HRP20170446T1 - Postupak pripreme spojeva korisnih kao inhibitori sglt2 - Google Patents
Postupak pripreme spojeva korisnih kao inhibitori sglt2 Download PDFInfo
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- HRP20170446T1 HRP20170446T1 HRP20170446TT HRP20170446T HRP20170446T1 HR P20170446 T1 HRP20170446 T1 HR P20170446T1 HR P20170446T T HRP20170446T T HR P20170446TT HR P20170446 T HRP20170446 T HR P20170446T HR P20170446 T1 HRP20170446 T1 HR P20170446T1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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- 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
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/7036—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (30)
1. Postupak pripreme spojeva formule (I)
[image]
pri čemu su Prsten A i Prsten B jedan od sljedećih:
(1) Prsten A je opciono supstituirani nezasićeni monciklično heterociklični prsten, i prsten B je opciono supstituirani nezasićeni monociklično heterociklični prsten, opciono supstituirani nezasićeni fuzirani heterobiciklični prsten ili opciono supstituirani benzenov prsten; ili
(2) Prsten A je opciono supstituirani benzenov prsten, i Prsten B je opciono supstituirani nezasićeni monociklično heterociklični prsten, ili opciono supstituirani nezasićeni fuzirani heterobiciklični prsten, pri čemu je Y povezan za heterociklični prsten fuziranog heterobicikličnog prstena; ili
(3) Prsten A je opciono supstituirani nezasićeni fuzirani heterobiciklični prsten, pri čemu su šećerni ostatak X-(šećer) i ostatak -Y- (Prsten B) oba na istom heterocikličnom prstenu fuziranog heterobicikličnog prstena, i Prsten B je opciono supstituirani nezasićeni monociklični heterociklični prsten, opciono supstituirani nezasićeni fuzirani heterobiciklični prsten, ili opciono supstituirani benzenov prsten;
X je atom ugljika;
Y je -(CH2)n-; pri čemu n je 1 ili 2;
pod uvjetom da je u Prstenu A, X dio nezasićene veze;
ili farmaceutski prihvatljiva sol ili njihov solvate; sadržavajući
[image]
reakciju spoja formule (VII), pri čemu je M2 vrsta cinka, sa spojem formule (VIII), pri čemu je svaka Z nezavisno izabrana zaštitna grupa kisika, i pri čemu je LG2odlazeća grupa; u smjesi eterskog otapala i ugljikovodičnog otapala; kako bi se dobio odgovarajući spoj formule (IX);
[image]
de-protektirajući spoj formule (IX); kako bi se dobio odgovarajući spoj formule (I).
2. Postupak kao u patentnom zahtjevu 1, naznačen time da dalje sadrži
[image]
reakciju spoja formule (V), pri čemu je LG1 odlazeća grupa, s organo-litijevim reagensom; u smjesi eterskog otapala i ugljikovodičnog otapala; kako bi se dobio odgovarajući spoj formule (VI), pri čemu je M1 litij;
[image]
reakcija spoja formule (VI) s cinkovom soli ili kompleksom amina od cink halida; u smjesi eterskog otapala i ugljikovodičnog otapala; kako bi se dobio odgovarajući spoj formule (VII).
3. Postupak kao u patentnom zahtjevu 1, naznačen time da M2 je ZnBr, Z je pivaloil i LG2 je bromo.
4. Postupak kao u patentnom zahtjevu 1, naznačen time da je spoj formule (VIII) prisutan u količini u rasponu od oko 1.0 do oko 1.1 molarnih ekvivalenata.
5. Postupak kao u patentnom zahtjevu 2, naznačen time da organo-litijev reagens je n-heksil-litij; i pri čemu je n-heksil litij prisutan u količini u rasponu od oko 1.0 do oko 1.2 molarna ekvivalenta.
6. Postupak kao u patentnom zahtjevu 2, naznačen time da spoj formule (VI) reagira s cinkovom soli; pri čemu cinkova sol je cink dibromid i pri čemu je cink dibromid prisutan u količini u rasponu od oko 0.33 do oko 1.0 molarnih ekvivalenata.
