ZA200610589B - Gonadotropin Releasing Hormone receptor antagonists - Google Patents
Gonadotropin Releasing Hormone receptor antagonists Download PDFInfo
- Publication number
- ZA200610589B ZA200610589B ZA200610589A ZA200610589A ZA200610589B ZA 200610589 B ZA200610589 B ZA 200610589B ZA 200610589 A ZA200610589 A ZA 200610589A ZA 200610589 A ZA200610589 A ZA 200610589A ZA 200610589 B ZA200610589 B ZA 200610589B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazin
- methyl
- tert
- butylphenyl
- phenyl
- Prior art date
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- 229940127445 Gonadotropin Releasing Hormone Receptor Antagonists Drugs 0.000 title description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 100
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
- -1 homopiperazize Chemical compound 0.000 claims description 58
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 43
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 102000008238 LHRH Receptors Human genes 0.000 claims description 16
- 108010021290 LHRH Receptors Proteins 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 102000005962 receptors Human genes 0.000 claims description 9
- 108020003175 receptors Proteins 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000002464 receptor antagonist Substances 0.000 claims description 5
- 229940044551 receptor antagonist Drugs 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- ZYOYYQRWXITKFF-UHFFFAOYSA-N pyrazine-2,3-dione Chemical compound O=C1N=CC=NC1=O ZYOYYQRWXITKFF-UHFFFAOYSA-N 0.000 claims description 4
- MVILWLLYYQVYNH-UHFFFAOYSA-N pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC=N1.NC(=O)C1=CC=CC=N1 MVILWLLYYQVYNH-UHFFFAOYSA-N 0.000 claims description 4
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- QGDKDKDJDCRBJV-NRFANRHFSA-N 6-[[(2s)-4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]-2-methylpiperazin-1-yl]methyl]quinoxaline Chemical compound C([C@@H](N(CC1)CC=2C=C3N=CC=NC3=CC=2)C)N1C(C=1N=2)=CC=CC=1NC=2C1=CC=C(C(C)(C)C)C=C1 QGDKDKDJDCRBJV-NRFANRHFSA-N 0.000 claims description 3
- MUXKNZTVGWQCSI-UHFFFAOYSA-N 6-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-3-(2-methylpropyl)-3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC(CC)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5NC(CC(C)C)C(=O)NC5=CC=4)CC3)C=CC=C2N1 MUXKNZTVGWQCSI-UHFFFAOYSA-N 0.000 claims description 3
- MRQQGUMBFPBXJO-UHFFFAOYSA-N 6-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-3-(hydroxymethyl)-3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC(CC)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5NC(CO)C(=O)NC5=CC=4)CC3)C=CC=C2N1 MRQQGUMBFPBXJO-UHFFFAOYSA-N 0.000 claims description 3
- IFRHRAPSJRMCTF-UHFFFAOYSA-N 6-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5NC(=O)C(=O)NC5=CC=4)CC3)C=CC=C2N1 IFRHRAPSJRMCTF-UHFFFAOYSA-N 0.000 claims description 3
- 201000009273 Endometriosis Diseases 0.000 claims description 3
- 206010020112 Hirsutism Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 3
- 206010057644 Testis cancer Diseases 0.000 claims description 3
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
- 206010046798 Uterine leiomyoma Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 201000010260 leiomyoma Diseases 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 235000005152 nicotinamide Nutrition 0.000 claims description 3
- 239000011570 nicotinamide Substances 0.000 claims description 3
- 229960003966 nicotinamide Drugs 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 201000003120 testicular cancer Diseases 0.000 claims description 3
