HRP20110015T1 - DERIVATI IMIDAZO[1,2-a]PIRIDIN-2-KARBOKSAMIDA, NJIHOVO DOBIVANJE I NJIHOVA UPOTREBA U TERAPIJI - Google Patents
DERIVATI IMIDAZO[1,2-a]PIRIDIN-2-KARBOKSAMIDA, NJIHOVO DOBIVANJE I NJIHOVA UPOTREBA U TERAPIJI Download PDFInfo
- Publication number
- HRP20110015T1 HRP20110015T1 HR20110015T HRP20110015T HRP20110015T1 HR P20110015 T1 HRP20110015 T1 HR P20110015T1 HR 20110015 T HR20110015 T HR 20110015T HR P20110015 T HRP20110015 T HR P20110015T HR P20110015 T1 HRP20110015 T1 HR P20110015T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyridine
- carboxamide
- phenylimidazo
- group
- imidazo
- Prior art date
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- 239000003814 drug Substances 0.000 title 1
- BEHYAANJUKYBTH-UHFFFAOYSA-N imidazo[1,2-a]pyridine-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CN21 BEHYAANJUKYBTH-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 30
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 150000002367 halogens Chemical class 0.000 claims abstract 12
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 239000002253 acid Substances 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 6
- 125000004429 atom Chemical group 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- 229910052705 radium Inorganic materials 0.000 claims abstract 2
- 229910052701 rubidium Inorganic materials 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 230000002265 prevention Effects 0.000 claims 7
- PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 claims 3
- -1 6-Chloro-N-phenylimidazo[1,2-a]pyridine-2-carboxamide 6-Methyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide 6-(Dimethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide Chemical compound 0.000 claims 3
- LJHNQCYVAAPQRP-UHFFFAOYSA-N 6-(diethylamino)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide 6-(3-methylphenyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide Chemical compound CCN(CC)c1ccc2nc(cn2c1)C(=O)Nc1ccccc1.Cc1cccc(c1)-c1ccc2nc(cn2c1)C(=O)Nc1ccccc1 LJHNQCYVAAPQRP-UHFFFAOYSA-N 0.000 claims 1
- GEBMQUDYOROJBS-UHFFFAOYSA-N 6-(dimethylamino)-n-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C=1N2C=C(N(C)C)C=CC2=NC=1C(=O)NC1=CC=CC(C(F)(F)F)=C1 GEBMQUDYOROJBS-UHFFFAOYSA-N 0.000 claims 1
- ZWVHKKAQJYXIQM-UHFFFAOYSA-N 6-[3-(methylcarbamoyl)phenyl]-n-phenylimidazo[1,2-a]pyridine-2-carboxamide Chemical compound CNC(=O)C1=CC=CC(C2=CN3C=C(N=C3C=C2)C(=O)NC=2C=CC=CC=2)=C1 ZWVHKKAQJYXIQM-UHFFFAOYSA-N 0.000 claims 1
- LTIYHHOHZJJBFX-UHFFFAOYSA-N 6-acetyl-n-phenylimidazo[1,2-a]pyridine-2-carboxamide;hydrochloride Chemical compound Cl.C=1N2C=C(C(=O)C)C=CC2=NC=1C(=O)NC1=CC=CC=C1 LTIYHHOHZJJBFX-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
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- XELWDPKVWRLXGE-UHFFFAOYSA-N C(C)(=O)NC=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.OC(C)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1.C(C)(C)C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2 Chemical compound C(C)(=O)NC=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.OC(C)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1.C(C)(C)C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2 XELWDPKVWRLXGE-UHFFFAOYSA-N 0.000 claims 1
