AU2005247699A1 - Aminopyridine derivatives as selective dopamine D3 agonists - Google Patents
Aminopyridine derivatives as selective dopamine D3 agonists Download PDFInfo
- Publication number
- AU2005247699A1 AU2005247699A1 AU2005247699A AU2005247699A AU2005247699A1 AU 2005247699 A1 AU2005247699 A1 AU 2005247699A1 AU 2005247699 A AU2005247699 A AU 2005247699A AU 2005247699 A AU2005247699 A AU 2005247699A AU 2005247699 A1 AU2005247699 A1 AU 2005247699A1
- Authority
- AU
- Australia
- Prior art keywords
- formula
- compounds
- alkyl
- reaction
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000556 agonist Substances 0.000 title description 20
- 150000003927 aminopyridines Chemical class 0.000 title description 11
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title description 11
- 229960003638 dopamine Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 350
- 238000002360 preparation method Methods 0.000 claims description 112
- -1 OR 7 Chemical group 0.000 claims description 86
- 238000011282 treatment Methods 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 18
- WZAQGEYBXLKEDB-UHFFFAOYSA-N 5-morpholin-2-ylpyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1OCCNC1 WZAQGEYBXLKEDB-UHFFFAOYSA-N 0.000 claims description 13
- 201000001881 impotence Diseases 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- 208000020016 psychiatric disease Diseases 0.000 claims description 8
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 8
- 208000020401 Depressive disease Diseases 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- BWGDAGTZIVIBHX-MAUKXSAKSA-N 5-[(2s,5s)-5-methyl-4-(3-phenylpropyl)morpholin-2-yl]pyridin-2-amine Chemical compound C([C@@H](OC[C@@H]1C)C=2C=NC(N)=CC=2)N1CCCC1=CC=CC=C1 BWGDAGTZIVIBHX-MAUKXSAKSA-N 0.000 claims description 6
- PTLVHXZCCZEHPB-UHFFFAOYSA-N 5-[4-(3-phenylpropyl)morpholin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1OCCN(CCCC=2C=CC=CC=2)C1 PTLVHXZCCZEHPB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- MILNIPPOWYGNRP-RYUDHWBXSA-N 5-[(2r,5s)-4,5-diethylmorpholin-2-yl]pyridin-2-amine Chemical compound C1N(CC)[C@@H](CC)CO[C@@H]1C1=CC=C(N)N=C1 MILNIPPOWYGNRP-RYUDHWBXSA-N 0.000 claims description 5
- RPPCYSJLGJVJPM-OALUTQOASA-N 5-[(2r,5s)-5-(phenylmethoxymethyl)-4-propylmorpholin-2-yl]pyridin-2-amine Chemical compound C([C@H]1CO[C@@H](CN1CCC)C=1C=NC(N)=CC=1)OCC1=CC=CC=C1 RPPCYSJLGJVJPM-OALUTQOASA-N 0.000 claims description 5
- UXRVFSIWSWPXSI-CBAPKCEASA-N 5-[(2r,5s)-5-methylmorpholin-2-yl]pyridin-2-amine Chemical compound C1N[C@@H](C)CO[C@@H]1C1=CC=C(N)N=C1 UXRVFSIWSWPXSI-CBAPKCEASA-N 0.000 claims description 5
- MILNIPPOWYGNRP-NWDGAFQWSA-N 5-[(2s,5s)-4,5-diethylmorpholin-2-yl]pyridin-2-amine Chemical compound C1N(CC)[C@@H](CC)CO[C@H]1C1=CC=C(N)N=C1 MILNIPPOWYGNRP-NWDGAFQWSA-N 0.000 claims description 5
- WQEDAMLUPHXADE-WCQYABFASA-N 5-[(2s,5s)-4-butyl-5-methylmorpholin-2-yl]pyridin-2-amine Chemical compound O1C[C@H](C)N(CCCC)C[C@@H]1C1=CC=C(N)N=C1 WQEDAMLUPHXADE-WCQYABFASA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- GDJIKWMLGQXLIT-UHFFFAOYSA-N [6-(6-aminopyridin-3-yl)-4-propylmorpholin-3-yl]methanol Chemical compound O1CC(CO)N(CCC)CC1C1=CC=C(N)N=C1 GDJIKWMLGQXLIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- DWSKCUWWSWFKJO-UHFFFAOYSA-N 4-methyl-5-(4-propylmorpholin-2-yl)pyridin-2-amine Chemical compound C1N(CCC)CCOC1C1=CN=C(N)C=C1C DWSKCUWWSWFKJO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 276
