JP2011522889A5 - - Google Patents
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- Publication number
- JP2011522889A5 JP2011522889A5 JP2011513498A JP2011513498A JP2011522889A5 JP 2011522889 A5 JP2011522889 A5 JP 2011522889A5 JP 2011513498 A JP2011513498 A JP 2011513498A JP 2011513498 A JP2011513498 A JP 2011513498A JP 2011522889 A5 JP2011522889 A5 JP 2011522889A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- membered
- heterocyclyl
- groups
- cancer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 37
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims 25
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000002950 monocyclic group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000002619 bicyclic group Chemical group 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 10
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- -1 optionally Chemical group 0.000 claims 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 208000014018 liver neoplasm Diseases 0.000 claims 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
- 206010061424 Anal cancer Diseases 0.000 claims 1
- 208000007860 Anus Neoplasms Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 239000012623 DNA damaging agent Substances 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 1
- 206010019695 Hepatic neoplasm 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
- 208000032271 Malignant tumor of penis Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000002471 Penile Neoplasms Diseases 0.000 claims 1
- 206010034299 Penile cancer Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims 1
- 206010061934 Salivary gland cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010047741 Vulval cancer Diseases 0.000 claims 1
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 201000011165 anus cancer Diseases 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002357 endometrial effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 229960005277 gemcitabine Drugs 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
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 201000005243 lung squamous cell carcinoma Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000002628 peritoneum cancer Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- 201000005102 vulva cancer Diseases 0.000 claims 1
- 0 *C(c(cc1)ccc1-c1cc(c(cc(C#N)nc2)c2[n]2)c2nc1)N1CCCCC1 Chemical compound *C(c(cc1)ccc1-c1cc(c(cc(C#N)nc2)c2[n]2)c2nc1)N1CCCCC1 0.000 description 4
- WUUMJLOCXSNNCP-UHFFFAOYSA-N CCN(CC1)CCC1Oc1c(C#N)ncc([nH]2)c1c1c2ncc(-c(cn2)ccc2OC)c1 Chemical compound CCN(CC1)CCC1Oc1c(C#N)ncc([nH]2)c1c1c2ncc(-c(cn2)ccc2OC)c1 WUUMJLOCXSNNCP-UHFFFAOYSA-N 0.000 description 1
- BQYZWMICXAURNB-UHFFFAOYSA-N CCN(CC1)CCC1Oc1c(C#N)ncc([nH]2)c1c1c2ncc(-c2ccc(CN(CC3)CCC3(F)F)cc2)c1 Chemical compound CCN(CC1)CCC1Oc1c(C#N)ncc([nH]2)c1c1c2ncc(-c2ccc(CN(CC3)CCC3(F)F)cc2)c1 BQYZWMICXAURNB-UHFFFAOYSA-N 0.000 description 1
