HRP20100694T1 - Derivati adenozina kao agonisti a2a receptora - Google Patents
Derivati adenozina kao agonisti a2a receptora Download PDFInfo
- Publication number
- HRP20100694T1 HRP20100694T1 HR20100694T HRP20100694T HRP20100694T1 HR P20100694 T1 HRP20100694 T1 HR P20100694T1 HR 20100694 T HR20100694 T HR 20100694T HR P20100694 T HRP20100694 T HR P20100694T HR P20100694 T1 HRP20100694 T1 HR P20100694T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- optionally substituted
- group
- ring
- membered heterocyclic
- Prior art date
Links
- 101150051188 Adora2a gene Proteins 0.000 title 1
- 150000003835 adenosine derivatives Chemical class 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 13
- 239000001301 oxygen Substances 0.000 claims abstract 13
- 229910052717 sulfur Chemical group 0.000 claims abstract 12
- 239000011593 sulfur Chemical group 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- -1 carboxy, amino Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000012907 medicinal substance Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000005864 Sulphur Substances 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000000954 anitussive effect Effects 0.000 claims 1
- 230000001387 anti-histamine Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 229940124584 antitussives Drugs 0.000 claims 1
- 229940124630 bronchodilator Drugs 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Spoj formule (Ia) ili njegovih stereoizomera ili farmaceutski prihvatljivih soli, naznacen time, da R1a i R1b su neovisno odabrani od 3-do 12-clane heterociklicke skupine koja sadrzi od 1 do 4 prstena atoma dusika i opcijski sadrzi od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaca kisik i sumpor, a ta skupina se opcijski supstituira sa okso, O-C1-C8-alkilom, C6-C10-arilom, R1c ili sa C1-C8-alkilom opcijski supstituiranim sa OH, ili R1a i R1b su neovisno odabrani od -NR4R4, i -NR5-C1-C8-alkilkarbonila; R2 je C1-C8-alkil opcijski supstituiran sa OH, halogen, C6-C10-aril opcijski supstituiran sa OH, SC1-C8-alkilom, CN, halogenom, O-C7-C14-aralkilom, ili O-C1-C8-alkilom, C3-C15-karbociklicka skupina opcijski supstituirana sa O-C7-C14 aralkilom, C3-C15-karbociklickom skupinom, O-C1-C8-alkilom, C2-C8-alkenilom, C2-C8-alkinilom ili C1-C8-alkilom, O-C1-C8-alkil, -SO2-C1-C8-alkil, 3- do12-clana heterociklicka skupina koja sadrzi 1 do 4 prstena dusikovih atoma i opcijski sadrzi od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaca kisik i sumpor, a ta skupina se opcijski supstituira sa 3- do 12-clanom heterociklickom skupinom koja sadrzi od 1 do 4 prstena dusikovih atoma i opcijski sadrzi od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaca kisik i sumpor, C7-C14-aralkil, ili C6-C14-aril opcijski supstituiran sa O-C7-C14-aralkilom, iliR3 je vodik, halo, C2-C8-alkenil, C2-C8-alkynil ili C1-C8-alkoksikarbonil, iliR3je C1-C8-alkilamino opcijski supstituiran sa OH, R3b, amino, di(C1-C8-alkil)amino, -NH-C(=O)-C1-C8-alkil,
Claims (6)
1. Spoj formule (Ia) ili njegovih stereoizomera ili farmaceutski prihvatljivih soli,
[image]
naznačen time, da
R1a i R1b su neovisno odabrani od 3-do 12-člane heterocikličke skupine koja sadrži od 1 do 4 prstena atoma dušika i opcijski sadrži od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaća kisik i sumpor, a ta skupina se opcijski supstituira sa okso, O-C1-C8-alkilom, C6-C10-arilom, R1c ili sa C1-C8-alkilom opcijski supstituiranim sa OH, ili R1a i R1b su neovisno odabrani od -NR4R4, i -NR5-C1-C8-alkilkarbonila;
