AU2013266110C1 - Heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators - Google Patents
Heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators Download PDFInfo
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- AU2013266110C1 AU2013266110C1 AU2013266110A AU2013266110A AU2013266110C1 AU 2013266110 C1 AU2013266110 C1 AU 2013266110C1 AU 2013266110 A AU2013266110 A AU 2013266110A AU 2013266110 A AU2013266110 A AU 2013266110A AU 2013266110 C1 AU2013266110 C1 AU 2013266110C1
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- Australia
- Prior art keywords
- methanone
- sulfonyl
- fluorophenyl
- isoquinolin
- hexahydro
- Prior art date
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- 229940117965 Glucocorticoid receptor modulator Drugs 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 238
- -1 heteroaryl ketone Chemical class 0.000 claims abstract description 187
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 278
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 189
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 188
- 229910052731 fluorine Inorganic materials 0.000 claims description 138
- 239000000203 mixture Substances 0.000 claims description 106
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 68
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 67
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 66
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 54
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 40
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 39
- 208000035475 disorder Diseases 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 34
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 30
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 27
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 22
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 17
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 17
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
- 239000003862 glucocorticoid Substances 0.000 claims description 16
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229930192474 thiophene Chemical group 0.000 claims description 14
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 13
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 10
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 10
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
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- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 claims description 6
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- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 5
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
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Classifications
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- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| US201361781629P | 2013-03-14 | 2013-03-14 | |
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| PCT/US2013/042732 WO2013177559A2 (en) | 2012-05-25 | 2013-05-24 | Heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators |
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| US8859774B2 (en) | 2012-05-25 | 2014-10-14 | Corcept Therapeutics, Inc. | Heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators |
| US12226412B2 (en) | 2012-05-25 | 2025-02-18 | Corcept Therapeutics, Inc. | Heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators |
| ES2743620T3 (es) | 2013-11-25 | 2020-02-20 | Corcept Therapeutics Inc | Moduladores del receptor de glucocorticoides de azadecalina condensada con octahidro |
| AU2016226451B2 (en) * | 2015-03-02 | 2019-12-19 | Corcept Therapeutics, Inc. | Use of glucocorticoid receptor antagonist and somatostatin analogues to treat ACTH-secreting tumors |
| ES2906778T3 (es) | 2015-03-30 | 2022-04-20 | Corcept Therapeutics Inc | Uso de antagonistas del receptor de glucocorticoides en combinación con glucocorticoides para tratar la insuficiencia suprarrenal |
| IL309712A (en) | 2015-05-18 | 2024-02-01 | Corcept Therapeutics Inc | Methods for diagnosing and determining treatment for Cushing's syndrome |
| AU2016305092B2 (en) * | 2015-08-13 | 2022-01-27 | Corcept Therapeutics, Inc. | Method for differentially diagnosing ACTH-dependent Cushing's syndrome |
