JP2010540612A - グルココルチコイド活性を有するステロイド［３，２−ｃ］ピラゾール化合物 - Google Patents
グルココルチコイド活性を有するステロイド［３，２−ｃ］ピラゾール化合物 Download PDFInfo
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- JP2010540612A JP2010540612A JP2010527546A JP2010527546A JP2010540612A JP 2010540612 A JP2010540612 A JP 2010540612A JP 2010527546 A JP2010527546 A JP 2010527546A JP 2010527546 A JP2010527546 A JP 2010527546A JP 2010540612 A JP2010540612 A JP 2010540612A
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- JP
- Japan
- Prior art keywords
- hydroxy
- naphtho
- dimethyl
- tetradecahydrocyclopenta
- carbonyl
- 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.)
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- 150000003431 steroids Chemical class 0.000 title description 11
- 230000000694 effects Effects 0.000 title description 10
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- 150000001875 compounds Chemical class 0.000 claims abstract description 373
- 238000000034 method Methods 0.000 claims abstract description 257
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 8
- -1 cyano, hydroxymethyl Chemical group 0.000 claims description 432
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 379
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 256
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 179
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 162
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 144
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 133
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 117
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 86
- 235000019260 propionic acid Nutrition 0.000 claims description 82
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 78
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 26
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 208000006673 asthma Diseases 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
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- 229910052731 fluorine Chemical group 0.000 claims description 20
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 19
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- UJJLJRQIPMGXEZ-SCSAIBSYSA-N tetrahydrofuran-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCO1 UJJLJRQIPMGXEZ-SCSAIBSYSA-N 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000002837 carbocyclic group Chemical group 0.000 claims description 13
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 12
- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 claims description 12
- IUIMIEZFBMVFBM-UHFFFAOYSA-N 8H-naphtho[1,2-f]indazole-1-carboxylic acid Chemical compound C1=C2NN=CC2=CC2=C3C(C(=O)O)=CC=CC3=CC=C21 IUIMIEZFBMVFBM-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 10
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims description 9
- SBUXBHALPHVDFT-UHFFFAOYSA-N 1-methyltriazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)N=N1 SBUXBHALPHVDFT-UHFFFAOYSA-N 0.000 claims description 9
- CFGQZVOVFIZRMN-UHFFFAOYSA-N 2-methylfuran-3-carboxylic acid Chemical compound CC=1OC=CC=1C(O)=O CFGQZVOVFIZRMN-UHFFFAOYSA-N 0.000 claims description 9
- BNYIQEFWGSXIKQ-UHFFFAOYSA-N 3-methylfuran-2-carboxylic acid Chemical compound CC=1C=COC=1C(O)=O BNYIQEFWGSXIKQ-UHFFFAOYSA-N 0.000 claims description 9
- ZGWGSEUMABQEMD-UHFFFAOYSA-N 4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=CSC=1C(O)=O ZGWGSEUMABQEMD-UHFFFAOYSA-N 0.000 claims description 9
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 claims description 7
- BOTREHHXSQGWTR-UHFFFAOYSA-N oxolane-3-carboxylic acid Chemical compound OC(=O)C1CCOC1 BOTREHHXSQGWTR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 6
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 6
- YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-UHFFFAOYSA-N 0.000 claims description 6
