HRP20150702T1 - Supstituirani 4-aril-1,4-dihidro-1,6-naftiridinamidi i njihova uporaba - Google Patents
Supstituirani 4-aril-1,4-dihidro-1,6-naftiridinamidi i njihova uporaba Download PDFInfo
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- HRP20150702T1 HRP20150702T1 HRP20150702TT HRP20150702T HRP20150702T1 HR P20150702 T1 HRP20150702 T1 HR P20150702T1 HR P20150702T T HRP20150702T T HR P20150702TT HR P20150702 T HRP20150702 T HR P20150702T HR P20150702 T1 HRP20150702 T1 HR P20150702T1
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- 150000001875 compounds Chemical class 0.000 claims 22
- 150000003839 salts Chemical group 0.000 claims 11
- 239000012453 solvate Chemical group 0.000 claims 10
- 239000012442 inert solvent Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- -1 for example Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 206010020571 Hyperaldosteronism Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 102220475869 Keratin, type I cytoskeletal 10_R12A_mutation Human genes 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 229940122434 Calcium sensitizer Drugs 0.000 claims 1
- 241000208011 Digitalis Species 0.000 claims 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 229960004676 antithrombotic agent Drugs 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 claims 1
- 229960005156 digoxin Drugs 0.000 claims 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 150000007928 imidazolide derivatives Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002461 renin inhibitor Substances 0.000 claims 1
- 229940086526 renin-inhibitors Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Claims (10)
1. Spoj s formulom (I)
[image]
u kojoj
D je C-R4 u kojem
R4 je vodik ili metil,
Ar je skupina s formulom
[image]
u kojoj
* je spojnica
i
R9 je etil, metoksi ili trifluorometoksi,
R1 je metil ili trifluorometil,
R2 je metil, etil, n-propil ili izopropil
i
R3 je vodik ili metil,
i soli, solvati i solvati njihovih soli.
2. Spoj prema zahtjevu 1 naznačen time da ima jednu od slijedećih struktura:
[image]
i
[image]
i soli, solvati i solvati njihovih soli.
3. Spoj prema zahtjevu 1 ili 2 naznačen time da ima jednu od slijedećih struktura:
[image]
[image]
[image]
i soli, solvati i solvati njihovih soli.
4. Spoj prema zahtjevu 1, 2 ili 3 naznačen time da ima slijedeću strukturu:
[image]
i soli, solvati i solvati njegovih soli.
5. Postupak za pripravu spojeva formule (I) kako je definirano u zahtjevima 1 do 4, naznačen time da spoj s formulom (II)
[image]
u kojoj Ar ima značenje navedeno u zahtjevima 1 do 4,
reagira u inertnom otapalu, gdje je prikladno u prisutnosti kiseline, u kombinaciji kiselina/baza i/ili u sredstvu za dehidraciju, sa spojem s formulom (III)
[image]
u kojoj R1 ima značenje navedeno u zahtjevima 1 do 4, i
T je alil ili 2-cijanoetil,
da se dobije spoj s formulom (IV)
[image]
u kojoj Ar, T i R1 svaki imaju gore navedena značenja,
potonji se zatim kondenzira u inertnom otapalu sa spojem s formulom (V)
[image]
u kojoj D i R3 imaju značenja navedena u zahtjevima 1 do 4,
da se dobije spoj s formulom (VI)
[image]
u kojoj Ar, D, T, R1 i R3 svaki imaju gore navedena značenja,
zatim spojevi formule (VI) alkiliraju u inertnom otapalu, gdje je prikladno u prisutnosti baze, sa spojem s formulom (VII) ili trialkiloksonijevom soli s formulom (VIII)
[image]
u kojoj
R12 je (C1-C6)-alkil koji može biti supstituiran s (C3-C7)-cikloalkilom ili do tri puta s fluorom,
R12A je metil ili etil,
X je izlazna skupina kao, na primjer, halogen, mesilat, tozilat ili triflat,
i