R2 je C1-C8-alkil opcijski supstituiran sa OH, halogen, C6-C10-aril opcijski supstituiran sa OH, SC1-C8-alkilom, CN, halogenom, O-C7-C14-aralkilom, ili O-C1-C8-alkilom, C3-C15-karbociklička skupina opcijski supstituirana sa O-C7-C14 aralkilom, C3-C15-karbocikličkom skupinom, O-C1-C8-alkilom, C2-C8-alkenilom, C2-C8-alkinilom ili C1-C8-alkilom, O-C1-C8-alkil, -SO2-C1-C8-alkil, 3- do12-člana heterociklička skupina koja sadrži 1 do 4 prstena dušikovih atoma i opcijski sadrži od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaća kisik i sumpor, a ta skupina se opcijski supstituira sa 3- do 12-članom heterocikličkom skupinom koja sadrži od 1 do 4 prstena dušikovih atoma i opcijski sadrži od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaća kisik i sumpor, C7-C14-aralkil, ili C6-C14-aril opcijski supstituiran sa O-C7-C14-aralkilom, ili
R3 je vodik, halo, C2-C8-alkenil, C2-C8-alkynil ili C1-C8-alkoksikarbonil, ili
R3je C1-C8-alkilamino opcijski supstituiran sa OH, R3b, amino, di(C1-C8-alkil)amino, -NH-C(=O)-C1-C8-alkil, -NH-SO2-C1-C8-alkil, -NH-C(=O)-NH-R3c, -NH-C(=O)-NH-C1-C8-alkil-R3b, C3-C15-karbociklička group ili C6-C10-aril opcijski supstituiran sa C6-C10- ariloksi, ili
R3 je 3- do 12-člana heterociklička skupina koja sadrži od 1 do 4 prstena dušikovih atoma i opcijski sadrži od 1 do 4 drugih heteroatoma odabranih iz skupine koja obuhvaća kisik i sumpor, a ta skupina je opcijski supstituirana sa 0-3R4;
R3a i R3b su svaki neovisno 3- do 12-člana heterociklička skupina koja sadrži najmanje jedan prsten heteroatoma odabranih iz skupine koja obuhvaća dušik, kisik i sumpor; opcijski supstituirani sa halo, cijano, okso, OH, karboksi, nitro, C1-C8-alkil, C1-C8-alkilkarbonil, OH-C1-C8-alkil, C1-C8-haloalkil, aminoC1-C8-alkil, amino(OH)C1-C8- alkil i C1-C8-alkoksi opcijski supstituiran sa aminokarbonilom;
R3c je 5- ili 6-člana heterociklička skupina koja sadrži najmanje jedan prsten heteroatoma odabranih iz skupine koja obuhvaća dušik, kisik i sumpor, koja je opcijski supstituirana sa 5- ili 6-članom heterocikličkom skupinom koja obuhvaća najmanje jedan prsten heteroatoma odabranih iz skupine koja obuhvaća dušik, kisik i sumpor;
R3d je neovisno 5- ili 6-člani heterociklički prsten koji sadrži najmanje jedan prsten heteroatoma odabranih iz skupine koja obuhvaća dušik, kisik i sumpor, a spomenuti 5-ili 6-člani heterociklički prsten je opcijski supstituiran sa halo, cijano, okso, OH, karboksi, amino, nitro, C1-C8-alkil, C1-C8-alkilsulfonil, aminokarbonil, C1-C8-alkilkarbonil, C1-C8-alkoksi opcijski supstituiran sa aminokarbonilom, ili 5- ili 6-člani heterociklički prsten sadrži najmanje jedan prsten heteroatoma odabranih iz skupine koja obuhvaća dušik, kisik i sumpor, a spomenuti prsten je također opcijski supstituiran sa halo, cijano, okso, OH, karboksi, amino, nitro, C1-C8-alkil, C1-C8alkilsulfonil, aminokarbonil, C1-C8-alkilkarbonil, ili C1-C8-alkoksi opcijski supstituiran sa aminokarbonilom;
R4je odabran između OH, C1-C8-alkila opcijski supstituiranog sa OH, C1-C8-alkoksi, C7-C14-aralkila opcijski supstituiranog sa OH, O-C1-C8-alkilom, halogenom, C6-C10-arilom, ili O-C6-C10-arilom, C1-C8-alkoksi, C6-C10-arila opcijski supstituiranog sa OH, C1-C8-alkilom, O-C1-C8-alkilom ili -halogenom, O-C6-C10-arila opcijski supstituiranog sa OH, C1-C8-alkilom, O-C1-C8-alkilom ili -halogenom, i NR4fC(O)NR4gR4h;
R4f i R4h su neovisno, H, ili C1-C8-alkil;
R4g je a 3- do 12-člana heterociklička skupina koja sadrži najmanje jedan prsten heteroatoma odabranih iz skupine koja obuhvaća dušik, kisik i sumpor;
dok je A odabran od
[image]
