JP2007508314A5 - - Google Patents
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- Publication number
- JP2007508314A5 JP2007508314A5 JP2006534415A JP2006534415A JP2007508314A5 JP 2007508314 A5 JP2007508314 A5 JP 2007508314A5 JP 2006534415 A JP2006534415 A JP 2006534415A JP 2006534415 A JP2006534415 A JP 2006534415A JP 2007508314 A5 JP2007508314 A5 JP 2007508314A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- phenyl
- pentan
- pyrrolidin
- pharmaceutical composition
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims 25
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 11
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 6
- 230000004064 dysfunction Effects 0.000 claims 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- 101710164184 Synaptic vesicular amine transporter Proteins 0.000 claims 3
- 102100034333 Synaptic vesicular amine transporter Human genes 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229960003638 dopamine Drugs 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- HHSYAWUBPBEDMP-UHFFFAOYSA-N 1-(3-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=CC(C)=CC=1C(=O)C(CCC)N1CCCC1 HHSYAWUBPBEDMP-UHFFFAOYSA-N 0.000 claims 2
- XCHIECWEKDGHNL-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(O)C=CC=1C(=O)C(CCC)N1CCCC1 XCHIECWEKDGHNL-UHFFFAOYSA-N 0.000 claims 2
- HWYVHRCKBXGZLV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(OC)C=CC=1C(=O)C(CCC)N1CCCC1 HWYVHRCKBXGZLV-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 claims 2
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 claims 2
- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 claims 2
- 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims 2
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 230000001722 neurochemical effect Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 229940076279 serotonin Drugs 0.000 claims 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- SWUVZKWCOBGPTH-HNNXBMFYSA-N (2s)-1-(4-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound N1([C@@H](CCC)C(=O)C=2C=CC(C)=CC=2)CCCC1 SWUVZKWCOBGPTH-HNNXBMFYSA-N 0.000 claims 1
- VVIVTDYOMWHKAE-UHFFFAOYSA-N 1-(2-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=CC=C(C)C=1C(=O)C(CCC)N1CCCC1 VVIVTDYOMWHKAE-UHFFFAOYSA-N 0.000 claims 1
- OUSCITCGPKFWDH-UHFFFAOYSA-N 1-(2-pyrrolidin-1-ylphenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=CC=C1N1CCCC1 OUSCITCGPKFWDH-UHFFFAOYSA-N 0.000 claims 1
- OYYFMZJTKZIRQM-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)C(CCC)N1CCCC1 OYYFMZJTKZIRQM-UHFFFAOYSA-N 0.000 claims 1
- KKTUFJIEHNEGDF-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(O)C(O)=CC=1C(=O)C(CCC)N1CCCC1 KKTUFJIEHNEGDF-UHFFFAOYSA-N 0.000 claims 1
- NYDUTEZMPZHSRY-UHFFFAOYSA-N 1-(3-iodophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=CC(I)=CC=1C(=O)C(CCC)N1CCCC1 NYDUTEZMPZHSRY-UHFFFAOYSA-N 0.000 claims 1
- RAHKQMUBMIJUFG-UHFFFAOYSA-N 1-(4-bromophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(Br)C=CC=1C(=O)C(CCC)N1CCCC1 RAHKQMUBMIJUFG-UHFFFAOYSA-N 0.000 claims 1
- NIGBFBTVONRYQN-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(CCC)N1CCCC1 NIGBFBTVONRYQN-UHFFFAOYSA-N 0.000 claims 1
- BQLSUBYYRRZHRK-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(F)C=CC=1C(=O)C(CCC)N1CCCC1 BQLSUBYYRRZHRK-UHFFFAOYSA-N 0.000 claims 1
- QXBWECFEEZMKTN-UHFFFAOYSA-N 1-(4-iodophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(I)C=CC=1C(=O)C(CCC)N1CCCC1 QXBWECFEEZMKTN-UHFFFAOYSA-N 0.000 claims 1
- WXZXQKCLNSPXHL-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyrrolidin-1-ylhexan-1-one Chemical compound C=1C=C(OC)C=CC=1C(=O)C(CCCC)N1CCCC1 WXZXQKCLNSPXHL-UHFFFAOYSA-N 0.000 claims 1
- NAHZCGQMXZCULW-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=O)C(CCC)N1CCCC1 NAHZCGQMXZCULW-UHFFFAOYSA-N 0.000 claims 1
- FCINLQHPPAWABH-UHFFFAOYSA-N 1-(4-prop-1-ynylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(C#CC)C=CC=1C(=O)C(CCC)N1CCCC1 FCINLQHPPAWABH-UHFFFAOYSA-N 0.000 claims 1
- ULUHBYVKNOUSDX-UHFFFAOYSA-N 1-[4-(furan-2-yl)phenyl]-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(C=2OC=CC=2)C=CC=1C(=O)C(CCC)N1CCCC1 ULUHBYVKNOUSDX-UHFFFAOYSA-N 0.000 claims 1
- FDCLNKXJEZCPEW-UHFFFAOYSA-N 1-[4-(hydroxymethyl)phenyl]-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(CO)C=CC=1C(=O)C(CCC)N1CCCC1 FDCLNKXJEZCPEW-UHFFFAOYSA-N 0.000 claims 1
- DLRWKNLMJAIFQB-UHFFFAOYSA-N 1-phenyl-2-pyrrolidin-1-ylheptan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(CCCCC)N1CCCC1 DLRWKNLMJAIFQB-UHFFFAOYSA-N 0.000 claims 1
