KR20100087147A - 글루코코르티코이드 활성을 갖는 스테로이드성 [3,2-ｃ]피라졸 화합물 - Google Patents
글루코코르티코이드 활성을 갖는 스테로이드성 [3,2-ｃ]피라졸 화합물 Download PDFInfo
- Publication number
- KR20100087147A KR20100087147A KR1020107009780A KR20107009780A KR20100087147A KR 20100087147 A KR20100087147 A KR 20100087147A KR 1020107009780 A KR1020107009780 A KR 1020107009780A KR 20107009780 A KR20107009780 A KR 20107009780A KR 20100087147 A KR20100087147 A KR 20100087147A
- Authority
- KR
- South Korea
- Prior art keywords
- naphtho
- dimethyl
- hydroxy
- tetradecahydrocyclopenta
- indazol
- 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.)
- Withdrawn
Links
- 230000000694 effects Effects 0.000 title description 13
- 239000003862 glucocorticoid Substances 0.000 title description 10
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 230000003637 steroidlike Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 465
- 238000000034 method Methods 0.000 claims abstract description 327
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- -1 cyano, hydroxymethyl Chemical group 0.000 claims description 495
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 453
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 232
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 174
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 170
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 155
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 34
- VFKABQOFAOFUHF-UHFFFAOYSA-N 8H-naphtho[1,2-f]indazol-1-yl furan-2-carboxylate Chemical compound O1C(=CC=C1)C(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC=4C=3)C1=2 VFKABQOFAOFUHF-UHFFFAOYSA-N 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- DMATWGSZZMUSOI-UHFFFAOYSA-N 8h-naphtho[1,2-f]indazol-1-yl cyclopropanecarboxylate Chemical compound C=1C=CC2=CC=C3C=C4NN=CC4=CC3=C2C=1OC(=O)C1CC1 DMATWGSZZMUSOI-UHFFFAOYSA-N 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 21
- 229910052731 fluorine Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 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 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- UNBHZBCTYNSIOO-UHFFFAOYSA-N 8H-naphtho[1,2-f]indazol-1-yl 2-methoxyacetate Chemical compound COCC(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC=4C=3)C1=2 UNBHZBCTYNSIOO-UHFFFAOYSA-N 0.000 claims description 16
- GMOJRIKGRQZTOX-UHFFFAOYSA-N O1C=NC(=C1)C(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC4C3)C12 Chemical compound O1C=NC(=C1)C(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC4C3)C12 GMOJRIKGRQZTOX-UHFFFAOYSA-N 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
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- 208000006673 asthma Diseases 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- LXPGKWOKTBQYHF-UHFFFAOYSA-N C(CC)(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC4C3)C12 Chemical compound C(CC)(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC4C3)C12 LXPGKWOKTBQYHF-UHFFFAOYSA-N 0.000 claims description 11
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
- 125000005518 carboxamido group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims description 7
- CQVGIPQCLGQRBX-GOSISDBHSA-N 8H-naphtho[1,2-f]indazol-1-yl (2R)-oxolane-2-carboxylate Chemical compound O1[C@H](CCC1)C(=O)OC1=CC=CC=2C=CC=3C(=CC=4C=NNC=4C=3)C1=2 CQVGIPQCLGQRBX-GOSISDBHSA-N 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl 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
- 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 6
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 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 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- IEUYPFMAPQGANZ-UHFFFAOYSA-N indazol-1-yl propanoate Chemical compound C1=CC=C2N(OC(=O)CC)N=CC2=C1 IEUYPFMAPQGANZ-UHFFFAOYSA-N 0.000 claims description 4