2. Spoj prema zahtjevu 1, naznačen time, da se koristi kao farmaceutski pripravak.
3. Spoj prema zahtjevu 1, naznačen time, da se koristi u kombinaciji s protuupalnom, bronhodilatornom, antihistaminskom ili antitusivnom ljekovitom tvari, a spomenuti spoj i spomenuta ljekovita tvar se nalaze u istom ili različitom farmaceutskom sastavu.
4. Farmaceutski sastav, naznačen time, da sadrži spoj prema zahtjevu 1 kao aktivni sastojak, opcijski zajedno sa farmaceutski prihvatljivim razrjeđivačem ili nosačem.
5. Uporaba spoja prema zahtjevu 1, naznačena time, da se koristi u proizvodnji lijeka za liječenje upalnih ili opstruktivnih oboljenja dišnog sustava.
6. Postupak za proizvodnju spojeva formule (Ia) kao što je određeno u zahtjevu 1, ili njihovih stereoizomera ili farmaceutski prihvatljivih soli, naznačen time, da obuhvaća korake
(i) reakcije spoja formule (II)
[image]
gdje su
R1a, R1b, R2, U1, U2 kao što su prethodno određeni;
a T je preostala skupina,
sa spojem formule (III)
H-R3 (III)
gdje je
R3 kao što je određen u zahtjevu 1; i
(ii) odstranjivanja bilo koje zaštitne skupine i ponovno oporavljanje rezultirajućeg spoja formule (II) u slobodnom obliku ili u obliku farmaceutski prihvatljive soli.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06120706A EP1903044A1 (en) | 2006-09-14 | 2006-09-14 | Adenosine Derivatives as A2A Receptor Agonists |
PCT/EP2007/059666 WO2008031875A1 (en) | 2006-09-14 | 2007-09-13 | Adenosine derivatives as a2a receptor agonists |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20100694T1 true HRP20100694T1 (hr) | 2011-01-31 |
Family
ID=37622170
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20100694T HRP20100694T1 (hr) | 2006-09-14 | 2010-12-14 | Derivati adenozina kao agonisti a2a receptora |
Country Status (31)
Country | Link |
---|---|
US (1) | US8188100B2 (hr) |
EP (2) | EP1903044A1 (hr) |
JP (1) | JP2010503639A (hr) |
KR (1) | KR20090040386A (hr) |
CN (1) | CN101511831B (hr) |
AR (1) | AR062768A1 (hr) |
AT (1) | ATE481404T1 (hr) |
AU (1) | AU2007296227A1 (hr) |
BR (1) | BRPI0716936A2 (hr) |
CA (1) | CA2662104A1 (hr) |
CL (1) | CL2007002658A1 (hr) |
CR (1) | CR10621A (hr) |
CY (1) | CY1110990T1 (hr) |
DE (1) | DE602007009272D1 (hr) |
DK (1) | DK2066669T3 (hr) |
ES (1) | ES2353141T3 (hr) |
HK (1) | HK1131392A1 (hr) |
HR (1) | HRP20100694T1 (hr) |
IL (1) | IL197153A0 (hr) |
MA (1) | MA30722B1 (hr) |
MX (1) | MX2009002811A (hr) |
NO (1) | NO20091244L (hr) |
PE (1) | PE20081151A1 (hr) |
PL (1) | PL2066669T3 (hr) |
PT (1) | PT2066669E (hr) |
RU (1) | RU2009113668A (hr) |
SI (1) | SI2066669T1 (hr) |
TN (1) | TN2009000084A1 (hr) |
TW (1) | TW200821324A (hr) |
WO (1) | WO2008031875A1 (hr) |
ZA (1) | ZA200901036B (hr) |
Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002362443B2 (en) * | 2001-10-01 | 2008-05-15 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having A2A agonist activity and compositions thereof |
GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
WO2006068760A2 (en) | 2004-11-19 | 2006-06-29 | The Regents Of The University Of California | Anti-inflammatory pyrazolopyrimidines |
GB0500785D0 (en) | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
WO2007120972A2 (en) * | 2006-02-10 | 2007-10-25 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
