HRP20140830T1 - Sulfoksimin supstituirani derivati anilin pirimidina kao inhibitori cdk, njihova proizvodnja i uporaba kao lijeka - Google Patents
Sulfoksimin supstituirani derivati anilin pirimidina kao inhibitori cdk, njihova proizvodnja i uporaba kao lijeka Download PDFInfo
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- HRP20140830T1 HRP20140830T1 HRP20140830AT HRP20140830T HRP20140830T1 HR P20140830 T1 HRP20140830 T1 HR P20140830T1 HR P20140830A T HRP20140830A T HR P20140830AT HR P20140830 T HRP20140830 T HR P20140830T HR P20140830 T1 HRP20140830 T1 HR P20140830T1
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- 125000005555 sulfoximide group Chemical group 0.000 title claims 7
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 150000008059 anilinopyrimidines Chemical class 0.000 title 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 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 7
- 150000003839 salts Chemical class 0.000 claims 7
- 150000003462 sulfoxides Chemical class 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 238000007866 imination reaction Methods 0.000 claims 4
- 238000003776 cleavage reaction Methods 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 230000007017 scission Effects 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 238000007306 functionalization reaction Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229940127554 medical product Drugs 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- IDRUEHMBFUJKAK-UHFFFAOYSA-N 2,4-dichloro-5-(trifluoromethyl)pyrimidine Chemical group FC(F)(F)C1=CN=C(Cl)N=C1Cl IDRUEHMBFUJKAK-UHFFFAOYSA-N 0.000 claims 1
- RGJNPJRAXMSHKN-UHFFFAOYSA-N 2,4-dichloro-5-iodopyrimidine Chemical group ClC1=NC=C(I)C(Cl)=N1 RGJNPJRAXMSHKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000002009 diols 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
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (13)
1. Spojevi opće formule (I)
[image]
naznačeni time da
X predstavlja -O- ili -NH-, i
R1 predstavlja metil, etil, propil ili izopropil skupinu, i
R2 i R3 međusobno neovisno, predstavljaju vodik, metil ili etil skupinu, te
R4 predstavlja C1-C6-alkil skupinu ili C3-C7-cikloalkil prsten,
i njihove soli, diastereomeri i enantiomeri.
2. Spojevi prema zahtjevu 1, naznačeni time da X predstavlja -O-, i njihove soli, diastereomeri i enantiomeri.
3. Spojevi prema jednom od zahtjeva 1 ili 2, naznačeni time da R1 predstavlja metil skupinu, i njihove soli, diastereomeri i enantiomeri.
4. Spojevi prema jednom od zahtjeva 1 do 3, naznačeni time da R2 predstavlja metil skupinu, i njihove soli, diastereomeri i enantiomeri.
5. Spojevi prema jednom od zahtjeva 1 do 4, naznačeni time da R3 predstavlja vodik ili metil skupinu, i njihove soli, diastereomeri i enantiomeri.
6. Spojevi prema jednom od zahtjeva 1 do 5, naznačeni time da R4 predstavlja metil ili etil skupinu ili ciklopropil prsten, i njihove soli, diastereomeri i enantiomeri.
7. Spojevi sa općom formulom (I) prema zahtjevu 1, naznačeni time da
X predstavlja -O- ili -NH-, i
R1 predstavlja metil skupinu, i
R2 predstavlja metil skupinu, i
R3 predstavlja vodik ili metil skupinu, i
R4 predstavlja metil ili etil skupinu ili ciklopropil prsten,
i njihove soli, diastereomeri i enantiomeri.
8. Postupak za proizvodnju spojeva sa općom formulom (Ia), naznačen time da sadrži barem jedan od koraka a)-h)
a) oksidaciju spoja sa formulom (IVd) u sulfoksid sa formulom (IVc)
[image]
b1) izravnu iminaciju sulfoksida sa formulom (IVc) u zaštićeni sulfoksimin sa formulom (IVa)
[image]
ili
b2) iminaciju sulfoksida sa formulom (IVc) u nezaštićeni sulfoksimin sa formulom (IVb) i naknadno uvođenje zaštitne skupine u spoj sa formulom (IVa)
[image]
c) redukciju spoja sa formulom (IVa) u spoj sa formulom (IV)
[image]
d) funkcionalizaciju 4-položaja od 2,4-dikloro-5-jodo-pirimidina (VII) pomoću reakcije sa mono-zaštićenim diolom sa formulom (VI) uz tvorbu intermedijera sa formulom (Va),
[image]
e) dobivanje 5-CF3 intermedijera (V)
[image]
f) spajanje spojeva formule (IV) i (V) da se dobije intermedijer sa formulom (III)
[image]
g) cijepanje zaštitne skupine PG uz tvorbu (II),
[image]
h) cijepanje zaštitne skupine na sulfoksiminu uz tvorbu (Ia),
[image]
pri čemu supstituenti R1, R2, R3 i R4 imaju značenja dodijeljena u općoj formuli (I) prema zahtjevima od 1 do 7.