- AQRQFJWAOACBGD-UHFFFAOYSA-N CCN(CC1)CCC1Oc1c(C#N)ncc([nH]2)c1c1c2ncc(-c2cccnc2)c1 Chemical compound CCN(CC1)CCC1Oc1c(C#N)ncc([nH]2)c1c1c2ncc(-c2cccnc2)c1 AQRQFJWAOACBGD-UHFFFAOYSA-N 0.000 description 1
- NMZXUFOJFYOUQA-UHFFFAOYSA-N CCN(CC1)CCC1Oc1c(N)ncc([nH]2)c1c1c2ncc(-c2ccc(CN(CC3)CCC3C(F)(F)F)cc2)c1 Chemical compound CCN(CC1)CCC1Oc1c(N)ncc([nH]2)c1c1c2ncc(-c2ccc(CN(CC3)CCC3C(F)(F)F)cc2)c1 NMZXUFOJFYOUQA-UHFFFAOYSA-N 0.000 description 1
- JOWIDRLNQQLHBC-UHFFFAOYSA-N CCN(CC1)CCC1Oc1c(c2c([nH]3)ncc(-c4c[n](C)nc4)c2)c3cnc1C#N Chemical compound CCN(CC1)CCC1Oc1c(c2c([nH]3)ncc(-c4c[n](C)nc4)c2)c3cnc1C#N JOWIDRLNQQLHBC-UHFFFAOYSA-N 0.000 description 1
- BDQOEXCIDXVHMO-UHFFFAOYSA-N CCN(CC1)CCC1Oc1c(c2cc(C#N)cnc2[nH]2)c2cnc1C#N Chemical compound CCN(CC1)CCC1Oc1c(c2cc(C#N)cnc2[nH]2)c2cnc1C#N BDQOEXCIDXVHMO-UHFFFAOYSA-N 0.000 description 1
- YKTZRIMZDGTGQO-UHFFFAOYSA-N CCN(CC1)Cc2c1cc(-c1cc(c(cc(C#N)nc3)c3[nH]3)c3nc1)[s]2 Chemical compound CCN(CC1)Cc2c1cc(-c1cc(c(cc(C#N)nc3)c3[nH]3)c3nc1)[s]2 YKTZRIMZDGTGQO-UHFFFAOYSA-N 0.000 description 1
- NHIZPKZPCIKYTF-UHFFFAOYSA-N CN(C)C1CCN(Cc(cc2)ccc2-c2cc(c3cc(C#N)ncc3[nH]3)c3nc2)CC1 Chemical compound CN(C)C1CCN(Cc(cc2)ccc2-c2cc(c3cc(C#N)ncc3[nH]3)c3nc2)CC1 NHIZPKZPCIKYTF-UHFFFAOYSA-N 0.000 description 1
- BOAFQZWUOJZNFV-UHFFFAOYSA-N CN(CC1)CCC1Oc1cc(-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)cc(Br)c1 Chemical compound CN(CC1)CCC1Oc1cc(-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)cc(Br)c1 BOAFQZWUOJZNFV-UHFFFAOYSA-N 0.000 description 1
- XDZCGZUSXWUNCC-UHFFFAOYSA-N CN(CC1)CCC1Oc1cc(OC)cc(-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)c1 Chemical compound CN(CC1)CCC1Oc1cc(OC)cc(-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)c1 XDZCGZUSXWUNCC-UHFFFAOYSA-N 0.000 description 1
- TTYHMBOHDSEZSR-UHFFFAOYSA-N CN(CC1)CCN1c(cc1)ccc1-c(cc1c2c3)cnc1[nH]c2cnc3Cl Chemical compound CN(CC1)CCN1c(cc1)ccc1-c(cc1c2c3)cnc1[nH]c2cnc3Cl TTYHMBOHDSEZSR-UHFFFAOYSA-N 0.000 description 1
- OXYGNHXZDLZMHI-UHFFFAOYSA-N CN(CC1)CCN1c(cc1)ccc1-c(cc1c2c3)cnc1[nH]c2cnc3OC Chemical compound CN(CC1)CCN1c(cc1)ccc1-c(cc1c2c3)cnc1[nH]c2cnc3OC OXYGNHXZDLZMHI-UHFFFAOYSA-N 0.000 description 1
- VXFICAIVTPNEHD-UHFFFAOYSA-N CN(CCc1cc(C2=CC3c4cc(C#N)ncc4NC3N=C2)c2)Cc1c2OC Chemical compound CN(CCc1cc(C2=CC3c4cc(C#N)ncc4NC3N=C2)c2)Cc1c2OC VXFICAIVTPNEHD-UHFFFAOYSA-N 0.000 description 1
- YXEHPUNPSRNFKC-UHFFFAOYSA-N COc(nc1)cc(c2c3)c1[nH]c2ncc3-c1ccc(CN2CCCCC2)cc1 Chemical compound COc(nc1)cc(c2c3)c1[nH]c2ncc3-c1ccc(CN2CCCCC2)cc1 YXEHPUNPSRNFKC-UHFFFAOYSA-N 0.000 description 1
- WWFGJJXAAWQFJQ-CALCHBBNSA-N C[C@H]1CN(Cc(cc2)ccc2-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)C[C@@H](C)C1 Chemical compound C[C@H]1CN(Cc(cc2)ccc2-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)C[C@@H](C)C1 WWFGJJXAAWQFJQ-CALCHBBNSA-N 0.000 description 1