- 206010046766 uterine cancer Diseases 0.000 claims description 3
- QKNFIJZSZFYMPI-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-[4-[4-(quinoxalin-6-ylmethyl)piperazin-1-yl]-1h-benzimidazol-2-yl]phenyl]ethane-1,1-diol Chemical compound C1=CC(C(O)(O)C(F)(F)F)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5N=CC=NC5=CC=4)CC3)C=CC=C2N1 QKNFIJZSZFYMPI-UHFFFAOYSA-N 0.000 claims description 2
- MRZOKEUZLDYYGD-LJQANCHMSA-N 2-(4-tert-butylphenyl)-4-[(3r)-4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]-3-methylpiperazin-1-yl]-1h-benzimidazole Chemical compound N1C(CC)=NC(CN2[C@@H](CN(CC2)C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1C MRZOKEUZLDYYGD-LJQANCHMSA-N 0.000 claims description 2
- IFOXKEWSLUUKPW-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]-1h-benzimidazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=C(N3CCN(CC=4N=CC=CC=4)CC3)C=CC=C2N1 IFOXKEWSLUUKPW-UHFFFAOYSA-N 0.000 claims description 2
- FHNLXZPCCFYREW-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-(pyridin-3-ylmethyl)piperazin-1-yl]-1h-benzimidazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=C(N3CCN(CC=4C=NC=CC=4)CC3)C=CC=C2N1 FHNLXZPCCFYREW-UHFFFAOYSA-N 0.000 claims description 2
- XITZFKMHZPUYRC-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(1,2-diethyl-5-methylimidazol-4-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound CCN1C(CC)=NC(CN2CCN(CC2)C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1C XITZFKMHZPUYRC-UHFFFAOYSA-N 0.000 claims description 2
- XAOOUYUAIIYQHQ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(1-ethylimidazol-4-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound CCN1C=NC(CN2CCN(CC2)C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 XAOOUYUAIIYQHQ-UHFFFAOYSA-N 0.000 claims description 2
- OQKKUHXPDMTOFE-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(2-ethyl-1,5-dimethylimidazol-4-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound CN1C(CC)=NC(CN2CCN(CC2)C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1C OQKKUHXPDMTOFE-UHFFFAOYSA-N 0.000 claims description 2
- MOPYTTWBRBUOEQ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound N1C(CC)=NC(C)=C1CN1CCN(C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)CC1 MOPYTTWBRBUOEQ-UHFFFAOYSA-N 0.000 claims description 2
- SJGWHQQAMPXTJX-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(2-methyl-3-propylimidazol-4-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound CCCN1C(C)=NC=C1CN1CCN(C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)CC1 SJGWHQQAMPXTJX-UHFFFAOYSA-N 0.000 claims description 2
- YZVAULLPLORWKB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(2-phenyl-1h-imidazol-5-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=C(N3CCN(CC=4N=C(NC=4)C=4C=CC=CC=4)CC3)C=CC=C2N1 YZVAULLPLORWKB-UHFFFAOYSA-N 0.000 claims description 2
- JWTRASPFJYREGL-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[(2-pyrrolidin-1-ylpyrimidin-4-yl)methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=CC=CC(N3CCN(CC=4N=C(N=CC=4)N4CCCC4)CC3)=C2N1 JWTRASPFJYREGL-UHFFFAOYSA-N 0.000 claims description 2
- VLJPORAUZNWOSC-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[4-[[2-(pyridin-2-ylmethoxy)pyrimidin-4-yl]methyl]piperazin-1-yl]-1h-benzimidazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=CC=CC(N3CCN(CC=4N=C(OCC=5N=CC=CC=5)N=CC=4)CC3)=C2N1 VLJPORAUZNWOSC-UHFFFAOYSA-N 0.000 claims description 2