9. Postupak za proizvodnju spojeva sa općom formulom (Ib), naznačen time da sadrži barem jedan od koraka a)-f)
a) oksidaciju spoja sa formulom (IVd) u sulfoksid sa formulom (IVc)
[image]
b1) izravnu iminaciju sulfoksida sa formulom (IVc) da se dobije zaštićeni sulfoksimin sa formulom (IVa)
[image]
ili
b2) Iminaciju sulfoksida sa formulom (IVc) da se dobije nezaštićeni sulfoksimin sa formulom (IVb) i naknadno uvođenje zaštitne skupine u spoj sa formulom (IVa)
[image]
c) redukciju spoja sa formulom (IVa) u spoj sa formulom (IV)
[image]
d) funkcionalizaciju 4-položaja od 2,4-dikloro-5-trifluorometil-pirimidina (VIIb) reakcijom sa aminom prema formuli (VIa) uz tvorbu intermedijara sa formulom (Vb)
[image]
e) spajanje spojeva formule (Vb) i (IV) da se dobije intermedijer sa formulom (IIb)
[image]
f) cijepanje zaštitne skupine na sulfoksiminu uz tvorbu (Ib)
[image]
pri čemu supstituenti R1, R2, R3 i R4 imaju značenja dodijeljena u općoj formuli (I) prema zahtjevima 1 do 7.
10. Spojevi prema jednom od zahtjeva 1 do 7 naznačeni time da su za uporabu kao medicinski proizvodi.
11. Uporaba spoja prema jednom zahtjevu od 1 do 7 naznačena time da je za proizvodnju medicinskog proizvoda za liječenje karcinoma.
12. Spojevi prema jednom od zahtjeva 1 do 7 naznačeni time da su za uporabu kao medicinski proizvodi protiv karcinoma.
13. Farmaceutska formulacija naznačena time da sadrži spoj prema jednom zahtjevu od 1 do 7.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08167113A EP2179991A1 (de) | 2008-10-21 | 2008-10-21 | Sulfoximinsubstituierte Anilino-Pyrimidinderivate als CDK-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
PCT/EP2009/007247 WO2010046035A1 (de) | 2008-10-21 | 2009-10-09 | Sulfoximinsubstituierte anilinopyrimidinderative als cdk-inhibitoren, deren herstellung und verwendung als arzeinmittel |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20140830T1 true HRP20140830T1 (hr) | 2014-11-21 |
Family
ID=40282208
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20140830AT HRP20140830T1 (hr) | 2008-10-21 | 2014-09-03 | Sulfoksimin supstituirani derivati anilin pirimidina kao inhibitori cdk, njihova proizvodnja i uporaba kao lijeka |
Country Status (38)
Country | Link |
---|---|
US (1) | US8735412B2 (hr) |
EP (2) | EP2179991A1 (hr) |
JP (1) | JP5564054B2 (hr) |
KR (1) | KR20110069115A (hr) |
CN (1) | CN102197029B (hr) |
AR (1) | AR074053A1 (hr) |
AU (1) | AU2009306733C1 (hr) |
BR (1) | BRPI0920112A2 (hr) |
CA (1) | CA2739739C (hr) |
CO (1) | CO6361926A2 (hr) |
CR (1) | CR20110210A (hr) |
CU (1) | CU24052B1 (hr) |
CY (1) | CY1115590T1 (hr) |
DK (1) | DK2350026T3 (hr) |
DO (1) | DOP2011000107A (hr) |
EA (1) | EA019230B1 (hr) |
EC (1) | ECSP11010992A (hr) |
ES (1) | ES2499028T3 (hr) |
HN (1) | HN2011001019A (hr) |
HR (1) | HRP20140830T1 (hr) |
IL (1) | IL211713A (hr) |
MA (1) | MA32723B1 (hr) |
MX (1) | MX2011004238A (hr) |
MY (1) | MY155230A (hr) |
NZ (1) | NZ592314A (hr) |
PA (1) | PA8846201A1 (hr) |
PE (1) | PE20110546A1 (hr) |
PL (1) | PL2350026T3 (hr) |
PT (1) | PT2350026E (hr) |
RS (1) | RS53523B1 (hr) |
SA (1) | SA109300632B1 (hr) |
SI (1) | SI2350026T1 (hr) |
TN (1) | TN2011000199A1 (hr) |
TW (2) | TWI496774B (hr) |
UA (1) | UA103500C2 (hr) |
UY (1) | UY32190A (hr) |
WO (1) | WO2010046035A1 (hr) |
ZA (1) | ZA201103727B (hr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2464633A1 (en) | 2009-08-14 | 2012-06-20 | Boehringer Ingelheim International GmbH | Regioselective preparation of 2-amino-5-trifluoromethylpyrimidine derivatives |