- ZNUSBHGXUCYXKB-IYBDPMFKSA-N C[C@H]1O[C@@H](C)CN(Cc(cc2)ccc2-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)C1 Chemical compound C[C@H]1O[C@@H](C)CN(Cc(cc2)ccc2-c2cc(c(cc(C#N)nc3)c3[nH]3)c3nc2)C1 ZNUSBHGXUCYXKB-IYBDPMFKSA-N 0.000 description 1
- YMANDCYDGJUYIB-UHFFFAOYSA-N C[n]1ncc(-c(cc2c3c4)cnc2[nH]c3cnc4Cl)c1 Chemical compound C[n]1ncc(-c(cc2c3c4)cnc2[nH]c3cnc4Cl)c1 YMANDCYDGJUYIB-UHFFFAOYSA-N 0.000 description 1
- FBPATNKKBYBXCK-UHFFFAOYSA-N C[n]1ncc(-c2cc(c(C(C(C#N)N=C3)OC4CNC4)c3[nH]3)c3nc2)c1 Chemical compound C[n]1ncc(-c2cc(c(C(C(C#N)N=C3)OC4CNC4)c3[nH]3)c3nc2)c1 FBPATNKKBYBXCK-UHFFFAOYSA-N 0.000 description 1
- ORGPRBJUQNAXQB-UHFFFAOYSA-N C[n]1ncc(-c2cc(c(c(OC3CCNCC3)c(C#N)nc3)c3[nH]3)c3nc2)c1 Chemical compound C[n]1ncc(-c2cc(c(c(OC3CCNCC3)c(C#N)nc3)c3[nH]3)c3nc2)c1 ORGPRBJUQNAXQB-UHFFFAOYSA-N 0.000 description 1
- IGKCVXYKFMUKST-AWEZNQCLSA-N C[n]1ncc(-c2cc(c(c(O[C@@H]3CNCCC3)c(C#N)nc3)c3[nH]3)c3nc2)c1 Chemical compound C[n]1ncc(-c2cc(c(c(O[C@@H]3CNCCC3)c(C#N)nc3)c3[nH]3)c3nc2)c1 IGKCVXYKFMUKST-AWEZNQCLSA-N 0.000 description 1
- JFMZVSXHQKUXTI-UHFFFAOYSA-N C[n]1ncc(-c2cc(c(cc(-c3c[n](C)nc3)nc3)c3[nH]3)c3nc2)c1 Chemical compound C[n]1ncc(-c2cc(c(cc(-c3c[n](C)nc3)nc3)c3[nH]3)c3nc2)c1 JFMZVSXHQKUXTI-UHFFFAOYSA-N 0.000 description 1
- NQFSLNFYSRONPJ-UHFFFAOYSA-N Fc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cc1 Chemical compound Fc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cc1 NQFSLNFYSRONPJ-UHFFFAOYSA-N 0.000 description 1
- NDLWAVWPZSWZDO-UHFFFAOYSA-N N#Cc(cc1c2c3)ncc1[nH]c2ncc3-c1ncc[nH]1 Chemical compound N#Cc(cc1c2c3)ncc1[nH]c2ncc3-c1ncc[nH]1 NDLWAVWPZSWZDO-UHFFFAOYSA-N 0.000 description 1
- BOIVMJXJOVNQQN-UHFFFAOYSA-N N#Cc(nc1)cc(c2c3)c1[nH]c2ncc3-c1ccc(CN2CCCCC2)nc1 Chemical compound N#Cc(nc1)cc(c2c3)c1[nH]c2ncc3-c1ccc(CN2CCCCC2)nc1 BOIVMJXJOVNQQN-UHFFFAOYSA-N 0.000 description 1
- LWTJVUBDEHASBX-UHFFFAOYSA-N N#Cc(nc1)cc(c2c3)c1[nH]c2ncc3C1=CCC(CN2CC3(CC3)CC3(CC3)C2)C=C1 Chemical compound N#Cc(nc1)cc(c2c3)c1[nH]c2ncc3C1=CCC(CN2CC3(CC3)CC3(CC3)C2)C=C1 LWTJVUBDEHASBX-UHFFFAOYSA-N 0.000 description 1
- VHYWVLFRESEOCS-UHFFFAOYSA-N N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1cc(Cl)c(CN2CCCCC2)cc1 Chemical compound N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1cc(Cl)c(CN2CCCCC2)cc1 VHYWVLFRESEOCS-UHFFFAOYSA-N 0.000 description 1
- ZVVXABOIOCBCJC-UHFFFAOYSA-N N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1cc(F)c(CN2CCCCC2)c(F)c1 Chemical compound N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1cc(F)c(CN2CCCCC2)c(F)c1 ZVVXABOIOCBCJC-UHFFFAOYSA-N 0.000 description 1
- MILNVUVREACQML-UHFFFAOYSA-N N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCC2)cc1 Chemical compound N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCC2)cc1 MILNVUVREACQML-UHFFFAOYSA-N 0.000 description 1
