CA2700181A1 - Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity - Google Patents
Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity Download PDFInfo
- Publication number
- CA2700181A1 CA2700181A1 CA2700181A CA2700181A CA2700181A1 CA 2700181 A1 CA2700181 A1 CA 2700181A1 CA 2700181 A CA2700181 A CA 2700181A CA 2700181 A CA2700181 A CA 2700181A CA 2700181 A1 CA2700181 A1 CA 2700181A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- dimethyl
- naphtho
- 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.)
- Abandoned
Links
- 230000000694 effects Effects 0.000 title description 13
- 239000003862 glucocorticoid Substances 0.000 title description 9
- 230000003637 steroidlike Effects 0.000 title description 5
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 409
- 238000000034 method Methods 0.000 claims abstract description 267
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 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 423
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 413
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 185
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 153
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 120
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims description 69
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 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 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 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 35
- 150000003839 salts Chemical class 0.000 claims description 32
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 28
- 150000002367 halogens Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 23
- HCAYHTNEDNLVLV-UHFFFAOYSA-N indazol-1-yl 1,3-oxazole-4-carboxylate Chemical compound O1C=NC(=C1)C(=O)ON1N=CC2=CC=CC=C12 HCAYHTNEDNLVLV-UHFFFAOYSA-N 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000004184 methoxymethyl group Chemical group [H]C([H])([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
- GOYBQMCJAXTSPY-UHFFFAOYSA-N indazol-1-yl cyclopropanecarboxylate Chemical compound N1=CC2=CC=CC=C2N1OC(=O)C1CC1 GOYBQMCJAXTSPY-UHFFFAOYSA-N 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- ULURQBQIQKKDEL-UHFFFAOYSA-N indazol-1-yl acetate Chemical compound C1=CC=C2N(OC(=O)C)N=CC2=C1 ULURQBQIQKKDEL-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 8
- 239000002253 acid Substances 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
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 8
- AQOIJXWJIVQFIK-UHFFFAOYSA-N indazol-1-yl 1,3-thiazole-2-carboxylate Chemical compound S1C(=NC=C1)C(=O)ON1N=CC2=CC=CC=C12 AQOIJXWJIVQFIK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 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
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 125000006577 C1-C6 hydroxyalkyl 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
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- CRVRKXJPZKOONL-UHFFFAOYSA-N 6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-1,3,5,7,9,11,13,15,17,19-decaen-17-yl 2-methoxyacetate Chemical compound C=1C2=CN=NC2=CC2=CC=C3C4=CC=C(OC(=O)COC)C4=CC=C3C2=1 CRVRKXJPZKOONL-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 2
- USWNZZLMPPLBCC-DCSWNHFHSA-N (1S,2R,13S,14S,17R,18S,20S)-7-(4-fluorophenyl)-17,20-dihydroxy-N,2,18-trimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-triene-17-carboxamide Chemical compound C([C@H]1[C@@H]2CC[C@]([C@]2(C[C@H](O)[C@@H]1[C@@]1(C)C2)C)(O)C(=O)NC)CC1=CC1=C2C=NN1C1=CC=C(F)C=C1 USWNZZLMPPLBCC-DCSWNHFHSA-N 0.000 claims 1
- 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 1
- CPANRTZZCSPEJT-UUSZPLOPSA-N (1r,3as,10ar,10bs,11s,12as)-7-(3-bromophenyl)-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 C1([C@@H]([C@]2(C3)C)[C@@H](O)C[C@]4([C@H]1CC[C@]4(OC(=O)C=1OC=CC=1)C(=O)SCF)C)CCC2=CC1=C3C=NN1C1=CC=CC(Br)=C1 CPANRTZZCSPEJT-UUSZPLOPSA-N 0.000 claims 1
- 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 1
- 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 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
- BUYJGYLCOOWYDN-GAVKLOIFSA-N C([C@H]1[C@@H]2CC[C@]([C@]2(C[C@H](O)[C@@H]1[C@@]1(C)C2)C)(O)C(=O)OCC)CC1=CC1=C2C=NN1C1=CC=C(F)C=C1 Chemical compound C([C@H]1[C@@H]2CC[C@]([C@]2(C[C@H](O)[C@@H]1[C@@]1(C)C2)C)(O)C(=O)OCC)CC1=CC1=C2C=NN1C1=CC=C(F)C=C1 BUYJGYLCOOWYDN-GAVKLOIFSA-N 0.000 claims 1
- BAMKSEGSQXVVOX-SGSTZZQFSA-N 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)CCl)CC1=CC1=C2C=NN1C1=CC=C(F)C=C1 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)CCl)CC1=CC1=C2C=NN1C1=CC=C(F)C=C1 BAMKSEGSQXVVOX-SGSTZZQFSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 8
