JP2010540612A5 - - Google Patents
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- Publication number
- JP2010540612A5 JP2010540612A5 JP2010527546A JP2010527546A JP2010540612A5 JP 2010540612 A5 JP2010540612 A5 JP 2010540612A5 JP 2010527546 A JP2010527546 A JP 2010527546A JP 2010527546 A JP2010527546 A JP 2010527546A JP 2010540612 A5 JP2010540612 A5 JP 2010540612A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- naphtho
- dimethyl
- carbonyl
- tetradecahydrocyclopenta
- 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.)
- Pending
Links
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 137
- -1 cyano, hydroxymethyl Chemical group 0.000 claims 114
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 82
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 73
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 56
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 38
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 31
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 30
- 235000019260 propionic acid Nutrition 0.000 claims 29
- 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 28
- 150000001875 compounds Chemical class 0.000 claims 21
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 21
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims 17
- 229960000583 acetic acid Drugs 0.000 claims 14
- JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- UJJLJRQIPMGXEZ-SCSAIBSYSA-N tetrahydrofuran-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCO1 UJJLJRQIPMGXEZ-SCSAIBSYSA-N 0.000 claims 5
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 4
- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 claims 3
- ILAOVOOZLVGAJF-UHFFFAOYSA-N 1-methylpyrrole-2-carboxylic acid Chemical compound CN1C=CC=C1C(O)=O ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 claims 3
- SBUXBHALPHVDFT-UHFFFAOYSA-N 1-methyltriazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)N=N1 SBUXBHALPHVDFT-UHFFFAOYSA-N 0.000 claims 3
- CFGQZVOVFIZRMN-UHFFFAOYSA-N 2-methylfuran-3-carboxylic acid Chemical compound CC=1OC=CC=1C(O)=O CFGQZVOVFIZRMN-UHFFFAOYSA-N 0.000 claims 3
- BNYIQEFWGSXIKQ-UHFFFAOYSA-N 3-methylfuran-2-carboxylic acid Chemical compound CC=1C=COC=1C(O)=O BNYIQEFWGSXIKQ-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 3
- 229910052731 fluorine Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 2
- YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- BOTREHHXSQGWTR-UHFFFAOYSA-N oxolane-3-carboxylic acid Chemical compound OC(=O)C1CCOC1 BOTREHHXSQGWTR-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- KSJJMSKNZVXAND-UHFFFAOYSA-N 1-cyanocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C#N)CC1 KSJJMSKNZVXAND-UHFFFAOYSA-N 0.000 claims 1
- HPOWDCXQUZLJRQ-UHFFFAOYSA-N 1-methoxycyclopropane-1-carboxylic acid Chemical compound COC1(C(O)=O)CC1 HPOWDCXQUZLJRQ-UHFFFAOYSA-N 0.000 claims 1
- WLDPWZQYAVZTTP-UHFFFAOYSA-N 1-methyl-imidazole-2-carboxylic acid Chemical compound CN1C=CN=C1C(O)=O WLDPWZQYAVZTTP-UHFFFAOYSA-N 0.000 claims 1
- WZTRQGJMMHMFGH-UHFFFAOYSA-N 1-methyl-imidazole-4-carboxylic acid Chemical compound CN1C=NC(C(O)=O)=C1 WZTRQGJMMHMFGH-UHFFFAOYSA-N 0.000 claims 1
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- WMQAQMYIZDJCDJ-UHFFFAOYSA-N 2-methyloxolane-2-carboxylic acid Chemical compound OC(=O)C1(C)CCCO1 WMQAQMYIZDJCDJ-UHFFFAOYSA-N 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 1
- BNMPIJWVMVNSRD-UHFFFAOYSA-N 5-methyl-1,2-oxazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NO1 BNMPIJWVMVNSRD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- MQAYFGXOFCEZRW-UHFFFAOYSA-N oxane-2-carboxylic acid Chemical compound OC(=O)C1CCCCO1 MQAYFGXOFCEZRW-UHFFFAOYSA-N 0.000 claims 1
- YEWPVCUHKJABMV-UHFFFAOYSA-N oxane-3-carboxylic acid Chemical compound OC(=O)C1CCCOC1 YEWPVCUHKJABMV-UHFFFAOYSA-N 0.000 claims 1
- AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- 238000006467 substitution reaction Methods 0.000 claims 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 1
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 |
|---|---|
| JP2010540612A JP2010540612A (ja) | 2010-12-24 |
| JP2010540612A5 true JP2010540612A5 (https=) | 2011-11-10 |
Family
ID=40328402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US8163724B2 (https=) |