US7585868B2 (en) | 2006-04-04 | 2009-09-08 | The Regents Of The University Of California | Substituted pyrazolo[3,4-D]pyrimidines as kinase antagonists |
GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
PL2322525T3 (pl) | 2006-04-21 | 2014-03-31 | Novartis Ag | Pochodne puryny do zastosowania jako agoniści receptora adenozyny A<sub>2A</sub> |
US8188063B2 (en) | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
ATE500263T1 (de) * | 2006-06-27 | 2011-03-15 | Cbt Dev Ltd | Neue 2',3'-methylidenacetyladenosine prodrugs zur verwendung als adenosinrezeptoragonisten |
EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
CN101553459A (zh) * | 2006-11-10 | 2009-10-07 | 诺瓦提斯公司 | 环戊烯二醇单乙酸酯衍生物 |
US20110160232A1 (en) | 2007-10-04 | 2011-06-30 | Pingda Ren | Certain chemical entities and therapeutic uses thereof |
KR20100068286A (ko) * | 2007-10-17 | 2010-06-22 | 노파르티스 아게 | 아데노신 a1 수용체 리간드로서의 퓨린 유도체 |
US8058259B2 (en) | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
WO2009088990A1 (en) | 2008-01-04 | 2009-07-16 | Intellikine, Inc. | Certain chemical entities, compositions and methods |
US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
WO2009114874A2 (en) | 2008-03-14 | 2009-09-17 | Intellikine, Inc. | Benzothiazole kinase inhibitors and methods of use |
US8637542B2 (en) | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
WO2010006072A2 (en) | 2008-07-08 | 2010-01-14 | The Regents Of The University Of California | Mtor modulators and uses thereof |
CN102124009B (zh) | 2008-07-08 | 2014-07-23 | 因特利凯公司 | 激酶抑制剂及其使用方法 |
WO2010036380A1 (en) | 2008-09-26 | 2010-04-01 | Intellikine, Inc. | Heterocyclic kinase inhibitors |
DK2358720T3 (en) | 2008-10-16 | 2016-06-06 | Univ California | Heteroarylkinaseinhibitorer fused-ring |
US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
WO2010129816A2 (en) | 2009-05-07 | 2010-11-11 | Intellikine, Inc. | Heterocyclic compounds and uses thereof |
JP5819831B2 (ja) | 2009-08-17 | 2015-11-24 | インテリカイン, エルエルシー | 複素環式化合物およびそれらの使用 |
WO2011047384A2 (en) | 2009-10-16 | 2011-04-21 | The Regents Of The University Of California | Methods of inhibiting ire1 |
WO2011146882A1 (en) | 2010-05-21 | 2011-11-24 | Intellikine, Inc. | Chemical compounds, compositions and methods for kinase modulation |
EP2637669A4 (en) | 2010-11-10 | 2014-04-02 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and their use |
NZ612909A (en) | 2011-01-10 | 2015-09-25 | Infinity Pharmaceuticals Inc | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
AR085397A1 (es) | 2011-02-23 | 2013-09-25 | Intellikine Inc | Combinacion de inhibidores de quinasa y sus usos |
TWI565709B (zh) | 2011-07-19 | 2017-01-11 | 英菲尼提製藥股份有限公司 | 雜環化合物及其用途 |
US8969363B2 (en) | 2011-07-19 | 2015-03-03 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
AR091790A1 (es) | 2011-08-29 | 2015-03-04 | Infinity Pharmaceuticals Inc | Derivados de isoquinolin-1-ona y sus usos |
JP6342805B2 (ja) | 2011-09-02 | 2018-06-13 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 置換ピラゾロ[3,4−d]ピリミジンおよびその用途 |
US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
SG11201502331RA (en) | 2012-09-26 | 2015-04-29 | Univ California | Modulation of ire1 |
US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