- FEKXTZGJWXJSNN-UHFFFAOYSA-N N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cn1 Chemical compound N#Cc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cn1 FEKXTZGJWXJSNN-UHFFFAOYSA-N 0.000 description 1
- SJQDZGJVQOTWKD-UHFFFAOYSA-N N#Cc(ncc([nH]1)c2c3c1ncc(-c1ccc(CN(CC4)CCC4(F)F)cc1)c3)c2OC1CCNCC1 Chemical compound N#Cc(ncc([nH]1)c2c3c1ncc(-c1ccc(CN(CC4)CCC4(F)F)cc1)c3)c2OC1CCNCC1 SJQDZGJVQOTWKD-UHFFFAOYSA-N 0.000 description 1
- UMIZHRHUKHOMJU-UHFFFAOYSA-N N#Cc(ncc([nH]1)c2c3c1ncc(-c1ccc(CN4CCOCC4)cc1)c3)c2OC1CCNCC1 Chemical compound N#Cc(ncc([nH]1)c2c3c1ncc(-c1ccc(CN4CCOCC4)cc1)c3)c2OC1CCNCC1 UMIZHRHUKHOMJU-UHFFFAOYSA-N 0.000 description 1
- GZZASBMXAPVEHC-UHFFFAOYSA-N N#Cc1ncc2[nH]c3ncccc3c2c1CC1CCN(CC(F)(F)F)CC1 Chemical compound N#Cc1ncc2[nH]c3ncccc3c2c1CC1CCN(CC(F)(F)F)CC1 GZZASBMXAPVEHC-UHFFFAOYSA-N 0.000 description 1
- PMBMWAUXJPACJZ-UHFFFAOYSA-N Nc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cc1 Chemical compound Nc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cc1 PMBMWAUXJPACJZ-UHFFFAOYSA-N 0.000 description 1
- FCQLKAWVWVURRM-UHFFFAOYSA-N O=C1NC=C2Nc(ncc(-c3ccc(CN4CCCCC4)cc3)c3)c3C2=C1 Chemical compound O=C1NC=C2Nc(ncc(-c3ccc(CN4CCCCC4)cc3)c3)c3C2=C1 FCQLKAWVWVURRM-UHFFFAOYSA-N 0.000 description 1
- DRTVBSHSKXKMDM-UHFFFAOYSA-N O=SNc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cc1 Chemical compound O=SNc(nc1)cc2c1[nH]c(nc1)c2cc1-c1ccc(CN2CCCCC2)cc1 DRTVBSHSKXKMDM-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6074608P | 2008-06-11 | 2008-06-11 | |
| US61/060,746 | 2008-06-11 | ||
| US14800109P | 2009-01-28 | 2009-01-28 | |
| US61/148,001 | 2009-01-28 | ||
| PCT/US2009/003492 WO2009151598A1 (en) | 2008-06-11 | 2009-06-10 | Diazacarbazoles and methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014165224A Division JP2015028027A (ja) | 2008-06-11 | 2014-08-14 | ジアザカルバゾール類と使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011522889A JP2011522889A (ja) | 2011-08-04 |
| JP2011522889A5 true JP2011522889A5 (OSRAM) | 2012-07-26 |
| JP5599784B2 JP5599784B2 (ja) | 2014-10-01 |
Family
ID=41066724
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011513498A Active JP5599784B2 (ja) | 2008-06-11 | 2009-06-10 | ジアザカルバゾール類と使用方法 |
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| US8003625B2 (en) | 2005-06-29 | 2011-08-23 | Threshold Pharmaceuticals, Inc. | Phosphoramidate alkylator prodrugs |
| US8501765B2 (en) * | 2008-06-11 | 2013-08-06 | Genentech, Inc. | Diazacarbazoles and methods of use |
| AR072084A1 (es) * | 2008-06-12 | 2010-08-04 | Sanofi Aventis | Derivados de azacarbolinas, su preparacion y su utilizacion terapeutica como inhibidores de las quinasas pim |
| FR2950891B1 (fr) * | 2009-10-06 | 2012-11-09 | Sanofi Aventis | Derives d'azacarbolines 9h-pyrrolo[2,3-b:5,4-c']dipyridine, leur preparation et leur utilisation therapeutique |