- 238000006243 chemical reaction Methods 0.000 description 200
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
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- 238000000034 method Methods 0.000 description 57
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
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- 150000001299 aldehydes Chemical class 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 35
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 34
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 150000001408 amides Chemical class 0.000 description 32
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- 150000002825 nitriles Chemical class 0.000 description 29
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- 239000012442 inert solvent Substances 0.000 description 26
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- 230000015572 biosynthetic process Effects 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 22
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- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 17
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- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 12
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Landscapes
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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GB0411891.5 | 2004-05-27 | ||
GB0411891A GB0411891D0 (en) | 2004-05-27 | 2004-05-27 | New aminopyridine derivatives and their use as pharmaceuticals |
GB0412463A GB0412463D0 (en) | 2004-06-03 | 2004-06-03 | New aminopyridine derivatives and their use as pharmaceuticals |
GB0412463.2 | 2004-06-03 | ||
PCT/IB2005/001554 WO2005115985A1 (en) | 2004-05-27 | 2005-05-17 | Aminopyridine derivatives as selective dopamine d3 agonists |
Publications (1)
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AU2005247699A1 true AU2005247699A1 (en) | 2005-12-08 |
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AU2005247699A Abandoned AU2005247699A1 (en) | 2004-05-27 | 2005-05-17 | Aminopyridine derivatives as selective dopamine D3 agonists |
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EP (1) | EP1758862A1 (ja) |
JP (1) | JP4198183B2 (ja) |
AP (1) | AP2006003824A0 (ja) |
AR (1) | AR049548A1 (ja) |
AU (1) | AU2005247699A1 (ja) |
BR (1) | BRPI0511571A (ja) |
CA (1) | CA2567935C (ja) |
EA (1) | EA200601982A1 (ja) |
EC (1) | ECSP067029A (ja) |
GT (1) | GT200500125A (ja) |
IL (1) | IL179314A0 (ja) |
MA (1) | MA28607B1 (ja) |
MX (1) | MXPA06013786A (ja) |
NL (1) | NL1029139C2 (ja) |
NO (1) | NO20065326L (ja) |
PA (1) | PA8635101A1 (ja) |
PE (1) | PE20060366A1 (ja) |
SV (1) | SV2005002129A (ja) |
TW (1) | TW200609216A (ja) |
UY (1) | UY28925A1 (ja) |
WO (1) | WO2005115985A1 (ja) |
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GB0502509D0 (en) * | 2005-02-07 | 2005-03-16 | Pfizer Ltd | Novel salt form of a dopamine agonist |
ES2580779T3 (es) | 2009-02-13 | 2016-08-26 | Bayer Intellectual Property Gmbh | Pirimidinas fusionadas |
MX2012011821A (es) * | 2010-04-12 | 2012-11-30 | Supernus Pharmaceuticals Inc | Metodos para producir sales de viloxazina y polimorfos novedosos de las mismas. |
WO2013003769A2 (en) | 2011-06-30 | 2013-01-03 | Donaldson Company, Inc. | Air/oil separator assemblies; components; and, methods |
GB2543296A (en) | 2015-10-13 | 2017-04-19 | Indivior Uk Ltd | Dopamine D3 receptor antagonists having a morpholine moiety |
