O)2R22; i
R3 je -H ili -C(O)R33 ili -S(O)R33 ili -S(O)2R33; i
pri čemu R111, R22 i R33 su nezavisno odabrani sa popisa koji sadrži -H, -CH3, -CH2X, -CHX2, -CX3, -C6H6, -C6H5X, -C6H4X2, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika i aril, gdje X predstavlja Br, CH3, C2H5, Cl, F ili I, uz uvjet da R2 i R3 nisu -H kada Z je S i R11 je -C(O)CH3; i
pri čemu R7 je odabran sa popisa koji sadrži -CH3, -CH2CH3, -CH2CH2CH3, -C6H6, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika, aril i njegove supstituirane derivate.
2. Spoj prema zahtjevu 1 naznačen time da R1 je -Z-R11, gdje Z je O ili S ili S(O) ili S(O)2 i R11 je -C(O)R111 ili -S(O)R111 ili -S(O)2 R111.
3. Spoj prema zahtjevu 2 naznačen time da R1 je -Z-R11 i Z je O i R11 je -C(O)H ili -C(O)CH3 i R2 i R3 su oba -H ili oba su isto kao R11.
4. Spoj prema zahtjevu 2 naznačen time da R1 je -Z-R11 i Z je S i R11, R2 i R3 su -C(O)CH3.
5. Postupak za dobivanje spoja prema bilo kojem od zahtjeva 2 do 4 naznačen time da sadrži kontakt spoja formule [2]
[image]
pri čemu Z je O ili S
sa spojem formule R111C(O)Y
gdje R111 je odabran sa popisa koji sadrži -H, -CH3, -CH2X, -CHX2, -CX3, -C6H6, -C6H5X, -C6H4X2, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika i aril, pri čemu X predstavlja Br, CH3, C2H5, Cl, F ili I i Y predstavlja Br, Cl, F, I, OH ili OC(O)R111, ili
sa spojem formule R111S(O)nY gdje n je 1 ili 2,
pri čemu R111 je odabran sa popisa koji sadrži -H, -CH3, -CH2X, -CHX2, -CX3, -C6H6, -C6H5X, -C6H4X2, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika i aril, pri čemu X predstavlja Br, CH3, C2H5, Cl, F ili I i Y predstavlja Br, Cl, F, I, OH ili OS(O)nR111.
6. Postupak prema zahtjevu 5 naznačen time da nadalje sadrži kontakt produkta dobivenog u (a) ili (b) sa enaminom opće formule [3] ili ketoesterom opće formule [3a]
[image]
pri čemu p ima vrijednost 1, 2, 3, 4, 5 ili 6 i pri čemu R4 i R5 su nezavisno odabrani sa popisa koji sadrži -CH3, -CH2CH3, -CH2CH2CH3, -C6H6, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika, aril ili pri čemu R4 i R5 su vezani jedan na drugoga da formiraju prsten koji je odabran sa popisa koji sadrži -CH2CH2-,-CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- i -CH2ACH2- pri čemu A je -(CH2)qO-, -(CH2)qS-, -(CH2)qS(O)-, -(CH2)qS(O)2- gdje q je 0, 1, 2, 3 ili 4, i R7 je odabran sa popisa koji sadrži -CH3, -CH2CH3, -CH2CH2CH3, -C6H6, ravni ili razgranati, zasićeni ili nezasićeni ugljikovodik sa do 10 atoma ugljika, aril i njegove supstituirane derivate, zatim sa hidrolizom da se dobije spoj opće formule [4]
[image]
pri čemu p ima gore definirano značenje.
7. Postupak prema zahtjevu 6 naznačen time da nadalje sadrži kontakt navedenog spoja opće formule [4] sa hidantoinazom, karbamoilazom i hidantoin racemazom da se dobije spoj opće formule [5]
[image]
pri čemu p ima vrijednost 1, 2, 3, 4, 5 ili 6.
8. Postupak prema zahtjevu 7 naznačen time da nadalje sadrži podvrgavanje navedenog spoja opće formule [5] hidrogenaciji da se dobije spoj opće formule [6]
[image]
pri čemu p ima vrijednost 1, 2, 3, 4, 5 ili 6.
9. Postupak prema zahtjevu 8 naznačen time da nadalje sadrži kontakt navedenog spoja opće formule [6] sa spojem opće formule [7] ili spojem opće formule [8]
[image]
pri čemu R6 je -CH3 ili fenil, da se dobije spoj opće formule [9]
pri čemu p ima vrijednost 1, 2, 3, 4, 5 ili 6.
