DK2938609T3 - Fremgangsmåde til fremstillingen af 1-([1,3]dioxolan-4-ylmethyl)-1h-pyrazol-3-ylamin - Google Patents
Fremgangsmåde til fremstillingen af 1-([1,3]dioxolan-4-ylmethyl)-1h-pyrazol-3-ylamin Download PDFInfo
- Publication number
- DK2938609T3 DK2938609T3 DK13811542.3T DK13811542T DK2938609T3 DK 2938609 T3 DK2938609 T3 DK 2938609T3 DK 13811542 T DK13811542 T DK 13811542T DK 2938609 T3 DK2938609 T3 DK 2938609T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- compound
- solvent
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (15)
1. Fremgangsmåde til fremstillingen afen forbindelse med formlen Patentkrav
i G) hvor R1 og R2 er uafhængigt valgt fra hydrogen, Ci-ealkyl, C3-7Cycloalkyl, C3-6alkenyl, eller phenyl; hvor Ci-6alkyl, cycloalkyl, C3-6alkenyl eller phenyl eventuelt kan være substitueret med halogen, hydroxyl, Ci-6alkoxycarbonyl, eller phenyl; eller R1 og R2, sammen med det carbonatom til hvilket de er bundet, danner C3-7cycloalkyl; omfattende følgende trin a) beskyttelse af 3-aminopyrazol med et carboxyleringsmiddel i et opløsningsmiddel ved en reaktionstemperatur mellem 20 og 100°C for at danne en forbindelse med formel (II);
(II) hvor R3 er Ci-ealkyl, cycloalkyl eller phenyl; b) 1-substitution af den beskyttede 3-aminopyrazol med formlen (II) for at danne en forbindelse med formel (III);
(III) c) hydrolyse af den beskyttede 3-aminopyrazol med formel (III) under basiske betingelser for at danne en forbindelse med formel (I);
O)·
2. Fremgangsmåde ifølge krav 1, til fremstillingen af en forbindelse med formel (la)
(la).
3. Fremgangsmåde ifølge krav 1 eller 2, hvor forbindelsen med formlen (I) eller (la) er l-((R)2,2-dimethyl-[l,3]dioxolan-4-ylmethyl)-lH-pyrazol-3-ylamin.
4. Fremgangsmåde ifølge krav 1, hvor trin a) udføres i et opløsningsmiddel valgt fra tetrahydrofuran, eddikesyre, vand, iso-propylacetat eller ethylacetat.
5. Fremgangsmåde ifølge krav 1 eller 4, hvor carboxyleringsmidlet er eddikesyreanhydrid, acetylchlorid, benzoesyreanhydrid, benzoylchlorid eller pivaloylchlorid.
6. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor trin b) udføres med et alkyleringsmiddel i et organisk opløsningsmiddel med en base og et lithiumsaltadditiv ved en temperatur på 70 til 150°C.
7. Fremgangsmåde ifølge krav 6, hvor opløsningsmidlet anvendt i trin b) er dimethylformamid, dimethylacetamid, N-methylpyrrolidinon eller dimethylsulfoxid.
8. Fremgangsmåde ifølge krav 6 eller 7, hvor basen i trin b) er natrium, lithium eller kaliumsalte af alkoxid.
9. Fremgangsmåde ifølge et hvilket som helst af kravene 6 til 8, hvor lithiumsaltet anvendt i trin b) er lithiumchlorid, lithiumbromid eller lithiumiodid.
10. Fremgangsmåde ifølge et hvilket som helst af kravene 6 til 9, hvor alkyleringsmidlet i trin b) er
hvor R1 og R2 er som defineret som i krav 1 eller 3; R4 er chlor, brom, iod eller -O-SO2-R5, hvor R5 er Ci-6alkyl, phenyl eller phenyl substitueret med en til tre substituenter uafhængigt valgt fra Ci-6alkyl, halogen eller nitro.
11. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 10, hvor alkyleringsmidlet i trin b) er
hvor R1, R2 og R4 er defineret som i krav 10.
12. Fremgangsmåde ifølge et hvilket som helst af kravene 1 to 10, hvor trin c) udføres i opløsningsmiddel med en base ved en temperatur på 40 til 100°C.