- NBCRAXITIQGRSB-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=O)C=1N=C2N(C=C(C=C2)C=C)C1.C1(=CC=CC=C1)NC(=O)C=1N=C2N(C=C(C=C2)C2=CC=CC=C2)C1.ClC=1C=CC=2N(C1)C=C(N2)C(=O)NC2=C(C=CC=C2)Cl Chemical compound C1(=CC=CC=C1)NC(=O)C=1N=C2N(C=C(C=C2)C=C)C1.C1(=CC=CC=C1)NC(=O)C=1N=C2N(C=C(C=C2)C2=CC=CC=C2)C1.ClC=1C=CC=2N(C1)C=C(N2)C(=O)NC2=C(C=CC=C2)Cl NBCRAXITIQGRSB-UHFFFAOYSA-N 0.000 claims 1
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- BJSHMZLZUNRCGU-UHFFFAOYSA-N CN(C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC(=CC=C2)F)C.C(N)(=O)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1 Chemical compound CN(C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC(=CC=C2)F)C.C(N)(=O)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1 BJSHMZLZUNRCGU-UHFFFAOYSA-N 0.000 claims 1
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- 208000022306 Cerebral injury Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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- KMEZENUTTJRIRO-UHFFFAOYSA-N FC=1C=C(C=C(C1)F)NC(=O)C=1N=C2N(C=C(C=C2)N(C)C)C1.ClC=1C=C(C=CC1)NC(=O)C=1N=C2N(C=C(C=C2)C2=CC(=CC=C2)CO)C1 Chemical compound FC=1C=C(C=C(C1)F)NC(=O)C=1N=C2N(C=C(C=C2)N(C)C)C1.ClC=1C=C(C=CC1)NC(=O)C=1N=C2N(C=C(C=C2)C2=CC(=CC=C2)CO)C1 KMEZENUTTJRIRO-UHFFFAOYSA-N 0.000 claims 1
- KZXLZYDINXQBHC-UHFFFAOYSA-N FC=1C=C(C=CC1)NC(=O)C=1N=C2N(C=C(C=C2)C2=CC(=CC=C2)CO)C1.CN(C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=C(C=CC=C2)F)C Chemical compound FC=1C=C(C=CC1)NC(=O)C=1N=C2N(C=C(C=C2)C2=CC(=CC=C2)CO)C1.CN(C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=C(C=CC=C2)F)C KZXLZYDINXQBHC-UHFFFAOYSA-N 0.000 claims 1
- KEMFSVLMLCQIAQ-UHFFFAOYSA-N FC=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.BrC=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1.CC1=CC=2N(C=C1)C=C(N2)C(=O)NC2=CC=CC=C2 Chemical compound FC=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.BrC=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1.CC1=CC=2N(C=C1)C=C(N2)C(=O)NC2=CC=CC=C2 KEMFSVLMLCQIAQ-UHFFFAOYSA-N 0.000 claims 1
- ICFCQBOWXWGCJV-UHFFFAOYSA-N N-(3-chloro-2-fluorophenyl)-6-(dimethylamino)imidazo[1,2-a]pyridine-2-carboxamide N-[3-(difluoromethoxy)phenyl]-6-(dimethylamino)imidazo[1,2-a]pyridine-2-carboxamide Chemical compound FC(OC=1C=C(C=CC1)NC(=O)C=1N=C2N(C=C(C=C2)N(C)C)C1)F.ClC=1C(=C(C=CC1)NC(=O)C=1N=C2N(C=C(C=C2)N(C)C)C1)F ICFCQBOWXWGCJV-UHFFFAOYSA-N 0.000 claims 1
- BQKFKIFSXKOKDS-UHFFFAOYSA-N N1(CCOCC1)C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.ClC=2C=CC(=C(C2)NC(=O)C=2N=C1N(C=C(C=C1)C1=CC(=CC=C1)CO)C2)F Chemical compound N1(CCOCC1)C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.ClC=2C=CC(=C(C2)NC(=O)C=2N=C1N(C=C(C=C1)C1=CC(=CC=C1)CO)C2)F BQKFKIFSXKOKDS-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- UKQPYPFTSUNKJJ-UHFFFAOYSA-N OC(C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2)C2=CC=CC=C2.OC(C)(C)C=2C=C(C=CC2)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1 Chemical compound OC(C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2)C2=CC=CC=C2.OC(C)(C)C=2C=C(C=CC2)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1 UKQPYPFTSUNKJJ-UHFFFAOYSA-N 0.000 claims 1