10. Postupak prema zahtjevu 9 naznačen time da R6 je -CH3 i p ima vrijednost 4 ili pri čemu R6 je fenil i p ima vrijednost 3.
11. Uporaba spoja dobivenog postupkom prema bilo kojem od zahtjeva 9 do 10 naznačena time da je za dobivanje lijeka.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07109684 | 2007-06-06 | ||
| PCT/EP2008/056841 WO2008148755A2 (en) | 2007-06-06 | 2008-06-03 | Novel 5-substituted hydantoins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120460T1 true HRP20120460T1 (hr) | 2012-06-30 |
Family
ID=38802392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120460AT HRP20120460T1 (hr) | 2007-06-06 | 2012-05-29 | Novi 5-supstituirani hidantoini |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8420683B2 (hr) |
| EP (1) | EP2150538B1 (hr) |
| CN (1) | CN101679295A (hr) |
| AT (1) | ATE551328T1 (hr) |
| HK (1) | HK1141029A1 (hr) |
| HR (1) | HRP20120460T1 (hr) |
| SI (1) | SI2150538T1 (hr) |
| WO (1) | WO2008148755A2 (hr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2271625B1 (en) | 2008-04-01 | 2012-09-12 | Abbott GmbH & Co. KG | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN103889968A (zh) | 2011-08-05 | 2014-06-25 | 艾伯维德国有限责任两合公司 | 氨基苯并二氢吡喃、氨基苯并二氢噻喃及氨基-1,2,3,4-四氢喹啉衍生物，包含这些化合物的药用组合物，及其在治疗中的用途 |
| CA2853254A1 (en) | 2011-11-18 | 2013-05-23 | Abbvie Inc. | N-substituted aminobenzocycloheptene, aminotetraline, aminoindane and phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| JP2016537323A (ja) | 2013-10-17 | 2016-12-01 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミノクロマン誘導体、アミノチオクロマン誘導体およびアミノ−１，２，３，４−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、および治療におけるこれらの使用 |
| EP3057958B1 (en) | 2013-10-17 | 2019-05-01 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| EP3229807A4 (en) | 2014-12-11 | 2018-10-17 | President and Fellows of Harvard College | Inhibitors of cellular necrosis and related methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4316928C2 (de) | 1993-05-19 | 1995-03-16 | Degussa | Neue Mikroorganismen, deren Verwendung und Verfahren zur Herstellung von L-alpha-Aminosäuren |
| AR036187A1 (es) | 2001-07-24 | 2004-08-18 | Adir | Un proceso para la preparacion de perindopril, compuestos analogos y sus sales, compuesto intermediario 2,5-dioxo-oxazolidina y proceso para preparar un intermediario |
| PL367931A1 (en) | 2004-05-12 | 2005-11-14 | Instytut Farmaceutyczny | Method for manufacture of 2-[n-[(s)-1- etoxycarbonyl-3-phenyl propyl]-(s)-alanyl] -(1s,3s,5s)-2-azabicyclo [3.3.0] octane-3-carboxylic acid |
| EP2267144A3 (en) * | 2006-12-04 | 2011-05-25 | DSM IP Assets B.V. | Whole-cell catalytic system comprising a hydantoinase, a racemase and a carbamoylase |
-
2008
- 2008-06-03 EP EP08760425A patent/EP2150538B1/en not_active Not-in-force
- 2008-06-03 AT AT08760425T patent/ATE551328T1/de active
- 2008-06-03 CN CN200880019177A patent/CN101679295A/zh active Pending
- 2008-06-03 US US12/601,304 patent/US8420683B2/en not_active Expired - Fee Related
- 2008-06-03 SI SI200830641T patent/SI2150538T1/sl unknown
- 2008-06-03 WO PCT/EP2008/056841 patent/WO2008148755A2/en active Application Filing
-
2010
- 2010-08-09 HK HK10107574.7A patent/HK1141029A1/xx not_active IP Right Cessation
-
2012
- 2012-05-29 HR HRP20120460AT patent/HRP20120460T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008148755A2 (en) | 2008-12-11 |
| EP2150538B1 (en) | 2012-03-28 |
| US20100174092A1 (en) | 2010-07-08 |
| ATE551328T1 (de) | 2012-04-15 |
| SI2150538T1 (sl) | 2012-07-31 |
| CN101679295A (zh) | 2010-03-24 |
| WO2008148755A3 (en) | 2009-02-12 |
| EP2150538A2 (en) | 2010-02-10 |
| HK1141029A1 (en) | 2010-10-29 |
| US8420683B2 (en) | 2013-04-16 |
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