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
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- 125000004122 cyclic group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 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 description 5
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
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- WZTRQGJMMHMFGH-UHFFFAOYSA-N 1-methyl-imidazole-4-carboxylic acid Chemical compound CN1C=NC(C(O)=O)=C1 WZTRQGJMMHMFGH-UHFFFAOYSA-N 0.000 claims description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
- 238000013459 approach Methods 0.000 description 10
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229960000443 hydrochloric acid Drugs 0.000 description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
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- 201000010099 disease Diseases 0.000 description 9
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 8
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0047—Nitrogen only at position 2(3)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
- A61P5/44—Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97741607P | 2007-10-04 | 2007-10-04 | |
| PCT/GB2008/050890 WO2009044200A1 (en) | 2007-10-04 | 2008-10-02 | Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity |
Publications (2)
| Publication Number | Publication Date |
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| JP2010540612A true JP2010540612A (ja) | 2010-12-24 |
| JP2010540612A5 JP2010540612A5 (https=) | 2011-11-10 |
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| JP2010527546A Pending JP2010540612A (ja) | 2007-10-04 | 2008-10-02 | グルココルチコイド活性を有するステロイド［３，２−ｃ］ピラゾール化合物 |
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| EP (1) | EP2207788A1 (https=) |
| JP (1) | JP2010540612A (https=) |
| KR (1) | KR20100087147A (https=) |
| CN (1) | CN101883778A (https=) |
| AR (1) | AR068734A1 (https=) |
| AU (1) | AU2008306593C1 (https=) |
| BR (1) | BRPI0817941A2 (https=) |
| CA (1) | CA2700181A1 (https=) |
| CL (1) | CL2008002954A1 (https=) |
| CO (1) | CO6270214A2 (https=) |
| CR (1) | CR11345A (https=) |
| DO (1) | DOP2010000094A (https=) |
| EA (1) | EA201000436A1 (https=) |
| IL (1) | IL204611A0 (https=) |
| MX (1) | MX2010003698A (https=) |
| NI (1) | NI201000043A (https=) |
| NZ (1) | NZ584160A (https=) |
| PE (1) | PE20090776A1 (https=) |
| TW (1) | TW200918047A (https=) |
| UY (1) | UY31375A1 (https=) |
| WO (1) | WO2009044200A1 (https=) |
| ZA (1) | ZA201002223B (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012522766A (ja) * | 2009-04-03 | 2012-09-27 | アストラゼネカ・アクチエボラーグ | グルココルチコイド活性を有するステロイド性［３，２−ｃ］ピラゾール化合物の新規アミド誘導体 |
| JP2012522768A (ja) * | 2009-04-03 | 2012-09-27 | アストラゼネカ・アクチエボラーグ | グルココルチコイド活性を有するステロイド性［３，２−ｃ］ピラゾール化合物の新規誘導体 |
| JP2016531852A (ja) * | 2013-09-25 | 2016-10-13 | ヴァン アンデル リサーチ インスティテュート | 非常に強力なグルココルチコイド |
| JP2019532071A (ja) * | 2016-10-14 | 2019-11-07 | ヴァン アンデル リサーチ インスティテュート | 非常に強力な糖質コルチコイドの構造およびデザインのための機構 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA201000436A1 (ru) | 2007-10-04 | 2010-10-29 | Астразенека Аб | Стероидные [3,2-с]пиразольные соединения, обладающие глюкокортикоидной активностью |
| JP2011507836A (ja) * | 2007-12-20 | 2011-03-10 | アストラゼネカ・アクチエボラーグ | グルココルチコステロイド受容体アゴニストとして作用するステロイド誘導体 |
| UY32523A (es) * | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticosteroides |
| UY32521A (es) * | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Combinación para emplear en el tratamiento de enfermedades respiratorias |
| CN102834406A (zh) * | 2009-06-16 | 2012-12-19 | 默沙东公司 | 作为糖皮质激素受体激动剂的新的[3.2-c]杂芳基甾体、其组合物和用途 |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| CA2802294C (en) | 2010-06-11 | 2016-05-10 | Rhodes Technologies | Process for n-dealkylation of tertiary amines |