- JYFWRZSLYABYED-UHFFFAOYSA-N OCC=1C=C(C=CC1)C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.OCC2=C(C=CC=C2)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1 Chemical compound OCC=1C=C(C=CC1)C=1C=CC=2N(C1)C=C(N2)C(=O)NC2=CC=CC=C2.OCC2=C(C=CC=C2)C=2C=CC=1N(C2)C=C(N1)C(=O)NC1=CC=CC=C1 JYFWRZSLYABYED-UHFFFAOYSA-N 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000034799 Tauopathies Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000013043 chemical agent Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- NWJXSOPECLIQJJ-UHFFFAOYSA-N n-(2,5-difluorophenyl)-6-(dimethylamino)imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C=1N2C=C(N(C)C)C=CC2=NC=1C(=O)NC1=CC(F)=CC=C1F NWJXSOPECLIQJJ-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
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Abstract
Spojevi formule (I): naznačeni time što: X predstavlja jednu ili više sljedećih skupina: • fenilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se, međusobno neovisno, bira između sljedećih atoma ili skupina: halogena, (C1-C6)alkoksi, (C1-C6)alkila, (C3-C7)cikloalkil(C1-C6)alkila, (C3-C7)cikloalkil(C1-C6)alkoksi ili NRaRb, R1 predstavlja atom vodika, halogen, (C1-C6)alkoksi skupinu, (C1-C6)alkilnu skupinu, (C3-C7)cikloalkil(C1-C6)alkilnu skupinu, (C3-C7)cikloalkil(C1-C6)alkoksi skupinu, amino ili NRcRd skupinu; alkilne i alkoksi skupine mogu izborno biti supstituirane s jednim ili više halogena, hidroksilnih, amino ili (C1-C6)alkoksi skupina, R2 predstavlja jednu od sljedećih skupina: • atom vodika, • (C1-C6)alkilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se, međusobno neovisno, bira između hidroksilne skupine, halogena, amino, NRaRb skupine ili fenilne skupine, • (C1-C6)alkoksi skupina, izborno supstituirana s jednom ili više skupina, koje se, međusobno neovisno, bira između hidroksilne skupine, halogena, amino ili NRaRb skupine, • (C3-C7)cikloalkil(C1-C6)alkilnu skupinu, • (C3-C7)cikloalkil(C1-C6)alkoksi skupinu, • (C2-C6)alkenilnu skupinu, • (C2-C6)alkinilnu skupinu, • -CO-R5 skupinu, • -CO-NR6R7 skupinu, • -CO-O-R8 skupinu, • -NR9-CO-R10 skupinu, • -NR11R12 skupinu, • atom halogena, • cijano skupinu, • fenilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se, međusobno neovisno, bira između sljedećih atoma ili skupina: halogena, (C1-C6)alkoksi, NRaRb, -CO-R5, -CO-NR6R7, -CO-O-R5, (C3-C7)cikloalkil(C1-C6)alkilne, (C3-C7)cikloalkil(C1-C6)alkoksi, (C1-C6)alkilne skupine, izborno supstituirane s jednim ili više hidroksila ili NRaRb, R3 predstavlja atom vodika, (C1-C6)alkilnu skupinu, (C1-C6)alkoksi skupinu ili atom halogena, R4 predstavlja atom vodika, (C1-C4)alkilnu skupinu, (C1-C4)alkoksi skupinu ili atom fluora, R5 predstavlja atom vodika, fenilnu skupinu ili (C1-C6)alkilnu skupinu, R6 i R7, koji su isti ili različiti, predstavljaju atom vodika ili (C1-C6)alkilna skupina ili tvore, s atomom dušika, 4- do 7-eročlani prsten, koji izborno sadrži dodatni heteroatom, kojeg se bira između N, O ili S, R8 predstavlja (C1-C6)alkilnu skupinu, R9 i R10, koji su isti ili različiti, predstavljaju atom vodika ili (C1-C6)alkilnu skupinu, R11 i R12, koji su isti ili različiti, predstavljaju (C1-C6)alkilnu skupinu ili tvore, s atomom dušika, 4- do 7-eročlani prsten, koji izborno sadrži dodatni heteroatom, kojeg se bira između N, O ili S, Ra i Rb su, međusobno neovisno, vodik ili (C1-C6)alkil ili tvore, s atomom dušika, 4- do 7-eročlani prsten, Rc je vodik, a Rd je (C1-C6)alkil, i najmanje jedan od supstituenata R1, R2, R3 i R4 nije vodik; i, kada R3 je metil, X nije supstituiran; kada R1 je metil, X nije supstituiran; kada R2 je klor, X nije para-fluorfenil; u obliku baze ili adicijske soli s kiselinom. Paten