7. Postupak kao u patentnom zahtjevu 1, naznačen time da
X je atom ugljika;
Prsten A je izabran iz grupe koja se sastoji od 4-metilfenila i 4-klorofenila;
Y je -CH2- i vezan je na poziciji 3 Prstena A; i
Prsten B je izabran iz grupe koja se sastoji od 2-(5-(4-fluorofenil)-tienila) i 2-(5-(6-fluoro-pirid-3-il)-tienila).
8. Postupak kao u patentnom zahtjevu 1, naznačen time da je X atom ugljika; Prsten A je 4-metil-fenil; Y je -CH2- i vezan je na poziciji 3 Prstena A; i Prsten B je 5-(4-fluorofenil)-tien-2-il.
9. Postupak prema patentnom zahtjevu 1 za pripremu spoja formule (I-S)
[image]
ili njegov solvat; sadržavajući
[image]
reakciju spoja formule (VII-S), pri čemu je M2 vrsta cinka, sa spojem formule (VIII-S), pri čemu je svaka Z nezavisno izabrana zaštitna grupa kisika, i pri čemu je LG2 odlazeća grupa;
u smjesi eterskog otapala i ugljikovodičnog otapala; kako bi se dobio odgovarajući spoj formule (IX-S);
[image]
uklanjajući zaštitu spoja formula (IX-S); kako bi se dobio odgovarajući spoj formule (I-S).
10. Postupak kao u patentnom zahtjevu 9, naznačen time da M2 je ZnBr.
11. Postupak kao u patentnom zahtjevu 9, naznačen time da svaka Z je pivaloil i pri čemu LG2 je bromo.
12. Postupak kao u patentnom zahtjevu 9, naznačen time da je spoj formule (VIII-S) prisutan u količini u rasponu od oko 0.8 do oko 1.25 molarnih ekvivalenata.
13. Postupak kao u patentnom zahtjevu 12, naznačen time da je spoj formule (VIII-S) prisutan u količini u rasponu od oko 1.0 do oko 1.1 molarnih ekvivalenata.
14. Postupak kao u patentnom zahtjevu 9, naznačen time da je spoj formule (VIII-S) u otopini ugljikovodičnog otapala dodan u spoj formule (VII-S) u otopini eterskog otapala.
15. Postupak kao u patentnom zahtjevu 9, naznačen time da je spoj formule (VII-S) reagirao sa spojem formule (VIII-S) na temperaturi u rasponu od oko 60°C do oko 95°C.
16. Postupak kao u patentnom zahtjevu 9, naznačen time da dalje sadrži
[image]
reakciju spoja formule (V-S), pri čemu je LG1odlazeća grupa; s organo-litijevim reagensom; u smjesi eterskog otapala i ugljikovodičnog otapala; kako bi se dobio odgovarajući spoj formule (VI-S), pri čemu je M1 litij;
[image]
reakciju spoja formule (VI-S) sa soli cinka ili kompleksom amina od cink halida; u smjesi eterskog otapala i ugljikovodičnog otapala; kako bi se dobio odgovarajući spoj formule (VII-S).
17. Postupak kao u patentnom zahtjevu 16, naznačen time da je organo-litijev reagens n-heksil litij.
18. Postupak kao u patentnom zahtjevu 16, naznačen time da je organo-litijev reagens prisutan u količini u rasponu od oko 0.5 do oko 2.0 molarna ekvivalenta.
19. Postupak kao u patentnom zahtjevu 18, naznačen time da je organo-litijev reagens prisutan u količini u rasponu od oko 1.0 do oko 1.2 molarna ekvivalenta.
20. Postupak kao u bilo kojem od patentnog zahtjeva 1, patentnog zahtjeva 2, patentnog zahtjeva 9 ili patentnog zahtjeva 16, naznačen time da je etersko otapalo di-n-butil eter ili ciklopentil metil eter i pri čemu je ugljikovodično otapalo toluen.
21. Postupak kao u patentnom zahtjevu 16, naznačen time da je spoj formule (V-S) reagirao s organo-litijevim reagensom, na temperaturi u rasponu od oko -78°C do oko sobne temperature.