US9751888B2 (en) | 2013-10-04 | 2017-09-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
EA201690713A1 (ru) | 2013-10-04 | 2016-08-31 | Инфинити Фармасьютикалз, Инк. | Гетероциклические соединения и их применения |
CA2943075C (en) | 2014-03-19 | 2023-02-28 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
CN105012318B (zh) * | 2014-04-17 | 2020-02-11 | 沈华浩 | 磺酰胺类化合物在气道慢性炎症性疾病中的应用 |
US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
NZ740616A (en) | 2015-09-14 | 2023-05-26 | Infinity Pharmaceuticals Inc | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
HRP20230537T1 (hr) * | 2016-03-16 | 2023-08-04 | Kura Oncology, Inc. | Supstituirani derivati tieno[2,3-d]pirimidina kao inhibitori za menin-mll i postupci za uporabu |
JP7000333B2 (ja) | 2016-03-16 | 2022-02-10 | クラ オンコロジー,インク. | メニン-mllの架橋された二環式阻害剤及びその使用方法 |
WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
CN109640999A (zh) | 2016-06-24 | 2019-04-16 | 无限药品股份有限公司 | 组合疗法 |
EP3601249A4 (en) | 2017-03-24 | 2020-12-16 | Kura Oncology, Inc. | METHODS OF TREATMENT OF MALIGNANT HEMOPATHIES AND EWING'S SARCOMA |
US11542248B2 (en) | 2017-06-08 | 2023-01-03 | Kura Oncology, Inc. | Methods and compositions for inhibiting the interaction of menin with MLL proteins |
TW201920170A (zh) | 2017-09-20 | 2019-06-01 | 美商庫拉腫瘤技術股份有限公司 | 經取代之menin-mll 抑制劑及使用方法 |
EP3686199B9 (en) | 2017-09-28 | 2022-12-07 | Cstone Pharmaceuticals (Suzhou) Co., Ltd. | Fused ring derivative as a2a receptor inhibitor |
Family Cites Families (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1528382A (en) * | 1974-12-26 | 1978-10-11 | Teijin Ltd | Cyclopentene diols and acyl esters thereof and processes for their preparation |
US4738954A (en) * | 1985-11-06 | 1988-04-19 | Warner-Lambert Company | Novel N6 -substituted-5'-oxidized adenosine analogs |
US4873360A (en) * | 1986-07-10 | 1989-10-10 | Board Of Governors Of Wayne State University | Process for the preparation of cyclopentanoids and novel intermediates produced thereby |
EP0267878A1 (en) | 1986-11-14 | 1988-05-18 | Ciba-Geigy Ag | N9-cyclopentyl-substituted adenine derivatives |
US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
JP2586897B2 (ja) | 1987-03-09 | 1997-03-05 | 富士薬品工業株式会社 | 光学活性なシス−シクロペンテン−3,5−ジオ−ルモノエステルの製造法 |
WO1992005177A1 (en) | 1990-09-25 | 1992-04-02 | Rhone-Poulenc Rorer International (Holdings) Inc. | Compounds having antihypertensive and anti-ischemic properties |
IT1254915B (it) | 1992-04-24 | 1995-10-11 | Gloria Cristalli | Derivati di adenosina ad attivita' a2 agonista |
US5688774A (en) * | 1993-07-13 | 1997-11-18 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
US5691188A (en) * | 1994-02-14 | 1997-11-25 | American Cyanamid Company | Transformed yeast cells expressing heterologous G-protein coupled receptor |
WO1997024327A1 (en) * | 1996-01-02 | 1997-07-10 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Process for preparing 2,4-dihydroxypyridine and 2,4-dihydroxy-3-nitropyridine |
US6376472B1 (en) * | 1996-07-08 | 2002-04-23 | Aventis Pharmaceuticals, Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
WO1998050047A1 (en) * | 1997-05-09 | 1998-11-12 | Trustees Of The University Of Pennsylvania | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
