HRP20170653T1 - Postupak za pripremanje 1-([1,3]dioksolan-4-ilmetil)-1h-pirazol-3-ilamina - Google Patents
Postupak za pripremanje 1-([1,3]dioksolan-4-ilmetil)-1h-pirazol-3-ilamina Download PDFInfo
- Publication number
- HRP20170653T1 HRP20170653T1 HRP20170653TT HRP20170653T HRP20170653T1 HR P20170653 T1 HRP20170653 T1 HR P20170653T1 HR P20170653T T HRP20170653T T HR P20170653TT HR P20170653 T HRP20170653 T HR P20170653T HR P20170653 T1 HRP20170653 T1 HR P20170653T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- image
- compound
- phenyl
- lithium
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (15)
1. Postupak za pripremanje spoja s formulom
[image]
pri čemu su R1 i R2 neovisno odabrani od vodika, C1-6alkila, C3-7cikloalkila, C3-6alkenila, ili fenila; pri čemu C1-6alkil, cikloalkil, C3-6alkenil ili fenil mogu proizvoljno biti supstituirani s halogenom, hidroksilom, C1-6alkoksikarbonilom, ili fenilom; ili
R1 i R2, zajedno s ugljikom na koji su oni spojeni, tvore C3-7cikloalkil;
naznačen time da sadrži slijedeće korake
a) zaštitu 3-aminopirazola sa sredstvom za karboksilaciju u otapalu kod temperature reakcije između 20 i 100 °C da se dobije spoj s formulom (II);
[image]
pri čemu R3 je C1-6alkil, cikloalkil ili fenil;
b) 1-supstituciju zaštićenog 3-aminopirazola s formulom (II) da se dobije spoj s formulom (III);
[image]
c) hidrolizu zaštićenog 3-aminopirazola s formulom (III) pod bazičnim uvjetima da se dobije spoj s formulom (I):
[image]
2. Postupak prema zahtjevu 1, naznačen time da je za pripremanje spoja s formulom (Ia)
[image]
3. Postupak prema zahtjevu 1 ili 2, naznačen time da spoj s formulom (I) ili (Ia) je 1-((R)2,2-dimetil-[1,3]dioksolan-4-ilmetil)-1H-pirazol-3-ilamin.
[image]
4. Postupak prema zahtjevu 1, naznačen time da se korak a) provodi u otapalu koje je odabrano od tetrahidrofurana, octene kiseline, vode, izo-propil acetata ili etil acetata.
5. Postupak prema zahtjevima 1 ili 4, naznačen time da sredstvo za karboksilaciju je octeni anhidrid, acetil klorid, benzojev anhidrid, benzoil klorid ili pivaloil klorid.
6. Postupak prema bilo kojem od zahtjeva 1 do 5, naznačen time da se korak b) provodi sa sredstvom za alkilaciju u organskom otapalu s bazom i dodatkom litijeve soli kod temperature od 70 do 150 °C.
7. Postupak prema zahtjevu 6, naznačen time da je otapalo koje se koristi u koraku b) dimetilformamid, dimetilacetamid, N-metilpirolidinon ili dimetilsulfoksid.
8. Postupak prema zahtjevu 6 ili 7, naznačen time da baza u koraku b) je natrijeva, litijeva ili kalijeva sol alkoksida.
9. Postupak prema bilo kojem od zahtjeva 6 do 8, naznačen time da je litijeva sol koja se koristi u koraku b) litijev klorid, litijev bromid ili litijev jodid.
10. Postupak prema bilo kojem od zahtjeva 6 do 9, naznačen time da je sredstvo za alkilaciju u koraku b)
[image]
pri čemu su R1 i R2 definirani kao u zahtjevu 1 ili 3;
R4 je klor, brom, jod ili -O-SO2-R5, pri čemu R5 je C1-6alkil, fenil ili fenil supstituiran s jednim do tri supstituenta koji su neovisno odabrani od C1-6alkila, halogena ili nitro.
11. Postupak prema bilo kojem od zahtjeva 1 do 10, naznačen time da sredstvo za alkilaciju u koraku b) je
[image]
pri čemu su R1, R2 i R4 definirani kao u zahtjevu 10.
12. Postupak prema bilo kojem od zahtjeva 1 do 10, naznačen time da se korak c) provodi u otapalu s bazom kod temperature od 40 do 100 °C.
13. Postupak prema zahtjevu 12, naznačen time da je otapalo korišteno u koraku c) metanol, etanol ili voda, ili njihova smjesa.
14. Postupak prema zahtjevima 12 ili 13, naznačen time da je baza korištena u koraku c) natrijev hidroksid, litijev hidroksid ili kalijev hidroksid.
