HRP20171914T1 - Postupak za dobivanje spojeva koji su korisni kao inhibitori sglt - Google Patents
Postupak za dobivanje spojeva koji su korisni kao inhibitori sglt Download PDFInfo
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- HRP20171914T1 HRP20171914T1 HRP20171914TT HRP20171914T HRP20171914T1 HR P20171914 T1 HRP20171914 T1 HR P20171914T1 HR P20171914T T HRP20171914T T HR P20171914TT HR P20171914 T HRP20171914 T HR P20171914T HR P20171914 T1 HRP20171914 T1 HR P20171914T1
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- 150000001875 compounds Chemical class 0.000 title claims 50
- 238000000034 method Methods 0.000 title claims 19
- 239000003112 inhibitor Substances 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 33
- 239000003960 organic solvent Substances 0.000 claims 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 6
- -1 alkyl lithium Chemical compound 0.000 claims 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052744 lithium Inorganic materials 0.000 claims 6
- 238000010511 deprotection reaction Methods 0.000 claims 4
- KVWLUDFGXDFFON-UHFFFAOYSA-N lithium;methanidyl(trimethyl)silane Chemical compound [Li+].C[Si](C)(C)[CH2-] KVWLUDFGXDFFON-UHFFFAOYSA-N 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 150000007530 organic bases Chemical class 0.000 claims 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- FYCMEIAQPYJEOX-UHFFFAOYSA-N [Li]C[Si](CC)(CC)CC Chemical compound [Li]C[Si](CC)(CC)CC FYCMEIAQPYJEOX-UHFFFAOYSA-N 0.000 claims 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 3
- 239000012346 acetyl chloride Substances 0.000 claims 3
- 150000001555 benzenes Chemical group 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 3
- RQLKAKQYERUOJD-UHFFFAOYSA-N lithium;1,3,5-trimethylbenzene-6-ide Chemical compound [Li+].CC1=CC(C)=[C-]C(C)=C1 RQLKAKQYERUOJD-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
Classifications
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
-
- 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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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (18)
1. Postupak za dobivanje spoja formule (I)
[image]
naznačen time da su prsten A i prsten B jedan od slijedećih:
(1) prsten A je proizvoljno supstituiran nezasićeni monociklički heterociklički prsten, i prsten B je proizvoljno supstituiran nezasićeni monociklički heterociklički prsten, proizvoljno supstituiran nezasićeni kondenzirani heterobiciklički prsten, ili proizvoljno supstituiran benzenov prsten; ili
(2) prsten A je proizvoljno supstituiran benzenov prsten, i prsten B je proizvoljno supstituiran nezasićeni monociklički heterociklički prsten, ili proizvoljno supstituiran nezasićeni kondenzirani heterobiciklički prsten, pri čemu je Y vezan za heterociklički prsten kondenziranog heterobicikličkog prstena; ili
(3) prsten A je proizvoljno supstituiran nezasićeni kondenzirani heterobiciklički prsten, pri čemu su šećerni dio X-(šećer) i dio -Y-(prsten B) oba na istom heterocikličkom prstenu kondenziranog heterobicikličkog prstena, i prsten B je proizvoljno supstituiran nezasićeni monociklički heterociklički prsten, proizvoljno supstituiran nezasićeni kondenzirani heterobiciklički prsten, ili proizvoljno supstituiran benzenov prsten;
X je ugljikov atom;
Y je -(CH2)n-; pri čemu n je 1 ili 2;
uz uvjet da u prstenu A, X je dio nezasićene veze;
ili njegova farmaceutski prihvatljiva sol;
koji obuhvaća
[image]
reagiranje spoja formule (V) sa spojem formule (VI-S), u prisutnosti alkil litija izabranog iz skupine koji čine skupina koju čine (trimetilsilil)metil litij, 2,4,6-trimetilfenil litij i (trietilsilil)metil litij u organskom otapalu, na temperaturi u rasponu od 0°C do -78°C; da se dobije odgovarajući spoj s formulom (VII);
i pri čemu je alkil litij dodan u smjesu spoja formule (V) i spoja formule (VI-S);
[image]
reagiranje spoja formule (VII) sa BF3OEt2, u prisutnosti trialkilsilana u organskom otapalu, da se dobije odgovarajući spoj s formulom (VIII);
[image]
reagiranje spoja formule (VIII) s acetanhidridom ili acetil kloridom, u prisutnosti organske baze, čiste ili u organskom otapalu, da se dobije odgovarajući spoj s formulom (IX); i
[image]
uklanjanje zaštite sa spoja formule (IX), da se dobije odgovarajući spoj s formulom (I).
