DE69711845T2

DE69711845T2 - Neue tricyclische verbindungen mit ice/ced-3 protease familie-hemmenden eigenschaften

Neue tricyclische verbindungen mit ice/ced-3 protease familie-hemmenden eigenschaften

Info

Publication number: DE69711845T2
Authority: DE; Germany
Prior art keywords: alkyl; group; formula; compound according; phenyl
Prior art date: 1996-09-12
Legal status : Expired - Fee Related

Application number

DE69711845T

Other languages

German (de)

English (en)

Other versions

DE69711845D1 (de

Inventor

S. Karanewsky

D. Linton

Current Assignee

Idun Pharmaceuticals Inc

Original Assignee

Idun Pharmaceuticals Inc

Priority date

1996-09-12

Filing date

1997-09-12

Publication date

2002-10-31

1997-09-12 Application filed by Idun Pharmaceuticals Inc filed Critical Idun Pharmaceuticals Inc

2002-05-16 Publication of DE69711845D1 publication Critical patent/DE69711845D1/de

2002-10-31 Application granted granted Critical

2002-10-31 Publication of DE69711845T2 publication Critical patent/DE69711845T2/de

2017-09-13 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 131
101150055276 ced-3 gene Proteins 0.000 title abstract description 9
108091005804 Peptidases Proteins 0.000 title description 7
239000004365 Protease Substances 0.000 title description 6
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 60
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
208000037906 ischaemic injury Diseases 0.000 claims abstract description 12
208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 8
230000004770 neurodegeneration Effects 0.000 claims abstract description 8
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
-1 2-(carboxy)eth-1-yl Chemical group 0.000 claims description 151
125000000217 alkyl group Chemical group 0.000 claims description 109
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 98
125000000753 cycloalkyl group Chemical group 0.000 claims description 52
125000001072 heteroaryl group Chemical group 0.000 claims description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
125000003884 phenylalkyl group Chemical group 0.000 claims description 31
238000000034 method Methods 0.000 claims description 28
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
201000010099 disease Diseases 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 12
150000001413 amino acids Chemical class 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 4
229910052805 deuterium Inorganic materials 0.000 claims description 3
125000004970 halomethyl group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
125000003275 alpha amino acid group Chemical group 0.000 claims 1
125000004431 deuterium atom Chemical group 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 11
230000001363 autoimmune Effects 0.000 abstract description 3
230000002757 inflammatory effect Effects 0.000 abstract description 2
230000002265 prevention Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 169
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 86
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 80
229910052757 nitrogen Inorganic materials 0.000 description 41
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
238000003756 stirring Methods 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 35
229910002027 silica gel Inorganic materials 0.000 description 35
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 34
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 27
239000012043 crude product Substances 0.000 description 26
238000001819 mass spectrum Methods 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 25
238000003818 flash chromatography Methods 0.000 description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
125000006239 protecting group Chemical group 0.000 description 24
238000000746 purification Methods 0.000 description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 22
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
229910000343 potassium bisulfate Inorganic materials 0.000 description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
ZCLSQRQRWNDNLV-UHFFFAOYSA-N acetic acid;dichloromethane;methanol Chemical compound OC.ClCCl.CC(O)=O ZCLSQRQRWNDNLV-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
239000000499 gel Substances 0.000 description 14
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
235000002639 sodium chloride Nutrition 0.000 description 13
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical class OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 13
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000003556 assay Methods 0.000 description 10
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
102000000589 Interleukin-1 Human genes 0.000 description 9
108010002352 Interleukin-1 Proteins 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
239000006260 foam Substances 0.000 description 9
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 8
125000003277 amino group Chemical group 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
229960003767 alanine Drugs 0.000 description 7
229940024606 amino acid Drugs 0.000 description 7
235000001014 amino acid Nutrition 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
238000004108 freeze drying Methods 0.000 description 7
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 7
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239000000758 substrate Substances 0.000 description 7
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
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HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 6
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 6
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 6
102000035195 Peptidases Human genes 0.000 description 6
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235000004279 alanine Nutrition 0.000 description 6
229960005261 aspartic acid Drugs 0.000 description 6
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
229940088598 enzyme Drugs 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
230000001404 mediated effect Effects 0.000 description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 6
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125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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CWRATHCADZOYAT-UHFFFAOYSA-N methyl quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OC)=CN=C21 CWRATHCADZOYAT-UHFFFAOYSA-N 0.000 description 3
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
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