- WIMPHPOBUYEDQI-UHFFFAOYSA-N 2-[4-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-2-methylimidazol-1-yl]-n-(cyclohexylmethyl)acetamide Chemical compound C=1N(CC(=O)NCC2CCCCC2)C(C)=NC=1CN(CC1)CCN1C(C=1N=2)=CC=CC=1NC=2C1=CC=C(C(C)(C)C)C=C1 WIMPHPOBUYEDQI-UHFFFAOYSA-N 0.000 claims description 2
- NUMHRVULCLMMCM-UHFFFAOYSA-N 2-[4-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-2-methylimidazol-1-yl]-n-phenylacetamide Chemical compound C=1N(CC(=O)NC=2C=CC=CC=2)C(C)=NC=1CN(CC1)CCN1C(C=1N=2)=CC=CC=1NC=2C1=CC=C(C(C)(C)C)C=C1 NUMHRVULCLMMCM-UHFFFAOYSA-N 0.000 claims description 2
- IRRYYNVBCQAKPR-UHFFFAOYSA-N 2-butyl-5-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-4-methyl-1,3-thiazole Chemical compound S1C(CCCC)=NC(C)=C1CN1CCN(C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)CC1 IRRYYNVBCQAKPR-UHFFFAOYSA-N 0.000 claims description 2
- LBQIQASDMMRGOU-UHFFFAOYSA-N 2-ethyl-5-[4-[4-(pyridin-2-ylmethyl)piperazin-1-yl]-1h-benzimidazol-2-yl]phenol Chemical compound C1=C(O)C(CC)=CC=C1C1=NC2=C(N3CCN(CC=4N=CC=CC=4)CC3)C=CC=C2N1 LBQIQASDMMRGOU-UHFFFAOYSA-N 0.000 claims description 2
- BKAMTODNAPWGHG-UHFFFAOYSA-N 3-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]pyrido[2,3-b]pyrazine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=C(N3CCN(CC=4N=C5N=CC=CC5=NC=4)CC3)C=CC=C2N1 BKAMTODNAPWGHG-UHFFFAOYSA-N 0.000 claims description 2
- BTYBUIUHUFFYBX-UHFFFAOYSA-N 3-benzyl-6-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC(CC)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5NC(CC=6C=CC=CC=6)C(=O)NC5=CC=4)CC3)C=CC=C2N1 BTYBUIUHUFFYBX-UHFFFAOYSA-N 0.000 claims description 2
- DXOOFFGXUPBEDI-UHFFFAOYSA-N 4-[4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]piperazin-1-yl]-2-(4-propan-2-ylphenyl)-1h-benzimidazole Chemical compound N1C(CC)=NC(CN2CCN(CC2)C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)C)=C1C DXOOFFGXUPBEDI-UHFFFAOYSA-N 0.000 claims description 2
- RAJTYETWUKNJOU-UHFFFAOYSA-N 4-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-n-(cyclohexylmethyl)pyrimidin-2-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=CC=CC(N3CCN(CC=4N=C(NCC5CCCCC5)N=CC=4)CC3)=C2N1 RAJTYETWUKNJOU-UHFFFAOYSA-N 0.000 claims description 2
- BPRYGQVSIJTOLH-UHFFFAOYSA-N 4-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-n-ethylpyrimidin-2-amine Chemical compound CCNC1=NC=CC(CN2CCN(CC2)C=2C=3NC(=NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=N1 BPRYGQVSIJTOLH-UHFFFAOYSA-N 0.000 claims description 2
- XIZPDZRWNIKPCE-UHFFFAOYSA-N 4-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-n-methyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(CN2CCN(CC2)C=2C=3NC(=NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 XIZPDZRWNIKPCE-UHFFFAOYSA-N 0.000 claims description 2
- IUKWVCDXPNGBDV-UHFFFAOYSA-N 4-cyclobutyl-7-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1h-quinoxaline-2,3-dione Chemical compound C1=CC(CC)=CC=C1C1=NC2=CC=CC(N3CCN(CC=4C=C5NC(=O)C(=O)N(C6CCC6)C5=CC=4)CC3)=C2N1 IUKWVCDXPNGBDV-UHFFFAOYSA-N 0.000 claims description 2
- QPVIHFCXQANBCV-UHFFFAOYSA-N 4-cyclohexyl-6-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1h-quinoxaline-2,3-dione Chemical compound C1=CC(CC)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5N(C6CCCCC6)C(=O)C(=O)NC5=CC=4)CC3)C=CC=C2N1 QPVIHFCXQANBCV-UHFFFAOYSA-N 0.000 claims description 2
- YXADJYMQNFFKTQ-UHFFFAOYSA-N 4-ethyl-6-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1h-quinoxaline-2,3-dione Chemical compound C1=CC(CC)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5N(CC)C(=O)C(=O)NC5=CC=4)CC3)C=CC=C2N1 YXADJYMQNFFKTQ-UHFFFAOYSA-N 0.000 claims description 2
