HRP20150068T1 - Sinteza aliskirena - Google Patents
Sinteza aliskirena Download PDFInfo
- Publication number
- HRP20150068T1 HRP20150068T1 HRP20150068AT HRP20150068T HRP20150068T1 HR P20150068 T1 HRP20150068 T1 HR P20150068T1 HR P20150068A T HRP20150068A T HR P20150068AT HR P20150068 T HRP20150068 T HR P20150068T HR P20150068 T1 HRP20150068 T1 HR P20150068T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- alkyl
- alkoxy
- image
- Prior art date
Links
- UXOWGYHJODZGMF-QORCZRPOSA-N Aliskiren Chemical compound COCCCOC1=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)C(C)C)=CC=C1OC UXOWGYHJODZGMF-QORCZRPOSA-N 0.000 title claims 3
- 229960004601 aliskiren Drugs 0.000 title claims 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 238000000034 method Methods 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- VFJGAQNGDVAFIC-UHFFFAOYSA-N 3-amino-2,2-dimethylpropanenitrile Chemical compound NCC(C)(C)C#N VFJGAQNGDVAFIC-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000004508 fractional distillation Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/08—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated
- C07C247/10—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (10)
1. Postupak za dobivanje aliskirena ili njegovih farmaceutski prihvatljivih soli koji sadrži korake:
a) prevođenje cijano grupe u spoju formule-III u amidnu grupu kako bi se dobio spoj formule-IV;
[image]
naznačen time da su R1 i R2 nezavisno jedan od drugog H, C1-C6 alkil, C1-C6 halogen alkil, C1-C6alkoksi, C1-C6alkoksi-C1-C6alkil, ili C1-C6alkoksi-C1-C6alkiloksi, R3 je C1-C6alkil i R4 je C1-C6alkil,
b) redukciju azidne grupe u spoju formule-IV da bi se dobila amino grupa i izolirao spoj formule-Ia; i
[image]
c) po želji prevođenje spoja formule-Ia u farmaceutski prihvatljivu sol.
2. Postupak prema zahtjevu 1, naznačen time da se spoj formule-III dobiva reakcijom spoja formule-II s 3-amino-2,2-dimetil-propionitrilom
[image]
pri čemu su R1 i R2 nezavisno jedan od drugog H, C1-C6alkil, C1-C6halogen alkil, C1-C6alkoksi, C1-C6alkoksi-C1-C6alkil, ili C1-C6alkoksi-C1-C6alkiloksi, R3 je C1-C6alkil, R4 je C1-C6alkil.
3. Postupak prema zahtjevu 1, naznačen time da se redukcija azidne grupe u spoju formule-IV provodi uz korištenje Pd/C.
4. Postupak prema zahtjevu 1 naznačen time da se redukcija azidne grupe u spoju formule-IV provodi u prisutnosti alkoholnog otapala.
5. Postupak prema zahtjevu 4, naznačen time da je alkoholno otapalo koje se upotrebljava za redukciju azidne grupe u spoju formule-IV izabrano između etanola, metanola i izopropanola.
6. Postupak prema zahtjevu 2, naznačen time da se spoj formule-II dobiva iz spoja formule-V.
[image]
pri čemu su R1 i R2 nezavisno jedan od drugog H, C1-C6alkil, C1-C6halogen alkil, C1-C6alkoksi, C1-C6alkoksi-C1-C6alkil, ili C1-C6alkoksi-C1-C6alkiloksi, R3 je C1-C6alkil, R4 je C1-C6alkil, R6 je C1-C6alkil i R7 je C1-C6alkil ili C1-C6alkoksi.
7. Postupak prema zahtjevu 6, naznačen time da se spoj formule-V pročišćava frakcijskom destilacijom.
8. Spoj formule-III
[image]
naznačen time da su R1 i R2 nezavisno jedan od drugog H, C1-C6alkil, C1-C6halogen alkil, C1-C6alkoksi, C1-C6alkoksi-C1-C6alkil, ili C1-C6alkoksi-C1-C6alkiloksi, R3 je C1-C6alkil, i R4 je C1-C6alkil.
