HRP20000825A2 - 2-aminopyridines containing fused ring substituents as nitric oxide synthase inhibitors - Google Patents
2-aminopyridines containing fused ring substituents as nitric oxide synthase inhibitors Download PDFInfo
- Publication number
- HRP20000825A2 HRP20000825A2 HR20000825A HRP20000825A HRP20000825A2 HR P20000825 A2 HRP20000825 A2 HR P20000825A2 HR 20000825 A HR20000825 A HR 20000825A HR P20000825 A HRP20000825 A HR P20000825A HR P20000825 A2 HRP20000825 A2 HR P20000825A2
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- Prior art keywords
- alkyl
- ring
- substituents
- phenyl
- disease
- Prior art date
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- 150000003930 2-aminopyridines Chemical class 0.000 title description 2
- 239000000236 nitric oxide synthase inhibitor Substances 0.000 title 1
- CSYSULGPHGCBQD-UHFFFAOYSA-N s-ethylisothiouronium diethylphosphate Chemical compound CCSC(N)=N.CCOP(O)(=O)OCC CSYSULGPHGCBQD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 46
- -1 nitro, hydroxy, cyano, amino Chemical group 0.000 claims description 42
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 25
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 25
- 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 25
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 241000124008 Mammalia Species 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
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- 239000001257 hydrogen Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
- 230000001154 acute effect Effects 0.000 claims description 16
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- 125000001624 naphthyl group Chemical group 0.000 claims description 15
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
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- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
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- MNUHYQZBNHDABI-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexan-6-amine Chemical class C1NCC2C(N)C21 MNUHYQZBNHDABI-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- ULTXUNMYXMQFOT-UHFFFAOYSA-N 6-[6-(2-pyrrolidin-1-ylethoxy)-1,8,9,10,11,12-hexahydrotricyclo[6.2.2.0^{2,7}]dodeca-3,9-dien-3-yl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C=3C4CCC(CC4)C=3C(OCCN3CCCC3)=CC=2)=N1 ULTXUNMYXMQFOT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 63
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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ES2200813T3 (es) * | 1999-02-25 | 2004-03-16 | Pfizer Products Inc. | 2-aminopiridinas que contienen sustituyentes de anillo condesado. |
GB0004151D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
GB0004153D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
GB0004149D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
GB0004152D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
SE0102640D0 (sv) | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
UA105182C2 (ru) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
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TW432073B (en) * | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
HN1996000101A (es) * | 1996-02-28 | 1997-06-26 | Inc Pfizer | Terapia combinada para la osteoporosis |
EP1471055A1 (en) * | 1996-03-29 | 2004-10-27 | Pfizer Inc. | 6-phenylpyridyl-2-amine derivatives |
AU744313B2 (en) * | 1997-02-10 | 2002-02-21 | Pfizer Products Inc. | 2-amino-6-(2-substituted-4-phenoxy)-substituted-pyridines |
HN1998000118A (es) * | 1997-08-27 | 1999-02-09 | Pfizer Prod Inc | 2 - aminopiridinas que contienen sustituyentes de anillos condensados. |
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