| BRPI0924844A2 (pt) * | 2009-03-24 | 2016-01-26 | Sanofi Sa | derivados de azacarbolinas 9h-pirrol[2,3-b:5,4-c']dipiridina, sua preparação e sua utilização terapêutica. |
| US20110183938A1 (en) * | 2009-12-16 | 2011-07-28 | Genentech, Inc. | 1,7-diazacarbazoles and methods of use |
| EP2640386B1 (en) | 2010-11-16 | 2017-01-18 | Array Biopharma Inc. | Combination of checkpoint kinase 1 inhibitors and wee 1 kinase inhibitors |
| CN102503959B (zh) * | 2011-10-25 | 2015-04-08 | 南方医科大学 | 一种稠三环类化合物及其制备方法、以及含该类化合物的药物组合物及其应用 |
| JP6073910B2 (ja) * | 2011-11-09 | 2017-02-01 | キャンサー・リサーチ・テクノロジー・リミテッド | ５−（ピリジン−２−イル−アミノ）−ピラジン−２−カルボニトリル化合物及びその治療使用 |
| WO2013096687A1 (en) * | 2011-12-22 | 2013-06-27 | Threshold Pharmaceuticals, Inc. | Administration of hypoxia activated prodrugs in combination with chk1 inhibitors for treating cancer |
| CA2869954C (en) | 2012-04-20 | 2023-01-03 | Advinus Therapeutics Limited | Substituted hetero-bicyclic compounds, compositions and medicinal applications thereof in medical conditions related to modulation of bruton's tyrosine kinase activity |
| EP2671881A1 (en) | 2012-06-07 | 2013-12-11 | Syngenta Participations AG. | Pesticidally active pyridyl- and pyrimidyl- substituted thiazole derivatives |
| CA2928568A1 (en) | 2013-07-26 | 2015-01-29 | Update Pharma Inc. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| WO2015069489A1 (en) | 2013-11-06 | 2015-05-14 | Merck Patent Gmbh | Predictive biomarker for hypoxia-activated prodrug therapy |
| WO2015154064A2 (en) | 2014-04-04 | 2015-10-08 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| CN107118207B (zh) * | 2017-05-22 | 2020-10-02 | 苏州东南药业股份有限公司 | 一类cdk抑制剂的制备方法 |
| SG11202010882XA (en) | 2018-05-04 | 2020-11-27 | Incyte Corp | Salts of an fgfr inhibitor |
| WO2020061377A1 (en) * | 2018-09-19 | 2020-03-26 | Genentech, Inc. | Spirocyclic 2,3-dihydro-7-azaindole compounds and uses thereof |
| EP3860996A4 (en) | 2018-10-02 | 2022-08-31 | Northwestern University | BETA-CARBOLINES AS POSITIVE ALLOSTERIC MODULATORS OF HUMAN SEROTONIN RECEPTOR 2C (5-HT2C) |
| EP3894403A1 (en) | 2018-12-13 | 2021-10-20 | Intervet International B.V. | Process for preparing 1-[(3r,4s)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl)amino]p yrazole-4-carboxamide |
| WO2021113462A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Derivatives of an fgfr inhibitor |
| US12168662B1 (en) | 2023-12-15 | 2024-12-17 | King Faisal University | Pyrido[4′,3′:4,5]pyrrolo[2,3-c][2,7]naphthyridines compounds as CK2 inhibitors |
| US12129252B1 (en) | 2024-02-15 | 2024-10-29 | King Faisal University | Pyrrolo[2,3-c][2,6]naphthyridine-8-carboxylic acids as CK2 inhibitors |
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| JP5000828B2 (ja) * | 2000-03-15 | 2012-08-15 | サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ＩｋＢキナーゼ阻害活性を有する置換ベーターカルボリン |