2. Postupak za dobivanje spoja formule (I-S)
[image]
ili njegove farmaceutski prihvatljive soli;
naznačen time da sadrži
[image]
reagiranje spoja formule (V-S), sa spojem formule (VI-S), u prisutnosti alkil litija izabranog iz skupine koju čine (trimetilsilil)metil litij, 2,4,6-trimetilfenil litij i (trietilsilil)metil litij, u organskom otapalu, na temperaturi u rasponu od 0°C do -78°C, da se dobije odgovarajući spoj s formulom (VII-S);
i pri čemu je doda alkil litij u smjesu spoja formule (V-S) i spoja formule (VI-S);
[image]
reagiranje spoja formule (VII-S) sa BF3OEt2, u prisutnosti trialkilsilana, u organskom otapalu, da se dobije odgovarajući spoj s formulom (VIII-S);
[image]
reagiranje spoja formule (VIII-S) sa acetanhidridom ili acetil kloridom, u prisutnosti organske baze, čiste ili u organskom otapalu, da se dobije odgovarajući spoj s formulom (IX-S); i
[image]
uklanjanje zaštite sa spoja formule (IX-S) da se dobije odgovarajući spoj s formulom (I-S).
3. Postupak dobivanja spoja formule (I-K)
[image]
ili njegova farmaceutski prihvatljiva sol;
naznačen time da sadrži
[image]
reagiranje spoja formule (V-K), sa spojem formule (VI-S), u prisutnosti alkil litija izabranog iz skupine koju čine (trimetilsilil)metil litij, 2,4,6-trimetilfenil litij i (trietilsilil)metil litij, u organskom otapalu, na temperaturi u rasponu od 0°C do -78°C, da se dobije odgovarajući spoj s formulom (VII-K);
i pri čemu je alkil litij dodan u smjesu spoja formule (V-K) i spoja formule (VI-S);
[image]
uklanjanje zaštite spoja formule (VII-K) da se dobije odgovarajući spoj s formulom (X-K);
[image]
reagiranje spoja formule (X-K) sa BF3OEt2, u prisutnosti trialkilsilana, u organskom otapalu, da se dobije odgovarajući spoj s formulom (VIII-K);
[image]
reagiranje spoja formule (VIII-K) sa acetanhidridom ili acetilkloridom, u prisutnosti organske baze, čiste ili u organskom otapalu, da se dobije odgovarajući spoj s formulom (IX-K); i
[image]
uklanjanje zaštite sa spoja formule (IX-K) da bi se dobilo spoj s formulom (I-K).
4. Postupak prema zahtjevu 1, zahtjevu 2 ili zahtjevu 3, naznačen time da je spoj s formulom (VI-S) prisutan u količini u rasponu od 1,0 do 1,25 molarnih ekvivalenata.
5. Postupak prema zahtjevu 1, zahtjevu 2 ili zahtjevu 3, naznačen time da alkillitij je (trimetilsilil)metil litij i pri čemu je alkil litij u količini u rasponu od 2,0 do 2,5 molarna ekvivalenta.
6. Postupak prema zahtjevu 1, zahtjevu 2 ili zahtjevu 3, naznačen time da je BF3OEt2 prisutan u količini u rasponu od 2,0 do 6,0 molarnih ekvivalenata i pri čemu trialkilsilan je Et3SiH i prisutan je u količini u rasponu od 2,0 do 6,0 molarnih ekvivalenata.
7. Postupak prema zahtjevu 6, naznačen time da molarni omjer BF3OEt2 : Et3SiH je 1:1.
8. Postupak prema zahtjevu 1, zahtjevu 2 ili zahtjevu 3, naznačen time da je organska baza NMM.
9. Postupak prema zahtjevu 1, naznačen time da spoj s formulom (VIII) reagira s acetanhidridom i pri čemu je acetandhidrid prisutan u količini u rasponu od 4,5 do 5,0 molarnih ekvivalenata.
10. Postupak prema zahtjevu 1, naznačen time da spoj s formulom (VIII) reagira s acetanhidridom u prisutnosti katalitičke količine DMAP.
