OA11595A - New pharmaceutical uses for NOS inhibitors. - Google Patents
New pharmaceutical uses for NOS inhibitors. Download PDFInfo
- Publication number
- OA11595A OA11595A OA1200100036A OA1200100036A OA11595A OA 11595 A OA11595 A OA 11595A OA 1200100036 A OA1200100036 A OA 1200100036A OA 1200100036 A OA1200100036 A OA 1200100036A OA 11595 A OA11595 A OA 11595A
- Authority
- OA
- OAPI
- Prior art keywords
- formula
- compound
- pyridin
- ylamine
- phenyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 344
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 18
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- 230000001149 cognitive effect Effects 0.000 claims description 9
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- 108010021487 Nitric Oxide Synthase Proteins 0.000 abstract description 40
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- 238000000034 method Methods 0.000 description 65
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- 125000000217 alkyl group Chemical group 0.000 description 61
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- 125000001424 substituent group Chemical group 0.000 description 56
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- 239000001257 hydrogen Substances 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 34
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 21
- 125000003710 aryl alkyl group Chemical group 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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- 125000001624 naphthyl group Chemical group 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- 125000003282 alkyl amino group Chemical group 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
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- 238000005481 NMR spectroscopy Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
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- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
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- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 9
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- 230000007062 hydrolysis Effects 0.000 description 8
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
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- 230000002829 reductive effect Effects 0.000 description 8
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 7
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 238000005804 alkylation reaction Methods 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
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- 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 description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
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- 229910052760 oxygen Inorganic materials 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- 229910000085 borane Inorganic materials 0.000 description 5
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
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- 201000010099 disease Diseases 0.000 description 4
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- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
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- RHMXSUBWYGIKPK-UHFFFAOYSA-N (6-phenylmethoxy-3-tricyclo[6.2.1.02,7]undeca-2,4,6-trienyl)boronic acid Chemical compound C1=2C(C3)CCC3C=2C(B(O)O)=CC=C1OCC1=CC=CC=C1 RHMXSUBWYGIKPK-UHFFFAOYSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
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- JXTLYBKAQQBEGK-UHFFFAOYSA-N n-[6-(4-formyl-2-propan-2-yloxyphenyl)pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound CC(C)OC1=CC(C=O)=CC=C1C1=CC=CC(NC(=O)C(C)(C)C)=N1 JXTLYBKAQQBEGK-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical compound CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- JAKNYTQAGPEFJB-UHFFFAOYSA-N piperidin-2-amine Chemical group NC1CCCCN1 JAKNYTQAGPEFJB-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
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- KWQRKOSMSFLBTJ-UHFFFAOYSA-N tert-butyl 3-methylsulfonyloxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)C1 KWQRKOSMSFLBTJ-UHFFFAOYSA-N 0.000 description 1
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- SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 1
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- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
Classifications
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Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
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US9615298P | 1998-08-11 | 1998-08-11 |
Publications (1)
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OA11595A true OA11595A (en) | 2004-08-19 |
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Family Applications (1)
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OA1200100036A OA11595A (en) | 1998-08-11 | 1999-08-05 | New pharmaceutical uses for NOS inhibitors. |