GB9813554D0 (en) * | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
JP3933870B2 (ja) | 1998-06-23 | 2007-06-20 | グラクソ グループ リミテッド | 2−(プリン−9−イル)−テトラヒドロフラン−3,4−ジオール誘導体 |
GB9813540D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
GB9813535D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
ES2264826T3 (es) | 1998-10-16 | 2007-01-16 | Pfizer Inc. | Derivados de adenina. |
ES2228163T3 (es) * | 1998-12-31 | 2005-04-01 | Aventis Pharmaceuticals Inc. | Procedimiento para preparar derivados de desaza-adenosina n6-sustituidos. |
US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
US6403567B1 (en) * | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
US6214807B1 (en) * | 1999-06-22 | 2001-04-10 | Cv Therapeutics, Inc. | C-pyrazole 2A A receptor agonists |
US6586413B2 (en) * | 1999-11-05 | 2003-07-01 | The United States Of America As Represented By The Department Of Health And Human Services | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
GB0003960D0 (en) | 2000-02-18 | 2000-04-12 | Pfizer Ltd | Purine derivatives |
GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
JP4012070B2 (ja) | 2001-01-16 | 2007-11-21 | カン−フィテ・バイオファーマ・リミテッド | ウイルスの複製を阻害するためのアデノシンa3受容体アゴニストの使用 |
GB2372741A (en) | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,8-Disubstituted adenosine derivatives and their different uses |
US20040162422A1 (en) * | 2001-03-20 | 2004-08-19 | Adrian Hall | Chemical compounds |
EP1258247A1 (en) * | 2001-05-14 | 2002-11-20 | Aventis Pharma Deutschland GmbH | Adenosine analogues for the treatment of insulin resistance syndrome and diabetes |
AU2002362443B2 (en) | 2001-10-01 | 2008-05-15 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having A2A agonist activity and compositions thereof |
US7414036B2 (en) * | 2002-01-25 | 2008-08-19 | Muscagen Limited | Compounds useful as A3 adenosine receptor agonists |
JP2006515829A (ja) | 2002-04-10 | 2006-06-08 | ユニバーシティ オブ バージニア パテント ファウンデーション | 炎症性疾病の処置のための、a2aアデノシン受容体アゴニストの使用 |
DE602004006895T2 (de) | 2003-12-29 | 2008-01-31 | Can-Fite Biopharma Ltd. | Verfahren zur behandlung von multipler sklerose |
CA2557285A1 (en) | 2004-03-05 | 2005-09-15 | Cambridge Biotechnology Limited | Adenosine receptor agonists |
EP1746885A4 (en) | 2004-05-03 | 2010-09-08 | Univ Virginia | ADENOSINE A2A RECEPTOR AGONISTS FOR THE TREATMENT OF DIABETIC NEPHROPATHY |
PE20060272A1 (es) * | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a |
US7825102B2 (en) * | 2004-07-28 | 2010-11-02 | Can-Fite Biopharma Ltd. | Treatment of dry eye conditions |
JP4642847B2 (ja) | 2004-07-28 | 2011-03-02 | キャン−ファイト・バイオファーマ・リミテッド | シェーグレン症候群を含むドライアイ疾患治療用アデノシンa3レセプターアゴニスト |
EP1794162A1 (en) * | 2004-09-09 | 2007-06-13 | The Government of the United States of America, as repres. by the Secretary of Health and Human Services, Nat. Inst. of Health | Purine derivatives as a3 and a1 adenosine receptor agonists |
GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
US20080051364A1 (en) * | 2004-11-08 | 2008-02-28 | Pninna Fishman | Therapeutic Treatment of Accelerated Bone Resorption |
GB0500785D0 (en) | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
DK1848718T3 (da) * | 2005-02-04 | 2012-08-27 | Millennium Pharm Inc | E1 aktiveringsenzymhæmmere |
GB0505219D0 (en) * | 2005-03-14 | 2005-04-20 | Novartis Ag | Organic compounds |