| SG11201807421TA (en) | 2016-03-01 | 2018-09-27 | Corcept Therapeutics Inc | The use of glucocorticoid receptor modulators to potentiate checkpoint inhibitors |
| US9943505B2 (en) * | 2016-09-09 | 2018-04-17 | Corcept Therapeutics, Inc. | Glucocorticoid receptor modulators to treat pancreatic cancer |
| SG11201908790PA (en) | 2017-03-31 | 2019-10-30 | Corcept Therapeutics Inc | Glucocorticoid receptor modulators to treat cervical cancer |
| EP3641780B1 (en) * | 2017-06-20 | 2025-09-10 | Corcept Therapeutics Incorporated | Treatment of neuroepithelial tumors using selective glucocorticoid receptor modulators |
| IL278125B (en) * | 2018-04-23 | 2022-09-01 | Corcept Therapeutics Inc | Methods for the preparation of regioselective n-alkyl triazoles |
| AU2019377864B2 (en) | 2018-11-09 | 2023-03-16 | Corcept Therapeutics Incorporated | Methods for shrinking pituitary tumors |
| CN117281790A (zh) | 2018-12-19 | 2023-12-26 | 科塞普特治疗公司 | 含有瑞拉可兰、杂芳基-酮稠合的氮杂十氢化萘化合物的药物制剂 |
| WO2020132046A1 (en) | 2018-12-19 | 2020-06-25 | Corcept Therapeutics Incorporated | Methods of treating cancer comprising administration of a glucocorticoid receptor modulator and a cancer chemotherapy agent |
| US11234971B2 (en) | 2018-12-19 | 2022-02-01 | Corcept Therapeutics Incorporated | Methods of treating cancer comprising administration of a glucocorticoid receptor modulator and a cancer chemotherapy agent |
| IL284237B2 (en) * | 2018-12-20 | 2025-02-01 | Corcept Therapeutics Inc | Imaging and treatment of tumors expressing the somatostatin receptor |
| CN113490496A (zh) | 2019-02-22 | 2021-10-08 | 科赛普特治疗学股份有限公司 | 一种杂芳基-酮稠合氮杂萘烷糖皮质激素受体调节剂瑞拉可兰的治疗用途 |
| WO2021076565A1 (en) | 2019-10-16 | 2021-04-22 | Corcept Therapeutics Incorporated | Method of normalizing the neutrophil to lymphocyte ratio in cancer patients with a selective glucocorticoid receptor antagonist |
| KR20220113767A (ko) | 2019-12-11 | 2022-08-16 | 코어셉트 쎄라퓨틱스 인코포레이티드 | 미리코릴란트로 항정신병약-유도 체중 증가를 치료하는 방법 |
| AU2020408057A1 (en) | 2019-12-21 | 2022-06-16 | Corcept Therapeutics Incorporated | Treatment of, and differential diagnosis between, ACTH-Dependent Cushing's syndrome and ACTH-Independent Cushing's syndrome |
| WO2021163058A1 (en) * | 2020-02-10 | 2021-08-19 | Corcept Therapeutics Incorporated | Methods of stimulating an anti-tumor response using a selective glucocorticoid receptor modulator |
| WO2022134033A1 (en) * | 2020-12-25 | 2022-06-30 | Corcept Therapeutics Incorporated | Methods of preparing heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators |
| CN116829556A (zh) * | 2021-02-03 | 2023-09-29 | 江苏恒瑞医药股份有限公司 | 稠合的氮杂三环类衍生物、其制备方法及其在医药上的应用 |
| KR20250073629A (ko) | 2022-10-06 | 2025-05-27 | 코어셉트 쎄라퓨틱스 인코포레이티드 | 글루코코르티코이드 수용체 조절제의 제형 |
| AU2023367284A1 (en) | 2022-10-28 | 2025-05-29 | Corcept Therapeutics Incorporated | Treatments for amyotrophic lateral sclerosis using dazucorilant |
| WO2024173745A1 (en) * | 2023-02-17 | 2024-08-22 | Corcept Therapeutics Incorporated | Methods and compositions for treating huntington's disease and its symptoms |
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| WO2005087769A1 (en) * | 2004-03-09 | 2005-09-22 | Corcept Therapeutics, Inc. | Fused ring azadecalin glucocorticoid receptor modulators |
| WO2012027702A1 (en) * | 2010-08-27 | 2012-03-01 | Corcept Therapeutics, Inc. | Pyridyl-amine fused azadecalin modulators |
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| US4391904A (en) | 1979-12-26 | 1983-07-05 | Syva Company | Test strip kits in immunoassays and compositions therein |
| GB8828669D0 (en) * | 1988-12-08 | 1989-01-11 | Lilly Industries Ltd | Organic compounds |
| US7640389B2 (en) | 2006-02-28 | 2009-12-29 | Freescale Semiconductor, Inc. | Non-volatile memory having a multiple block erase mode and method therefor |
| EP1932843A1 (en) * | 2006-12-14 | 2008-06-18 | sanofi-aventis | Sulfonyl-phenyl-2H-(1,2,4) oxadiazole-5-one derivatives, processes for their preparation and their use as pharmaceuticals |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2005087769A1 (en) * | 2004-03-09 | 2005-09-22 | Corcept Therapeutics, Inc. | Fused ring azadecalin glucocorticoid receptor modulators |
| WO2012027702A1 (en) * | 2010-08-27 | 2012-03-01 | Corcept Therapeutics, Inc. | Pyridyl-amine fused azadecalin modulators |
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