Claims (13)
1. Spojevi formule (I):
[image]
naznačeni time što:
X predstavlja jednu ili više sljedećih skupina:
• fenilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se, međusobno neovisno, bira između sljedećih atoma ili skupina: halogena, (C1-C6)alkoksi, (C1-C6)alkila, (C3-C7)cikloalkil(C1-C6)alkila, (C3-C7)cikloalkil(C1-C6)alkoksi ili NRaRb,
R1 predstavlja atom vodika, halogen, (C1-C6)alkoksi skupinu, (C1-C6)alkilnu skupinu, (C3-C7)cikloalkil(C1-C6)alkilnu skupinu, (C3-C7)cikloalkil(C1-C6)alkoksi skupinu, amino ili NRcRd skupinu; alkilne i alkoksi skupine mogu izborno biti supstituirane s jednim ili više halogena, hidroksilnih, amino ili (C1-C6)alkoksi skupina,
R2 predstavlja jednu od sljedećih skupina:
• atom vodika,
• (C1-C6)alkilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se, međusobno neovisno, bira između hidroksilne skupine, halogena, amino, NRaRb skupine ili fenilne skupine,
• (C1-C6)alkoksi skupina, izborno supstituirana s jednom ili više skupina, koje se, međusobno neovisno, bira između hidroksilne skupine, halogena, amino ili NRaRb skupine,
• (C3-C7)cikloalkil(C1-C6)alkilnu skupinu,
• (C3-C7)cikloalkil(C1-C6)alkoksi skupinu,
• (C2-C6)alkenilnu skupinu,
• (C2-C6)alkinilnu skupinu,
• -CO-R5 skupinu,
• -CO-NR6R7 skupinu,
• -CO-O-R8 skupinu,
• -NR9-CO-R10 skupinu,
• -NR11R12 skupinu,
• atom halogena,
• cijano skupinu,
• fenilnu skupinu, izborno supstituiranu s jednom ili više skupina, koje se, međusobno neovisno, bira između sljedećih atoma ili skupina: halogena, (C1-C6)alkoksi, NRaRb, -CO-R5, -CO-NR6R7, -CO-O-R5, (C3-C7)cikloalkil(C1-C6)alkilne, (C3-C7)cikloalkil(C1-C6)alkoksi, (C1-C6)alkilne skupine, izborno supstituirane s jednim ili više hidroksila ili NRaRb,
R3 predstavlja atom vodika, (C1-C6)alkilnu skupinu, (C1-C6)alkoksi skupinu ili atom halogena,
R4 predstavlja atom vodika, (C1-C4)alkilnu skupinu, (C1-C4)alkoksi skupinu ili atom fluora,
R5 predstavlja atom vodika, fenilnu skupinu ili (C1-C6)alkilnu skupinu,
R6 i R7, koji su isti ili različiti, predstavljaju atom vodika ili (C1-C6)alkilna skupina ili tvore, s atomom dušika, 4- do 7-eročlani prsten, koji izborno sadrži dodatni heteroatom, kojeg se bira između N, O ili S,
R8 predstavlja (C1-C6)alkilnu skupinu,
R9 i R10, koji su isti ili različiti, predstavljaju atom vodika ili (C1-C6)alkilnu skupinu,
R11 i R12, koji su isti ili različiti, predstavljaju (C1-C6)alkilnu skupinu ili tvore, s atomom dušika, 4- do 7-eročlani prsten, koji izborno sadrži dodatni heteroatom, kojeg se bira između N, O ili S,
Ra i Rb su, međusobno neovisno, vodik ili (C1-C6)alkil ili tvore, s atomom dušika, 4- do 7-eročlani prsten,
Rc je vodik, a Rd je (C1-C6)alkil,
i najmanje jedan od supstituenata R1, R2, R3 i R4 nije vodik;
i, kada R3 je metil, X nije supstituiran;
kada R1 je metil, X nije supstituiran;
kada R2 je klor, X nije para-fluorfenil;
u obliku baze ili adicijske soli s kiselinom.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što spojevi formule (I), u kojoj: X je fenilna skupina
u obliku baze ili adicijske soli s kiselinom.
3. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što spojevi formule (I), u kojoj: R1, R3 i R4 su atomi vodika
u obliku baze ili adicijske soli s kiselinom.