- SDJHWWKYUXAOLQ-UHFFFAOYSA-N 4-ethyl-7-[[4-[2-(4-ethylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1h-quinoxaline-2,3-dione Chemical compound C1=CC(CC)=CC=C1C1=NC2=C(N3CCN(CC=4C=C5NC(=O)C(=O)N(CC)C5=CC=4)CC3)C=CC=C2N1 SDJHWWKYUXAOLQ-UHFFFAOYSA-N 0.000 claims description 2
- ULRYXVDXGZHINN-UHFFFAOYSA-N 5-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1,3-diethylpyrimidine-2,4-dione Chemical compound O=C1N(CC)C(=O)N(CC)C=C1CN1CCN(C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)CC1 ULRYXVDXGZHINN-UHFFFAOYSA-N 0.000 claims description 2
- POFFHRQCFDSGST-UHFFFAOYSA-N 5-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1,3-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)N(C)C=C1CN1CCN(C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)CC1 POFFHRQCFDSGST-UHFFFAOYSA-N 0.000 claims description 2
- MVEKHLDVWXAEJF-UHFFFAOYSA-N 5-[[4-[2-(4-tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl]methyl]-1-hexylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(CCCCCC)C=C1CN1CCN(C=2C=3N=C(NC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)CC1 MVEKHLDVWXAEJF-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003431 steroids Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
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EP (1) | EP1758895A1 (ko) |
JP (1) | JP2008503469A (ko) |
KR (1) | KR20070027584A (ko) |
CN (1) | CN101006078A (ko) |
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RU (1) | RU2007101544A (ko) |
WO (1) | WO2006009734A1 (ko) |
ZA (1) | ZA200610589B (ko) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2570693A1 (en) * | 2004-06-17 | 2006-01-26 | Wyeth | Processes for preparing gonadotropin releasing hormone receptor antagonists |
JP2008503469A (ja) | 2004-06-17 | 2008-02-07 | ワイス | ゴナドトロピン放出ホルモン受容体アンタゴニスト |
EA012178B1 (ru) * | 2004-09-03 | 2009-08-28 | Лаборатуар Сероно Са | Пиридинметиленазолидиноны и их применение |
EP2269610A3 (en) | 2004-09-20 | 2011-03-09 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
AU2005286648A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
JP2008520732A (ja) * | 2004-11-23 | 2008-06-19 | ワイス | ゴナドトロピン放出ホルモン受容体アンタゴニスト |
US7582634B2 (en) * | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US7538113B2 (en) * | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US7534796B2 (en) * | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
US20060189619A1 (en) * | 2005-02-24 | 2006-08-24 | Wyeth | 3-({4-[2-(4-Tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl}methyl)pyrido[2,3-b]]pyrazi ne compounds |
CA2601978A1 (en) * | 2005-03-07 | 2006-09-14 | Wyeth | Quinoxaline dihydrohalide dihydrates and synthetic methods therefor |
US7531542B2 (en) * | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
US7582636B2 (en) * | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
CA2618646A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
DE102006032589A1 (de) * | 2006-07-13 | 2008-01-17 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Formylpyridin-2-carbonitril |
US8308582B2 (en) * | 2007-02-20 | 2012-11-13 | E & F Co., Ltd. | Golf club head, and method for manufacturing the golf club head |
KR101524817B1 (ko) | 2007-04-18 | 2015-06-01 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 축합환 유도체, 그것을 함유하는 의약 조성물 및 그 의약 용도 |
KR20100017766A (ko) | 2007-05-10 | 2010-02-16 | 에이엠알 테크놀로지, 인크. | 아릴- 및 헤테로아릴-치환된 테트라히드로벤조-1,4-디아제핀 및 노르에피네프린, 도파민 및 세로토닌의 재흡수를 차단하기 위한 이의 용도 |
KR20100052482A (ko) * | 2007-08-23 | 2010-05-19 | 사노피-아벤티스 | 아졸로아린 유도체, 이의 제조 방법, 이들 화합물을 함유하는 약제 및 이의 용도 |
