HRP20220114T1 - Spojevi s anti-tumoralnim djelovanjem - Google Patents
Spojevi s anti-tumoralnim djelovanjem Download PDFInfo
- Publication number
- HRP20220114T1 HRP20220114T1 HRP20220114TT HRP20220114T HRP20220114T1 HR P20220114 T1 HRP20220114 T1 HR P20220114T1 HR P20220114T T HRP20220114T T HR P20220114TT HR P20220114 T HRP20220114 T HR P20220114T HR P20220114 T1 HRP20220114 T1 HR P20220114T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- ethoxymethyl
- methyl
- oxazol
- amine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 13
- 230000000259 anti-tumor effect Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- -1 oxotriazolyl Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 208000014951 hematologic disease Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 230000002062 proliferating effect Effects 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- QRCSISPIJNVFQQ-MRXNPFEDSA-N (5R)-1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-5-methylimidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NC[C@H]1C)=O)C QRCSISPIJNVFQQ-MRXNPFEDSA-N 0.000 claims 1
- GSYUXXIWIAFEEC-UHFFFAOYSA-N 1-(2-aminoethyl)-3-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound NCCN1C(N(CC1)C1=CC=C(C=C1)C1=CN=C(O1)NC1=C(C=CC(=C1)COCC)C)=O GSYUXXIWIAFEEC-UHFFFAOYSA-N 0.000 claims 1
- SBJGWUJYRDHDBQ-UHFFFAOYSA-N 1-[4-[2-[3,5-bis(ethoxymethyl)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=CC(COCC)=C1 SBJGWUJYRDHDBQ-UHFFFAOYSA-N 0.000 claims 1
- FIJFTLZRJFJJHH-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-(2-hydroxyethoxy)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC(OCCO)=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=C1 FIJFTLZRJFJJHH-UHFFFAOYSA-N 0.000 claims 1
- RQPXDZRYAPBRHH-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-(2-methoxyethoxy)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC(OCCOC)=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=C1 RQPXDZRYAPBRHH-UHFFFAOYSA-N 0.000 claims 1
- LLZOOVAINRMGQZ-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-methylanilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=C(C=C(C=1)C)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O LLZOOVAINRMGQZ-UHFFFAOYSA-N 0.000 claims 1
- LAKSUMNYPLRTDS-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)-5-methylanilino]-1,3-thiazol-4-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=C(C=C(C=1)C)NC=1SC=C(N=1)C1=CC=C(C=C1)N1C(NCC1)=O LAKSUMNYPLRTDS-UHFFFAOYSA-N 0.000 claims 1
- QGBQAFISZCLPMZ-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)anilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC=CC(NC2=NC=C(O2)C2=CC=C(C=C2)N2CCNC2=O)=C1 QGBQAFISZCLPMZ-UHFFFAOYSA-N 0.000 claims 1
- ZXWMOVQGEFDBGU-UHFFFAOYSA-N 1-[4-[2-[3-(ethoxymethyl)anilino]-1,3-thiazol-4-yl]phenyl]imidazolidin-2-one Chemical compound CCOCC1=CC=CC(NC2=NC(=CS2)C2=CC=C(C=C2)N2CCNC2=O)=C1 ZXWMOVQGEFDBGU-UHFFFAOYSA-N 0.000 claims 1
- HFPQVVDIBFNORW-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-3-methylimidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(N(CC1)C)=O)C HFPQVVDIBFNORW-UHFFFAOYSA-N 0.000 claims 1
- ZBAFYGYLXHEICJ-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O)C ZBAFYGYLXHEICJ-UHFFFAOYSA-N 0.000 claims 1
- WPTJLPQUUQBCGM-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]pyridin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(C=CC=C1)=O)C WPTJLPQUUQBCGM-UHFFFAOYSA-N 0.000 claims 1