- 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 319
- 238000005160 1H NMR spectroscopy Methods 0.000 description 141
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 137
- 101150041968 CDC13 gene Proteins 0.000 description 136
- 239000000203 mixture Substances 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 107
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 99
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 89
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 88
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 76
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- 239000002904 solvent Substances 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000012074 organic phase Substances 0.000 description 38
- 239000003112 inhibitor Substances 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- 239000012267 brine Substances 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000001914 filtration Methods 0.000 description 30
- 238000002953 preparative HPLC Methods 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 description 26
- 238000001704 evaporation Methods 0.000 description 26
- 230000008020 evaporation Effects 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- DIDJZJDDXQPTLN-UHFFFAOYSA-N indazole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)N=CC2=C1 DIDJZJDDXQPTLN-UHFFFAOYSA-N 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
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- 239000003795 chemical substances by application Substances 0.000 description 19
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- 239000011541 reaction mixture Substances 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 15
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000011737 fluorine Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 238000013459 approach Methods 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 10
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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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97741607P | 2007-10-04 | 2007-10-04 | |
| US60/977,416 | 2007-10-04 | ||
| PCT/GB2008/050890 WO2009044200A1 (en) | 2007-10-04 | 2008-10-02 | Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2700181A1 true CA2700181A1 (en) | 2009-04-09 |
Family
ID=40328402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2700181A Abandoned CA2700181A1 (en) | 2007-10-04 | 2008-10-02 | Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US8163724B2 (https=) |
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| 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 |
| 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 |
| 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 |
| 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 |
| EP3525870B1 (en) * | 2016-10-14 | 2023-05-10 | Van Andel Research Institute | Highly potent glucocorticoids |
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| DE2727367A1 (de) * | 1977-06-14 | 1979-01-04 | Schering Ag | Neue kortikoide |
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| KR100831534B1 (ko) * | 2001-04-30 | 2008-05-22 | 글락소 그룹 리미티드 | 17.알파 위치에 시클릭 에스테르기를 지닌 항염증성의안드로스탄의 17.베타.-카르보티오에이트 에스테르 유도체 |
| 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 |
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| 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 |
| WO2009108118A1 (en) | 2008-02-27 | 2009-09-03 | Astrazeneca Ab | 16 alpha, 17 alpa-acetal glucocorticosteroidal derivatives and their use |
| UY32523A (es) | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticosteroides |
| UY32520A (es) | 2009-04-03 | 2010-10-29 | Astrazeneca Ab | Compuestos que tienen actividad agonista del receptor de glucocorticoesteroides |
| 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 KR KR1020107009780A patent/KR20100087147A/ko not_active Withdrawn
- 2008-10-02 CN CN2008801190932A patent/CN101883778A/zh active Pending
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- 2008-10-02 NZ NZ584160A patent/NZ584160A/en not_active IP Right Cessation
- 2008-10-03 PE PE2008001725A patent/PE20090776A1/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
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2010
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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 |
| JP2010540612A (ja) | 2010-12-24 |
| AU2008306593C1 (en) | 2012-10-04 |
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