TW200922570A - Organic compounds - Google Patents

Info

Publication number

TW200922570A

TW200922570A TW097139735A TW97139735A TW200922570A TW 200922570 A TW200922570 A TW 200922570A TW 097139735 A TW097139735 A TW 097139735A TW 97139735 A TW97139735 A TW 97139735A TW 200922570 A TW200922570 A TW 200922570A

Authority

TW

Taiwan

Prior art keywords

group

doc

imidazolium

alkyl

pyridine

Prior art date

2007-10-17

Links

• Espacenet
• Global Dossier
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• 150000002894 organic compounds Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 139
• 238000000034 method Methods 0.000 claims abstract description 63
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 201000010099 disease Diseases 0.000 claims abstract description 29
• 102100034134 Activin receptor type-1B Human genes 0.000 claims abstract description 10
• 230000001404 mediated effect Effects 0.000 claims abstract description 8
• 102100033456 TGF-beta receptor type-1 Human genes 0.000 claims abstract description 7
• 101710173011 Activin receptor type-1B Proteins 0.000 claims abstract description 6
• 101000712674 Homo sapiens TGF-beta receptor type-1 Proteins 0.000 claims abstract description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• -1 c--C7 alkyl Chemical group 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 58
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 49
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 48
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 27
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 230000005764 inhibitory process Effects 0.000 claims description 24
• 239000007789 gas Substances 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 14
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 13
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
• 229910052707 ruthenium Inorganic materials 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 12
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 11
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 11
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000003277 amino group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
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• 210000000988 bone and bone Anatomy 0.000 claims description 8
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 208000017169 kidney disease Diseases 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 208000029578 Muscle disease Diseases 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
• 229910052791 calcium Inorganic materials 0.000 claims description 5
• 239000011575 calcium Substances 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
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• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
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• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 208000020832 chronic kidney disease Diseases 0.000 claims description 4
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052762 osmium Inorganic materials 0.000 claims description 4
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
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• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
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• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
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• 125000004018 acid anhydride group Chemical group 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 230000004221 bone function Effects 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims description 2
• 208000002672 hepatitis B Diseases 0.000 claims description 2
• 210000001117 keloid Anatomy 0.000 claims description 2
• 230000000926 neurological effect Effects 0.000 claims description 2
• 230000009759 skin aging Effects 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• 150000003573 thiols Chemical class 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
• 206010019280 Heart failures Diseases 0.000 claims 1
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• 241000256011 Sphingidae Species 0.000 claims 1
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• 150000003973 alkyl amines Chemical class 0.000 claims 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
• 230000004968 inflammatory condition Effects 0.000 claims 1
• 239000012528 membrane Substances 0.000 claims 1
• 108090000765 processed proteins & peptides Proteins 0.000 claims 1
• 150000003254 radicals Chemical class 0.000 claims 1
• 230000004936 stimulating effect Effects 0.000 claims 1
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
• 150000003462 sulfoxides Chemical class 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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• 239000012453 solvate Chemical group 0.000 abstract description 10
• 230000008569 process Effects 0.000 abstract description 7
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 187
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
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• 239000000543 intermediate Substances 0.000 description 114
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• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 28
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