- ILSJJAHMDZLZCZ-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]pyrrolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(CCC1)=O)C ILSJJAHMDZLZCZ-UHFFFAOYSA-N 0.000 claims 1
- HKHLLEPTTVBSDM-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-thiazol-4-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC=C(N=1)C1=CC=C(C=C1)N1C(NCC1)=O)C HKHLLEPTTVBSDM-UHFFFAOYSA-N 0.000 claims 1
- YYHQBSIXIZKFNY-UHFFFAOYSA-N 1-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-thiazol-5-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC(=CN=1)C1=CC=C(C=C1)N1C(NCC1)=O)C YYHQBSIXIZKFNY-UHFFFAOYSA-N 0.000 claims 1
- VOKVJCQSCHSFJP-UHFFFAOYSA-N 1-[4-[5-[5-(ethoxymethyl)-2-methylanilino]-1,2,4-thiadiazol-3-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC1=NC(=NS1)C1=CC=C(C=C1)N1C(NCC1)=O)C VOKVJCQSCHSFJP-UHFFFAOYSA-N 0.000 claims 1
- XGESFNUMDHJAJS-UHFFFAOYSA-N 1-[4-[5-[5-(ethoxymethyl)-2-methylanilino]-1,3,4-oxadiazol-2-yl]phenyl]imidazolidin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC1=NN=C(O1)C1=CC=C(C=C1)N1C(NCC1)=O)C XGESFNUMDHJAJS-UHFFFAOYSA-N 0.000 claims 1
- GVJOWQGYKUBCQE-UHFFFAOYSA-N 2-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-4H-1,2,4-triazol-3-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CNC1=O)C GVJOWQGYKUBCQE-UHFFFAOYSA-N 0.000 claims 1
- JSWUEYLOGRTPSD-UHFFFAOYSA-N 3-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-1H-pyridin-2-one Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)C=1C(NC=CC=1)=O)C JSWUEYLOGRTPSD-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia 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
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- JNBIUWYKWYDSPW-UHFFFAOYSA-N N-[2-[3-[4-[2-[5-(ethoxymethyl)-2-methylanilino]-1,3-oxazol-5-yl]phenyl]-2-oxoimidazolidin-1-yl]ethyl]acetamide Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C(N(CC1)CCNC(C)=O)=O)C JNBIUWYKWYDSPW-UHFFFAOYSA-N 0.000 claims 1
- QRSGFQDESJIFLU-UHFFFAOYSA-N N-[3,5-bis(ethoxymethyl)phenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=C(C=C(C=1)COCC)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 QRSGFQDESJIFLU-UHFFFAOYSA-N 0.000 claims 1
- WUCHRJRDCNDMFS-UHFFFAOYSA-N N-[3-(ethoxymethyl)-5-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=C(C=C(C=1)C)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 WUCHRJRDCNDMFS-UHFFFAOYSA-N 0.000 claims 1
- ANBIJEYNXHJRIP-UHFFFAOYSA-N N-[3-(ethoxymethyl)phenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=C(C=CC=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1 ANBIJEYNXHJRIP-UHFFFAOYSA-N 0.000 claims 1
- ZPQNZRRKCVTTFS-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-4-(4-pyrazol-1-ylphenyl)-1,3-thiazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC=C(N=1)C1=CC=C(C=C1)N1N=CC=C1)C ZPQNZRRKCVTTFS-UHFFFAOYSA-N 0.000 claims 1
- RMOPBHDDDOXMEO-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(4-imidazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1C=NC=C1)C RMOPBHDDDOXMEO-UHFFFAOYSA-N 0.000 claims 1
- NCICENINCLNAMJ-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3,4-oxadiazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=NN=1)C1=CC=C(C=C1)N1N=CC=C1)C NCICENINCLNAMJ-UHFFFAOYSA-N 0.000 claims 1
- CIPHHAYPPQTPKX-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1)C CIPHHAYPPQTPKX-UHFFFAOYSA-N 0.000 claims 1
