JP2009536220A5 - - Google Patents
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- JP2009536220A5 JP2009536220A5 JP2009510112A JP2009510112A JP2009536220A5 JP 2009536220 A5 JP2009536220 A5 JP 2009536220A5 JP 2009510112 A JP2009510112 A JP 2009510112A JP 2009510112 A JP2009510112 A JP 2009510112A JP 2009536220 A5 JP2009536220 A5 JP 2009536220A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- halo
- substituted
- hedgehog
- 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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- 150000003839 salts Chemical class 0.000 claims description 6
- VZZJRYRQSPEMTK-CALCHBBNSA-N sonidegib Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(N=C1)=CC=C1NC(=O)C1=CC=CC(C=2C=CC(OC(F)(F)F)=CC=2)=C1C VZZJRYRQSPEMTK-CALCHBBNSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 18
- 125000001475 halogen functional group Chemical group 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 206010004146 Basal cell carcinoma Diseases 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000009459 hedgehog signaling Effects 0.000 description 3
- 230000008410 smoothened signaling pathway Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 1
- 101710133394 POU domain, class 3, transcription factor 2 Proteins 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
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- 229920001615 Tragacanth Polymers 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
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- 239000002671 adjuvant Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
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- 239000000556 agonist Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
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- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- -1 methyl-piperazinyl Chemical group 0.000 description 1
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- 230000035772 mutation Effects 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
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- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79794906P | 2006-05-05 | 2006-05-05 | |
| US60/797,949 | 2006-05-05 | ||
| PCT/US2007/068292 WO2007131201A2 (en) | 2006-05-05 | 2007-05-04 | Compounds and compositions as hedgehog pathway modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011189963A Division JP5603308B2 (ja) | 2006-05-05 | 2011-08-31 | ヘッジホッグ経路調節剤としての化合物および組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009536220A JP2009536220A (ja) | 2009-10-08 |
| JP2009536220A5 true JP2009536220A5 (enExample) | 2011-10-20 |
| JP4891396B2 JP4891396B2 (ja) | 2012-03-07 |
Family
ID=38668605
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009510112A Active JP4891396B2 (ja) | 2006-05-05 | 2007-05-04 | ヘッジホッグ経路調節剤としての化合物および組成物 |
| JP2011189963A Active JP5603308B2 (ja) | 2006-05-05 | 2011-08-31 | ヘッジホッグ経路調節剤としての化合物および組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011189963A Active JP5603308B2 (ja) | 2006-05-05 | 2011-08-31 | ヘッジホッグ経路調節剤としての化合物および組成物 |
Country Status (44)
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA93548C2 (uk) * | 2006-05-05 | 2011-02-25 | Айерем Елелсі | Сполуки та композиції як модулятори хеджхогівського сигнального шляху |
| TWI433674B (zh) | 2006-12-28 | 2014-04-11 | Infinity Discovery Inc | 環杷明（ｃｙｃｌｏｐａｍｉｎｅ）類似物類 |
| US8507471B2 (en) * | 2007-06-07 | 2013-08-13 | Irm Llc | Biphenylcarboxamide derivatives as hedgehod pathway modulators |
| AU2014280951B2 (en) * | 2007-06-07 | 2016-10-13 | Sun Pharmaceutical Industries Limited | Biphenylcarboxamide derivatives as hedgehog pathway modulators |
| EP2222638A2 (en) * | 2007-11-21 | 2010-09-01 | Decode Genetics EHF | Biaryl pde4 inhibitors for treating inflammation |
| CN104059124A (zh) | 2007-12-27 | 2014-09-24 | 无限药品股份有限公司 | 立体选择性还原的方法 |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| US20090281089A1 (en) * | 2008-04-11 | 2009-11-12 | Genentech, Inc. | Pyridyl inhibitors of hedgehog signalling |
| KR20120015363A (ko) * | 2008-09-17 | 2012-02-21 | 노파르티스 아게 | Ｎ-［6-(시스-2,6-디메틸모르폴린-4-일)피리딘-3-일］-2-메틸-4'-(트리플루오로메톡시)［1,1'-비페닐］-3-카르복스아미드의 염 |