22. Postupak kao u patentnom zahtjevu 2 ili patentnom zahtjevu 16, naznačen time da je cinkova sol izabrana iz grupe koja se sastoji od cink dibromida (ZnBr2), cink dijodida (Znl2) i cink ditriflata; i pri čemu je kompleks amina od cink halida izabran iz grupe koja se sastoji od kompleksa piridin cink bromida i kompleksa N-metilmorfolin cink bromida.
23. Postupak kao u patentnom zahtjevu 16, naznačen time da je spoj formule (VI-S) reagiralo s cinkovom soli; i pri čemu je cinkova sol cink dibromid.
24. Postupak kao u patentnom zahtjevu 23, naznačen time da je zink dibromid prisutan u količini u rasponu od oko 0.33 do oko 1.0 molarnog ekvivalenta.
25. Postupak kao u patentnom zahtjevu 24, naznačen time da je zink dibromid prisutan u količini od oko 0.5 molarnih ekvivalenata.
26. Postupak kao u patentnom zahtjevu 16, naznačen time da je spoj formule (VI-S) reagiralo sa soli cinka u prisustvu soli amina ili litija.
27. Postupak kao u patentnom zahtjevu 26, naznačen time da je sol amina ili litija izabrana iz grupe koja se sastoji od litij bromida, litij jodida, piridina, N-metil morfolina, 2,6-lutidina i TMEDA; i pri čemu je sol amina ili litija poželjno prisutna u količini u rasponu od oko 1.0 do oko 2.0 molarna ekvivalenata.
28. Postupak za pripremu spoja formule (X-P)
[image]
pri čemu su obje Q1 grupe iste i jesu
[image]
i pri čemu su Prsten A i Prsten B jedan od sljedećeg:
(1) Prsten A je opciono supstituirani nezasićeni monociklično heterociklični prsten, i Prsten B je opciono supstituirani nezasićeni monociklično heterociklični prsten, opciono supstituirani nezasićeni fuzirani heterobiciklični prsten ili opciono supstituirani benzenov prsten; ili
(2) Prsten A je opciono supstituirani benzenov prsten, i Prsten B je opciono supstituirani nezasićeni monociklični heterociklični prsten, ili opciono supstituirani nezasićeni fuzirani heterobiciklični prsten, pri čemu je Y povezan za heterociklični prsten fuziranog heterobicikličnog prstena; ili
(3) Prsten A je opciono supstituirani nezasićeni fuzirani heterobiciklični prsten, pri čemu su ostatak šećera X-(šećer) i ostatak -Y-(Prsten B) oba na istom heterocikličnom prstenu fuziranog heterobicikličnog prstena, i Prsten B je opciono supstituirani nezasićeni monociklični heterociklični prsten, opciono supstituirani nezasićeni fuzirani heterobiciklični prsten, ili opciono supstituirani benzenov prsten;
X je atom ugljika;
Y je -(CH2)n-; pri čemu n je 1 ili 2;
pod uvjetom da je u Prstenu A, X dio nezasićene veze;
[image]
reakciju spoja formule (Z1), pri čemu Ha2 je halogen, sa litij trialkil magnezatom, spojem formule (Z2); u pogodno izabranom anhidridnom organskom otapalu ili smjesi ili anhidridnim organskim otapalima; kako bi se dobio odgovarajući spoj formule (Z3);
[image]
reakciju spoja formule (Z3) sa kompleksom cinka halida-litij halida, spoja formule (Z4 ), pri čemu je Ha1 halogen; u pogodno izabranom anhidridnom organskom otapalu ili smjesi ili anhidridnim organskim otapalima; kako bi se dobio odgovarajući spoj formule (X-P).
29. Postupak kao u patentnom zahtjevu 28, naznačen time da je spoj formule (Z2) litij dibutil heksilmagnezat; i pri čemu je spoj formule (Z4) kompleks cink bromid-litij bromida.