- ZPMUGFCTFPDKHI-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(4-pyrazol-1-ylphenyl)-1,3-thiazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1SC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1)C ZPMUGFCTFPDKHI-UHFFFAOYSA-N 0.000 claims 1
- CHNMIPRFUCPMKF-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-(4-pyridin-2-ylphenyl)-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)C1=NC=CC=C1)C CHNMIPRFUCPMKF-UHFFFAOYSA-N 0.000 claims 1
- VXTMJCUGYPDWOT-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(1,2,4-triazol-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CN=C1)C VXTMJCUGYPDWOT-UHFFFAOYSA-N 0.000 claims 1
- LJSZVNPEBAZKPB-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(1,3-thiazol-2-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)C=1SC=CN=1)C LJSZVNPEBAZKPB-UHFFFAOYSA-N 0.000 claims 1
- QGUZRIQSXXKNJL-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(1H-pyrazol-4-yl)phenyl]-1,3-oxazol-2-amine Chemical compound N1N=CC(=C1)C1=CC=C(C=C1)C1=CN=C(O1)NC1=C(C=CC(=C1)COCC)C QGUZRIQSXXKNJL-UHFFFAOYSA-N 0.000 claims 1
- KAFCXUQOMWBXEU-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(1H-pyrazol-5-yl)phenyl]-1,3-oxazol-2-amine Chemical compound N1N=CC=C1C1=CC=C(C=C1)C1=CN=C(O1)NC1=C(C=CC(=C1)COCC)C KAFCXUQOMWBXEU-UHFFFAOYSA-N 0.000 claims 1
- PCSPJWVWQVRWNQ-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(2-methylpyrazol-3-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)C1=CC=NN1C)C PCSPJWVWQVRWNQ-UHFFFAOYSA-N 0.000 claims 1
- HVDYDLAZKVAIDL-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(3-methoxypyrazol-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=C(C=C1)OC)C HVDYDLAZKVAIDL-UHFFFAOYSA-N 0.000 claims 1
- IDSVPEUUTLWJBT-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(3-methylpyrazol-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=C(C=C1)C)C IDSVPEUUTLWJBT-UHFFFAOYSA-N 0.000 claims 1
- URNDZGDIXCGGGO-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(4-methylpyrazol-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC(=C1)C)C URNDZGDIXCGGGO-UHFFFAOYSA-N 0.000 claims 1
- WDXVGLKCUPRDAT-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(5-methylpyrazol-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=C1C)C WDXVGLKCUPRDAT-UHFFFAOYSA-N 0.000 claims 1
- HEMVWJHGOITMEG-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(triazol-1-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=NC=C1)C HEMVWJHGOITMEG-UHFFFAOYSA-N 0.000 claims 1
- VYVOOYRFWHJRTD-UHFFFAOYSA-N N-[5-(ethoxymethyl)-2-methylphenyl]-5-[4-(triazol-2-yl)phenyl]-1,3-oxazol-2-amine Chemical compound C(C)OCC=1C=CC(=C(C=1)NC=1OC(=CN=1)C1=CC=C(C=C1)N1N=CC=N1)C VYVOOYRFWHJRTD-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010028537 myelofibrosis Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 230000003381 solubilizing effect Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Claims (13)
1. Spoj formule (III):
[image]
ili njegova farmaceutski prihvatljiva sol, pri čemu:
R1 i R2 su svaki neovisno odabrani od: vodika; heterocikla; cijano; -CF3; -NRR’; -OH; halogena;
alkil grupa izborno supstituirana s jednom ili više skupina odabranih od heterocikla, NRR', OR i vodo-solubilizirajuće skupine; alkoksi skupina izborno supstituirana s jednom ili više skupina odabranih od heterocikla, NRR', OR i vodo-solubilizirajuće skupine; -CO-NRR’; - SO2-NRR’; -NR-CO-R’ i -NR-SO2R’;
