HRP20210066T1 - Proces pripreme spoja indol karboksamida - Google Patents
Proces pripreme spoja indol karboksamida Download PDFInfo
- Publication number
- HRP20210066T1 HRP20210066T1 HRP20210066TT HRP20210066T HRP20210066T1 HR P20210066 T1 HRP20210066 T1 HR P20210066T1 HR P20210066T T HRP20210066T T HR P20210066TT HR P20210066 T HRP20210066 T HR P20210066T HR P20210066 T1 HRP20210066 T1 HR P20210066T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- image
- converting
- group
- Prior art date
Links
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 30
- 238000000034 method Methods 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- -1 -SO)2R Chemical group 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Claims (6)
1. Proces pripreme spoja Formule (V):
[image]
koji obuhvaća korake:
(a) reagiranje spoja Formule (I) i spoja Formule (II):
[image]
da se dobije spoj Formule (III):
[image]
i
(b) pretvaranje navedenog spoja Formule (III) u spomenuti spoj Formule (V) koracima (b1), (b2) i (b3), u bilo kojem redoslijedu:
(b1) formiranje indolne grupe reakcijom sa spojem Formule (IVa) ili spojem Formule (IVb):
[image]
(b2) pretvaranje navedene -NR4R5 grupe u -NH2; i
(b3) pretvaranje navedene -OR3 grupe u -NH2; pri čemu:
X1 je halo, -NO2, -OS(O)2R, ili -N2+;
X2 je Cl, Br, I, -OH, -OS(O)2R, aciloksi, ili trialkilsiloksi;
R1 i R2 su nezavisno izabrani od H, benzila, supstituisanog benzila, 4-metoksifenila, acila, -S(O)2Ar, terc-butoksikarbonila, ili benziloksikarbonila;
R3 je H, C1-8 alkil, aril, ili heteroaril;
R4 i R5 su nezavisno izabrani od H, benzila, 4-metoksibenzila, 4-metoksifenila, acila, -SO)2R, terc-butoksikarbonila, ili benziloksikarbonila;
R8 je H, C1-3 alkil, ili aril; i
svaki R je nezavisno C1-3 alkil ili aril.
2. Proces prema patentnom zahtjevu 1 pri čemu u Koraku (b), navedeni spoj Formule (III) se pretvara u spomenuti spoj Formule (V):
reagiranjem navedenog spoja Formule (III) sa navedenim spojem Formule (IVa) ili navedenim spojem Formule (IVb) i pretvaranjem navedene -NR4R5 grupe u -NH2, bilo uzastopnim ili istovremenim redoslijedom, bilo oboma, da se dobije spoj Formule (Va)
[image]
i pretvaranjem navedene -OR3 grupe koja je vezana za spomenuti spoj Formule (Va) u -NH2 da se dobije spomenuti spoj Formule (V).
3. Proces prema patentnom zahtjevu 1 pri čemu u Koraku (b), navedeno spoj Formule (III) se pretvara u spomenuti spoj Formule (V):
pretvaranjem navedene -OR3 grupe koja je vezana za spomenuti spoj Formule (III) u -NR6R7 da se dobije spomenuti spoj Formule (IIIa):
[image]
reagiranjem spomenutog spoja Formule (IIIa) sa spomenutim spojem Formule (IVa) ili spomenutim spojem Formule (IVb) da se dobije spoj Formule (Vb):
[image]
i pretvaranjem svake od spomenute -NR4R5 grupe i spomenute -NR6R7 grupe koja je vezana za spoj Formule (Vb) u -NH2, bilo uzastopnim ili istovremenim redoslijedom, bilo oboma; pri čemu R6 i R7 su pojedinačno izabrani od H, benzila, 4-metoksibenzil 4-metoksifenila, alila, acila, formila, -OH, -OR, terc-butoksikarbonila, benziloksikarbonila ili -S(O)2R.
4. Proces prema patentnom zahtjevu 1 pri čemu u Koraku (b1), spomenuta indol grupa je formirana reakcijom sa spomenutim spojem Formule (IVa).
5. Proces prema patentnom zahtjevu 1 pri čemu u Koraku (b1), spomenuta indol grupa je formirana reakcijom sa spomenutim spojem Formule (IVb).