Y- je ne-nukleofilni anion kao, na primjer, tetrafluoroborat,
ili u prisutnosti kiseline s trialkil ortoformatom s formulom (IX)
[image]
u kojoj R12A ima gore navedeno značenje,
da se dobiju spojevi s formulom (X-A)
[image]
u kojoj Ar, D, T, R1, R3 i R12 svaki imaju gore navedena značenja,
ili spojevi s formulom (VI) reagiraju u inertnom otapalu u prisutnosti baze sa spojem s formulom (XI)
[image]
u kojoj R11 ima značenje navedeno u zahtjevu 1 ili 2,
da se dobiju spojevi s formulom (X-B)
[image]
u kojoj Ar, D, T, R1, R3 i R11 svaki imaju gore navedena značenja,
zatim ester skupina T u spojevima s formulom (X-A) ili (X-B) je uklonjena da se dobiju karboksilne kiseline s formulom (XII)
[image]
u kojoj Ar, D, R1, R2 i R3 svaki imaju značenja navedena u zahtjevima 1 do 4,
tada se pretvara s 1,1'-karbonildiimidazolom u imidazolide s formulom (XIII)
[image]
u kojoj Ar, D, R1, R2 i R3 svaki imaju gore navedena značenja,
i potonji zatim reagiraju u inertnom otapalu, kada je to prikladno u prisutnosti pomoćne baze, s amonijakom da se dobiju amidi s formulom (I),
i gdje je to prikladno spojevi formule (I) se odvajaju postupcima poznatim stručnjaku u njihove enantiomere i/ili diastereomere, i/ili se pretvaraju s prikladnim (i) otapalima i/ili (ii) bazama ili kiselinama u solvate, soli i/ili solvate njihovih soli.
6. Spoj s formulom (I) kako je definirano u zahtjevima 1 do 4 naznačen time da je za uporabu kod liječenja i/ili sprječavanja bolesti.
7. Uporaba spoja s formulom (I) kako je definirano u zahtjevima 1 do 4 naznačena time da je za proizvodnju lijeka za liječenje i/ili sprječavanje aldosteronizma, visokog krvnog tlaka, kroničnog zatajenja srca, posljedica infarkta miokarda, ciroze jetre, zatajenja bubrega i moždanog udara.
8. Lijek naznačen time da sadrži spoj s formulom (I) kako je definirano u zahtjevima 1 do 4 u kombinaciji s inertnom, ne-toksičnom, farmaceutski prikladnom pomoćnom tvari.
9. Lijek naznačen time da sadrži spoj s formulom (I) kako je definirano u zahtjevima 1 do 4 u kombinaciji s jednom ili više dodatnih aktivnih tvari odabranih iz skupine koju čine inhibitori ACE, inhibitori renina, antagonisti receptora angiotenzina II, beta-blokatori, acetilsalicilna kiselina, diuretici, antagonisti kalcija, statini, derivati digitalisa (digoksina), senzibilizatori kalcija, nitrati i antitrombotici.
10. Lijek prema zahtjevima 8 ili 9 naznačen time da je za uporabu kod liječenja i/ili sprječavanja aldosteronizma, visokog krvnog tlaka, kroničnog zatajenja srca, posljedica infarkta miokarda, ciroze jetre, zatajenja bubrega i moždanog udara.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007009494A DE102007009494A1 (de) | 2007-02-27 | 2007-02-27 | Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung |
| PCT/EP2008/001257 WO2008104306A2 (de) | 2007-02-27 | 2008-02-19 | Substituierte 4-aryl-1,4-dihydro-1,6-naphthyridinamide und ihre verwendung |
| EP08715849.9A EP2132206B1 (de) | 2007-02-27 | 2008-02-19 | Substituierte 4-aryl-1,4-dihydro-1,6-naphthyridinamide und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150702T1 true HRP20150702T1 (hr) | 2015-08-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150702TT HRP20150702T1 (hr) | 2007-02-27 | 2015-06-30 | Supstituirani 4-aril-1,4-dihidro-1,6-naftiridinamidi i njihova uporaba |
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Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011150286A2 (en) | 2010-05-26 | 2011-12-01 | Satiogen Pharmaceuticals,Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
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