pri čemu su R i R' svaki neovisno odabrani od vodika, cikloalkila, heterocikla, vodo-solubilizirajuće skupine i alkilne skupine izborno supstituirane s jednom ili više skupina odabranih od OR", NR"R'", NR"COR'" i vodo-solubilizirajuće skupine; pri čemu su R" i R'" svaki neovisno odabrani od vodika, alkila ili cikloalkila;
A je heterociklična skupina, odabrana od triazolila, oksotriazolila, imidazolila, oksoimidazolidinila, pirazolila, piridila, oksopiridila, tiazolila i oksopirolidinila, izborno supstituirana s jednom ili više skupina odabranih od halogena, alkila, arila, hidroksila, alkoksi, nitro, tiola, heterocikloalkila, heteroarila, cijano, cikloalkila, vodo-solubilizirajuće skupine, -NRR', -alkil-NRR'; -NR-CO-R’, -alkil-NR-CO-R’, -CONRR’ i -SO2NRR’ skupine;
pri čemu su R i R' svaki neovisno odabrani od vodikovih, alkilnih, cikloalkilnih, arilnih, heterocikloalkilnih i heteroarilnih skupina;
B je peteročlana prstenasta heteroarilna skupina; pri čemu je svaka vodo-solubilizirajuća skupina neovisno odabrana od:
(i) karboksilnih kiselina, sulfonskih kiselina, fosfornih kiselina, amina i kvarternih amonijevih skupina;
(ii) -N-(CH2)zR; -N-(CH2)z-C(O)R; -N-(CH2)z-C(O)OR; -N-(CH2)z-S(O)2R; -N-(CH2)z-S(O)2OR i -N-(CH2)z-C(O)NRR’;
gdje je z cijeli broj u rasponu od 0 do 6; i R i R' su svaki neovisno odabrani od vodika;
C1-C10 alkil izborno supstituiran s najmanje jednim heteroatomom odabranim od F, Cl, Br, I, O i N; C1-C10 alkoksi; aril i heteroaril; i
(iii) bilo koje od formula:
[image]
[image]
[image]
pri čemu:
L je odabran iz skupine koju čine CH i N;
M je odabrano od -CH(R)-, -CH2-, -O-, -S-, -NH-, -N(-(CH2)zR)-, -N(-(CH2)zC(O)R)-, -N(-(CH2)zC(O)OR)-, -N(-(CH2)z-S(O)2R)-, -N(-(CH2)z-S(O)2OR)- i -N (-(CH2)z-C(O)NRR')-;
z je cijeli broj u rasponu od 0 do 6;
R i R' su svaki neovisno odabrani od vodika; C1-C10 alkil izborno supstituiran s najmanje jednim heteroatomom odabranim od F, Cl, Br, I, O, ili N; C1-C10 alkoksi; NR’"R"" grupa u kojoj R'" i R"" su svaki neovisno odabrani od vodika i C1-C10 alkila izborno supstituiranog s najmanje jednim heteroatomom odabranim od F, Cl, Br, I, O, ili N; aril i heteroaril;
uz uvjet da L i M nisu oba istovremeno CH i CH2, redom;
s tim da:
B nije triazolil;
ako je B tiazolil, A nije imidazolil ili triazolil.
2. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je A odabran od 2-oksoimidazolidinila i pirazolila.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, ili njegova farmaceutski prihvatljiva sol, naznačen time što R1 je metil i R2 je vodik.
4. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, odabran od:
1-{4-[2-(5-etoksimetil-2-metil-fenilamino)-tiazol-4-il]-fenil}-imidazolidin-2-on;
(5-etoksimetil-2-metil-fenil)-[5-(4-pirazol-1-il-fenil)-tiazol-2-il]-amin;
1-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-imidazolidin-2-on;
1-{4-[5-(5-etoksimetil-2-metil-fenilamino)-[1,3,4]oksadiazol-2-il]-fenil}-imidazolidin-2-on;
(5-etoksimetil-2-metil-fenil)-[5-(4-pirazol-1-il-fenil)-[1,3,4]oksadiazol-2-il]-amin;
1-{4-[5-(5-etoksimetil-2-metil-fenilamino)-[1,2,4]tiadiazol-3-il]-fenil}-imidazolidin-2-on;
1-{4-[2-(5-etoksimetil-2-metil-fenilamino)-tiazol-5-il]-fenil}-imidazolidin-2-on;
(5-etoksimetil-2-metil-fenil)-[4-(4-pirazol-1-il-fenil)-tiazol-2-il]-amin;
1-{4-[2-(3-etoksimetil-5-metil-fenilamino)-tiazol-4-il]-fenil}-imidazolidin-2-on;
1-{4-[2-(3-etoksimetil-5-metil-fenilamino)-oksazol-5-il]-fenil}-imidazolidin-2-on;
(3-etoksimetil-fenil)-[5-(4-pirazol-1-il-fenil)-oksazol-2-il]-amin;