4. Spojevi u skladu s patentnim zahtjevom 1, naznačeni time što su:
6-Klor-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(Dimetilamino)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(1-Hidroksi-1-metiletil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
N-(4-Fluorfenil)-6-isopropenilimidazo[1,2-a]piridin-2-karboksamid
6-Klor-N-(2-klorfenil)imidazo[1,2-a]piridin-2-karboksamid
N,6-Difenilimidazo[1,2-a]piridin-2-karboksamid
N-Fenil-6-vinilimidazo[1,2-a]piridin-2-karboksamid
6-Etil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Formil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Etinil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-[3-(1-Hidroksi-1-metiletil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-[Hidroksi(fenil)metil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Acetil-N-fenilimidazo[1,2-a]piridin-2-karboksamid-hidroklorid (1:1)
6-Izopropil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(1-Hidroksietil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Acetamido-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(Dimetilamino)-5-metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
5-Metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
7-Metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Brom-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Fluor-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6,8-Difluor-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Brom-5-metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Jod-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Cijano-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(Hidroksimetil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Metoksi-N-fenilimidazo[1,2-a]piridin-2-karboksamid
N-(4-Fluorfenil)-6-(1-hidroksi-1-metiletil)imidazo[1,2-a]piridin-2-karboksamid
6-Benzoil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Izopropenil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Klor-N-(3-fluorfenil)imidazo[1,2-a]piridin-2-karboksamid
6-Klor-N-(3-klorfenil)imidazo[1,2-a]piridin-2-karboksamid
6-Klor-N-(3-metoksifenil)imidazo[1,2-3]piridin-2-karboksamid
6-Klor-N-[4-(dimetilamino)fenil]imidazo[1,2-a]piridin-2-karboksamid
6-Klor-N-(4-klorfenil)imidazo[1,2-a]piridin-2-karboksamid
6-[2-(Hidroksimetil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-[3-(Hidroksimetil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-[4-(Hidroksimetil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(2-Formilfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(3-Formilfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
5,6-Dimetil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
Metil-3-[2-(anilinokarbonil)imidazo[1,2-a]piridin-6-il]benzoate
6-(3-Acetilfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(3-Fluorfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(4-Metilfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(3-Metoksifenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-[3-(Aminometil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(3-Klorfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(3-Karbamoilfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-[3-(1-Hidroksietil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(3-Metilfenil)-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(Dietilamino)-N-fenilimidazo[1,2-a]piridin-2-karboksamid i njegov hidroklorid (1:1)
6-[3-(Metilkarbamoil)fenil]-N-fenilimidazo[1,2-a]piridin-2-karboksamid i njegov hidroklorid (1:1)
6-Karbamoil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-(Dimetilamino)-N-(3-fluorfenil)imidazo[1,2-a]piridin-2-karboksamid
N-(2,5-Difluorfenil)-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
N-(2,3-Difluorfenil)-6-(dimetilamino)imidazo[1,2-a]pirldine-2-karboksamid
6-(Dimetilamino)-N-(2-fluorfenil)imidazo[1,2-a]piridin-2-karboksamid
N-(3-Fluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(3,5-Difluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(2-Klorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
6-[3-(Hidroksimetil)fenil]-N-(3-metilfenil)imidazo[1,2-a]piridin-2-karboksamid
N-(2,5-Difluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(2,3-Difluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(2-Fluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(5-Klor-2-fluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
6-Morfolin-4-il-N-fenilimidazo[1,2-a]piridin-2-karboksamid i njegov hidroklorid (1:1)
6-Azetidin-1-il-N-fenilimidazo[1,2-a]piridin-2-karboksamid
6-Jod-5-metil-N-fenilimidazo[1,2-a]piridin-2-karboksamid
N-(3,5-Difluorfenil)-6-jodimidazo[1,2-a]piridin-2-karboksamid
N-(3-Klorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(3,5-Difluorfenil)-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
N-(2-Klorfenil)-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
6-(Dimetilamino)-N-[3-(trifluormetoksi)fenil]imidazo[1,2-a]piridin-2-karboksamid
N-(3-Klor-2-fluorfenil)-6-[3-(hidroksimetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
6-(Dimetilamino)-N-(3-metilfenil)imidazo[1,2-a]piridin-2-karboksamid
N-(3-Klorfenil)-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
N-(5-Klor-2-fluorfenil)-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
N-(3-Klor-2-fluorfenil)-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
N-[3-(Difluormetoksi)fenil]-6-(dimetilamino)imidazo[1,2-a]piridin-2-karboksamid
6-(Dimetilamino)-N-[3-(trifluormetil)fenil]imidazo[1,2-a]piridin-2-karboksamid
u obliku baze ili adicijske soli s kiselinom.
5. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili adicijsku sol ovog spoja s farmaceutski prihvatljivom kiselinom.
6. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili farmaceutski prihvatljivu sol ovog spoja, a također i najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
7. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju neurodegenerativnih bolesti.
8. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju multiple skleroze, ozljeda velikog mozga i epilepsije.
9. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju psihijatrijskih bolesti.
10. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju upalnih bolesti.
11. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju osteoporoze i raka.
12. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju Parkinsonove bolesti, Alzheimerove bolesti ili tauopatija.
13. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je namijenjen upotrebi u liječenju i sprječavanju shizofrenije, depresije, ovisnosti o kemijskim sredstvima ili poremećaja nedostatka pažljivosti s hiperaktivnošću.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0606012A FR2903107B1 (fr) | 2006-07-03 | 2006-07-03 | Derives d'imidazopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
PCT/FR2007/001125 WO2008003856A1 (fr) | 2006-07-03 | 2007-07-03 | Dérivés d'imidazo[1,2-a]pyridine-2-carboxamides leur préparation et leur application en thérapeutique |
Publications (1)
Publication Number | Publication Date |
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HRP20110015T1 true HRP20110015T1 (hr) | 2011-02-28 |
Family
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Family Applications (1)
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HR20110015T HRP20110015T1 (hr) | 2006-07-03 | 2011-01-11 | DERIVATI IMIDAZO[1,2-a]PIRIDIN-2-KARBOKSAMIDA, NJIHOVO DOBIVANJE I NJIHOVA UPOTREBA U TERAPIJI |
Country Status (24)
Country | Link |
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US (2) | US7704989B2 (hr) |
EP (1) | EP2041133B1 (hr) |
JP (1) | JP5259587B2 (hr) |
KR (1) | KR20090024776A (hr) |
CN (1) | CN101484453B (hr) |
AT (1) | ATE484504T1 (hr) |
AU (1) | AU2007271008B2 (hr) |
BR (1) | BRPI0714320A2 (hr) |
CA (1) | CA2655713C (hr) |
CY (1) | CY1111868T1 (hr) |
DE (1) | DE602007009839D1 (hr) |
DK (1) | DK2041133T3 (hr) |
ES (1) | ES2354482T3 (hr) |
FR (1) | FR2903107B1 (hr) |
HK (1) | HK1135964A1 (hr) |
HR (1) | HRP20110015T1 (hr) |
IL (1) | IL195891A0 (hr) |
MX (1) | MX2008016546A (hr) |
PL (1) | PL2041133T3 (hr) |
PT (1) | PT2041133E (hr) |
RS (1) | RS51652B (hr) |
RU (1) | RU2441003C2 (hr) |
SI (1) | SI2041133T1 (hr) |
WO (1) | WO2008003856A1 (hr) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2903108B1 (fr) * | 2006-07-03 | 2008-08-29 | Sanofi Aventis Sa | Utilisation de derives d'imidazo[1,2-a] pyridine-2-carboxamides en therapeutique. |
TW200911798A (en) | 2007-08-02 | 2009-03-16 | Amgen Inc | PI3 kinase modulators and methods of use |
CA2710194C (en) * | 2007-12-19 | 2014-04-22 | Amgen Inc. | Inhibitors of p13 kinase |
FR2925906B1 (fr) * | 2008-01-02 | 2010-08-20 | Sanofi Aventis | COMPOSES DE N-PHENYL-IMIDAZO°1,2-a!PYRIDINE-2-CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
FR2925900B1 (fr) * | 2008-01-02 | 2011-03-04 | Sanofi Aventis | DERIVES DE N-PHENYL-IMIDAZO°1,2-a!PYRIDINE-2-CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