13. Fremgangsmåde ifølge krav 12, hvor opløsningsmidlet anvendt i trin c) er methanol, ethanol eller vand, eller en blanding deraf.
14. Fremgangsmåde ifølge krav 12 eller 13, hvor basen anvendt i trin c) er natriumhydroxid, lithiumhydroxid eller kaliumhydroxid.
15. Forbindelse med formel (III);
(ΠΙ) hvor R1 er methyl, R2 er methyl og R3 er methyl.
Applications Claiming Priority (2)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2938609T3 true DK2938609T3 (da) | 2017-05-15 |
Family
ID=49876646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13811542.3T DK2938609T3 (da) | 2012-12-25 | 2013-12-20 | Fremgangsmåde til fremstillingen af 1-([1,3]dioxolan-4-ylmethyl)-1h-pyrazol-3-ylamin |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US9388168B2 (da) |
| EP (1) | EP2938609B1 (da) |
| JP (1) | JP6297590B2 (da) |
| KR (1) | KR102122569B1 (da) |
| CN (1) | CN105051031B (da) |
| AU (1) | AU2013369473B2 (da) |
| BR (1) | BR112015015229B1 (da) |
| CA (1) | CA2896155C (da) |
| CY (1) | CY1119040T1 (da) |
| DK (1) | DK2938609T3 (da) |
| ES (1) | ES2629313T3 (da) |
| HK (1) | HK1213262A1 (da) |
| HR (1) | HRP20170653T1 (da) |
| HU (1) | HUE032621T2 (da) |
| IL (1) | IL239558A (da) |
| LT (1) | LT2938609T (da) |
| NZ (1) | NZ709362A (da) |
| PL (1) | PL2938609T3 (da) |
| PT (1) | PT2938609T (da) |
| RU (1) | RU2621725C2 (da) |
| SG (1) | SG11201504951TA (da) |
| SI (1) | SI2938609T1 (da) |
| WO (1) | WO2014102164A1 (da) |
| ZA (1) | ZA201504601B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109674752B (zh) | 2016-12-15 | 2022-10-11 | 华领医药技术（上海）有限公司 | 葡萄糖激酶激活剂的口服制剂及其制备方法 |
| CN113493442A (zh) * | 2020-04-03 | 2021-10-12 | 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 |
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 |
| BRPI0906888A2 (pt) * | 2008-01-18 | 2015-11-03 | Astellas Pharma Inc | derivado de fenilacetamida |
| 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 KR KR1020157019691A patent/KR102122569B1/ko active IP Right Grant
- 2013-12-20 HU HUE13811542A patent/HUE032621T2/en unknown
- 2013-12-20 EP EP13811542.3A patent/EP2938609B1/en active Active
- 2013-12-20 WO PCT/EP2013/077563 patent/WO2014102164A1/en active Application Filing
- 2013-12-20 SI SI201330684A patent/SI2938609T1/sl unknown
- 2013-12-20 DK DK13811542.3T patent/DK2938609T3/da active
- 2013-12-20 RU RU2015126911A patent/RU2621725C2/ru active
- 2013-12-20 NZ NZ709362A patent/NZ709362A/en unknown
- 2013-12-20 PL PL13811542T patent/PL2938609T3/pl unknown
- 2013-12-20 ES ES13811542.3T patent/ES2629313T3/es active Active
- 2013-12-20 LT LTEP13811542.3T patent/LT2938609T/lt unknown
- 2013-12-20 PT PT138115423T patent/PT2938609T/pt unknown
- 2013-12-20 SG SG11201504951TA patent/SG11201504951TA/en unknown
- 2013-12-20 CA CA2896155A patent/CA2896155C/en active Active
- 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 CN CN201380068179.8A patent/CN105051031B/zh active Active
- 2013-12-20 US US14/655,287 patent/US9388168B2/en active Active
- 2013-12-20 AU AU2013369473A patent/AU2013369473B2/en 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
-
2016
- 2016-02-04 HK HK16101337.2A patent/HK1213262A1/zh unknown
-
2017
- 2017-04-27 HR HRP20170653TT patent/HRP20170653T1/hr unknown
- 2017-07-10 CY CY20171100727T patent/CY1119040T1/el unknown
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