6. Proces prema patentnom zahtjevu 1 koji dalje obuhvaća korak reagiranja spoja Formule (V) sa spojem Formule (VI)
[image]
da se dobije spoj Formule (VII):
[image]
u kome X3 je -OH, halo, -OCH3, -O(aril), -OC(O)R, -OS(O)2R, -OS(O)R, -OP(O)R2, ili - OP(O)(OR)2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662382938P | 2016-09-02 | 2016-09-02 | |
| PCT/US2017/049589 WO2018045157A1 (en) | 2016-09-02 | 2017-08-31 | Process for preparing indole carboxamide compounds |
| EP17772790.6A EP3507282B1 (en) | 2016-09-02 | 2017-08-31 | Process for preparing indole carboxamide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210066T1 true HRP20210066T1 (hr) | 2021-03-05 |
Family
ID=59969218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210066TT HRP20210066T1 (hr) | 2016-09-02 | 2021-01-13 | Proces pripreme spoja indol karboksamida |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US11220489B2 (hr) |
| EP (1) | EP3507282B1 (hr) |
| JP (1) | JP7025411B2 (hr) |
| KR (1) | KR102477924B1 (hr) |
| CN (1) | CN109923107B (hr) |
| CY (1) | CY1123757T1 (hr) |
| DK (1) | DK3507282T3 (hr) |
| ES (1) | ES2837361T3 (hr) |
| HR (1) | HRP20210066T1 (hr) |
| HU (1) | HUE052941T2 (hr) |
| LT (1) | LT3507282T (hr) |
| PL (1) | PL3507282T3 (hr) |
| PT (1) | PT3507282T (hr) |
| RS (1) | RS61285B1 (hr) |
| SI (1) | SI3507282T1 (hr) |
| SM (1) | SMT202100043T1 (hr) |
| WO (1) | WO2018045157A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022089620A1 (zh) * | 2020-10-30 | 2022-05-05 | 苏州晶云药物科技股份有限公司 | 吲哚基甲酰胺类化合物的新晶型及其制备方法 |
| JP2024504602A (ja) * | 2021-01-12 | 2024-02-01 | ジービー００５， インコーポレイテッド | キナーゼ阻害剤としてのインドール誘導体 |
| CN114957241B (zh) * | 2021-02-23 | 2023-08-22 | 药雅科技(上海)有限公司 | 杂环类化合物作为激酶抑制剂的制备及其应用 |
| CN115141176B (zh) * | 2021-03-31 | 2023-08-22 | 药雅科技(上海)有限公司 | 炔代吲哚类fgfr抑制剂及其制备方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005082865A1 (ja) | 2004-02-27 | 2005-09-09 | Astellas Pharma Inc. | 縮合二環性ピリミジン誘導体 |
| KR102273997B1 (ko) * | 2013-06-26 | 2021-07-08 | 애브비 인코포레이티드 | Btk 억제제로서 1급 카복스아미드 |
| JP6517928B2 (ja) | 2014-10-24 | 2019-05-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | キナーゼ阻害剤として有用なインドールカルボキシアミド |
-
2017
- 2017-08-31 WO PCT/US2017/049589 patent/WO2018045157A1/en unknown
- 2017-08-31 CN CN201780067366.2A patent/CN109923107B/zh active Active
- 2017-08-31 JP JP2019511945A patent/JP7025411B2/ja active Active
- 2017-08-31 RS RS20210031A patent/RS61285B1/sr unknown
- 2017-08-31 SI SI201730541T patent/SI3507282T1/sl unknown
- 2017-08-31 US US16/328,447 patent/US11220489B2/en active Active
- 2017-08-31 EP EP17772790.6A patent/EP3507282B1/en active Active
- 2017-08-31 PT PT177727906T patent/PT3507282T/pt unknown
- 2017-08-31 DK DK17772790.6T patent/DK3507282T3/da active
- 2017-08-31 KR KR1020197008952A patent/KR102477924B1/ko active IP Right Grant
- 2017-08-31 SM SM20210043T patent/SMT202100043T1/it unknown
- 2017-08-31 HU HUE17772790A patent/HUE052941T2/hu unknown
- 2017-08-31 LT LTEP17772790.6T patent/LT3507282T/lt unknown
- 2017-08-31 ES ES17772790T patent/ES2837361T3/es active Active
- 2017-08-31 PL PL17772790T patent/PL3507282T3/pl unknown
-
2021
- 2021-01-13 HR HRP20210066TT patent/HRP20210066T1/hr unknown
- 2021-01-28 CY CY20211100073T patent/CY1123757T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3507282A1 (en) | 2019-07-10 |
| PT3507282T (pt) | 2020-12-23 |
| LT3507282T (lt) | 2021-01-25 |
| CN109923107B (zh) | 2022-06-14 |
| CN109923107A (zh) | 2019-06-21 |
| KR20190044652A (ko) | 2019-04-30 |
| ES2837361T3 (es) | 2021-06-30 |
| RS61285B1 (sr) | 2021-02-26 |
| PL3507282T3 (pl) | 2021-04-06 |
| DK3507282T3 (da) | 2021-02-01 |
| CY1123757T1 (el) | 2022-05-27 |
| JP7025411B2 (ja) | 2022-02-24 |
| EP3507282B1 (en) | 2020-11-04 |
| WO2018045157A1 (en) | 2018-03-08 |
| US11220489B2 (en) | 2022-01-11 |
| KR102477924B1 (ko) | 2022-12-14 |
| JP2019529378A (ja) | 2019-10-17 |
| SI3507282T1 (sl) | 2021-01-29 |
| SMT202100043T1 (it) | 2021-03-15 |
| HUE052941T2 (hu) | 2021-05-28 |
| US20210276970A1 (en) | 2021-09-09 |
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