FR2925901B1 (fr) * | 2008-01-02 | 2011-03-04 | Sanofi Aventis | DERIVES DE N-HETEROCYCLIQUE-IMIDAZO°1,2-a!PYRIDINE-2- CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
FR2925903B1 (fr) * | 2008-01-02 | 2011-01-21 | Sanofi Aventis | DERIVES 6-HETEROCYCLIQUE-IMIDAZO°1,2-a!PYRIDINE-2- CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
FR2925905B1 (fr) | 2008-01-02 | 2010-11-05 | Sanofi Aventis | DERIVES DE 2-BENZOYL-IMIDAZO°1,2-a!PYRIDINE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
FR2928923B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-heteroaryl-6-phenyl-imidazo °1,2-a!pyridines, leur preparation et leur application en therapeutiques |
FR2928922B1 (fr) | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines polysubstitues, leur preparation et leur application en therapeutique |
FR2928921B1 (fr) * | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines, leur preparation et leur application en therapeutique |
FR2928924B1 (fr) | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 6-heteroaryle-imidazo°1,2-a! pyridines, leur preparation et leur application en therapeutique |
FR2933609B1 (fr) | 2008-07-10 | 2010-08-27 | Fournier Lab Sa | Utilisation de derives d'indole comme activateurs de nurr-1, pour le traitement de la maladie de parkinson. |
CA2755768A1 (en) * | 2009-03-23 | 2010-09-30 | Merck Sharp & Dohme Corp. | P2x3, receptor antagonists for treatment of pain |
AU2010229142A1 (en) * | 2009-03-23 | 2011-10-13 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
FR2950053B1 (fr) | 2009-09-11 | 2014-08-01 | Fournier Lab Sa | Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
FR2955110A1 (fr) | 2010-01-08 | 2011-07-15 | Fournier Lab Sa | Nouveaux derives de type pyrrolopyridine benzoique |
WO2012026766A2 (ko) * | 2010-08-25 | 2012-03-01 | (주)네오팜 | 신규한 헤테로고리 화합물 및 이를 이용한 염증성 질환 치료용 조성물 |
WO2014103801A1 (ja) * | 2012-12-28 | 2014-07-03 | 株式会社新日本科学 | イミダゾピリジン誘導体を有効成分として含むoct3活性阻害剤又はoct3検出剤 |
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FR2638161B1 (fr) * | 1988-10-24 | 1991-01-11 | Centre Nat Rech Scient | Nouvelles benzoyl-2 imidazo (1,2-a) pyridines et leurs sels, leur procede de preparation, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
US6489337B1 (en) | 2000-03-31 | 2002-12-03 | Ortho-Mcneil Pharmaceutical, Inc. | Method for treating histamine H3 receptor-mediated disorders with 2- or 3-aryl substituted imidazo[1,2-a] pyridines |
DE10117184A1 (de) | 2001-04-05 | 2002-10-17 | Gruenenthal Gmbh | Substituierte Imidazol[1,2-a]-pyridin-3-yl-amid- und -aminverbindungen |
EP1465869B1 (en) | 2001-12-21 | 2013-05-15 | Exelixis Patent Company LLC | Modulators of lxr |
GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
JP2006522794A (ja) * | 2003-04-10 | 2006-10-05 | ファイザー株式会社 | Nr2b受容体拮抗物質としての二環系化合物 |
KR101153335B1 (ko) * | 2003-09-24 | 2012-07-05 | 메틸진 인코포레이티드 | 히스톤 데아세틸라제의 억제제 |
PE20050952A1 (es) | 2003-09-24 | 2005-12-19 | Novartis Ag | Derivados de isoquinolina como inhibidores de b-raf |
JP4842829B2 (ja) | 2003-10-31 | 2011-12-21 | 武田薬品工業株式会社 | 含窒素縮合複素環化合物 |
US20050171172A1 (en) * | 2003-11-13 | 2005-08-04 | Ambit Biosciences Corporation | Amide derivatives as PDGFR modulators |
KR20070048798A (ko) * | 2004-08-31 | 2007-05-09 | 아스트라제네카 아베 | 퀴나졸리논 유도체 및 이것의 b-raf 억제제로서의 용도 |