11. Postupak prema zahtjevu 1, naznačen time da se spoju s formulom (IX) uklanja zaštita reagiranjem sa bazom.
12. Postupak prema zahtjevu 2, naznačen time da spoj s formulom (VIII-S) reagira s acetanhidridom u prisutnosti količine u rasponu od 4,5 do 5,0 molarnih ekvivalenata.
13. Postupak prema zahtjevu 2, naznačen time da spoj s formulom (VIII-S) reagira s acetanhidridom u prisutnosti katalitičke količine DMAP.
14. Postupak prema zahtjevu 2, naznačen time da je spoj s formulom (IX-S) nadalje suspendiran u metanolu i filtriran.
15. Postupak prema zahtjevu 2, naznačen time da se sa spoja formule (IX-S) uklanja zaštita reagiranjem sa bazom.
16. Postupak prema zahtjevu 3, naznačen time da spoj s formulom (VIII-K) reagira s acetanhidridom i pri čemu je acetanhidrid prisutan u količini u rasponu od 4,5 do 5,0 molarnih ekvivalenata.
17. Postupak prema zahtjevu 3, naznačen time da spoj s formulom (VIII-K) reagira s acetanhidridom u prisutnosti katalitičke količine DMAP.
18. Postupak prema zahtjevu 3, naznačen time da se sa spoja formule (IX-K) uklanja zaštita reagiranjem sa bazom.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97106707P | 2007-09-10 | 2007-09-10 | |
| US1882208P | 2008-01-03 | 2008-01-03 | |
| PCT/US2008/075700 WO2009035969A1 (en) | 2007-09-10 | 2008-09-09 | Process for the preparation of compounds useful as inhibitors of sglt |
| EP08831144.4A EP2200606B1 (en) | 2007-09-10 | 2008-09-09 | Process for the preparation of compounds useful as inhibitors of sglt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171914T1 true HRP20171914T1 (hr) | 2018-03-23 |
Family
ID=40452424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171914TT HRP20171914T1 (hr) | 2007-09-10 | 2017-12-11 | Postupak za dobivanje spojeva koji su korisni kao inhibitori sglt |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US9024009B2 (hr) |
| EP (1) | EP2200606B1 (hr) |
| JP (2) | JP5596545B2 (hr) |
| KR (1) | KR101552187B1 (hr) |
| CN (1) | CN101801371B (hr) |
| AR (1) | AR071246A1 (hr) |
| AU (1) | AU2008299102B2 (hr) |
| BR (1) | BRPI0816258B8 (hr) |
| CA (1) | CA2699285C (hr) |
| CL (1) | CL2008002685A1 (hr) |
| CY (1) | CY1119706T1 (hr) |
| DK (1) | DK2200606T3 (hr) |
| EA (1) | EA020209B1 (hr) |
| ES (1) | ES2647504T3 (hr) |
| HK (1) | HK1144554A1 (hr) |
| HR (1) | HRP20171914T1 (hr) |
| HU (1) | HUE035130T2 (hr) |
| IL (1) | IL204145A (hr) |
| LT (1) | LT2200606T (hr) |
| ME (1) | ME03072B (hr) |
| MX (1) | MX2010002695A (hr) |
| MY (1) | MY162628A (hr) |
| NO (1) | NO2200606T3 (hr) |
| NZ (1) | NZ600110A (hr) |
| PL (1) | PL2200606T3 (hr) |
| PT (1) | PT2200606T (hr) |
| RS (1) | RS56990B1 (hr) |
| SI (1) | SI2200606T1 (hr) |
| TW (2) | TWI533870B (hr) |
| UA (1) | UA105480C2 (hr) |
| WO (1) | WO2009035969A1 (hr) |
| ZA (1) | ZA201002513B (hr) |
Families Citing this family (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7007443B2 (en) | 2003-06-27 | 2006-03-07 | Forhealth Technologies, Inc. | System and method for bandoliering syringes |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| UY30730A1 (es) † | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
| CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| MX2011001525A (es) | 2008-08-15 | 2011-03-29 | Boehringer Ingelheim Int | Derivados de purina para su uso en el tratamiento de enfermedades relacionadas con fab. |
| ME02702B (me) | 2008-08-22 | 2017-10-20 | Theracos Sub Llc | Postupci za pripremu inhibitora sgl t2 |
| US9056850B2 (en) * | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
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