WO2018014829A1 (en) | 2016-07-20 | 2018-01-25 | Novartis Ag | Aminopyridine derivatives and their use as selective alk-2 inhibitors |
AU2020270992A1 (en) * | 2019-04-12 | 2021-10-28 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | D3 receptor agonist compounds; methods of preparation; intermediates thereof; and methods of use thereof |
JP2023502742A (ja) | 2019-11-22 | 2023-01-25 | インサイト コーポレーション | Alk2阻害剤及びjak2阻害剤を含む併用療法 |
IL298767A (en) | 2020-06-16 | 2023-02-01 | Incyte Corp | ALK2 inhibitors for the treatment of anemia |
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US5077290A (en) * | 1990-10-11 | 1991-12-31 | Merck & Co., Inc. | Morpholine derivatives compositions and use |
GB0130219D0 (en) * | 2001-12-18 | 2002-02-06 | Pfizer Ltd | Compounds for the treatment of sexual dysfunction |
SI1572214T1 (sl) * | 2002-12-10 | 2010-07-30 | Pfizer Ltd | Derivati morfolina za uporabo kot dopaminski agonisti pri zdravljenju med drugim spolne disfunkcije |
-
2005
- 2005-05-17 CA CA002567935A patent/CA2567935C/en not_active Expired - Fee Related
- 2005-05-17 BR BRPI0511571-0A patent/BRPI0511571A/pt not_active Application Discontinuation
- 2005-05-17 EP EP05747191A patent/EP1758862A1/en not_active Withdrawn
- 2005-05-17 MX MXPA06013786A patent/MXPA06013786A/es not_active Application Discontinuation
- 2005-05-17 EA EA200601982A patent/EA200601982A1/ru unknown
- 2005-05-17 WO PCT/IB2005/001554 patent/WO2005115985A1/en active Application Filing
- 2005-05-17 AP AP2006003824A patent/AP2006003824A0/xx unknown
- 2005-05-17 AU AU2005247699A patent/AU2005247699A1/en not_active Abandoned
- 2005-05-17 JP JP2007514200A patent/JP4198183B2/ja not_active Expired - Fee Related
- 2005-05-24 GT GT200500125A patent/GT200500125A/es unknown
- 2005-05-25 PE PE2005000583A patent/PE20060366A1/es not_active Application Discontinuation
- 2005-05-26 UY UY28925A patent/UY28925A1/es not_active Application Discontinuation
- 2005-05-26 TW TW094117274A patent/TW200609216A/zh unknown
- 2005-05-26 AR ARP050102169A patent/AR049548A1/es unknown
- 2005-05-26 PA PA20058635101A patent/PA8635101A1/es unknown
- 2005-05-26 NL NL1029139A patent/NL1029139C2/nl not_active IP Right Cessation
- 2005-05-27 SV SV2005002129A patent/SV2005002129A/es not_active Application Discontinuation
-
2006
- 2006-11-15 IL IL179314A patent/IL179314A0/en unknown
- 2006-11-20 NO NO20065326A patent/NO20065326L/no unknown
- 2006-11-27 EC EC2006007029A patent/ECSP067029A/es unknown
- 2006-11-27 MA MA29488A patent/MA28607B1/fr unknown
Also Published As
Publication number | Publication date |
---|---|
AP2006003824A0 (en) | 2006-12-31 |
NL1029139C2 (nl) | 2006-06-19 |
EP1758862A1 (en) | 2007-03-07 |
ECSP067029A (es) | 2006-12-29 |
PA8635101A1 (es) | 2006-05-16 |
SV2005002129A (es) | 2005-12-13 |
CA2567935A1 (en) | 2005-12-08 |
BRPI0511571A (pt) | 2008-01-02 |
MXPA06013786A (es) | 2007-01-25 |
JP4198183B2 (ja) | 2008-12-17 |
IL179314A0 (en) | 2007-03-08 |
TW200609216A (en) | 2006-03-16 |
WO2005115985A1 (en) | 2005-12-08 |
UY28925A1 (es) | 2005-12-30 |
NO20065326L (no) | 2006-12-19 |
JP2008500331A (ja) | 2008-01-10 |
GT200500125A (es) | 2006-01-10 |
NL1029139A1 (nl) | 2005-11-30 |
AR049548A1 (es) | 2006-08-16 |
MA28607B1 (fr) | 2007-05-02 |
PE20060366A1 (es) | 2006-05-15 |
CA2567935C (en) | 2009-10-27 |
EA200601982A1 (ru) | 2007-04-27 |
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