DE602005013819D1 (de) * | 2004-12-22 | 2009-05-20 | Astrazeneca Ab | Pyridincarbonsäureamidderivate zur verwendung als antikrebsmittel |
TW200635899A (en) * | 2004-12-22 | 2006-10-16 | Astrazeneca Ab | Chemical compounds |
FR2903108B1 (fr) * | 2006-07-03 | 2008-08-29 | Sanofi Aventis Sa | Utilisation de derives d'imidazo[1,2-a] pyridine-2-carboxamides en therapeutique. |
-
2006
- 2006-07-03 FR FR0606012A patent/FR2903107B1/fr not_active Expired - Fee Related
-
2007
- 2007-07-03 BR BRPI0714320-6A2A patent/BRPI0714320A2/pt not_active IP Right Cessation
- 2007-07-03 DK DK07803833.8T patent/DK2041133T3/da active
- 2007-07-03 KR KR1020097000050A patent/KR20090024776A/ko not_active Application Discontinuation
- 2007-07-03 DE DE602007009839T patent/DE602007009839D1/de active Active
- 2007-07-03 SI SI200730465T patent/SI2041133T1/sl unknown
- 2007-07-03 ES ES07803833T patent/ES2354482T3/es active Active
- 2007-07-03 CA CA2655713A patent/CA2655713C/fr not_active Expired - Fee Related
- 2007-07-03 JP JP2009517332A patent/JP5259587B2/ja not_active Expired - Fee Related
- 2007-07-03 RS RS20110009A patent/RS51652B/en unknown
- 2007-07-03 WO PCT/FR2007/001125 patent/WO2008003856A1/fr active Application Filing
- 2007-07-03 CN CN200780025234XA patent/CN101484453B/zh not_active Expired - Fee Related
- 2007-07-03 AT AT07803833T patent/ATE484504T1/de active
- 2007-07-03 EP EP07803833A patent/EP2041133B1/fr active Active
- 2007-07-03 RU RU2009103307/04A patent/RU2441003C2/ru not_active IP Right Cessation
- 2007-07-03 PL PL07803833T patent/PL2041133T3/pl unknown
- 2007-07-03 AU AU2007271008A patent/AU2007271008B2/en not_active Ceased
- 2007-07-03 PT PT07803833T patent/PT2041133E/pt unknown
- 2007-07-03 MX MX2008016546A patent/MX2008016546A/es active IP Right Grant
-
2008
- 2008-12-11 IL IL195891A patent/IL195891A0/en unknown
- 2008-12-17 US US12/337,007 patent/US7704989B2/en not_active Expired - Fee Related
-
2010
- 2010-01-05 HK HK10100041.7A patent/HK1135964A1/xx not_active IP Right Cessation
- 2010-02-24 US US12/711,779 patent/US8404848B2/en not_active Expired - Fee Related
-
2011
- 2011-01-11 HR HR20110015T patent/HRP20110015T1/hr unknown
- 2011-01-12 CY CY20111100038T patent/CY1111868T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
US7704989B2 (en) | 2010-04-27 |
MX2008016546A (es) | 2009-02-06 |
PT2041133E (pt) | 2011-01-10 |
US20100168155A1 (en) | 2010-07-01 |
FR2903107B1 (fr) | 2008-08-22 |
RU2009103307A (ru) | 2010-08-10 |
CA2655713C (fr) | 2015-05-05 |
PL2041133T3 (pl) | 2011-04-29 |
BRPI0714320A2 (pt) | 2014-06-24 |
HK1135964A1 (en) | 2010-06-18 |
RS51652B (en) | 2011-10-31 |
WO2008003856A1 (fr) | 2008-01-10 |
KR20090024776A (ko) | 2009-03-09 |
CY1111868T1 (el) | 2015-11-04 |
CN101484453A (zh) | 2009-07-15 |
CN101484453B (zh) | 2012-07-04 |
DE602007009839D1 (de) | 2010-11-25 |
CA2655713A1 (fr) | 2008-01-10 |
JP2009541471A (ja) | 2009-11-26 |
US20090149441A1 (en) | 2009-06-11 |
FR2903107A1 (fr) | 2008-01-04 |
ATE484504T1 (de) | 2010-10-15 |
ES2354482T3 (es) | 2011-03-15 |
JP5259587B2 (ja) | 2013-08-07 |
EP2041133A1 (fr) | 2009-04-01 |
AU2007271008A1 (en) | 2008-01-10 |
SI2041133T1 (sl) | 2011-02-28 |
DK2041133T3 (da) | 2011-02-07 |
US8404848B2 (en) | 2013-03-26 |
IL195891A0 (en) | 2009-09-01 |
RU2441003C2 (ru) | 2012-01-27 |
EP2041133B1 (fr) | 2010-10-13 |
AU2007271008B2 (en) | 2012-10-11 |
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