CA2461363A1 - Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors - Google Patents
Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors Download PDFInfo
- Publication number
- CA2461363A1 CA2461363A1 CA002461363A CA2461363A CA2461363A1 CA 2461363 A1 CA2461363 A1 CA 2461363A1 CA 002461363 A CA002461363 A CA 002461363A CA 2461363 A CA2461363 A CA 2461363A CA 2461363 A1 CA2461363 A1 CA 2461363A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridyl
- indole
- alkyl
- bromo
- methyl
- 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.)
- Abandoned
Links
- 150000002473 indoazoles Chemical class 0.000 title abstract description 12
- KDWAJWXWMMNKHA-UHFFFAOYSA-N 2-pyridin-3-yl-1h-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CN=C1 KDWAJWXWMMNKHA-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000002697 lyase inhibitor Substances 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 89
- 102000004317 Lyases Human genes 0.000 claims abstract description 41
- 108090000856 Lyases Proteins 0.000 claims abstract description 41
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 26
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 26
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 20
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 19
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 127
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 241000282465 Canis Species 0.000 claims description 4
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- 241000282324 Felis Species 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 35
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 5
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 20
- 102000004190 Enzymes Human genes 0.000 abstract description 17
- 108090000790 Enzymes Proteins 0.000 abstract description 17
- 239000003112 inhibitor Substances 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
- 235000019439 ethyl acetate Nutrition 0.000 description 82
- 238000005160 1H NMR spectroscopy Methods 0.000 description 58
- 239000000203 mixture Substances 0.000 description 56
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 53
- 125000000217 alkyl group Chemical group 0.000 description 51
- -1 cortisol) Chemical compound 0.000 description 49
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 41
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- CSDIPVWFZZEUMT-UHFFFAOYSA-N 5-bromo-1-pyridin-3-ylindole Chemical compound C1=CC2=CC(Br)=CC=C2N1C1=CC=CN=C1 CSDIPVWFZZEUMT-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 29
- 201000010099 disease Diseases 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
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- 101150041968 CDC13 gene Proteins 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 22
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- 239000000243 solution Substances 0.000 description 21
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- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 20
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
- 239000000499 gel Substances 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 19
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 18
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- WPGZNPGXADYGMZ-UHFFFAOYSA-N 5-bromo-1-(4-methylpyridin-3-yl)indole Chemical compound CC1=CC=NC=C1N1C2=CC=C(Br)C=C2C=C1 WPGZNPGXADYGMZ-UHFFFAOYSA-N 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
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- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 description 16
- 239000000262 estrogen Substances 0.000 description 16
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- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
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- 125000003545 alkoxy group Chemical group 0.000 description 14
- 229940030486 androgens Drugs 0.000 description 14
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- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
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- 125000001424 substituent group Chemical group 0.000 description 10
- KOUOYJYRICGOSC-UHFFFAOYSA-N 5-pyridin-3-yl-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1C1=CC=CN=C1 KOUOYJYRICGOSC-UHFFFAOYSA-N 0.000 description 9
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 9
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- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ASXFMIDIRZPCGK-UHFFFAOYSA-N (4-methylpyridin-3-yl)boronic acid Chemical compound CC1=CC=NC=C1B(O)O ASXFMIDIRZPCGK-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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Classifications
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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
- C07D401/14—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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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
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Engineering & Computer Science (AREA)
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- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32499301P | 2001-09-26 | 2001-09-26 | |
| US60/324,993 | 2001-09-26 | ||
| PCT/US2002/030482 WO2003027094A2 (en) | 2001-09-26 | 2002-09-26 | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461363A1 true CA2461363A1 (en) | 2003-04-03 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461363A Abandoned CA2461363A1 (en) | 2001-09-26 | 2002-09-26 | Substituted 3-pyridyl indoles and indazoles as c17,20 lyase inhibitors |
| CA002461360A Abandoned CA2461360A1 (en) | 2001-09-26 | 2002-09-26 | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461360A Abandoned CA2461360A1 (en) | 2001-09-26 | 2002-09-26 | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors |
Country Status (5)
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|---|---|
| EP (2) | EP1432698A2 (enExample) |
| JP (2) | JP2005528325A (enExample) |
