HRP20130040T1 - 4-piridinon spojevi i njihova uporaba kod karcinoma - Google Patents
4-piridinon spojevi i njihova uporaba kod karcinoma Download PDFInfo
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- HRP20130040T1 HRP20130040T1 HRP20130040AT HRP20130040T HRP20130040T1 HR P20130040 T1 HRP20130040 T1 HR P20130040T1 HR P20130040A T HRP20130040A T HR P20130040AT HR P20130040 T HRP20130040 T HR P20130040T HR P20130040 T1 HRP20130040 T1 HR P20130040T1
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- Prior art keywords
- amino
- cancer
- fluorophenyl
- chloropyridin
- yloxy
- Prior art date
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- 206010028980 Neoplasm Diseases 0.000 title claims 4
- 201000011510 cancer Diseases 0.000 title claims 4
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- BOGJDTOFGQXALT-UHFFFAOYSA-N 1-[3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]ethyl piperidine-4-carboxylate Chemical compound C1=C(C(=O)NC=2C=C(F)C(OC=3C(=C(N)N=CC=3)Cl)=CC=2)C(=O)C(C=2C=CC(F)=CC=2)=CN1C(C)OC(=O)C1CCNCC1 BOGJDTOFGQXALT-UHFFFAOYSA-N 0.000 claims 2
- DQJMJJVJQGNYCV-VWLOTQADSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl (2s)-2-amino-3-methylbutanoate Chemical compound O=C1C(C=2C=CC(F)=CC=2)=CN(COC(=O)[C@@H](N)C(C)C)C=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC(N)=C1Cl DQJMJJVJQGNYCV-VWLOTQADSA-N 0.000 claims 2
- RPWXHBDMGSUEKP-QHCPKHFHSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl (2s)-2-amino-4-methylpentanoate Chemical compound O=C1C(C=2C=CC(F)=CC=2)=CN(COC(=O)[C@@H](N)CC(C)C)C=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC(N)=C1Cl RPWXHBDMGSUEKP-QHCPKHFHSA-N 0.000 claims 2
- DAPPNDREFUZNSA-AWEZNQCLSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl (2s)-2-aminopropanoate Chemical compound O=C1C(C=2C=CC(F)=CC=2)=CN(COC(=O)[C@@H](N)C)C=C1C(=O)NC(C=C1F)=CC=C1OC1=CC=NC(N)=C1Cl DAPPNDREFUZNSA-AWEZNQCLSA-N 0.000 claims 2
- JZMFOKBMMZHEOO-QFIPXVFZSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl (2s)-pyrrolidine-2-carboxylate Chemical compound NC1=NC=CC(OC=2C(=CC(NC(=O)C=3C(C(C=4C=CC(F)=CC=4)=CN(COC(=O)[C@H]4NCCC4)C=3)=O)=CC=2)F)=C1Cl JZMFOKBMMZHEOO-QFIPXVFZSA-N 0.000 claims 2
- KXDZWUPUSDCGDD-UHFFFAOYSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl dihydrogen phosphate Chemical compound NC1=NC=CC(OC=2C(=CC(NC(=O)C=3C(C(C=4C=CC(F)=CC=4)=CN(COP(O)(O)=O)C=3)=O)=CC=2)F)=C1Cl KXDZWUPUSDCGDD-UHFFFAOYSA-N 0.000 claims 2
- LADCXWSDWZWZGQ-UHFFFAOYSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl piperidine-3-carboxylate Chemical compound NC1=NC=CC(OC=2C(=CC(NC(=O)C=3C(C(C=4C=CC(F)=CC=4)=CN(COC(=O)C4CNCCC4)C=3)=O)=CC=2)F)=C1Cl LADCXWSDWZWZGQ-UHFFFAOYSA-N 0.000 claims 2
- BOHQBNXWTJDQSV-UHFFFAOYSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl piperidine-4-carboxylate Chemical compound NC1=NC=CC(OC=2C(=CC(NC(=O)C=3C(C(C=4C=CC(F)=CC=4)=CN(COC(=O)C4CCNCC4)C=3)=O)=CC=2)F)=C1Cl BOHQBNXWTJDQSV-UHFFFAOYSA-N 0.000 claims 2
- BQIVJVAZDJHDJF-UHFFFAOYSA-N ethyl 2-amino-3-methylbutanoate Chemical compound CCOC(=O)C(N)C(C)C BQIVJVAZDJHDJF-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- PDYXPCKITKHFOZ-UHFFFAOYSA-N n-[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]-5-(4-fluorophenyl)-4-oxo-1h-pyridine-3-carboxamide Chemical compound NC1=NC=CC(OC=2C(=CC(NC(=O)C=3C(C(C=4C=CC(F)=CC=4)=CNC=3)=O)=CC=2)F)=C1Cl PDYXPCKITKHFOZ-UHFFFAOYSA-N 0.000 claims 2
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 201000008808 Fibrosarcoma Diseases 0.000 claims 1
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- OOIORTLXTFQSHA-UHFFFAOYSA-N [3-[[4-(2-amino-3-chloropyridin-4-yl)oxy-3-fluorophenyl]carbamoyl]-5-(4-fluorophenyl)-4-oxopyridin-1-yl]methyl 1-methylpiperidine-4-carboxylate Chemical compound C1CN(C)CCC1C(=O)OCN1C=C(C=2C=CC(F)=CC=2)C(=O)C(C(=O)NC=2C=C(F)C(OC=3C(=C(N)N=CC=3)Cl)=CC=2)=C1 OOIORTLXTFQSHA-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 201000010175 gallbladder cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (13)
1. Spoj sljedeće Formule (I):
[image]
ili njegova sol, gdje:
G je H, -CHX-OP(=O)(OH)2, ili -CHX-OC(=O)Z;
X je H ili alkil po izboru supstituiran jednim ili više od OH, halogen, cijano, i/ili -NR1R2;
Z je alkil, cikloalkil, aril, ili heterociklo po izboru supstituiran jednim ili više od alkil, OH, halogen, cijano, i/ili -NR3R4; i
R1, R2, R3, i R4 su nezavisno H i/ili alkil.