GB0514809D0 (en) * | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
JP5339916B2 (ja) * | 2005-11-30 | 2013-11-13 | キャン−ファイト・バイオファーマ・リミテッド | 骨関節炎の治療におけるa3アデノシン受容体アゴニストの使用 |
DK1983990T3 (da) * | 2006-01-26 | 2011-07-11 | Us Gov Health & Human Serv | Allosteriske A3-adenosin-receptormodulatorer |
EA031335B1 (ru) * | 2006-02-02 | 2018-12-28 | Миллениум Фармасьютикалз, Инк. | Производные пирролопиримидинов |
WO2007092936A2 (en) * | 2006-02-08 | 2007-08-16 | University Of Virginia Patent Foundation | Method to treat gastric lesions |
GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607951D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607953D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
PL2322525T3 (pl) | 2006-04-21 | 2014-03-31 | Novartis Ag | Pochodne puryny do zastosowania jako agoniści receptora adenozyny A<sub>2A</sub> |
GB0607948D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
GB0607945D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
EP1889846A1 (en) * | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
US8008307B2 (en) * | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
CN101553459A (zh) * | 2006-11-10 | 2009-10-07 | 诺瓦提斯公司 | 环戊烯二醇单乙酸酯衍生物 |
US20080312160A1 (en) * | 2007-04-09 | 2008-12-18 | Guerrant Richard L | Method of treating enteritis, intestinal damage, and diarrhea from c. difficile with an a2a adenosine receptor agonist |
US20080262001A1 (en) * | 2007-04-23 | 2008-10-23 | Adenosine Therapeutics, Llc | Agonists of a2a adenosine receptors for treating recurrent tumor growth in the liver following resection |
AU2008270735C1 (en) * | 2007-06-29 | 2014-03-06 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Dendrimer conjugates of agonists and antagonists of the GPCR superfamily |
US20090181934A1 (en) * | 2007-10-17 | 2009-07-16 | Novartis Ag | Organic Compounds |
KR20100068286A (ko) * | 2007-10-17 | 2010-06-22 | 노파르티스 아게 | 아데노신 a1 수용체 리간드로서의 퓨린 유도체 |
WO2009061516A1 (en) * | 2007-11-08 | 2009-05-14 | New York University School Of Medicine | Medical implants containing adenosine receptor agonists and methods for inhibiting medical implant loosening |
EP2240020A4 (en) * | 2008-01-09 | 2011-05-11 | Trovis Pharmaceuticals Llc | INTRATHEAL TREATMENT OF NEUROPATHIC PAIN WITH A2AR AGONISTS |
-
2006
- 2006-09-14 EP EP06120706A patent/EP1903044A1/en not_active Ceased
-
2007
- 2007-09-12 AR ARP070104040A patent/AR062768A1/es not_active Application Discontinuation
- 2007-09-12 PE PE2007001224A patent/PE20081151A1/es not_active Application Discontinuation
- 2007-09-13 JP JP2009527828A patent/JP2010503639A/ja not_active Withdrawn
- 2007-09-13 CA CA002662104A patent/CA2662104A1/en not_active Abandoned
- 2007-09-13 RU RU2009113668/04A patent/RU2009113668A/ru unknown
- 2007-09-13 PL PL07803477T patent/PL2066669T3/pl unknown
- 2007-09-13 SI SI200730448T patent/SI2066669T1/sl unknown
- 2007-09-13 DE DE602007009272T patent/DE602007009272D1/de active Active
- 2007-09-13 AT AT07803477T patent/ATE481404T1/de active
- 2007-09-13 CN CN2007800333258A patent/CN101511831B/zh not_active Expired - Fee Related
- 2007-09-13 MX MX2009002811A patent/MX2009002811A/es not_active Application Discontinuation
- 2007-09-13 US US12/310,254 patent/US8188100B2/en not_active Expired - Fee Related