| GB201016912D0 (en) * | 2010-10-07 | 2010-11-24 | Astrazeneca Ab | Novel combination |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| US8829024B2 (en) * | 2011-01-07 | 2014-09-09 | Corcept Therapeutics, Inc. | Combination steroid and glucocorticoid receptor antagonist therapy |
| CN103502221B (zh) | 2011-03-18 | 2016-03-30 | 拜耳知识产权有限责任公司 | N-(3-氨甲酰基苯基)-1h-吡唑-5-甲酰胺衍生物及其用于防治动物害虫的用途 |
| US9526729B2 (en) * | 2013-01-29 | 2016-12-27 | Hsiao Lily Yu | Medicament for treating peripheral neuropathies |
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| JP2004528354A (ja) * | 2001-04-30 | 2004-09-16 | グラクソ グループ リミテッド | 抗炎症性の、１７α位に環状エステル基を有するアンドロスタンの１７β−カルボチオ酸エステル誘導体 |
| WO2006108572A2 (en) * | 2005-04-08 | 2006-10-19 | Glaxo Group Limited | Novel crystalline pharmaceutical product |
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| US3471477A (en) | 1967-10-18 | 1969-10-07 | Syntex Corp | 6-gem-difluoro (3,2-c) and (2,3-d) pyrazole steroids |
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| JPS6067495A (ja) | 1983-09-22 | 1985-04-17 | Ota Seiyaku Kk | ピラゾール誘導体 |
| SE8306370D0 (sv) | 1983-11-18 | 1983-11-18 | Draco Ab | Novel androstane-17beta-carboxylic acid esters, a process and intermediates for their preparation, compositions and method for the treatment of inflammatory conditions |
| WO1994025478A1 (en) | 1993-04-29 | 1994-11-10 | Instytut Farmaceutyczny | 16α,17α-ACETAL GLUCOCORTICOSTEROIDAL DERIVATIVES |
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| DE69720965T2 (de) | 1996-02-13 | 2004-02-05 | Astrazeneca Ab | Chinazolinderivate und deren verwendung als vegf hemmer |
| NZ331191A (en) | 1996-03-05 | 2000-03-27 | Zeneca Ltd | 4-anilinoquinazoline derivatives and pharmaceutical compositions thereof |
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- 2008-10-02 JP JP2010527546A patent/JP2010540612A/ja active Pending
- 2008-10-02 KR KR1020107009780A patent/KR20100087147A/ko not_active Withdrawn
- 2008-10-02 CN CN2008801190932A patent/CN101883778A/zh active Pending
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- 2008-10-03 PE PE2008001725A patent/PE20090776A1/es not_active Application Discontinuation
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- 2008-10-03 US US12/245,275 patent/US8163724B2/en not_active Expired - Fee Related
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012522766A (ja) * | 2009-04-03 | 2012-09-27 | アストラゼネカ・アクチエボラーグ | グルココルチコイド活性を有するステロイド性［３，２−ｃ］ピラゾール化合物の新規アミド誘導体 |
| JP2012522768A (ja) * | 2009-04-03 | 2012-09-27 | アストラゼネカ・アクチエボラーグ | グルココルチコイド活性を有するステロイド性［３，２−ｃ］ピラゾール化合物の新規誘導体 |
| JP2016531852A (ja) * | 2013-09-25 | 2016-10-13 | ヴァン アンデル リサーチ インスティテュート | 非常に強力なグルココルチコイド |
| JP2019532071A (ja) * | 2016-10-14 | 2019-11-07 | ヴァン アンデル リサーチ インスティテュート | 非常に強力な糖質コルチコイドの構造およびデザインのための機構 |
| JP7146750B2 (ja) | 2016-10-14 | 2022-10-04 | ヴァン アンデル リサーチ インスティテュート | 非常に強力な糖質コルチコイドの構造およびデザインのための機構 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8163724B2 (en) | 2012-04-24 |
| MX2010003698A (es) | 2010-04-21 |
| CO6270214A2 (es) | 2011-04-20 |
| PE20090776A1 (es) | 2009-07-23 |
| EP2207788A1 (en) | 2010-07-21 |
| EA201000436A1 (ru) | 2010-10-29 |
| AU2008306593A1 (en) | 2009-04-09 |
| BRPI0817941A2 (pt) | 2015-05-05 |
| NI201000043A (es) | 2012-09-10 |
| UY31375A1 (es) | 2009-05-29 |
| CL2008002954A1 (es) | 2010-01-15 |
| AR068734A1 (es) | 2009-12-02 |
| KR20100087147A (ko) | 2010-08-03 |
| US20090286835A1 (en) | 2009-11-19 |
| IL204611A0 (en) | 2010-11-30 |
| CN101883778A (zh) | 2010-11-10 |
| AU2008306593B2 (en) | 2012-04-12 |
| CR11345A (es) | 2010-07-15 |
| NZ584160A (en) | 2011-05-27 |
| DOP2010000094A (es) | 2012-08-15 |
| TW200918047A (en) | 2009-05-01 |
| ZA201002223B (en) | 2010-12-29 |
| WO2009044200A1 (en) | 2009-04-09 |
| US20120178726A1 (en) | 2012-07-12 |
| CA2700181A1 (en) | 2009-04-09 |
| AU2008306593C1 (en) | 2012-10-04 |
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