HRP20210438T1 - Racemični beta-aminosulfonski spojevi - Google Patents
Racemični beta-aminosulfonski spojevi Download PDFInfo
- Publication number
- HRP20210438T1 HRP20210438T1 HRP20210438TT HRP20210438T HRP20210438T1 HR P20210438 T1 HRP20210438 T1 HR P20210438T1 HR P20210438T T HRP20210438T T HR P20210438TT HR P20210438 T HRP20210438 T HR P20210438T HR P20210438 T1 HRP20210438 T1 HR P20210438T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- formula
- image
- aminosulfone
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 8
- 238000000034 method Methods 0.000 claims 11
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims 10
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 150000002466 imines Chemical class 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- BXUJVINGXQGNFD-UHFFFAOYSA-N 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine Chemical compound CCOC1=CC(C(N)CS(C)(=O)=O)=CC=C1OC BXUJVINGXQGNFD-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000003457 sulfones Chemical class 0.000 claims 3
- VAMZHXWLGRQSJS-UHFFFAOYSA-N 3-ethoxy-4-methoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC=C1OC VAMZHXWLGRQSJS-UHFFFAOYSA-N 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- -1 amino tert-butoxycarbonyl group Chemical group 0.000 claims 1
- IMOZEMNVLZVGJZ-QGZVFWFLSA-N apremilast Chemical compound C1=C(OC)C(OCC)=CC([C@@H](CS(C)(=O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 IMOZEMNVLZVGJZ-QGZVFWFLSA-N 0.000 claims 1
- 229960001164 apremilast Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical compound [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001979 organolithium group Chemical group 0.000 claims 1
- 125000002734 organomagnesium group Chemical group 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/28—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Postupak u dobivanju racemičnog β-aminosulfona (1)
[image]
,
naznačen time što se sastoji u koracima:
a) reakcije 3-etoksi-4-metoksibenzaldehida (9) sa spojem formule R1-NH2 i spojem formule R2-S(O)OH, ili njegovom solju, kako bi se dobilo aminosulfon formule (2):
[image]
gdje:
R1 je zaštitna skupina za amino; i
R2 je C1-C6 alkil, supstituirani C1-C6 alkil, C6-C10 aril ili supstituirani C6-C10 aril;
b) prevođenja aminosulfona formule (2) u sulfon formule (3) obradom karbanionom dobivenim iz dimetil-sulfona:
[image]
c) skidanja zaštite sa sulfona (3) kako bi se dobilo 1-(3-etoksi-4-metoksifenil)-2-(metilsulfonil)etan-1-amin (1) u obliku racemične smjese.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se, u koraku a), sulfinat upotrebljava kao spoj formule R2-S(O)OH.
3. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 i 2, naznačen time što se, u koraku a), natrijev p-toluensulfinat upotrebljava kao spoj formule R2-S(O)OH.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što se kiselinu upotrebljava u koraku a).
5. Postupak u skladu s patentnim zahtjevom 4, naznačen time što se navedenu kiselinu bira iz skupine koju čine karboksilne kiseline i Lewisove kiseline.
6. Postupak u skladu s bilo kojim od patentnih zahtjeva 4 i 5, naznačen time što je navedena kiselina mravlja kiselina.
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što je, u koraku a), zaštitna skupina za amino tert-butoksikarbonilna skupina ili benziloksikarbonilna skupina ili formilna skupina ili acetilna skupina.
8. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što se, u koraku b), karbanion dobiven iz dimetil-sulfona dobiva obradom dimetil-sulfona bazom koju se bira iz skupine koju čine organolitijevi reagensi, organomagnezijevi reagensi i natrijev, litijev, kalijev ili magnezijev amid.
9. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time što se aminosulfon formule (2), dobiven u koraku a) prevodi u odgovarajući imin (10) obradom bazom:
[image]
,
te zatim obradi karbanionom dobivenim iz dimetil-sulfona kako bi se dobilo spoj (3).
10. Postupak u skladu s patentnim zahtjevom 9, naznačen time što se istu baza upotrebljava za prevođenje aminosulfona formule (2) u imin (10) i u dobivanju karbaniona dobivenog iz dimetil-sulfona.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 10, naznačen time što dodatno uključuje prevođenje racemičnog 1-(3-etoksi-4-metoksifenil)-2-(metilsulfonil)etan-1-amina (1) u njegov enantiomerno obogaćeni ili enantiomerno čisti oblik.