(3-etoksimetil-5-metil-fenil)-[5-(4-pirazol-1-il-fenil)-oksazol-2-il]-amin;
(3,5-bis-(etoksimetil)-fenil)-[5-(4-pirazol-1-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-[5-(4-pirazol-1-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-[5-(4-[1,2,4]triazol-1-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-[5-(4-[1,2,3]triazol-1-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-[5-(4-[1,2,3]triazol-2-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-[5-(4-imidazol-1-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-[5-(4-tiazol-2-il-fenil)-oksazol-2-il]-amin;
(5-etoksimetil-2-metil-fenil)-{5-[4-(3-metil-pirazol-1-il)-fenil]-oksazol-2-il}-amin;
(5-etoksimetil-2-metil-fenil)-{5-[4-(4-metil-pirazol-1-il)-fenil]-oksazol-2-il}-amin;
(5-etoksimetil-2-metil-fenil)-{5-[4-(5-metil-pirazol-1-il)-fenil]-oksazol-2-il}-amin;
(5-etoksimetil-2-metil-fenil)-{5-[4-(3-metoksi-pirazol-1-il)-fenil]-oksazol-2-il}-amin;
2-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-2,4-dihidro-[1,2,4]triazol-3-on;
1-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-3-metil-imidazolidin-2-on;
1-(2-amino-etil)-3-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-imidazolidin-2-on;
N-[2-(3-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-2-okso-imidazolidin-1-il)-etil]-acetamid;
1-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-pirolidin-2-on;
(5-etoksimetil-2-metil-fenil)-[5-(4-piridin-2-il-fenil)-oksazol-2-il]-amin;
1-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-lH-piridin-2-on;
3-{4-[2-(5-etoksimetil-2-metil-fenilamino)-oksazol-5-il]-fenil}-lH-piridin-2-on;
(R)-1-(4-(2-((5-(etoksimetil)-2-metilfenil)amino)oksazol-5-il)fenil)-5-metilimidazolidin-2-on;
4-(4-(2-((5-(etoksimetil)-2-metilfenil)amino)oksazol-5-il)fenil)-5-metil-2,4-dihidro-3H-1,2,4 triazol - 3-on;
1-(4-(2-((3,5-bis(etoksimetil)fenil)amino)oksazol-5-il)fenil)imidazolidin-2-on;
1-(4-(2-((3-(etoksimetil)-5-(2-metoksietoksi)fenil)amino)oksazol-5-il)fenil)imidazolidin-2-on;
5-(4-(1H-pirazol-5-il)fenil)-N-(5-(etoksimetil)-2-metilfenil)oksazol-2-amin;
1-(4-(2-((3-(etoksimetil)-5-(2-hidroksietoksi)fenil)amino)oksazol-5-il)fenil)imidazolidin-2-on;
5-(4-(1H-pirazol-4-il)fenil)-N-(5-(etoksimetil)-2-metilfenil)oksazol-2-amin;
N-(5-(etoksimetil)-2-metilfenil)-5-(4-(1-metil-1H-pirazol-5-il)fenil)oksazol-2-amin;
1-(4-(2-((3-(etoksimetil)fenil)amino)oksazol-5-il)fenil)imidazolidin-2-on; i
1-(4-(2-((3-(etoksimetil)fenil)amino)tiazol-4-il)fenil)imidazolidin-2-on.
5. Farmaceutski pripravak sadrži spoj prema bilo kojem od zahtjeva 1 do 4 i najmanje jedan farmaceutski prihvatljiv ekscipijens i/ili nosač.
6. Farmaceutski pripravak prema zahtjevu 5, sadrži spoj prema bilo kojem od zahtjeva 1 do 4 kao jedini aktivni farmaceutski sastojak.
7. Farmaceutski pripravak prema zahtjevu 5, nadalje sadrži još jedno aktivno farmaceutsko sredstvo.
8. Spoj prema bilo kojem od zahtjeva 1 do 4 za uporabu kao lijek.
9. Spoj prema bilo kojem od zahtjeva 1 do 4 za uporabu u liječenju hematoloških poremećaja i/ili proliferativnih poremećaja.
10. Spoj za uporabu prema zahtjevu 9, naznačen time što je hematološki poremećaj odabran od limfoma; leukemija kao što je akutna mijeloična leukemija (AML), akutna limfoblastna leukemija (ALL), kronična limfoidna leukemija (CLL), ili kronična mijeloična leukemija (CML); multipli mijelom (MM); mijelodisplatični sindrom (MDS) i mijelodisplazija s mijelofibrozom.