- SBSLXCNVDNBFRN-YWTPUBSGSA-N (1r,10ar,11s,12as)-7-(3-ethenylphenyl)-1-{[(fluoromethyl)thio]carbonyl}-11-hydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,5,7,10,10a,10b,11,12,12a-tetradecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-yl furan-2-carboxylate Chemical compound C([C@@H](O)C[C@]1(C2CC[C@]1(OC(=O)C=1OC=CC=1)C(=O)SCF)C)([C@]1(C3)C)C2CCC1=CC1=C3C=NN1C1=CC=CC(C=C)=C1 SBSLXCNVDNBFRN-YWTPUBSGSA-N 0.000 claims description 3
- AOXIDDMEWXUHCM-SGSTZZQFSA-N (1r,3as,3bs,10ar,10bs,11s,12as)-7-(4-fluorophenyl)-11-hydroxy-1-(hydroxyacetyl)-10a,12a-dimethyl-1,2,3,3a,3b,4,5,7,10,10a,10b,11,12,12a-tetradecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-yl acetate Chemical compound C([C@H]1[C@@H]2CC[C@]([C@]2(C[C@H](O)[C@@H]1[C@@]1(C)C2)C)(OC(=O)C)C(=O)CO)CC1=CC1=C2C=NN1C1=CC=C(F)C=C1 AOXIDDMEWXUHCM-SGSTZZQFSA-N 0.000 claims description 3
- GKRRYJYPTGJUQO-VTIVGAPMSA-N (1r,3as,3bs,10ar,10bs,11s,12as)-7-{4-fluoro-3-[(prop-2-en-1-yloxy)methyl]phenyl}-11-hydroxy-10a,12a-dimethyl-1-(methylcarbamoyl)-1,2,3,3a,3b,4,5,7,10,10a,10b,11,12,12a-tetradecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-yl furan-2-carboxylate Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(C[C@H](O)[C@@H]1[C@@]1(C)C2)C)(C(=O)NC)OC(=O)C=3OC=CC=3)CC1=CC1=C2C=NN1C1=CC=C(F)C(COCC=C)=C1 GKRRYJYPTGJUQO-VTIVGAPMSA-N 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- BNYIQEFWGSXIKQ-UHFFFAOYSA-M 3-methylfuran-2-carboxylate Chemical compound CC=1C=COC=1C([O-])=O BNYIQEFWGSXIKQ-UHFFFAOYSA-M 0.000 claims description 3
- WMBHDSXWUULFCH-UHFFFAOYSA-N C=1(C=CC=C2C=CC=3C(=CC=4C=NNC4C3)C12)C(O)=S Chemical compound C=1(C=CC=C2C=CC=3C(=CC=4C=NNC4C3)C12)C(O)=S WMBHDSXWUULFCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- GOYBQMCJAXTSPY-UHFFFAOYSA-N indazol-1-yl cyclopropanecarboxylate Chemical compound N1=CC2=CC=CC=C2N1OC(=O)C1CC1 GOYBQMCJAXTSPY-UHFFFAOYSA-N 0.000 claims description 3
- NOQWKBWKXLLBAZ-UHFFFAOYSA-N indazol-1-yl furan-2-carboxylate Chemical compound O1C(=CC=C1)C(=O)ON1N=CC2=CC=CC=C12 NOQWKBWKXLLBAZ-UHFFFAOYSA-N 0.000 claims description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
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- 229960005419 nitrogen Drugs 0.000 description 10
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- 229960001262 tramazoline Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
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- 229940074410 trehalose Drugs 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 230000005951 type IV hypersensitivity Effects 0.000 description 1
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- 231100000397 ulcer Toxicity 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
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- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 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)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US97741607P | 2007-10-04 | 2007-10-04 | |
| US60/977,416 | 2007-10-04 |
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| KR20100087147A true KR20100087147A (ko) | 2010-08-03 |
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| AR (1) | AR068734A1 (https=) |
| AU (1) | AU2008306593C1 (https=) |
| BR (1) | BRPI0817941A2 (https=) |
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| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190068577A (ko) * | 2016-10-14 | 2019-06-18 | 반 안델 리서치 인스티튜트 | 고효능 글루코코르티코이드의 설계를 위한 구조 및 메커니즘 |
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| 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 |
