DK2571506T3 - Fremgangsmåder til fremstilling af makrolider og ketolider og mellemprodukter dertil - Google Patents
Fremgangsmåder til fremstilling af makrolider og ketolider og mellemprodukter dertil Download PDFInfo
- Publication number
- DK2571506T3 DK2571506T3 DK11784318.5T DK11784318T DK2571506T3 DK 2571506 T3 DK2571506 T3 DK 2571506T3 DK 11784318 T DK11784318 T DK 11784318T DK 2571506 T3 DK2571506 T3 DK 2571506T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- compound
- acid addition
- addition salt
- sodium
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (17)
1. Fremgangsmåde til fremstilling af en forbindelse med formlen (I),
_(!)_ eller et farmaceutisk acceptabelt salt deraf, hvor: R10 er hydrogen eller acyl; X er H; og Y er OR7; hvor R7 er monosaccharid, disaccharid, alkyl, arylalkyl eller heteroarylalkyl, der hver eventuelt et substitueret, eller acyl eller C(0)NR8R9; hvor R8 og R9 hver et uafhængigt udvalgt fra gruppen bestående af hydrogen, hydroxy, alkyl, heteroalkyl, alkoxy, aryl, arylalkyl, heteroaryl og heteroarylalkyl, der hver eventuelt er substitueret, og dimethylaminoalkyl, acyl, sulfonyl, ureido og carbamoyl; eller R8og R9 er taget sammen med det forbundne nitrogen for at danne en eventuelt substitueret heterocyklus; eller X og Y er taget sammen med det forbundne carbon for at danne carbonyl; V er C(O), C(=NR11), CH(NR12R13) eller N(R14)CH2; hvor N(R14) er bundet til C-10-carbon; hvor R11 er hydroxy eller alkoxy; R12 og R13 hver er uafhængigt udvalgt fra gruppen bestående af hydrogen, hydroxy, alkyl, alkoxy, heteroalkyl, aryl, arylalkyl, heteroaryl og heteroarylalkyl, der hver eventuelt er substitueret, og dimethylaminoalkyl, acyl, sulfonyl, ureido og carbamoyl; R14 er hydrogen, hydroxy, alkyl, alkoxy, heteroalkyl, aryl, arylalkyl, heteroaryl eller heteroarylalkyl, der hver eventuelt er substitueret, eller dimethylaminoalkyl, acyl, sulfonyl, ureido eller carbamoyl; W er H, F, Cl, Br, I eller OH; A er CH2, C(O), C(0)0, C(0)NH, S(0)2, S(0)2NH eller C(0)NHS(0)2; B er (CH2)n, hvor n er et heltal fra 0 til 10; eller en umættet carbonkæde med 2 til 10 carbonatomer; og C er hydrogen, hydroxy, alkyl, alkoxy, heteroalkyl, aryl, arylalkyl, heteroaryl eller heteroarylalkyl, der hver eventuelt er substitueret, eller acyl, acyloxy, sulfonyl, ureido eller carbamoyl; hvilken fremgangsmåde omfatter (at trinnet med
etahlerinn af kontakt mellem en forbindelse med formlen (III), eller et syreadditionssalt deraf, hvor Q i kombination med oximoxygenet danner et acetal eller ketal, eller Q er tropyl, og et acyleringsmiddel for at danne en forbindelse med formlen (IVt
eller et syreadditionssalt deraf, hvor R er en acylgruppe; (b) trinnet med etablering af kontakt mellem en forbindelse med formlen (IV), eller et syreadditionssalt deraf, og et methyleringsmiddel for at danne en forbindelse med formlen (V)_
eller et syreadditionssalt deraf; og (c) trinnet med etablering af kontakt mellem en forbindelse med formlen (V), eller et syreadditionssalt deraf, og et deoximeringsmiddel for at danne en forbindelse med formlen (II)
eller et syreadditionssalt deraf.
2. Fremgangsmåde ifølge krav 1, hvor R10 er hydrogen.
3. Fremgangsmåde ifølge krav 1 eller 2, hvor X og Y tages sammen med det forbundne carbon for at danne cabonyl.
4. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 3, hvor V er C(O).
5. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 4, hvor W er H eller F, fortrinsvis F.
6. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor A er CH2.
7. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 6, hvor B er (CH2)n, hvor n er 2 til 6, fortrinsvis 2 til 5, mere fortrinsvis 2 til 4, mere fortrinsvis 2 til 3 eller mere fortrinsvis 3.
8. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 7, hvor C er aminophenyl, fortrinsvis 3-aminophenyl.
9. Fremgangsmåde ifølge krav 1, hvor forbindelsen med formlen (I) er med formlen
eller et farmaceutisk acceptabelt salt deraf.
10. Fremgangsmåde ifølge krav 1, hvor forbindelsen med formlen (I) er med formlen
11. Fremgangsmåde til fremstil ing afen forbindelse med formlen (II);
eller et farmaceutisk acceptabelt salt deraf, hvor R er en acylgruppe; hvilken fremgangsmåde omfatter (a) trinnet med etablering af kontakt mellem en forbindelse med formlen (III),
eller et syreadditionssalt deraf, hvor Q i kombination med oximoxygenet danner et acetal eller ketal, eller Q er tropyl, og et acyleringsmiddel for at danne en forbindelse med formlen (IV)
_(IV)_ eller et syreadditionssalt deraf; (b) trinnet med etablering af kontakt mellem en forbindelse med formlen (IV), eller et syreadditionssalt deraf, og et methyleringsmiddel for at danne en forbindelse med formlen (V)
_(V)_ eller et syreadditionssalt deraf; og (c) trinnet med etablering af kontakt mellem en forbindelse med formlen (V), eller et syreadditionssalt deraf, og et deoximeringsmiddel for at danne en forbindelse med formlen (II).
12. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 11, hvor acyleringsmidlet er et anhydrid.
13. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 12, hvor methyleringsmidlet i trin (b) er methylbromid, methyliodid, dimethylsulfat, methyl p-toluensulfonat eller methylmethansulfonat; fortrinsvis methyliodid.
14. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 13, hvor deoximeringsmidlet i trin (c) omfatter et reduktionsmiddel.
15. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 13, hvor deoximeringsmidlet i trin (c) omfatter en uorganisk svovloxidforbindelse, fortrinsvis natriumhydrogensulfit, natriumpyrosulfat, natriumthiosulfat, natriumsulfit, natriumhydrosulfit, natriummetabisulfit, natriumbisulfit, natriumdithionat, kaliumhydrogensulfit, kaliumthiosulfat, kaliummetabisulfit, eller blandinger deraf, mere fortrinsvis natriummetabisulfit eller natriumbisulfit, eller en kombination deraf, og endnu mere fortrinsvis natriumbisulfit.
16. Fremgangsmåde eller forbindelse ifølge et hvilket som helst af kravene 1 til 15, hvor Q er 2-methoxy-2-propyl, 1-methoxycyclohexyl eller 1-isopropoxycyclohexyl, fortrinsvis 2-methoxy-2-propyl.