| 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=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ584160A (en) | 2007-10-04 | 2011-05-27 | Astrazeneca Ab | Steroidal [3,2-c] pyrazole compounds, with glucocorticoid activity |
| CN101945885A (zh) * | 2007-12-20 | 2011-01-12 | 阿斯利康(瑞典)有限公司 | 用作糖皮质激素受体激动剂的甾类衍生物 |
| UY32520A (es) | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticoesteroides |
| UY32525A (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 |
| UY32523A (es) * | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticosteroides |
| JP2012530140A (ja) | 2009-06-16 | 2012-11-29 | メルク・シャープ・アンド・ドーム・コーポレーション | グルココルチコイド受容体アゴニストとしての新規[3,2−c]ヘテロアリールステロイド、組成物およびこの使用 |
| 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 |
| AU2011263416B2 (en) | 2010-06-11 | 2014-04-10 | 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 |
| KR101834362B1 (ko) | 2011-03-18 | 2018-03-05 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | N-(3-카바모일페닐)-1h-피라졸-5-카복사미드 유도체 및 동물 해충을 구제하기 위한 그의 용도 |
| US9526729B2 (en) * | 2013-01-29 | 2016-12-27 | Hsiao Lily Yu | Medicament for treating peripheral neuropathies |
| 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 |
| CN110382033B (zh) * | 2016-10-14 | 2022-04-15 | 范安德尔研究所 | 用于设计高效力糖皮质激素的结构与机制 |
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| ITMI20022606A1 (it) | 2002-12-09 | 2004-06-10 | Farmabios Spa | Processo di sintesi di steroidi polialogenati. |
| WO2005028495A1 (en) | 2003-09-24 | 2005-03-31 | Glaxo Group Limited | Anti-inflammatory glucocorticoids |
| WO2005063777A1 (en) | 2003-12-23 | 2005-07-14 | Corus Pharma | Benzylphosphate and substituted benzylphosphate prodrugs for the treatment of pulmonary inflammation |
| GB0507165D0 (en) * | 2005-04-08 | 2005-05-18 | Glaxo Group Ltd | Novel crystalline pharmaceutical product |
| WO2007054974A2 (en) | 2005-09-28 | 2007-05-18 | Arch Pharmalab Limited | A green chemistry process for the preparation of pregnadiene esters |
| NZ584160A (en) | 2007-10-04 | 2011-05-27 | Astrazeneca Ab | Steroidal [3,2-c] pyrazole compounds, with glucocorticoid activity |
| CN101945885A (zh) | 2007-12-20 | 2011-01-12 | 阿斯利康(瑞典)有限公司 | 用作糖皮质激素受体激动剂的甾类衍生物 |
| BRPI0907789A2 (pt) | 2008-02-27 | 2019-01-22 | Astrazeneca Ab | derivaldos 16-alfa e 17-alfa de glicocorticosteroides e seus usos |
| UY32520A (es) | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticoesteroides |
| 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 |
| UY32525A (es) | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticosteroides |
-
2008
- 2008-10-02 NZ NZ584160A patent/NZ584160A/en not_active IP Right Cessation
- 2008-10-02 AU AU2008306593A patent/AU2008306593C1/en not_active Ceased
- 2008-10-02 JP JP2010527546A patent/JP2010540612A/ja active Pending
- 2008-10-02 CA CA2700181A patent/CA2700181A1/en not_active Abandoned
- 2008-10-02 KR KR1020107009780A patent/KR20100087147A/ko not_active Withdrawn
- 2008-10-02 EP EP08806706A patent/EP2207788A1/en not_active Ceased
- 2008-10-02 WO PCT/GB2008/050890 patent/WO2009044200A1/en not_active Ceased
- 2008-10-02 CN CN2008801190932A patent/CN101883778A/zh active Pending
- 2008-10-02 BR BRPI0817941 patent/BRPI0817941A2/pt not_active IP Right Cessation
- 2008-10-02 MX MX2010003698A patent/MX2010003698A/es active IP Right Grant
- 2008-10-02 EA EA201000436A patent/EA201000436A1/ru unknown
- 2008-10-03 AR ARP080104343A patent/AR068734A1/es not_active Application Discontinuation
- 2008-10-03 PE PE2008001725A patent/PE20090776A1/es not_active Application Discontinuation
- 2008-10-03 UY UY31375A patent/UY31375A1/es not_active Application Discontinuation
- 2008-10-03 TW TW097138109A patent/TW200918047A/zh unknown
- 2008-10-03 CL CL2008002954A patent/CL2008002954A1/es unknown
- 2008-10-03 US US12/245,275 patent/US8163724B2/en not_active Expired - Fee Related
-
2010
- 2010-03-18 IL IL204611A patent/IL204611A0/en unknown
- 2010-03-26 NI NI201000043A patent/NI201000043A/es unknown
- 2010-03-29 ZA ZA2010/02223A patent/ZA201002223B/en unknown
- 2010-03-31 DO DO2010000094A patent/DOP2010000094A/es unknown
- 2010-04-05 CO CO10037849A patent/CO6270214A2/es not_active Application Discontinuation
- 2010-04-05 CR CR11345A patent/CR11345A/es not_active Application Discontinuation
-
2012
- 2012-03-12 US US13/417,626 patent/US20120178726A1/en not_active Abandoned
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