| WO2001068648A1 (en) * | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| GB0116966D0 (en) * | 2001-07-11 | 2001-09-05 | Pharma Mar Sa | Anittumoral compounds |
| GB0121941D0 (en) | 2001-09-11 | 2001-10-31 | Astrazeneca Ab | Chemical compounds |
| WO2003039545A2 (en) * | 2001-11-07 | 2003-05-15 | Millennium Pharmaceuticals, Inc. | Carboline derivatives as inhibitors of ikb in the treatment of multiple myeloma and others cancers |
| US20060264493A1 (en) | 2003-02-17 | 2006-11-23 | Ermes Vanotti | Tetracyclic pyrazole derivatives as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| SE0401655D0 (sv) | 2004-06-24 | 2004-06-24 | Astrazeneca Ab | New compounds |
| WO2006131552A1 (de) * | 2005-06-09 | 2006-12-14 | Boehringer Ingelheim International Gmbh | Alpha-carboline als cdk-1 inhibitoren |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| WO2008045834A2 (en) | 2006-10-09 | 2008-04-17 | Takeda San Diego, Inc. | Kinase inhibitors |
| CA2666138A1 (en) | 2006-10-09 | 2008-05-08 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US8618121B2 (en) | 2007-07-02 | 2013-12-31 | Cancer Research Technology Limited | 9H-pyrimido[4,5-B]indoles, 9H-pyrido[4',3':4,5]pyrrolo[2,3-D]pyridines, and 9H 1,3,6,9 tetraaza-fluorenes as CHK1 kinase function inhibitors |
| US8133506B2 (en) | 2008-03-12 | 2012-03-13 | Aptalis Pharmatech, Inc. | Drug delivery systems comprising weakly basic drugs and organic acids |
| US20090312288A1 (en) | 2008-04-16 | 2009-12-17 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US8501765B2 (en) * | 2008-06-11 | 2013-08-06 | Genentech, Inc. | Diazacarbazoles and methods of use |
| AR072084A1 (es) | 2008-06-12 | 2010-08-04 | Sanofi Aventis | Derivados de azacarbolinas, su preparacion y su utilizacion terapeutica como inhibidores de las quinasas pim |
| WO2010015589A1 (en) | 2008-08-05 | 2010-02-11 | Nycomed Gmbh | Benzyl-substituted tetracyclic heterocyclic compounds as pde5 inhibitors |
| BRPI0924844A2 (pt) | 2009-03-24 | 2016-01-26 | Sanofi Sa | derivados de azacarbolinas 9h-pirrol[2,3-b:5,4-c']dipiridina, sua preparação e sua utilização terapêutica. |
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- 2009-06-10 DK DK09762894.5T patent/DK2300475T3/en active
- 2009-06-10 EP EP13191108.3A patent/EP2706059A1/en not_active Withdrawn
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- 2009-06-10 PE PE2010001127A patent/PE20110365A1/es not_active Application Discontinuation
- 2009-06-10 KR KR1020117000563A patent/KR101710732B1/ko not_active Expired - Fee Related
- 2009-06-10 RU RU2010154105/04A patent/RU2515972C2/ru not_active IP Right Cessation
- 2009-06-10 CA CA2725754A patent/CA2725754C/en not_active Expired - Fee Related
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- 2009-06-10 WO PCT/US2009/003492 patent/WO2009151598A1/en not_active Ceased
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