SK287766B6 - Metaloproteinázové inhibítory - Google Patents
Metaloproteinázové inhibítory Download PDFInfo
- Publication number
- SK287766B6 SK287766B6 SK1096-2003A SK10962003A SK287766B6 SK 287766 B6 SK287766 B6 SK 287766B6 SK 10962003 A SK10962003 A SK 10962003A SK 287766 B6 SK287766 B6 SK 287766B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- apci
- nmr
- methyl
- mmol
- Prior art date
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- 239000003475 metalloproteinase inhibitor Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 203
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- -1 phenyl-heteroalkyl Chemical group 0.000 claims description 89
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 28
- 238000001727 in vivo Methods 0.000 claims description 27
- 125000006413 ring segment Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 11
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- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
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- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
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- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000006168 tricyclic group Chemical group 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- SFJFBTPHDHUUPU-OAHLLOKOSA-N (5s)-5-[[4-(5-chloropyridin-2-yl)oxypiperidin-1-yl]sulfonylmethyl]-5-methylimidazolidine-2,4-dione Chemical compound C1CC(OC=2N=CC(Cl)=CC=2)CCN1S(=O)(=O)C[C@@]1(C)NC(=O)NC1=O SFJFBTPHDHUUPU-OAHLLOKOSA-N 0.000 claims description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 24
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Classifications
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| PCT/SE2002/000472 WO2002074767A1 (en) | 2001-03-15 | 2002-03-13 | Metalloproteinase inhibitors |
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| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20130313 |