US8933227B2 (en) | 2009-08-14 | 2015-01-13 | Boehringer Ingelheim International Gmbh | Selective synthesis of functionalized pyrimidines |
DE102010014427A1 (de) | 2010-04-01 | 2011-10-06 | Bayer Schering Pharma Aktiengesellschaft | Kombinationen neuer pan-CDK-Inhibitoren zur Behandlung von Tumoren |
DE102010014426A1 (de) * | 2010-04-01 | 2011-10-06 | Bayer Schering Pharma Aktiengesellschaft | Verwendung neuer pan-CDK-Inhibitoren zur Behandlung von Tumoren |
DE102010046720A1 (de) * | 2010-09-23 | 2012-03-29 | Bayer Schering Pharma Aktiengesellschaft | Verfahren zur Herstellung von pan-CDK-Inhibitoren der Formel (l), sowie Intermediate der Herstellung |
TWI555737B (zh) | 2011-05-24 | 2016-11-01 | 拜耳知識產權公司 | 含有硫醯亞胺基團之4-芳基-n-苯基-1,3,5-三氮雜苯-2-胺 |
DE102011080992A1 (de) * | 2011-08-16 | 2013-02-21 | Bayer Pharma AG | Verwendung von MAD2L2 als Stratifikationsmarker bei der Behandlung von Brusttumoren mit neuen pan-CDK-Inhibitoren |
DE102011080991A1 (de) * | 2011-08-16 | 2013-02-21 | Bayer Pharma AG | Verwendung von CCNE2 als Stratifikationsmarker bei der Behandlung von Brusttumoren mit neuen pan-CDK-Inhibitoren |
WO2013037894A1 (en) | 2011-09-16 | 2013-03-21 | Bayer Intellectual Property Gmbh | Disubstituted 5-fluoro pyrimidine derivatives containing a sulfoximine group |
EA201491732A1 (ru) * | 2012-03-21 | 2015-08-31 | Байер Интеллектуэль Проперти Гмбх | Применение (rs)-s-циклопропил-s-(4-{[4-{[(1r,2r)-2-гидрокси-1-метилпропил]окси}-5-(трифторметил)пиримидин-2-ил]амино}фенил)сульфоксимида для лечения специфических опухолей |
CA2964696C (en) * | 2014-10-16 | 2022-09-06 | Bayer Pharma Aktiengesellschaft | Fluorinated benzofuranyl-pyrimidine derivatives containing a sulfoximine group |
EP3849537A4 (en) | 2018-09-10 | 2022-06-29 | Mirati Therapeutics, Inc. | Combination therapies |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4029650A1 (de) | 1990-09-19 | 1992-03-26 | Hoechst Ag | 2-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltene mittel und ihre verwendung als fungizide |
AU744986B2 (en) | 1997-07-12 | 2002-03-07 | Cancer Research Technology Limited | Cyclin dependent kinase inhibiting purine derivatives |
US6440965B1 (en) | 1997-10-15 | 2002-08-27 | Krenitsky Pharmaceuticals, Inc. | Substituted pyrimidine derivatives, their preparation and their use in the treatment of neurodegenerative or neurological disorders of the central nervous system |
ES2270612T3 (es) | 1998-08-29 | 2007-04-01 | Astrazeneca Ab | Compuestos de pirimidina. |
GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
JP4291135B2 (ja) | 2001-05-29 | 2009-07-08 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | Cdk阻害性ピリミジン、それらの製造および薬剤としての使用 |
EP1483260A1 (de) * | 2002-03-11 | 2004-12-08 | Schering Aktiengesellschaft | Cdk inhibitorische 2-heteroaryl-pyrimidine, deren herstellung und verwendung als arzneimittel |
JP2006508997A (ja) | 2002-11-28 | 2006-03-16 | シエーリング アクチエンゲゼルシャフト | Chk−、Pdk−およびAkt−阻害性ピリミジン、それらの製造および薬剤としての使用 |
DE10349423A1 (de) | 2003-10-16 | 2005-06-16 | Schering Ag | Sulfoximinsubstituierte Parimidine als CDK- und/oder VEGF-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
JP2008514571A (ja) * | 2004-09-29 | 2008-05-08 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | 細胞周期−キナーゼまたはレセプター−チロシン−キナーゼインヒビターとしての置換2−置換アニリノピリミジン類、それらの製造および薬剤としての使用 |
DE102005062742A1 (de) * | 2005-12-22 | 2007-06-28 | Bayer Schering Pharma Ag | Sulfoximin substituierte Pyrimidine, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel |
DE102006027156A1 (de) * | 2006-06-08 | 2007-12-13 | Bayer Schering Pharma Ag | Sulfimide als Proteinkinaseinhibitoren |
EP2179992A1 (de) * | 2008-10-21 | 2010-04-28 | Bayer Schering Pharma Aktiengesellschaft | Sulfonsubstituierte Anlinopyrimidinderivative als CDK-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
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2008
- 2008-10-21 EP EP08167113A patent/EP2179991A1/de not_active Withdrawn
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2009
- 2009-10-09 BR BRPI0920112A patent/BRPI0920112A2/pt not_active IP Right Cessation
- 2009-10-09 SI SI200931004T patent/SI2350026T1/sl unknown
- 2009-10-09 MX MX2011004238A patent/MX2011004238A/es active IP Right Grant
- 2009-10-09 CN CN200980141978.7A patent/CN102197029B/zh not_active Expired - Fee Related
- 2009-10-09 PL PL09778874T patent/PL2350026T3/pl unknown
- 2009-10-09 PT PT97788749T patent/PT2350026E/pt unknown
- 2009-10-09 EP EP09778874.9A patent/EP2350026B1/de active Active
- 2009-10-09 AU AU2009306733A patent/AU2009306733C1/en not_active Ceased
- 2009-10-09 DK DK09778874.9T patent/DK2350026T3/da active
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- 2009-10-09 MY MYPI2011001632A patent/MY155230A/en unknown
- 2009-10-09 UA UAA201106183A patent/UA103500C2/uk unknown
- 2009-10-09 PE PE2011000917A patent/PE20110546A1/es not_active Application Discontinuation
- 2009-10-09 JP JP2011532519A patent/JP5564054B2/ja not_active Expired - Fee Related
- 2009-10-09 WO PCT/EP2009/007247 patent/WO2010046035A1/de active Application Filing
- 2009-10-09 CA CA2739739A patent/CA2739739C/en not_active Expired - Fee Related
- 2009-10-09 EA EA201100623A patent/EA019230B1/ru not_active IP Right Cessation
- 2009-10-09 NZ NZ592314A patent/NZ592314A/xx not_active IP Right Cessation
- 2009-10-09 ES ES09778874.9T patent/ES2499028T3/es active Active
- 2009-10-09 KR KR1020117009024A patent/KR20110069115A/ko active IP Right Grant
- 2009-10-09 RS RSP20140466 patent/RS53523B1/en unknown
- 2009-10-19 PA PA20098846201A patent/PA8846201A1/es unknown
- 2009-10-20 UY UY0001032190A patent/UY32190A/es not_active Application Discontinuation
- 2009-10-20 SA SA109300632A patent/SA109300632B1/ar unknown
- 2009-10-21 TW TW103126302A patent/TWI496774B/zh not_active IP Right Cessation
- 2009-10-21 AR ARP090104043A patent/AR074053A1/es not_active Application Discontinuation
- 2009-10-21 TW TW098135674A patent/TWI458716B/zh not_active IP Right Cessation
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2011
- 2011-03-14 IL IL211713A patent/IL211713A/en not_active IP Right Cessation
- 2011-04-15 HN HN2011001019A patent/HN2011001019A/es unknown
- 2011-04-20 EC EC2011010992A patent/ECSP11010992A/es unknown
- 2011-04-20 MA MA33786A patent/MA32723B1/fr unknown
- 2011-04-20 DO DO2011000107A patent/DOP2011000107A/es unknown
- 2011-04-20 TN TN2011000199A patent/TN2011000199A1/fr unknown
- 2011-04-20 CO CO11049624A patent/CO6361926A2/es active IP Right Grant
- 2011-04-20 CU CU2011000088A patent/CU24052B1/es active IP Right Grant
- 2011-04-25 CR CR20110210A patent/CR20110210A/es unknown
- 2011-05-20 ZA ZA2011/03727A patent/ZA201103727B/en unknown
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- 2014-09-03 HR HRP20140830AT patent/HRP20140830T1/hr unknown
- 2014-09-05 CY CY20141100717T patent/CY1115590T1/el unknown
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Publication | Publication Date | Title |
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