11. Spoj za uporabu prema zahtjevu 9, naznačen time što je proliferativni poremećaj rak.
12. Spoj za uporabu prema zahtjevu 11, naznačen time što je rak odabran od raka glave i vrata; melanoma; karcinoma bubrega; karcinoma želuca; karcinoma jetre; kolorektalnog karcinoma; karcinoma gušterače; karcinoma pluća; neuronskog karcinoma; multiformnog glioblastoma; osteosarkoma; Ewingovog sarkoma; karcinoma dojke; karcinoma jajnika i karcinoma prostate.
13. Farmaceutski pripravak prema zahtjevu 7, naznačen time što sadrži spoj prema bilo kojem od zahtjeva 1 do 4 i drugi aktivni farmaceutski sastojak kao kombinirani pripravak za sekvencijalnu, istodobnu ili odvojenu uporabu u liječenju poremećaja odabranog od hematoloških poremećaja i proliferativnih poremećaja.
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US3989816A (en) | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
CA1163561A (en) | 1979-11-06 | 1984-03-13 | Cyril Boroda | Preparation containing nitroglycerine and optionally other medicaments and preparation thereof |
US4460372A (en) | 1981-02-17 | 1984-07-17 | Alza Corporation | Percutaneous absorption enhancer dispenser for use in coadministering drug and percutaneous absorption enhancer |
US4379454A (en) | 1981-02-17 | 1983-04-12 | Alza Corporation | Dosage for coadministering drug and percutaneous absorption enhancer |
US4411893A (en) | 1981-08-14 | 1983-10-25 | Minnesota Mining And Manufacturing Company | Topical medicament preparations |
CA1236029A (en) | 1984-05-14 | 1988-05-03 | Edmund Sandborn | Pharmaceutical solutions comprising dimethyl sulfoxide |
US4615699A (en) | 1985-05-03 | 1986-10-07 | Alza Corporation | Transdermal delivery system for delivering nitroglycerin at high transdermal fluxes |
DE3815221C2 (de) | 1988-05-04 | 1995-06-29 | Gradinger F Hermes Pharma | Verwendung einer Retinol- und/oder Retinsäureester enthaltenden pharmazeutischen Zubereitung zur Inhalation zur Einwirkung auf die Schleimhäute des Tracheo-Bronchialtraktes einschließlich der Lungenalveolen |
GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
US5906202A (en) | 1996-11-21 | 1999-05-25 | Aradigm Corporation | Device and method for directing aerosolized mist to a specific area of the respiratory tract |
US6448272B1 (en) * | 1998-12-07 | 2002-09-10 | Smithkline Beecham Corporation | Myt1 kinase inhibitors |
JP4216947B2 (ja) * | 1999-05-18 | 2009-01-28 | 三井化学株式会社 | アミン化合物 |
CN100491374C (zh) * | 2002-08-02 | 2009-05-27 | Ab科学公司 | 2-(3-氨基芳基)氨基-4-芳基-噻唑及其作为c-kit抑制剂的应用 |
US8450302B2 (en) * | 2002-08-02 | 2013-05-28 | Ab Science | 2-(3-aminoaryl) amino-4-aryl-thiazoles and their use as c-kit inhibitors |
CA2525547C (en) * | 2003-05-14 | 2012-07-03 | Torreypines Therapeutics, Inc. | Compounds and uses thereof in modulating amyloid beta |
EP1684750B1 (en) * | 2003-10-23 | 2010-04-28 | AB Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
US20090196912A1 (en) * | 2004-07-30 | 2009-08-06 | Gpc Botech Ag | Pyridinylamines |
CA2578122A1 (en) | 2004-08-27 | 2006-03-02 | Gpc Biotech Ag | Pyrimidine derivatives |
WO2006106437A2 (en) * | 2005-04-04 | 2006-10-12 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
US8088806B2 (en) * | 2005-05-09 | 2012-01-03 | Achillion Pharmaceuticals, Inc. | Thiazole compounds and methods of use |
JP5214096B2 (ja) * | 2005-06-17 | 2013-06-19 | 富士フイルムファインケミカルズ株式会社 | 新規なビピリジン誘導体 |