17. Fremgangsmåde eller forbindelse ifølge et hvilket som helst af kravene 1 til 16, hvor R er benzoyl.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34666410P | 2010-05-20 | 2010-05-20 | |
PCT/US2011/037330 WO2011146829A1 (en) | 2010-05-20 | 2011-05-20 | Processes for preparing macrolides and ketolides and intermediates therefor |
Publications (1)
Publication Number | Publication Date |
---|---|
DK2571506T3 true DK2571506T3 (da) | 2017-08-28 |
Family
ID=44992076
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK11784318.5T DK2571506T3 (da) | 2010-05-20 | 2011-05-20 | Fremgangsmåder til fremstilling af makrolider og ketolider og mellemprodukter dertil |
Country Status (16)
Country | Link |
---|---|
US (4) | US9051346B2 (da) |
EP (1) | EP2571506B1 (da) |
JP (1) | JP6184319B2 (da) |
KR (1) | KR101945324B1 (da) |
CN (2) | CN105198944B (da) |
AU (1) | AU2011255464C1 (da) |
BR (1) | BR112012029586A2 (da) |
CA (1) | CA2799937A1 (da) |
DK (1) | DK2571506T3 (da) |
ES (1) | ES2636948T3 (da) |
HK (2) | HK1181672A1 (da) |
IL (1) | IL223161A0 (da) |
PL (1) | PL2571506T3 (da) |
RU (1) | RU2608390C2 (da) |
SI (1) | SI2571506T1 (da) |
WO (1) | WO2011146829A1 (da) |
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-
2011
- 2011-05-20 DK DK11784318.5T patent/DK2571506T3/da active
- 2011-05-20 CA CA 2799937 patent/CA2799937A1/en not_active Abandoned
- 2011-05-20 CN CN201510604701.0A patent/CN105198944B/zh not_active Expired - Fee Related
- 2011-05-20 KR KR1020127032834A patent/KR101945324B1/ko active IP Right Grant
- 2011-05-20 CN CN201180026739.4A patent/CN102917708B/zh not_active Expired - Fee Related
- 2011-05-20 EP EP11784318.5A patent/EP2571506B1/en not_active Not-in-force
- 2011-05-20 SI SI201131256T patent/SI2571506T1/sl unknown
- 2011-05-20 PL PL11784318T patent/PL2571506T3/pl unknown
- 2011-05-20 US US13/699,020 patent/US9051346B2/en not_active Expired - Fee Related
- 2011-05-20 RU RU2012150753A patent/RU2608390C2/ru not_active IP Right Cessation
- 2011-05-20 BR BR112012029586A patent/BR112012029586A2/pt not_active IP Right Cessation
- 2011-05-20 ES ES11784318.5T patent/ES2636948T3/es active Active
- 2011-05-20 WO PCT/US2011/037330 patent/WO2011146829A1/en active Application Filing
- 2011-05-20 AU AU2011255464A patent/AU2011255464C1/en not_active Ceased
- 2011-05-20 JP JP2013511385A patent/JP6184319B2/ja active Active
-
2012
- 2012-11-20 IL IL223161A patent/IL223161A0/en unknown
-
2013
- 2013-08-02 HK HK13109063.8A patent/HK1181672A1/zh not_active IP Right Cessation
-
2015
- 2015-05-01 US US14/702,004 patent/US20150232500A1/en not_active Abandoned
-
2016
- 2016-06-15 HK HK16106890.0A patent/HK1218919A1/zh not_active IP Right Cessation
-
2018
- 2018-03-06 US US15/913,650 patent/US20190048035A1/en not_active Abandoned
-
2019
- 2019-11-25 US US16/693,978 patent/US20200087335A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
KR20130120374A (ko) | 2013-11-04 |
WO2011146829A1 (en) | 2011-11-24 |
AU2011255464A1 (en) | 2012-12-13 |
PL2571506T3 (pl) | 2017-10-31 |
US20200087335A1 (en) | 2020-03-19 |
RU2608390C2 (ru) | 2017-01-18 |
SI2571506T1 (sl) | 2017-12-29 |
RU2012150753A (ru) | 2014-06-27 |
US9051346B2 (en) | 2015-06-09 |
US20190048035A1 (en) | 2019-02-14 |
KR101945324B1 (ko) | 2019-02-07 |
BR112012029586A2 (pt) | 2016-08-02 |
HK1218919A1 (zh) | 2017-03-17 |
EP2571506A4 (en) | 2014-04-02 |
EP2571506B1 (en) | 2017-05-10 |
JP2013527187A (ja) | 2013-06-27 |
AU2011255464B2 (en) | 2016-06-16 |
CN102917708B (zh) | 2015-11-25 |
US20150232500A1 (en) | 2015-08-20 |
IL223161A0 (en) | 2013-02-03 |
CN105198944A (zh) | 2015-12-30 |
HK1181672A1 (zh) | 2013-11-15 |
AU2011255464C1 (en) | 2017-02-23 |
CN105198944B (zh) | 2018-06-01 |
JP6184319B2 (ja) | 2017-08-23 |
ES2636948T3 (es) | 2017-10-10 |
CA2799937A1 (en) | 2011-11-24 |
EP2571506A1 (en) | 2013-03-27 |
US20130066056A1 (en) | 2013-03-14 |
CN102917708A (zh) | 2013-02-06 |
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