DE102008030091B4 (de) * | 2008-06-25 | 2011-03-03 | Resprotect Gmbh | Uracilderivate und deren Verwendung |
DE102008039083A1 (de) | 2008-08-21 | 2010-02-25 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Aminopyrazole und ihre Verwendung |
WO2010085570A1 (en) | 2009-01-23 | 2010-07-29 | Takeda Pharmaceutical Company Limited | Poly (ADP-Ribose) Polymerase (PARP) Inhibitors |
ES2882797T3 (es) | 2009-04-02 | 2021-12-02 | Merck Serono Sa | Inhibidores de dihidroorotato deshidrogenasa |
WO2011014681A1 (en) | 2009-07-30 | 2011-02-03 | Takeda Pharmaceutical Company Limited | Poly (ADP-Ribose) Polymerase (PARP) INHIBITORS |
JP5793505B2 (ja) | 2009-12-23 | 2015-10-14 | ジャスコ ファーマシューティカルズ, エルエルシー | アミノピリミジンキナーゼ阻害薬 |
KR20130043198A (ko) * | 2010-07-16 | 2013-04-29 | 피라말 엔터프라이지즈 리미티드 | 키나제 억제제로서 치환된 이미다조퀴놀린 유도체 |
EP2699569B1 (en) | 2011-04-22 | 2017-08-30 | Jasco Pharmaceuticals, LLC | Aminopyrimidine kinase inhibitors |
CA2853454C (en) | 2011-11-04 | 2020-01-21 | Jasco Pharmaceuticals, LLC | Aminopyrimidine kinase inhibitors |
CA2885969C (en) * | 2012-10-02 | 2021-04-06 | Epitherapeutics Aps | Substitued pyridine derivatives and compositions thereof useful as inhibitors of histone demethylases |
GB201321736D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
CN104277042A (zh) * | 2014-10-15 | 2015-01-14 | 湖南华腾制药有限公司 | 一种咪唑并吡啶衍生物的制备方法 |
CN104628721A (zh) * | 2015-01-22 | 2015-05-20 | 湖南华腾制药有限公司 | 一种咪唑并[1,2-a]吡啶衍生物的制备方法 |
CA3215823A1 (en) * | 2021-04-23 | 2022-10-27 | Peng Gao | Heterocyclic derivative inhibitor and preparation method therefor and application thereof |
CN113278019A (zh) * | 2021-05-31 | 2021-08-20 | 河南偶联生物科技有限公司 | 一种咪唑并[1,2-a]吡啶类化合物的合成方法 |
CN114478423A (zh) * | 2022-03-02 | 2022-05-13 | 八叶草健康产业研究院(厦门)有限公司 | 一种2,4-二甲基恶唑-5-甲酸的制备方法 |
WO2023207283A1 (en) * | 2022-04-28 | 2023-11-02 | Ningbo Newbay Technology Development Co., Ltd | Compounds as parp1 inhibitiors |
Family Cites Families (89)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL281104A (ko) | 1961-07-18 | 1900-01-01 | ||
GB1049330A (en) | 1962-08-13 | 1966-11-23 | Merck & Co Inc | Benzamidines and the preparation of 2-aryl benzimidazoles |
NL135043C (ko) | 1963-10-11 | |||
IL22369A (en) | 1963-11-19 | 1968-10-24 | Merck & Co Inc | 2-heteroaryl-5 and/or 6-substituted benzazoles |
US3996233A (en) | 1975-02-10 | 1976-12-07 | E. R. Squibb & Sons, Inc. | Amino derivatives of imidazo[4,5-b]pyridines |
FR2504532A1 (fr) * | 1981-04-24 | 1982-10-29 | Delalande Sa | Nouveaux derives heterocycliques du type benzimidazole, indole et purine, leur procede de preparation et leur application en therapeutique |
CH653021A5 (fr) | 1981-04-24 | 1985-12-13 | Delalande Sa | Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant. |
ZA848005B (en) * | 1983-10-17 | 1985-05-29 | Duphar Int Res | Blood-pressure lowering piperazine derivatives |
ATE81975T1 (de) | 1984-12-21 | 1992-11-15 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
US5057517A (en) | 1987-07-20 | 1991-10-15 | Merck & Co., Inc. | Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents |
NZ225447A (en) | 1987-07-20 | 1991-12-23 | Merck & Co Inc | Piperazinyl derivatives of purine and purine isosteres and pharmaceutical compositions |
IL94390A (en) | 1989-05-30 | 1996-03-31 | Merck & Co Inc | The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them |
DE3926770A1 (de) | 1989-08-12 | 1991-02-14 | Basf Ag | (1,2,4)triazolo(1,5-a)pyridine |