| WO2010037715A1 (en) | 2008-10-01 | 2010-04-08 | Novartis Ag | Smoothened antagonism for the treatment of hedgehog pathway-related disorders |
| WO2010052448A2 (en) * | 2008-11-05 | 2010-05-14 | Ucb Pharma S.A. | Fused pyrazine derivatives as kinase inhibitors |
| AR077490A1 (es) * | 2009-07-21 | 2011-08-31 | Novartis Ag | Composiciones farmaceuticas topicas para el tratamiento de una condicion hiperproliferativa de la piel |
| CA2769795C (en) | 2009-08-05 | 2020-01-07 | Infinity Pharmaceuticals, Inc. | Enzymatic transamination of cyclopamine analogs |
| US20110039850A1 (en) | 2009-08-12 | 2011-02-17 | Mhairi Copland | Leukemia Treatment |
| US20120232087A1 (en) | 2009-11-18 | 2012-09-13 | Silvia Buonamici | Methods and compositions for treating solid tumors and other malignancies |
| AU2011255218B2 (en) | 2010-05-21 | 2015-03-12 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| US9376447B2 (en) | 2010-09-14 | 2016-06-28 | Infinity Pharmaceuticals, Inc. | Transfer hydrogenation of cyclopamine analogs |
| CN101993415B (zh) * | 2010-09-15 | 2013-08-14 | 北京韩美药品有限公司 | 作为Hedgehog通路抑制剂的化合物以及包含该化合物的药物组合物及其应用 |
| AU2011326427B2 (en) | 2010-11-10 | 2016-01-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| PE20180318A1 (es) | 2011-01-10 | 2018-02-09 | Infinity Pharmaceuticals Inc | Procedimiento para preparar isoquinolinonas y formas solidas de isoquinolinonas |
| CN104975099A (zh) | 2011-06-02 | 2015-10-14 | 诺华股份有限公司 | Hedgehog抑制剂治疗的生物标志物 |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| WO2013012918A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| AR091790A1 (es) | 2011-08-29 | 2015-03-04 | Infinity Pharmaceuticals Inc | Derivados de isoquinolin-1-ona y sus usos |
| US9630979B2 (en) | 2011-09-29 | 2017-04-25 | Infinity Pharmaceuticals, Inc. | Inhibitors of monoacylglycerol lipase and methods of their use |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US9512106B2 (en) | 2012-09-17 | 2016-12-06 | Duke University | Smoothened modulators and methods of use thereof |
| LT2914296T (lt) | 2012-11-01 | 2018-09-25 | Infinity Pharmaceuticals, Inc. | Vėžio gydymas, panaudojant p13 kinazės izoformos moduliatorius |
| WO2014085523A1 (en) | 2012-11-29 | 2014-06-05 | Strasspharma Llc | Methods of modulating follicle stimulating hormone activity |
| CN103910736B (zh) * | 2013-01-08 | 2017-11-17 | 江苏先声药业有限公司 | 一类二氢吡喃并嘧啶衍生物及其医药应用 |
| US20160024051A1 (en) | 2013-03-15 | 2016-01-28 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| US9192609B2 (en) | 2013-04-17 | 2015-11-24 | Hedgepath Pharmaceuticals, Inc. | Treatment and prognostic monitoring of proliferation disorders using hedgehog pathway inhibitors |
| EP3003309B1 (en) | 2013-05-30 | 2020-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| WO2015051244A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US9751888B2 (en) | 2013-10-04 | 2017-09-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US20160244452A1 (en) | 2013-10-21 | 2016-08-25 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2015092720A1 (en) * | 2013-12-19 | 2015-06-25 | Novartis Ag | Metabolites of sonidegib (lde225) |
| JOP20200094A1 (ar) | 2014-01-24 | 2017-06-16 | Dana Farber Cancer Inst Inc | جزيئات جسم مضاد لـ pd-1 واستخداماتها |
| JOP20200096A1 (ar) | 2014-01-31 | 2017-06-16 | Children’S Medical Center Corp | جزيئات جسم مضاد لـ tim-3 واستخداماتها |
| EP3660050A1 (en) | 2014-03-14 | 2020-06-03 | Novartis AG | Antibody molecules to lag-3 and uses thereof |
| EP3119397B1 (en) | 2014-03-19 | 2022-03-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders |
| JP6377245B2 (ja) * | 2014-03-24 | 2018-08-22 | グアンドン ジョンシェン ファーマシューティカル カンパニー リミテッド | Ｓｍｏ阻害剤としてのキノリン誘導体 |
| US20150320754A1 (en) | 2014-04-16 | 2015-11-12 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| WO2015168079A1 (en) | 2014-04-29 | 2015-11-05 | Infinity Pharmaceuticals, Inc. | Pyrimidine or pyridine derivatives useful as pi3k inhibitors |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| MA41044A (fr) | 2014-10-08 | 2017-08-15 | Novartis Ag | Compositions et procédés d'utilisation pour une réponse immunitaire accrue et traitement contre le cancer |
| CN114920840A (zh) | 2014-10-14 | 2022-08-19 | 诺华股份有限公司 | 针对pd-l1的抗体分子及其用途 |
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