2. Spoj prema zahtjevu 1 ili njegova sol, gdje: G je H.
3. Spoj prema zahtjevu 1 ili njegova sol, gdje:
G je -CHX-OP(=O)(OH)2; i
X je H ili C1-C2alkil po izboru supstituiran jednim ili više od OH, halogen, cijano, i/ili -NR1R2.
4. Spoj prema zahtjevu 3 ili njegova sol, gdje:
X je H ili metil.
5. Spoj prema zahtjevu 4 ili njegova sol, gdje X je H.
6. Spoj prema zahtjevu 1 ili njegova sol, gdje:
G je -CHX-OC(=O)Z;
X je H, C1-C2alkil po izboru supstituiran jednim ili više od OH, halogen, cijano, i/ili -NR1R2;
Z je C1-C6alkil ili 5- do 6-eročlani heterociklo koji obuhvaća jedan dušikov heteroatom, po izboru supstituiran jednim ili više od alkil, OH, halogen, cijano, i/ili -NR3R4; i
R1, R2, R3, i R4 su nezavisno H i/ili C1-C4alkil.
7. Spoj prema zahtjevu 6 ili njegova sol, gdje X je H ili metil.
8. Spoj prema zahtjevu 7 ili njegova sol, gdje je G:
[image]
[image]
ili
[image]
9. Spoj prema zahtjevu 1 ili njegova sol, gdje je taj spoj:
N-(4-(2-Amino-3-kloropiridin-4-iloksi)-3-fluorofenil)-5-(4-fluorofenil)-4-okso-1,4-dihidropiridin-3-karboksamid (1);
(3-(4-(2-Amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil dihidrogen fosfat (2);
(S)-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil 2-aminopropanoat (3);
(S)-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil 2-amino-3-metilbutanoat (4);
(S)-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil 2-amino-4-metilpentanoat (5);
(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil piperidin-3-karboksilat (6);
(S)-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil pirolidin-2-karboksilat (7);
(S)-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil) pirolidin-3-karboksilat (8);
(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil piperidin-4-karboksilat (9);
1-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)etilpiperidin-4-karboksilat (10);
(2S)-1-(3-(4-(2-amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)etil 2-amino-3-metilbutanoat (11); ili
(3-(4-(2-Amino-3-kloropiridin-4-iloksi)-3-fluorofenilkarbamoil)-5-(4-fluorofenil)-4-oksopiridin-1(4H)-il)metil1-metilpiperidin-4-karboksilat (12).
10. Farmaceutska smjesa koja sadrži barem jedan spoj prema bilo kojem od zahtjeva 1 do 9 ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljivi nosač ili punilo.
11. Farmaceutska smjesa prema zahtjevu 10, gdje je taj barem jedan spoj:
[image]
ili njegova farmaceutski prihvatljiva sol.