US20080207572A1 (en) * | 2005-07-14 | 2008-08-28 | Ab Science | Use of Dual C-Kit/Fgfr3 Inhibitors for Treating Multiple Myeloma |
CA2617394C (en) * | 2005-09-13 | 2014-06-03 | Janssen Pharmaceutica N.V. | 2-aniline-4-aryl substituted thiazole derivatives |
GB0524436D0 (en) * | 2005-11-30 | 2006-01-11 | Novartis Ag | Organic compounds |
ES2375576T3 (es) * | 2006-03-31 | 2012-03-02 | Novartis Ag | Derivados del �?cido (4-(4-[6-(trifluorometil-piridin-3-ilamino)-heteroarilo con contenido de n]-fenil)-ciclohexil)-acético y sus usos farmacéuticos. |
JO3019B1 (ar) * | 2006-04-19 | 2016-09-05 | Janssen Pharmaceutica Nv | ثلاثي مستبدل 4،2،1-ثلاثي زولات |
WO2007131953A1 (en) | 2006-05-12 | 2007-11-22 | Ab Science | A new process for the synthesis of 2-aminoxazole compounds |
FR2901273B1 (fr) * | 2006-05-19 | 2010-12-24 | Anaconda Pharma | Inhibiteurs du virus du papillome humain et les compositions pharmaceutiques les contenant |
MX2009007302A (es) * | 2007-01-23 | 2009-07-15 | Palau Pharma Sa | Derivados de purina. |
MX2009008921A (es) * | 2007-02-22 | 2009-08-28 | Irm Llc | Derivados de tiazole en la forma de moduladores de receptores acoplados por proteina g. |
GB0709031D0 (en) * | 2007-05-10 | 2007-06-20 | Sareum Ltd | Pharmaceutical compounds |
CA2730010A1 (en) * | 2008-07-09 | 2010-01-14 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
JP2012180281A (ja) * | 2009-06-29 | 2012-09-20 | Dainippon Sumitomo Pharma Co Ltd | 新規オキサジアゾール誘導体 |
WO2011006903A1 (en) * | 2009-07-15 | 2011-01-20 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc | Substituted triazole and imidazole derivatives as gamma secretase modulators |
EP2499282B1 (en) * | 2009-11-09 | 2015-04-22 | NeuroGenetic Pharmaceuticals, Inc. | Gamma-secretase modulatory compounds, methods for identifying same, and uses therefor |
ES2539170T3 (es) * | 2010-01-12 | 2015-06-26 | Ab Science | Inhibidores de quinasas de oxazol |
GB201012105D0 (en) | 2010-07-19 | 2010-09-01 | Domainex Ltd | Novel pyrimidine compounds |
EP2616443A1 (en) * | 2010-09-14 | 2013-07-24 | Exelixis, Inc. | Phtalazine derivatives as jak1 inhibitors |
US20120129843A1 (en) * | 2010-11-18 | 2012-05-24 | Yan Zhang | Pyridyl-thiazolyl inhibitors of pro-matrix metalloproteinase activation |
US20120302569A1 (en) * | 2011-05-25 | 2012-11-29 | Paul Francis Jackson | Phenyl-thiazolyl inhibitors of pro-matrix metalloproteinase activation |
EP2714667B1 (en) * | 2011-05-27 | 2020-11-25 | Laxman S. DESAI | Aminooxazole inhibitors of cyclin dependent kinases |
EP2736904B1 (en) * | 2011-07-27 | 2016-03-16 | AB Science | Oxazole and thiazole derivatives as selective protein kinase inhibitors (c-kit) |
KR101896035B1 (ko) * | 2011-08-23 | 2018-09-07 | 덕산네오룩스 주식회사 | 유기전기소자용 신규 화합물, 이를 이용하는 유기전기소자 및 그 단말 |
CN103436048B (zh) * | 2013-08-08 | 2014-12-03 | 陕西师范大学 | 硫脲供体双桥链有机染料及其应用 |
US20150045353A1 (en) * | 2013-08-09 | 2015-02-12 | Neurogenetic Pharmaceuticals, Inc. | Formulations containing gamma secretase modulators, methods for preparation and delivery thereof |
RU2016139031A (ru) * | 2014-03-24 | 2018-04-25 | Аб Сьянс | Производные оксазола, замещенные диазаспироалкалоном, в качестве ингибиторов тирозинкиназы селезенки |
EP3144307A1 (en) * | 2015-09-18 | 2017-03-22 | AB Science | Novel oxazole derivatives that inhibit syk |
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