| AU (2) | AU2002362603A1 (enExample) |
| CA (2) | CA2461363A1 (enExample) |
| WO (8) | WO2003027105A1 (enExample) |
Families Citing this family (77)
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| ATE440096T1 (de) * | 2000-12-08 | 2009-09-15 | Takeda Pharmaceutical | Substituierte thiazolderivate mit 3- pyridylgruppen, verfahren zu deren herstellung und deren verwendung |
| JP4160295B2 (ja) * | 2000-12-08 | 2008-10-01 | 武田薬品工業株式会社 | 3−ピリジル基を有する置換チアゾール誘導体、その製造法および用途 |
| US20040147561A1 (en) * | 2002-12-27 | 2004-07-29 | Wenge Zhong | Pyrid-2-one derivatives and methods of use |
| US7244739B2 (en) * | 2003-05-14 | 2007-07-17 | Torreypines Therapeutics, Inc. | Compounds and uses thereof in modulating amyloid beta |
| ES2222827B1 (es) * | 2003-07-30 | 2006-03-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 5-indolilsulfonamidas, su preparacion y su aplicacion como medicamentos. |
| DE602004022319D1 (de) * | 2003-11-14 | 2009-09-10 | Vertex Pharma | Thiazole udn oxazole als modulatoren von atp-bindungs-kassetten-transportern |
| JP2007532669A (ja) * | 2004-04-13 | 2007-11-15 | イカジェン インコーポレイテッド | カリウムイオンチャネル調節剤としての多環式ピリミジン |
| JP4602686B2 (ja) * | 2004-04-15 | 2010-12-22 | 広栄化学工業株式会社 | 2,6−ジハロゲノ−4−アリールピリジン類の製造法 |
| EP2939674A1 (en) * | 2004-10-13 | 2015-11-04 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| PT1802579E (pt) * | 2004-10-20 | 2014-02-17 | Merck Serono Sa | Derivados da 3-arilaminopiridina |
| WO2006051723A1 (ja) * | 2004-11-09 | 2006-05-18 | Kaneka Corporation | 1-ハロ-3-アリール-2-プロパノン類の製造法 |
| GB0428514D0 (en) * | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| ZA200705827B (en) * | 2005-01-19 | 2008-10-29 | Biolipox Ab | Indoles useful in the treatment of inflammation |
| BRPI0608910A2 (pt) | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| AU2006278998A1 (en) * | 2005-07-29 | 2007-02-15 | 4Sc Ag | Novel heterocyclic NF-kB inhibitors |
| FR2889526B1 (fr) | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| KR20080066938A (ko) * | 2005-10-07 | 2008-07-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 복소환 화합물 및 그것을 함유하는 의약 조성물 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| AR056893A1 (es) * | 2005-12-28 | 2007-10-31 | Takeda Pharmaceutical | Compuestos heterociclicos fusionados y no fusionados, antagonistas de receptores mineralocorticoides |
| KR101081293B1 (ko) * | 2006-01-18 | 2011-11-08 | 에프. 호프만-라 로슈 아게 | 11 베타-에이치에스디1 억제제로서 티아졸 |
| CN101374808B (zh) | 2006-01-24 | 2011-05-25 | 伊莱利利公司 | 孕酮受体的吲哚磺酰胺调节剂 |
| PL2001849T3 (pl) * | 2006-03-29 | 2015-04-30 | Hoffmann La Roche | Pochodne pirydyny i pirymidyny jako antagoniści mGluR2 |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| US7652018B2 (en) | 2006-08-15 | 2010-01-26 | Wyeth Llc | Imidazolidin-2-one derivatives useful as PR modulators |
| US7538107B2 (en) | 2006-08-15 | 2009-05-26 | Wyeth | Oxazinan-2-one derivatives useful as PR modulators |
| US7618989B2 (en) | 2006-08-15 | 2009-11-17 | Wyeth | Tricyclic oxazolidone derivatives useful as PR modulators |
| JP5284788B2 (ja) * | 2006-09-21 | 2013-09-11 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロアリール環置換ピリジン誘導体およびそれらを含有する抗真菌剤 |
| EP2065377B1 (en) | 2006-09-21 | 2011-11-23 | Eisai R&D Management Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| EP2076265A4 (en) | 2006-10-02 | 2010-09-22 | Cortendo Invest Ab | KETOCONAZOLE ENANTIOMER IN HUMANS |
| WO2008070350A2 (en) | 2006-10-27 | 2008-06-12 | The Board Of Regents Of The University Of Texas System | Methods and compositions related to wrapping of dehydrons |
| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| BRPI0811939A2 (pt) | 2007-05-22 | 2014-11-25 | Achillion Pharmaceuticals Inc | Tiazóis substituídos por heteroarila |
| ES2542849T3 (es) | 2007-08-13 | 2015-08-12 | Monsanto Technology Llc | Composiciones y procedimientos de control de nematodos |
| AU2008310097B2 (en) | 2007-10-09 | 2013-05-16 | Merck Patent Gmbh | Pyridine derivatives useful as glucokinase activators |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
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-
2002
- 2002-09-26 WO PCT/US2002/030981 patent/WO2003027105A1/en not_active Ceased
- 2002-09-26 JP JP2003530682A patent/JP2005528325A/ja not_active Withdrawn
- 2002-09-26 JP JP2003530675A patent/JP2005532983A/ja not_active Withdrawn
- 2002-09-26 CA CA002461363A patent/CA2461363A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030982 patent/WO2003027095A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030983 patent/WO2003027096A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030483 patent/WO2003027085A2/en not_active Ceased
- 2002-09-26 AU AU2002362603A patent/AU2002362603A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030482 patent/WO2003027094A2/en not_active Ceased
- 2002-09-26 AU AU2002340010A patent/AU2002340010A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030979 patent/WO2003027101A1/en not_active Ceased
- 2002-09-26 CA CA002461360A patent/CA2461360A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030924 patent/WO2003027100A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030834 patent/WO2003027107A1/en not_active Ceased
- 2002-09-26 EP EP02778338A patent/EP1432698A2/en not_active Withdrawn
- 2002-09-26 EP EP02799636A patent/EP1432706A2/en not_active Withdrawn
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| WO2003027094A3 (en) | 2003-10-23 |
| AU2002340010A1 (en) | 2003-04-07 |
| WO2003027105A1 (en) | 2003-04-03 |
| EP1432706A2 (en) | 2004-06-30 |
| WO2003027096A1 (en) | 2003-04-03 |
| WO2003027085A3 (en) | 2003-12-04 |
| WO2003027107A1 (en) | 2003-04-03 |
| WO2003027085A2 (en) | 2003-04-03 |
| JP2005528325A (ja) | 2005-09-22 |
| JP2005532983A (ja) | 2005-11-04 |
| AU2002362603A1 (en) | 2003-04-07 |
| WO2003027094A2 (en) | 2003-04-03 |
| EP1432698A2 (en) | 2004-06-30 |
| WO2003027101A1 (en) | 2003-04-03 |
| CA2461360A1 (en) | 2003-04-03 |
| WO2003027100A1 (en) | 2003-04-03 |
| WO2003027095A1 (en) | 2003-04-03 |
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