9. Primjena spoja formule-III za dobivanje aliskirena ili njegovih farmaceutski prihvatljivih soli.
10. Spoj formule-A1
[image]
.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3087CH2010 | 2010-10-19 | ||
| IN2395CH2011 | 2011-07-13 | ||
| PCT/IB2011/002507 WO2012052829A1 (en) | 2010-10-19 | 2011-10-19 | Synthesis of aliskiren |
| EP11811559.1A EP2630118B1 (en) | 2010-10-19 | 2011-10-19 | Synthesis of aliskiren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150068T1 true HRP20150068T1 (hr) | 2015-04-10 |
Family
ID=45529137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150068AT HRP20150068T1 (hr) | 2010-10-19 | 2015-01-20 | Sinteza aliskirena |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9187409B2 (hr) |
| EP (1) | EP2630118B1 (hr) |
| CY (1) | CY1115983T1 (hr) |
| DK (1) | DK2630118T3 (hr) |
| ES (1) | ES2528701T3 (hr) |
| HR (1) | HRP20150068T1 (hr) |
| PL (1) | PL2630118T3 (hr) |
| PT (1) | PT2630118E (hr) |
| RS (1) | RS53772B1 (hr) |
| SI (1) | SI2630118T1 (hr) |
| SM (1) | SMT201500035B (hr) |
| WO (1) | WO2012052829A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013118138A1 (en) | 2011-12-13 | 2013-08-15 | Laboratories Ltd Mylan | Novel process for the preparation of renin inhibitors |
| WO2013124868A2 (en) | 2012-02-21 | 2013-08-29 | Mylan Laboratories Limited | Solid form of aliskiren intermediate |
| WO2013171767A1 (en) | 2012-05-18 | 2013-11-21 | Mylan Laboratories Limited | An improved process for the preparation of aliskiren |
| CN104592054A (zh) * | 2013-10-31 | 2015-05-06 | 徐州万邦金桥制药有限公司 | 一种高纯度半富马酸阿利吉仑的制备方法 |
| WO2018228984A1 (en) * | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY119161A (en) | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| US6777574B1 (en) | 1999-07-29 | 2004-08-17 | Speedel Pharma Ag | 2-alkyl-5-halogen-pent-4-ene carboxylic acids and their production |
| PL212898B1 (pl) * | 2000-07-05 | 2012-12-31 | Speedel Pharma Ag | Sposób otrzymywania podstawionych amidów oktanoilowych oraz zwiazki posrednie wykorzystane w tym sposobie |
| TR200401871T4 (tr) | 2000-07-25 | 2004-08-23 | Speedel Pharma Ag | Değiştirilen oktanoil amitlerin (octanoyl amides) hazırlanması |
| WO2011148392A1 (en) * | 2010-05-28 | 2011-12-01 | Msn Laboratories Limited | Process for the preparation of (2s,4s,5s,7s)-n-(2-carbamyl-2- methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-[4-methoxy-3-(3- methoxypropoxy)phenyl]-octanamide hemifumarate and its intermediates thereof |
-
2011
- 2011-10-19 PT PT118115591T patent/PT2630118E/pt unknown
- 2011-10-19 ES ES11811559.1T patent/ES2528701T3/es active Active
- 2011-10-19 PL PL11811559T patent/PL2630118T3/pl unknown
- 2011-10-19 RS RS20150062A patent/RS53772B1/en unknown
- 2011-10-19 US US13/879,849 patent/US9187409B2/en not_active Expired - Fee Related
- 2011-10-19 WO PCT/IB2011/002507 patent/WO2012052829A1/en active Application Filing
- 2011-10-19 SI SI201130373T patent/SI2630118T1/sl unknown
- 2011-10-19 DK DK11811559.1T patent/DK2630118T3/en active
- 2011-10-19 EP EP11811559.1A patent/EP2630118B1/en active Active
-
2015
- 2015-01-20 HR HRP20150068AT patent/HRP20150068T1/hr unknown
- 2015-02-02 CY CY20151100111T patent/CY1115983T1/el unknown
- 2015-02-12 SM SM201500035T patent/SMT201500035B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2630118T3 (pl) | 2015-04-30 |
| PT2630118E (pt) | 2015-02-10 |
| SI2630118T1 (sl) | 2015-03-31 |
| DK2630118T3 (en) | 2015-02-09 |
| EP2630118A1 (en) | 2013-08-28 |
| CY1115983T1 (el) | 2017-01-25 |
| WO2012052829A1 (en) | 2012-04-26 |
| RS53772B1 (en) | 2015-06-30 |
| US20130261324A1 (en) | 2013-10-03 |
| SMT201500035B (it) | 2015-03-05 |
| EP2630118B1 (en) | 2014-11-05 |
| ES2528701T3 (es) | 2015-02-11 |
| US9187409B2 (en) | 2015-11-17 |
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