15. Spoj s formulom (III);
[image]
naznačen time da R1 je metil, R2 je metil i R3 je metil.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012087380 | 2012-12-25 | ||
| PCT/EP2013/077563 WO2014102164A1 (en) | 2012-12-25 | 2013-12-20 | Process for the preparation of 1-([1,3]dioxolan-4-ylmethyl)-1h-pyrazol-3-ylamine |
| EP13811542.3A EP2938609B1 (en) | 2012-12-25 | 2013-12-20 | Process for the preparation of 1-([1,3]dioxolan-4-ylmethyl)-1h-pyrazol-3-ylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170653T1 true HRP20170653T1 (hr) | 2017-06-30 |
Family
ID=49876646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170653TT HRP20170653T1 (hr) | 2012-12-25 | 2013-12-20 | Postupak za pripremanje 1-([1,3]dioksolan-4-ilmetil)-1h-pirazol-3-ilamina |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9388168B2 (hr) |
| EP (1) | EP2938609B1 (hr) |
| JP (1) | JP6297590B2 (hr) |
| KR (1) | KR102122569B1 (hr) |
| CN (1) | CN105051031B (hr) |
| AU (1) | AU2013369473B2 (hr) |
| BR (1) | BR112015015229B1 (hr) |
| CA (1) | CA2896155C (hr) |
| CY (1) | CY1119040T1 (hr) |
| DK (1) | DK2938609T3 (hr) |
| ES (1) | ES2629313T3 (hr) |
| HR (1) | HRP20170653T1 (hr) |
| HU (1) | HUE032621T2 (hr) |
| IL (1) | IL239558A (hr) |
| LT (1) | LT2938609T (hr) |
| NZ (1) | NZ709362A (hr) |
| PL (1) | PL2938609T3 (hr) |
| PT (1) | PT2938609T (hr) |
| RU (1) | RU2621725C2 (hr) |
| SG (1) | SG11201504951TA (hr) |
| SI (1) | SI2938609T1 (hr) |
| WO (1) | WO2014102164A1 (hr) |
| ZA (1) | ZA201504601B (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11266630B2 (en) * | 2016-12-15 | 2022-03-08 | Hua Medicine (Shanghai) Ltd. | Oral preparation of glucokinase activator and preparation method therefor |
| CN113493442B (zh) * | 2020-04-03 | 2024-11-08 | 天津药物研究院有限公司 | 作为葡萄糖激酶活化剂的吡咯烷酮衍生物及其制备方法和用途 |
| WO2021212360A1 (en) * | 2020-04-22 | 2021-10-28 | Hua Medicine (Shanghai) Ltd. | Treating untreated or treatment-resistant diabetes with glucokinase activator and sodium-glucose cotransporter-2 inhibitor |
| US11813274B2 (en) | 2020-04-22 | 2023-11-14 | Hua Medicine (Shanghai) Ltd. | Treating untreated or treatment-resistant diabetes with glucokinase activator and sodium-glucose cotransporter-2 inhibitor |
| CN111732543A (zh) * | 2020-08-14 | 2020-10-02 | 浙江鼎龙科技有限公司 | 一种4,5-二氨基-1-（2-羟乙基）吡唑硫酸盐的制备方法 |
| CN113750100B (zh) * | 2021-08-31 | 2022-12-30 | 海南中济医药科技有限公司 | 一种含有多扎格列艾汀与西格列汀的药物组合物及其制备方法 |
| AR127064A1 (es) * | 2021-09-15 | 2023-12-13 | Hua Medicine Shanghai Ltd | Prodroga de derivados de pirrolidona como activador de glucoquinasa |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160841A (en) * | 1977-01-31 | 1979-07-10 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles |
| FR2748274B1 (fr) * | 1996-05-03 | 1998-06-12 | Oreal | Nouveaux diamino pyrazoles, leur synthese, compositions de teinture des fibres keratiniques les contenant, procede de teinture des fibres keratiniques |
| JP5287730B2 (ja) * | 2008-01-18 | 2013-09-11 | アステラス製薬株式会社 | フェニルアセトアミド誘導体 |
| US7741327B2 (en) * | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| US8178689B2 (en) * | 2010-06-17 | 2012-05-15 | Hoffman-La Roche Inc. | Tricyclic compounds |
-
2013
- 2013-12-20 BR BR112015015229-5A patent/BR112015015229B1/pt active IP Right Grant
- 2013-12-20 JP JP2015550041A patent/JP6297590B2/ja active Active
- 2013-12-20 PL PL13811542T patent/PL2938609T3/pl unknown
- 2013-12-20 CN CN201380068179.8A patent/CN105051031B/zh active Active
- 2013-12-20 US US14/655,287 patent/US9388168B2/en active Active
- 2013-12-20 DK DK13811542.3T patent/DK2938609T3/en active
- 2013-12-20 PT PT138115423T patent/PT2938609T/pt unknown
- 2013-12-20 AU AU2013369473A patent/AU2013369473B2/en active Active
- 2013-12-20 KR KR1020157019691A patent/KR102122569B1/ko active Active
- 2013-12-20 SG SG11201504951TA patent/SG11201504951TA/en unknown
- 2013-12-20 WO PCT/EP2013/077563 patent/WO2014102164A1/en active Application Filing
- 2013-12-20 HU HUE13811542A patent/HUE032621T2/en unknown
- 2013-12-20 NZ NZ709362A patent/NZ709362A/en unknown
- 2013-12-20 HR HRP20170653TT patent/HRP20170653T1/hr unknown
- 2013-12-20 SI SI201330684A patent/SI2938609T1/sl unknown
- 2013-12-20 CA CA2896155A patent/CA2896155C/en active Active
- 2013-12-20 RU RU2015126911A patent/RU2621725C2/ru active
- 2013-12-20 EP EP13811542.3A patent/EP2938609B1/en active Active
- 2013-12-20 LT LTEP13811542.3T patent/LT2938609T/lt unknown
- 2013-12-20 ES ES13811542.3T patent/ES2629313T3/es active Active
-
2015
- 2015-06-21 IL IL239558A patent/IL239558A/en active IP Right Grant
- 2015-06-25 ZA ZA2015/04601A patent/ZA201504601B/en unknown
-
2017
- 2017-07-10 CY CY20171100727T patent/CY1119040T1/el unknown
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