US5716964A (en) | 1989-12-04 | 1998-02-10 | G.D. Searle & Co. | Tetrazolyl substituted imidazo 1,2-a!pyridinylalkyl compounds for treatment of neurotoxic injury |
EP0434038A1 (en) | 1989-12-22 | 1991-06-26 | Takeda Chemical Industries, Ltd. | Fused imidazole derivatives, their production and use |
EP0471236B1 (en) | 1990-07-30 | 1995-03-15 | Takeda Chemical Industries, Ltd. | Imidazopyridine derivatives and their use |
US5502187A (en) | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
CZ236494A3 (en) | 1992-04-03 | 1994-12-15 | Upjohn Co | Pharmaceutically active bicyclic-heterocyclic amines |
US5338740A (en) | 1993-07-13 | 1994-08-16 | Pfizer Inc. | Angiotensin II receptor antagonists |
US5470847A (en) | 1993-12-10 | 1995-11-28 | Board Of Regents, The University Of Texas System | Ovulation control by regulating nitric oxide levels with arginine derivatives |
US5576460A (en) | 1994-07-27 | 1996-11-19 | Massachusetts Institute Of Technology | Preparation of arylamines |
AUPN449295A0 (en) * | 1995-07-28 | 1995-08-24 | Inner And Eastern Health Care Network, The | Radioprotectors |
US6720472B2 (en) * | 1996-07-12 | 2004-04-13 | University Of Medicine And Dentistry Of New Jersey | HMGI proteins in cancer and obesity |
JP3711238B2 (ja) | 1997-08-05 | 2005-11-02 | ファイザー・プロダクツ・インク | 神経ペプチドY受容体アンタゴニストとしての4−アミノピロ−ル(3,2−d)ピリミジン |
CA2303830A1 (en) | 1997-09-26 | 1999-04-08 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
IT1298727B1 (it) | 1998-03-12 | 2000-02-02 | Silvia Anna Barbesti | Procedimento per la determinazione della frazione cellulare vitale in un campione biologico e tipizzazione delle cellule in esame |
US6310066B1 (en) * | 1998-04-29 | 2001-10-30 | American Home Products Corp. | Antipsychotic indolyl derivatives |
AU3667899A (en) | 1998-04-29 | 1999-11-16 | American Home Products Corporation | Antipsychotic indolyl derivatives |
US6399629B1 (en) * | 1998-06-01 | 2002-06-04 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
PL345906A1 (en) | 1998-06-04 | 2002-01-14 | Abbott Lab | Cell adhesion-inhibiting antinflammatory compounds |
US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
US6307087B1 (en) | 1998-07-10 | 2001-10-23 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
JP5035813B2 (ja) | 1998-07-10 | 2012-09-26 | マサチューセッツ インスティテュート オブ テクノロジー | 金属用のリガンドおよびそれらに基づいて改善された金属触媒法 |
CN100396675C (zh) * | 1998-08-10 | 2008-06-25 | 加利福尼亚州大学董事会 | 质子泵抑制剂的前药 |
US6184226B1 (en) * | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
CA2341409A1 (en) | 1998-08-31 | 2000-03-09 | Merck And Co., Inc. | Novel angiogenesis inhibitors |
ATE269303T1 (de) | 1999-01-07 | 2004-07-15 | Wyeth Corp | Arylpiperazinyl-cyclohexyl indolderivate zur behandlung von depressionen |
US6313126B1 (en) * | 1999-01-07 | 2001-11-06 | American Home Products Corp | Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression |
US6306859B1 (en) * | 1999-03-02 | 2001-10-23 | American Home Products Corporation | N-substituted imide derivatives with serotonergic activity |
PE20010306A1 (es) * | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
WO2001002400A1 (fr) | 1999-07-02 | 2001-01-11 | Eisai Co., Ltd. | Composes imidazole fusionnes et medicaments contre le diabete sucre |
US20020147197A1 (en) * | 1999-10-08 | 2002-10-10 | Newman Michael J. | Methods and compositions for enhancing pharmaceutical treatments |
US6787302B2 (en) * | 1999-10-25 | 2004-09-07 | Genprime, Inc. | Method and apparatus for prokaryotic and eukaryotic cell quantitation |
US6620529B1 (en) | 1999-10-27 | 2003-09-16 | Fuji Photo Film Co., Ltd. | Materials for light emitting devices and light emitting devices using the same |