30. Postupak kao u patentnom zahtjevu 28, naznačen time da spoj formule (X-P) je spoj formule (X-S).
[image]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25137809P | 2009-10-14 | 2009-10-14 | |
| PCT/US2010/052598 WO2011047113A1 (en) | 2009-10-14 | 2010-10-14 | Process for the preparation of compounds useful as inhibitors of sglt2 |
| EP10768162.9A EP2488515B1 (en) | 2009-10-14 | 2010-10-14 | Process for the preparation of compounds useful as inhibitors of sglt2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170446T1 true HRP20170446T1 (hr) | 2017-05-19 |
Family
ID=43127364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170446TT HRP20170446T1 (hr) | 2009-10-14 | 2010-10-14 | Postupak pripreme spojeva korisnih kao inhibitori sglt2 |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US9174971B2 (hr) |
| EP (1) | EP2488515B1 (hr) |
| JP (1) | JP5833011B2 (hr) |
| KR (1) | KR101730920B1 (hr) |
| CN (1) | CN102648196B (hr) |
| AU (1) | AU2010306797B2 (hr) |
| BR (1) | BR112012008939B1 (hr) |
| CA (1) | CA2777528C (hr) |
| CL (1) | CL2012000929A1 (hr) |
| CY (1) | CY1118777T1 (hr) |
| DK (1) | DK2488515T3 (hr) |
| EA (1) | EA024368B1 (hr) |
| ES (1) | ES2620469T3 (hr) |
| HR (1) | HRP20170446T1 (hr) |
| HU (1) | HUE031375T2 (hr) |
| IL (1) | IL219094A (hr) |
| IN (1) | IN2012DN03299A (hr) |
| LT (1) | LT2488515T (hr) |
| ME (1) | ME02634B (hr) |
| MX (1) | MX340214B (hr) |
| NZ (1) | NZ599306A (hr) |
| PH (1) | PH12012500698A1 (hr) |
| PL (1) | PL2488515T3 (hr) |
| PT (1) | PT2488515T (hr) |
| RS (1) | RS55909B1 (hr) |
| SG (1) | SG10201500258WA (hr) |
| SI (1) | SI2488515T1 (hr) |
| SM (1) | SMT201700162T1 (hr) |
| UA (1) | UA109883C2 (hr) |
| WO (1) | WO2011047113A1 (hr) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA020209B1 (ru) * | 2007-09-10 | 2014-09-30 | Янссен Фармацевтика Н.В. | Способ получения соединений, применимых в качестве ингибиторов натрийзависимого переносчика глюкозы |
| US9056850B2 (en) * | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| US20110009347A1 (en) * | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| PT2451797E (pt) | 2009-07-10 | 2013-06-25 | Janssen Pharmaceutica Nv | Processo de cristalização para o 1-(β-d-glucopiranosilo)-4-metilo-3-[5-(4-fluorofenilo)-2-tienilometilo]benzeno |
| LT2568988T (lt) | 2010-05-11 | 2016-09-12 | Janssen Pharmaceutica, N.V. | Farmacinės kompozicijos, apimančios 1-(beta-d-gliukopiranozil)-2-tienilmetilbenzeno darinius kaip sglt inhibitorius |
| US10544135B2 (en) * | 2011-04-13 | 2020-01-28 | Janssen Pharmaceutica Nv | Process for the preparation of compounds useful as inhibitors of SGLT2 |
| US9035044B2 (en) | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| WO2013061105A2 (en) * | 2011-10-28 | 2013-05-02 | Debreceni Egyetem | Glycogen phosphorylase inhibitors |
| KR20140097258A (ko) | 2011-10-31 | 2014-08-06 | 시노팜 타이완 리미티드 | Sglt2 억제제의 결정성 및 비-결정성 형태 |
| US9193751B2 (en) | 2012-04-10 | 2015-11-24 | Theracos, Inc. | Process for the preparation of benzylbenzene SGLT2 inhibitors |
| WO2014132940A1 (ja) | 2013-02-26 | 2014-09-04 | 田辺三菱製薬株式会社 | α－ハロテトラアシルグルコースの製造方法 |
| MX355831B (es) | 2013-05-08 | 2018-05-02 | Lek Pharmaceuticals | NOVEDOSOS HIDRATOS CRISTALINOS DE 1-(ß-D-GLUCOPIRANOSIL)-4-METIL-3 -[5-(4-FLUORO-FENIL)-2-TIENIL-METIL]-BENCENO. |
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