12. Spoj prema bilo kojem od zahtjeva 1 do 9 ili njegova farmaceutski prihvatljiva sol za uporabu u liječenju raka.
13. Spoj prema zahtjevu 12 za uporabu u liječenju raka, gdje taj rak je rak mjehura, rak dojke, rak kolorektuma, rak želuca, rak glave i vrata, rak bubrega, rak jetre, rak pluća, rak jajnika, rak gušterače/žučnog mjehura, rak prostate, rak štitnjače, osteosarkom, rabdomiosarkom, melanom, glioblastomi/astrocitomi, MFH/fibrosarkom ili mezoteliom.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2284808P | 2008-01-23 | 2008-01-23 | |
| PCT/US2009/031649 WO2009094417A1 (en) | 2008-01-23 | 2009-01-22 | 4-pyridinone compounds and their use for cancer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20130040T1 true HRP20130040T1 (hr) | 2013-02-28 |
Family
ID=40637826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20130040AT HRP20130040T1 (hr) | 2008-01-23 | 2013-01-17 | 4-piridinon spojevi i njihova uporaba kod karcinoma |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8124768B2 (hr) |
| EP (1) | EP2235002B1 (hr) |
| JP (1) | JP5314050B2 (hr) |
| KR (1) | KR101596527B1 (hr) |
| CN (1) | CN101977906B (hr) |
| AU (1) | AU2009206440B2 (hr) |
| BR (1) | BRPI0906444B8 (hr) |
| CA (1) | CA2713111C (hr) |
| CO (1) | CO6230986A2 (hr) |
| CY (1) | CY1114140T1 (hr) |
| DK (1) | DK2235002T3 (hr) |
| EA (1) | EA017736B1 (hr) |
| ES (1) | ES2398335T3 (hr) |
| HK (1) | HK1143157A1 (hr) |
| HR (1) | HRP20130040T1 (hr) |
| IL (1) | IL207212A (hr) |
| NZ (1) | NZ586630A (hr) |
| PL (1) | PL2235002T3 (hr) |
| PT (1) | PT2235002E (hr) |
| SI (1) | SI2235002T1 (hr) |
| WO (1) | WO2009094417A1 (hr) |
| ZA (1) | ZA201005248B (hr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009303602B2 (en) | 2008-10-14 | 2012-06-14 | Sunshine Lake Pharma Co., Ltd. | Compounds and methods of use |
| EP2408300B1 (en) | 2009-03-21 | 2016-05-11 | Sunshine Lake Pharma Co., Ltd. | Amino ester derivatives, salts thereof and methods of use |
| EP2563773A1 (en) | 2010-04-29 | 2013-03-06 | Deciphera Pharmaceuticals, LLC | Pyridone amides and analogs exhibiting anti-cancer and anti-proliferative activites |
| RU2477723C2 (ru) | 2011-06-16 | 2013-03-20 | Общество С Ограниченной Ответственностью "Фьюжн Фарма" | Ингибиторы протеинкиназ (варианты), их применение для лечения онкологических заболеваний и фармацевтическая композиция на их основе |
| PT2810937T (pt) | 2012-01-31 | 2017-03-03 | Daiichi Sankyo Co Ltd | Derivado de piridona |
| EP2879677B1 (en) | 2012-07-28 | 2017-06-14 | Calitor Sciences, LLC | Substituted pyrazolone compounds and methods of use |
| US8975282B2 (en) | 2012-07-28 | 2015-03-10 | Sunshine Lake Pharma Co., Ltd. | Substituted pyrazolone compounds and methods of use |
| US20140057920A1 (en) | 2012-08-23 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| US20140057926A1 (en) * | 2012-08-23 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| US9102624B2 (en) * | 2012-08-23 | 2015-08-11 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| TWI723572B (zh) | 2014-07-07 | 2021-04-01 | 日商第一三共股份有限公司 | 具有四氫吡喃基甲基之吡啶酮衍生物及其用途 |
| CN105153026B (zh) * | 2015-08-21 | 2018-02-02 | 江西科技师范大学 | 含联芳基酰胺结构的索拉非尼衍生物及其制备方法和应用 |
| WO2024067783A1 (zh) * | 2022-09-28 | 2024-04-04 | 上海济煜医药科技有限公司 | 含磷类化合物及其制备方法和医药应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430885A3 (en) | 1989-12-01 | 1991-11-06 | Ciba-Geigy Ag | Anthelmintical compounds |
| US6143764A (en) | 1995-11-07 | 2000-11-07 | Kirin Beer Kabushiki Kaisha | Quinoline and quinazoline derivatives inhibiting platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing the same |
| EP1087937A1 (en) | 1998-06-17 | 2001-04-04 | Du Pont Pharmaceuticals Company | Cyclic hydroxamic acids as metalloproteinase inhibitors |
| US6355660B1 (en) | 1999-07-20 | 2002-03-12 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
| WO2001005769A2 (en) | 1999-07-20 | 2001-01-25 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
| WO2001021596A1 (en) | 1999-09-21 | 2001-03-29 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| WO2001070754A1 (en) * | 2000-03-22 | 2001-09-27 | Merck Frosst Canada & Co. | Sulfur substituted aryldifluoromethylphosphonic acids as ptp-1b inhibitors |
| FR2812633A1 (fr) | 2000-08-04 | 2002-02-08 | Aventis Cropscience Sa | Derives de phenyl(thio)urees et phenyl(thio)carbamates fongicides |
| SE0102384D0 (sv) | 2001-07-03 | 2001-07-03 | Pharmacia Ab | New compounds |
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| SE0302487D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
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| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| WO2007033196A1 (en) | 2005-09-14 | 2007-03-22 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| WO2007035428A1 (en) | 2005-09-15 | 2007-03-29 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| US7348325B2 (en) | 2005-11-30 | 2008-03-25 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| ES2531396T3 (es) | 2008-01-23 | 2015-03-13 | Bristol Myers Squibb Co | Proceso para preparar compuestos de piridinona |
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