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| GB933868A (en) | 1958-12-08 | 1963-08-14 | American Cyanamid Co | Process for fluorinating steroids |
| NL100550C (https=) | 1959-02-16 | |||
| US3129218A (en) | 1961-11-01 | 1964-04-14 | Merck & Co Inc | 2-alkoxymethylene steroids of the androstane and pregnane series |
| US3072639A (en) | 1962-03-05 | 1963-01-08 | Merck & Co Inc | 16-oxygenated-4-pregneno-[3, 2-c] pyrazoles and process of preparing them |
| US3364203A (en) | 1965-09-09 | 1968-01-16 | Syntex Corp | 6, 7-methylene and 6, 7-halomethylene pyrazole pregnanes and processes for their preparation |
| US3471477A (en) | 1967-10-18 | 1969-10-07 | Syntex Corp | 6-gem-difluoro (3,2-c) and (2,3-d) pyrazole steroids |
| DE2727367A1 (de) * | 1977-06-14 | 1979-01-04 | Schering Ag | Neue kortikoide |
| DE2735110A1 (de) | 1977-08-04 | 1979-02-15 | Hoechst Ag | Corticoid-17-alkylcarbonate und verfahren zu ihrer herstellung |
| DE2817988A1 (de) | 1978-04-25 | 1979-11-08 | Hoechst Ag | Corticoid 17-alkylcarbonate und verfahren zu deren herstellung |
| 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 |
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| US6291455B1 (en) | 1996-03-05 | 2001-09-18 | Zeneca Limited | 4-anilinoquinazoline derivatives |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
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| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| IL153484A0 (en) | 2000-07-07 | 2003-07-06 | Angiogene Pharm Ltd | Colchinol derivatives as angiogenesis inhibitors |
| CN1255392C (zh) | 2000-07-07 | 2006-05-10 | 安吉奥金尼药品有限公司 | 作为血管生成抑制剂的秋水仙醇衍生物 |
| GB0110411D0 (en) | 2001-04-27 | 2001-06-20 | Astrazeneca Ab | Chemical process |
| PT1383786E (pt) * | 2001-04-30 | 2008-12-30 | Glaxo Group Ltd | Derivados anti-inflamatórios de éster 17.beta-carbotioato de androstano com um grupo éster ciclíco na posição 17.alfa |
| 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 |
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- 2008-10-02 AU AU2008306593A patent/AU2008306593C1/en not_active Ceased
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- 2008-10-02 KR KR1020107009780A patent/KR20100087147A/ko not_active Withdrawn
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- 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
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- 2008-10-03 UY UY31375A patent/UY31375A1/es not_active Application Discontinuation
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2012
- 2012-03-12 US US13/417,626 patent/US20120178726A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190068577A (ko) * | 2016-10-14 | 2019-06-18 | 반 안델 리서치 인스티튜트 | 고효능 글루코코르티코이드의 설계를 위한 구조 및 메커니즘 |
Also Published As
| Publication number | Publication date |
|---|---|
| PE20090776A1 (es) | 2009-07-23 |
| AU2008306593B2 (en) | 2012-04-12 |
| CR11345A (es) | 2010-07-15 |
| EP2207788A1 (en) | 2010-07-21 |
| EA201000436A1 (ru) | 2010-10-29 |
| US8163724B2 (en) | 2012-04-24 |
| US20090286835A1 (en) | 2009-11-19 |
| WO2009044200A1 (en) | 2009-04-09 |
| NI201000043A (es) | 2012-09-10 |
| US20120178726A1 (en) | 2012-07-12 |
| AU2008306593A1 (en) | 2009-04-09 |
| BRPI0817941A2 (pt) | 2015-05-05 |
| CO6270214A2 (es) | 2011-04-20 |
| AR068734A1 (es) | 2009-12-02 |
| UY31375A1 (es) | 2009-05-29 |
| MX2010003698A (es) | 2010-04-21 |
| JP2010540612A (ja) | 2010-12-24 |
| CA2700181A1 (en) | 2009-04-09 |
| TW200918047A (en) | 2009-05-01 |
| CL2008002954A1 (es) | 2010-01-15 |
| AU2008306593C1 (en) | 2012-10-04 |
| IL204611A0 (en) | 2010-11-30 |
| DOP2010000094A (es) | 2012-08-15 |
| ZA201002223B (en) | 2010-12-29 |
| CN101883778A (zh) | 2010-11-10 |
| NZ584160A (en) | 2011-05-27 |
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