12. Imin (10):
[image]
,
naznačen time što je R1 zaštitna skupina za amino, koja, zajedno s atomom dušika na kojeg je vezana, tvori karbamatnu skupinu, amidnu skupinu ili fosfinoamidnu skupinu.
13. Aminosulfon formule (2):
[image]
,
naznačen time što je R1 zaštitna skupina za amino; i
R2 je C1-C6 alkil, supstituirani C1-C6 alkil, C6-C10 aril ili supstituirani C6-C10 aril.
14. Sulfon formule (3):
[image]
,
naznačen time što je R1 tert-butoksikarbonilna skupina ili benziloksikarbonilna skupina.
15. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 12 do 14, naznačena time što je navedeni spoj namijenjen dobivanju apremilasta, njegovog optičkog izomera, solvata, hidrata ili međuprodukta u njegovoj sintezi.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17382174 | 2017-04-04 | ||
| EP18716163.3A EP3606907B1 (en) | 2017-04-04 | 2018-03-28 | Racemic beta-aminosulfone compounds |
| PCT/EP2018/057894 WO2018184933A1 (en) | 2017-04-04 | 2018-03-28 | Racemic beta-aminosulfone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210438T1 true HRP20210438T1 (hr) | 2021-04-30 |
Family
ID=58501428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210438TT HRP20210438T1 (hr) | 2017-04-04 | 2021-03-16 | Racemični beta-aminosulfonski spojevi |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10689332B2 (hr) |
| EP (1) | EP3606907B1 (hr) |
| ES (1) | ES2866476T3 (hr) |
| HR (1) | HRP20210438T1 (hr) |
| HU (1) | HUE054270T2 (hr) |
| PL (1) | PL3606907T3 (hr) |
| PT (1) | PT3606907T (hr) |
| SI (1) | SI3606907T1 (hr) |
| WO (1) | WO2018184933A1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10689332B2 (en) | 2017-04-04 | 2020-06-23 | Quimica Sintetica, S.A. | Racemic beta-aminosulfone compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6020358A (en) | 1998-10-30 | 2000-02-01 | Celgene Corporation | Substituted phenethylsulfones and method of reducing TNFα levels |
| MX2011002589A (es) | 2008-09-10 | 2011-04-07 | Celgene Corp | Procesos para la preparacion de compuestos de aminosulfona. |
| AR090100A1 (es) | 2012-02-21 | 2014-10-22 | Celgene Corp | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| EP2949645A1 (en) * | 2014-05-28 | 2015-12-02 | LEK Pharmaceuticals d.d. | Processes for the preparation of ß-aminosulfone compounds |
| CN105348172B (zh) | 2015-12-04 | 2017-11-14 | 新发药业有限公司 | (s)‑1‑(4‑甲氧基‑3‑乙氧基)苯基‑2‑甲磺酰基乙胺的制备及阿普斯特的制备方法 |
| WO2018061034A1 (en) * | 2016-09-30 | 2018-04-05 | Sun Pharmaceutical Industries Limited | Novel process for the preparation of 1-(3-ethoxy-4-methoxy-phenyl)-2-methylsulfonyl-ethanamine |
| US10689332B2 (en) | 2017-04-04 | 2020-06-23 | Quimica Sintetica, S.A. | Racemic beta-aminosulfone compounds |
-
2018
- 2018-03-28 US US16/500,673 patent/US10689332B2/en active Active
- 2018-03-28 ES ES18716163T patent/ES2866476T3/es active Active
- 2018-03-28 SI SI201830269T patent/SI3606907T1/sl unknown
- 2018-03-28 WO PCT/EP2018/057894 patent/WO2018184933A1/en unknown
- 2018-03-28 EP EP18716163.3A patent/EP3606907B1/en active Active
- 2018-03-28 PT PT187161633T patent/PT3606907T/pt unknown
- 2018-03-28 PL PL18716163T patent/PL3606907T3/pl unknown
- 2018-03-28 HU HUE18716163A patent/HUE054270T2/hu unknown
-
2021
- 2021-03-16 HR HRP20210438TT patent/HRP20210438T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT3606907T (pt) | 2021-04-01 |
| EP3606907B1 (en) | 2021-01-20 |
| WO2018184933A1 (en) | 2018-10-11 |
| EP3606907A1 (en) | 2020-02-12 |
| SI3606907T1 (sl) | 2021-08-31 |
| ES2866476T3 (es) | 2021-10-19 |
| PL3606907T3 (pl) | 2021-07-12 |
| US10689332B2 (en) | 2020-06-23 |
| HUE054270T2 (hu) | 2021-08-30 |
| US20200087254A1 (en) | 2020-03-19 |
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