DE19963234A1 (de) | 1999-12-27 | 2002-01-24 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
US20020059365A1 (en) * | 2000-02-10 | 2002-05-16 | Martin King | System for delivery and exchange of electronic data |
EP1136483A1 (en) | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-[Piperazinyl]pyrimidone derivatives |
RU2182708C2 (ru) | 2000-04-17 | 2002-05-20 | Институт молекулярной биологии им. В.А. Энгельгардта РАН | Способ множественного параллельного скрининга специфичности связывания биологически активных соединений с нуклеиновыми кислотами с использованием биочипа (варианты) |
DE10030376A1 (de) | 2000-06-21 | 2002-01-24 | Bayer Ag | Neues Verfahren zum Auffinden neuer Wirkstoffe |
US6951947B2 (en) * | 2000-07-13 | 2005-10-04 | The Scripps Research Institute | Labeled peptides, proteins and antibodies and processes and intermediates useful for their preparation |
JP4745547B2 (ja) | 2000-07-14 | 2011-08-10 | 富山化学工業株式会社 | 新規ベンズイミダゾール誘導体またはその塩 |
US20030028018A1 (en) * | 2000-09-11 | 2003-02-06 | Chiron Coporation | Quinolinone derivatives |
FR2815345B1 (fr) | 2000-10-12 | 2002-12-13 | Servier Lab | Nouveaux derives de cyclobutene-dione, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
CA2426674A1 (en) | 2000-10-25 | 2002-05-02 | Takeda Chemical Industries, Ltd. | Agent for preventing or treating portal hypertension |
JP2002161084A (ja) | 2000-11-28 | 2002-06-04 | Sumitomo Pharmaceut Co Ltd | 複素環誘導体 |
EP2062593A3 (en) | 2000-12-01 | 2011-08-17 | Takeda Pharmaceutical Company Limited | Method for producing preparation containing bioactive peptide |
KR100394086B1 (ko) | 2000-12-04 | 2003-08-06 | 한국과학기술연구원 | 도파민 d3 및 d4 수용체의 선택적 활성을 지닌 신규이소옥사졸릴알킬피페라진 유도체와, 이의 제조방법 |
US20020072053A1 (en) * | 2000-12-08 | 2002-06-13 | Mcnally Alan J. | Immunoassay based on DNA replication using labeled primer |
GB2370270A (en) | 2000-12-20 | 2002-06-26 | Lilly Co Eli | Pharmaceutical compounds |
JP2002212101A (ja) | 2001-01-19 | 2002-07-31 | Takeda Chem Ind Ltd | 歯肉肥厚抑制剤 |
FR2821428B1 (fr) | 2001-02-23 | 2004-08-06 | Abx Sa | Reactif et procede pour l'identification et le comptage de cellules biologiques |
DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
EP1369130A1 (en) | 2001-03-16 | 2003-12-10 | Takeda Chemical Industries, Ltd. | Process for producing sustained release preparation |
US6689391B2 (en) * | 2001-03-30 | 2004-02-10 | Council Of Scientific & Industrial Research | Natural non-polar fluorescent dye from a non-bioluminescent marine invertebrate, compositions containing the said dye and its uses |
US6376141B1 (en) * | 2001-04-13 | 2002-04-23 | Xerox Corporation | Photoreceptor with layered charge generation section |
AR035543A1 (es) | 2001-06-26 | 2004-06-16 | Japan Tobacco Inc | Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con |
US6855714B2 (en) | 2001-07-06 | 2005-02-15 | Schering Aktiengesellschaft | 1-alkyl-2-aryl-benzimidazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives |
US6492517B1 (en) | 2001-07-19 | 2002-12-10 | Air Products And Chemicals, Inc. | Method for preparing halomethyl heterocyclic compounds |
JP2003040890A (ja) | 2001-07-31 | 2003-02-13 | Fuji Photo Film Co Ltd | ハロゲン化3H−ピロロ[2,3−b]ピリジン類及びその製造方法 |
WO2003013609A1 (en) | 2001-08-03 | 2003-02-20 | Takeda Chemical Industries, Ltd. | Sustained-release medicines |
JP2003083968A (ja) | 2001-09-14 | 2003-03-19 | Jsr Corp | Dnaチップおよびアッセイ方法 |
FR2831536A1 (fr) | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
