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 (enExample) | 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 |
| AR072092A1 (es) * | 2008-06-11 | 2010-08-04 | Genentech Inc | Diazacarbazoles y metodos de uso |
| 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 |
| UY32275A (es) * | 2009-03-24 | 2010-06-30 | Sanofi Aventis | DERIVADOS DE AZACARBOLINAS 9H-PIRROLO[2,3-b:5,4-c'] DIPIRIDINA, SU PREPARACION Y SU UTILIZACIÓN TERAPÉUTICA. |
| 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 |
| US20110183938A1 (en) * | 2009-12-16 | 2011-07-28 | Genentech, Inc. | 1,7-diazacarbazoles and methods of use |
| TW201304778A (zh) | 2010-11-16 | 2013-02-01 | Array Biopharma Inc | 檢查點激酶１抑制劑及ｗｅｅ１激酶抑制劑之組合 |
| 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 |
| US9254299B2 (en) | 2011-12-22 | 2016-02-09 | Threshold Pharmaceuticals, Inc. | Administration of hypoxia activated prodrugs in combination with Chk1 inhibitors for treating cancer |
| WO2013157022A1 (en) | 2012-04-20 | 2013-10-24 | Advinus Therapeutics Limited | Substituted hetero-bicyclic compounds, compositions and medicinal applications thereof |
| EP2671881A1 (en) | 2012-06-07 | 2013-12-11 | Syngenta Participations AG. | Pesticidally active pyridyl- and pyrimidyl- substituted thiazole derivatives |
| LT3495367T (lt) | 2012-06-13 | 2021-02-25 | Incyte Holdings Corporation | Pakeistieji tricikliniai junginiai, kaip fgfr inhibitoriai |
| CA2928568A1 (en) | 2013-07-26 | 2015-01-29 | Update Pharma Inc. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| US10071109B2 (en) | 2013-11-06 | 2018-09-11 | Molecular Templates, Inc. | Predictive biomarker for hypoxia-activated prodrug therapy |
| JP6783224B2 (ja) | 2014-04-04 | 2020-11-11 | デル マー ファーマシューティカルズ | 肺の非小細胞癌腫及び卵巣癌を処置するためのジアンヒドロガラクチトール及びその類縁体又は誘導体の使用 |
| 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 |
| MX2020011718A (es) | 2018-05-04 | 2021-02-15 | Incyte Corp | Formas solidas de un inhibidor de receptores del factor de crecimiento de fibroblastos (fgfr) y procesos para prepararlas. |
| ES3061844T3 (en) | 2018-05-04 | 2026-04-07 | 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 |
| WO2020072675A1 (en) | 2018-10-02 | 2020-04-09 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2c (5-ht2c) |
| WO2020120673A1 (en) * | 2018-12-13 | 2020-06-18 | 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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| WO2001068648A1 (en) * | 2000-03-15 | 2001-09-20 | Aventis Pharma Deutschland Gmbh | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| MEP28108A (en) * | 2000-03-15 | 2010-10-10 | Sanofi Aventis Deutschland | 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 |
| US9248124B2 (en) * | 2001-11-07 | 2016-02-02 | Millennium Pharmaceuticals, Inc. | Use of inhibitors of IκB kinase for the treatment of cancer |
| MXPA05008688A (es) | 2003-02-17 | 2005-10-05 | Pharmacia Italia Spa | Derivados tetraciclicos de pirazol como inhibidores de la cinasa, procedimiento para su preparacion y composiciones farmaceuticas que los comprenden. |
| SE0401655D0 (sv) | 2004-06-24 | 2004-06-24 | Astrazeneca Ab | New compounds |
| EP1896472A1 (de) * | 2005-06-09 | 2008-03-12 | Boehringer Ingelheim International GmbH | Alpha-carboline als cdk-1 inhibitoren |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP2079696A2 (en) | 2006-10-09 | 2009-07-22 | Takeda San Diego, Inc. | Kinase inhibitors |
| EP2081930A2 (en) | 2006-10-09 | 2009-07-29 | Takeda San Diego, Inc. | Kinase inhibitors |
| EP2170886A1 (en) | 2007-07-02 | 2010-04-07 | 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 |
| WO2009129401A1 (en) | 2008-04-16 | 2009-10-22 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| AR072092A1 (es) * | 2008-06-11 | 2010-08-04 | Genentech Inc | Diazacarbazoles y metodos de uso |
| 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 |
| UY32275A (es) | 2009-03-24 | 2010-06-30 | Sanofi Aventis | DERIVADOS DE AZACARBOLINAS 9H-PIRROLO[2,3-b:5,4-c'] DIPIRIDINA, SU PREPARACION Y SU UTILIZACIÓN TERAPÉUTICA. |
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