- 2007-09-13 BR BRPI0716936-1A2A patent/BRPI0716936A2/pt not_active IP Right Cessation
- 2007-09-13 EP EP07803477A patent/EP2066669B1/en active Active
- 2007-09-13 KR KR1020097005251A patent/KR20090040386A/ko active IP Right Grant
- 2007-09-13 AU AU2007296227A patent/AU2007296227A1/en not_active Abandoned
- 2007-09-13 PT PT07803477T patent/PT2066669E/pt unknown
- 2007-09-13 ES ES07803477T patent/ES2353141T3/es active Active
- 2007-09-13 WO PCT/EP2007/059666 patent/WO2008031875A1/en active Application Filing
- 2007-09-13 TW TW096134289A patent/TW200821324A/zh unknown
- 2007-09-13 DK DK07803477.4T patent/DK2066669T3/da active
- 2007-09-13 CL CL200702658A patent/CL2007002658A1/es unknown
-
2009
- 2009-02-13 ZA ZA200901036A patent/ZA200901036B/xx unknown
- 2009-02-19 CR CR10621A patent/CR10621A/es not_active Application Discontinuation
- 2009-02-19 IL IL197153A patent/IL197153A0/en unknown
- 2009-03-13 TN TN2009000084A patent/TN2009000084A1/fr unknown
- 2009-03-25 NO NO20091244A patent/NO20091244L/no not_active Application Discontinuation
- 2009-03-30 MA MA31736A patent/MA30722B1/fr unknown
- 2009-12-03 HK HK09111343.2A patent/HK1131392A1/xx unknown
-
2010
- 2010-12-14 HR HR20100694T patent/HRP20100694T1/hr unknown
- 2010-12-15 CY CY20101101154T patent/CY1110990T1/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20100694T1 (hr) | Derivati adenozina kao agonisti a2a receptora | |
AU2018272359B2 (en) | Lactam compound as FXR receptor agonist | |
CN110041327B (zh) | 吡啶酮衍生物、其组合物及作为抗流感病毒药物的应用 | |
JP4405602B2 (ja) | ヒストン脱アセチル化酵素阻害剤 | |
EP1935892B1 (en) | Glycyrrhetinic acid-30-amide derivatives and the uses thereof | |
EP3279188B1 (en) | Axially chiral isomers, and preparation methods therefor and pharmaceutical uses thereof | |
WO2019236483A1 (en) | Spirocyclic compounds | |
ES2881695T3 (es) | Derivado de 1,3,5-triazina y método de uso del mismo | |
EP3116509B1 (en) | A new class of mu-opioid receptor agonists | |
Chen et al. | Discovery of 2-chloro-N-((4, 4-difluoro-1-hydroxycyclohexyl) methyl)-5-(5-fluoropyrimidin-2-yl) benzamide as a potent and CNS penetrable P2X7 receptor antagonist | |
TWI630194B (zh) | 雙環止痛化合物 | |
WO2015130964A1 (en) | Therapeutic compounds | |
UY27781A1 (es) | Compuestos químicos. | |
AU2016382372B2 (en) | Sulfonamide derivative and preparation method and use thereof | |
MX369956B (es) | Metodos para preparar compuestos de benzoquinolina. | |
RU2009104764A (ru) | Производные пурина, как антангонисты a2a | |
WO2015069693A1 (en) | Inhibitors of histone deacetylase | |
EP3484858A1 (en) | Activators of hiv latency | |
MY140325A (en) | Indanyl-piperazine derivatives, process for their preparation and pharmaceutical compositions containing them | |
WO2018223030A1 (en) | Use of ezh2 inhibitors for treating cancer | |
CN107459476A (zh) | 反吲哚啉环丙胺类化合物及其制备方法、药物组合物和用途 | |
JP6033788B2 (ja) | 置換されたメチルアミン、セロトニン5−ht6受容体アンタゴニスト、製造のための方法及びその使用 | |
JP2015534990A (ja) | 誤制御されたeIF4Eに関連する疾患又は障害を治療又は予防するための組成物及び方法 | |
BR102014010331B1 (pt) | processo para a preparação de aminaftona, uso de aminaftona, uso do composto químico epóxido 2 e uso do composto químico 4 | |
Jaroch et al. | Dihydroquinolines with amine-containing side chains as potent n-NOS inhibitors |