WO2003045929A1 (fr) | 2001-11-26 | 2003-06-05 | Takeda Chemical Industries, Ltd. | Derive bicyclique, procede de production de ce derive et utilisation correspondante |
WO2003048140A1 (fr) | 2001-12-03 | 2003-06-12 | Japan Tobacco Inc. | Compose azole et utilisation medicinale de celui-ci |
FR2833948B1 (fr) * | 2001-12-21 | 2004-02-06 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et leur utilisation en tant que medicament |
JP2003231687A (ja) | 2002-02-04 | 2003-08-19 | Japan Tobacco Inc | ピラゾリル縮合環化合物及びその医薬用途 |
US6818420B2 (en) * | 2002-02-27 | 2004-11-16 | Biosource International, Inc. | Methods of using FET labeled oligonucleotides that include a 3′-5′ exonuclease resistant quencher domain and compositions for practicing the same |
SE0202462D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
GB0219457D0 (en) | 2002-08-21 | 2002-09-25 | Amersham Biosciences Uk Ltd | Fluorescence reference plate |
MXPA05003948A (es) | 2002-10-17 | 2005-06-17 | Amgen Inc | Derivados de bencimidazol y su uso como ligandos de receptor vaniloide. |
JP2008503469A (ja) | 2004-06-17 | 2008-02-07 | ワイス | ゴナドトロピン放出ホルモン受容体アンタゴニスト |
CA2570693A1 (en) * | 2004-06-17 | 2006-01-26 | Wyeth | Processes for preparing gonadotropin releasing hormone receptor antagonists |
JP2008520732A (ja) | 2004-11-23 | 2008-06-19 | ワイス | ゴナドトロピン放出ホルモン受容体アンタゴニスト |
US7582634B2 (en) * | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US7534796B2 (en) * | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
US7538113B2 (en) * | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US20060189619A1 (en) | 2005-02-24 | 2006-08-24 | Wyeth | 3-({4-[2-(4-Tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl}methyl)pyrido[2,3-b]]pyrazi ne compounds |
US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
-
2005
- 2005-06-16 JP JP2007516680A patent/JP2008503469A/ja active Pending
- 2005-06-16 MX MXPA06014798A patent/MXPA06014798A/es not_active Application Discontinuation
- 2005-06-16 WO PCT/US2005/021124 patent/WO2006009734A1/en active Application Filing
- 2005-06-16 AU AU2005264996A patent/AU2005264996A1/en not_active Abandoned
- 2005-06-16 KR KR1020067026441A patent/KR20070027584A/ko not_active Application Discontinuation
- 2005-06-16 EP EP05762686A patent/EP1758895A1/en not_active Withdrawn
- 2005-06-16 CA CA002570968A patent/CA2570968A1/en not_active Abandoned
- 2005-06-16 US US11/154,795 patent/US7696210B2/en not_active Expired - Fee Related
- 2005-06-16 CN CNA200580027480XA patent/CN101006078A/zh active Pending
- 2005-06-16 RU RU2007101544/04A patent/RU2007101544A/ru unknown
- 2005-06-16 BR BRPI0512261-9A patent/BRPI0512261A/pt not_active IP Right Cessation
-
2006
- 2006-12-07 CR CR8799A patent/CR8799A/es not_active Application Discontinuation
- 2006-12-15 ZA ZA200610589A patent/ZA200610589B/en unknown
- 2006-12-18 EC EC2006007090A patent/ECSP067090A/es unknown
-
2007
- 2007-01-16 NO NO20070294A patent/NO20070294L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2006009734A1 (en) | 2006-01-26 |
MXPA06014798A (es) | 2007-06-22 |
CA2570968A1 (en) | 2006-01-26 |
RU2007101544A (ru) | 2008-08-10 |
BRPI0512261A (pt) | 2008-02-26 |
NO20070294L (no) | 2007-02-28 |
CN101006078A (zh) | 2007-07-25 |
CR8799A (es) | 2007-08-28 |
US7696210B2 (en) | 2010-04-13 |
ECSP067090A (es) | 2007-01-26 |
KR20070027584A (ko) | 2007-03-09 |
JP2008503469A (ja) | 2008-02-07 |
EP1758895A1 (en) | 2007-03-07 |
WO2006009734A8 (en) | 2007-01-11 |
AU2005264996A1 (en) | 2006-01-26 |
US20060019965A1 (en) | 2006-01-26 |
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