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US (1) | US20020151572A1 (xx) |
EP (1) | EP1109556A2 (xx) |
JP (1) | JP2002522498A (xx) |
KR (1) | KR20010085364A (xx) |
CN (1) | CN1323211A (xx) |
AP (1) | AP2001002067A0 (xx) |
AR (1) | AR020009A1 (xx) |
AU (1) | AU749439B2 (xx) |
BR (1) | BR9912906A (xx) |
CA (1) | CA2340200A1 (xx) |
CO (1) | CO5130011A1 (xx) |
CR (1) | CR6302A (xx) |
CZ (1) | CZ2001486A3 (xx) |
DZ (1) | DZ2867A1 (xx) |
EA (1) | EA200100125A1 (xx) |
EE (1) | EE200100084A (xx) |
GE (1) | GEP20043252B (xx) |
GT (1) | GT199900127A (xx) |
HK (1) | HK1041819A1 (xx) |
HR (1) | HRP20010099A2 (xx) |
HU (1) | HUP0103113A3 (xx) |
ID (1) | ID28227A (xx) |
IL (1) | IL141031A0 (xx) |
IS (1) | IS5814A (xx) |
MA (1) | MA26670A1 (xx) |
NO (1) | NO20010685L (xx) |
NZ (1) | NZ509298A (xx) |
OA (1) | OA11595A (xx) |
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PE (1) | PE20001025A1 (xx) |
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TR (3) | TR200103661T2 (xx) |
WO (1) | WO2000009130A2 (xx) |
YU (1) | YU9601A (xx) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US20010049379A1 (en) | 1997-08-27 | 2001-12-06 | Lowe John Adams | 2-aminopyridines containing fused ring substituents |
US6586478B2 (en) | 2000-02-22 | 2003-07-01 | Cellegy Canada | Methods and compositions for improving sleep |
CA2479098A1 (en) * | 2002-03-20 | 2003-09-25 | Maree Therese Smith | Methods and compositions comprising nitric oxide donors and opioid analgesics |
WO2005007627A1 (ja) * | 2003-07-18 | 2005-01-27 | Nihon Nohyaku Co., Ltd. | フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤 |
US9120750B2 (en) | 2013-03-07 | 2015-09-01 | Northwestern University | 2-Aminopyridine-based selective neuronal nitric oxide synthase inhibitors |
US10759791B2 (en) | 2014-11-04 | 2020-09-01 | Northwestern University | Mammalian and bacterial nitric oxide synthase inhibitors |
US9951014B2 (en) | 2014-11-04 | 2018-04-24 | Northwestern University | Mammalian and bacterial nitric oxide synthase inhibitors |
Family Cites Families (6)
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ES2214604T3 (es) * | 1996-03-29 | 2004-09-16 | Pfizer Inc. | Derivados de la 6-fenilpiridil-2-amina. |
HN1997000027A (es) * | 1996-12-06 | 1997-06-05 | Pfizer Prod Inc | Derivados de 6-fenil piridil - 2 amina |
SK101199A3 (en) * | 1997-02-10 | 2000-10-09 | Pfizer Prod Inc | 2-amino-6-(2-substituted-4-phenoxy)-substituted-pyridines, their use and pharmaceutical compositions based thereupon |
HN1998000118A (es) * | 1997-08-27 | 1999-02-09 | Pfizer Prod Inc | 2 - aminopiridinas que contienen sustituyentes de anillos condensados. |
HN1998000125A (es) * | 1997-08-28 | 1999-02-09 | Pfizer Prod Inc | 2-aminopiridinas con sustituyentes alcoxi ramificados |
SE9703693D0 (sv) * | 1997-10-10 | 1997-10-10 | Astra Pharma Prod | Novel combination |
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1999
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- 1999-08-05 KR KR1020017001788A patent/KR20010085364A/ko not_active Application Discontinuation
- 1999-08-05 TR TR2001/03661T patent/TR200103661T2/xx unknown
- 1999-08-05 AU AU49248/99A patent/AU749439B2/en not_active Ceased
- 1999-08-05 BR BR9912906-0A patent/BR9912906A/pt not_active IP Right Cessation
- 1999-08-05 CA CA002340200A patent/CA2340200A1/en not_active Abandoned
- 1999-08-05 PL PL99346842A patent/PL346842A1/xx not_active Application Discontinuation
- 1999-08-05 CZ CZ2001486A patent/CZ2001486A3/cs unknown
- 1999-08-05 AP APAP/P/2001/002067A patent/AP2001002067A0/en unknown
- 1999-08-05 HU HU0103113A patent/HUP0103113A3/hu unknown
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- 1999-08-05 JP JP2000564633A patent/JP2002522498A/ja active Pending
- 1999-08-05 EE EEP200100084A patent/EE200100084A/xx unknown
- 1999-08-05 TR TR2001/00434T patent/TR200100434T2/xx unknown
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- 1999-08-05 EA EA200100125A patent/EA200100125A1/ru unknown
- 1999-08-05 TR TR2004/01803T patent/TR200401803T2/xx unknown
- 1999-08-05 SK SK170-2001A patent/SK1702001A3/sk unknown
- 1999-08-05 EP EP99933077A patent/EP1109556A2/en not_active Withdrawn
- 1999-08-05 CN CN99811907A patent/CN1323211A/zh active Pending
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- 1999-08-09 PE PE1999000801A patent/PE20001025A1/es not_active Application Discontinuation
- 1999-08-10 MA MA25724A patent/MA26670A1/fr unknown
- 1999-08-10 SV SV1999000121A patent/SV1999000121A/es not_active Application Discontinuation
- 1999-08-10 DZ DZ990167A patent/DZ2867A1/xx active
- 1999-08-10 TN TNTNSN99154A patent/TNSN99154A1/fr unknown
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- 1999-08-11 US US09/372,352 patent/US20020151572A1/en not_active Abandoned
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2001
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2002
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