- RYJXAZXFWIWTOJ-UHFFFAOYSA-N 1-phenyl-2-pyrrolidin-1-ylnonan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(CCCCCCC)N1CCCC1 RYJXAZXFWIWTOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- HEFDYDISPNHKAM-UHFFFAOYSA-N 2-pyrrolidin-1-yl-1-(4-thiophen-2-ylphenyl)pentan-1-one Chemical compound C=1C=C(C=2SC=CC=2)C=CC=1C(=O)C(CCC)N1CCCC1 HEFDYDISPNHKAM-UHFFFAOYSA-N 0.000 claims 1
- SLPVYNPNJIYANF-UHFFFAOYSA-N 3-methyl-1-phenyl-2-pyrrolidin-1-ylbutan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C(C)C)N1CCCC1 SLPVYNPNJIYANF-UHFFFAOYSA-N 0.000 claims 1
- GMWFVXBLHOYMAG-UHFFFAOYSA-N 4-methyl-1-(4-methylphenyl)-2-pyrrolidin-1-ylpentan-1-one Chemical compound C=1C=C(C)C=CC=1C(=O)C(CC(C)C)N1CCCC1 GMWFVXBLHOYMAG-UHFFFAOYSA-N 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical compound [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 201000001272 cocaine abuse Diseases 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000002825 dopamine reuptake Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- RUCXEVOCSDADAL-UHFFFAOYSA-N methyl 4-(2-pyrrolidin-1-ylpentanoyl)benzoate Chemical compound C=1C=C(C(=O)OC)C=CC=1C(=O)C(CCC)N1CCCC1 RUCXEVOCSDADAL-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- DSIUMNNVBQZCEG-UHFFFAOYSA-N n-[4-(2-pyrrolidin-1-ylpentanoyl)phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C=CC=1C(=O)C(CCC)N1CCCC1 DSIUMNNVBQZCEG-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003136 n-heptyl 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])* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- DTNUPBSOODGRKW-UHFFFAOYSA-N naphyrone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)C(CCC)N1CCCC1 DTNUPBSOODGRKW-UHFFFAOYSA-N 0.000 claims 1
- 230000019818 neurotransmitter uptake Effects 0.000 claims 1
- 229960002748 norepinephrine Drugs 0.000 claims 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
- SWUVZKWCOBGPTH-UHFFFAOYSA-N pyrovalerone Chemical compound C=1C=C(C)C=CC=1C(=O)C(CCC)N1CCCC1 SWUVZKWCOBGPTH-UHFFFAOYSA-N 0.000 claims 1
- 229950010600 pyrovalerone Drugs 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000000697 serotonin reuptake Effects 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- GSESDIFGJCCBHN-UHFFFAOYSA-N α-pyrrolidinobutiophenone Chemical compound C=1C=CC=CC=1C(=O)C(CC)N1CCCC1 GSESDIFGJCCBHN-UHFFFAOYSA-N 0.000 claims 1
- YDIIDRWHPFMLGR-UHFFFAOYSA-N α-pyrrolidinopentiophenone Chemical compound C=1C=CC=CC=1C(=O)C(CCC)N1CCCC1 YDIIDRWHPFMLGR-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50988203P | 2003-10-08 | 2003-10-08 | |
| PCT/US2004/033349 WO2005034878A2 (en) | 2003-10-08 | 2004-10-08 | Pyrovalerone analogs and therapeutic uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007508314A JP2007508314A (ja) | 2007-04-05 |
| JP2007508314A5 true JP2007508314A5 (https=) | 2007-11-22 |
Family
ID=34435034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006534415A Withdrawn JP2007508314A (ja) | 2003-10-08 | 2004-10-08 | ピロバレロン類縁体及びそれらの治療的使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20080234498A1 (https=) |
| EP (1) | EP1670755A4 (https=) |
| JP (1) | JP2007508314A (https=) |
| AU (1) | AU2004280256A1 (https=) |
| CA (1) | CA2542077A1 (https=) |
| WO (1) | WO2005034878A2 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI499414B (zh) | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ ２）的抑制物與其應用方法 |
| WO2008109591A1 (en) | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
| UA117095C2 (uk) | 2011-12-22 | 2018-06-25 | Аліос Біофарма, Інк. | Нуклеозидна сполука або її фармацевтично прийнятна сіль |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| SG11201407336PA (en) | 2012-05-25 | 2015-03-30 | Janssen Sciences Ireland Uc | Uracyl spirooxetane nucleosides |
| GEP201706757B (en) | 2012-12-21 | 2017-10-25 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| GB2530783A (en) * | 2014-10-02 | 2016-04-06 | Randox Lab Ltd | Improved immunoassay for pyrrolidinophenones |
| AU2020256166A1 (en) | 2019-04-02 | 2021-10-14 | Aligos Therapeutics, Inc. | Compounds targeting PRMT5 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3314970A (en) * | 1967-04-18 | Pykrolidino ketones | ||
| US3287217A (en) * | 1966-11-22 | Compositions and methods for stimulat- ing the central nervous system and in- creasing the blood pressure | ||
| US2369611A (en) * | 1938-12-24 | 1945-02-13 | Scheuing Georg | Analgetically effective tetrahydronaphthalene piperidyl derivatives |
| DE1161274B (de) * | 1960-04-07 | 1964-01-16 | Thomae Gmbh Dr K | Verfahren zur Herstellung von ª‡-Pyrrolidinoketonen und deren Salzen |
| CH395998A (de) * | 1961-05-05 | 1965-07-31 | Wander Ag Dr A | Verfahren zur Herstellung von a-Pyrrolidino-valerophenonen |
| FR2319332A1 (fr) * | 1975-07-28 | 1977-02-25 | Roussel Uclaf | Nouveaux derives de l'aminobenzocycloheptene et leurs sels, procede de preparation et application a titre de medicaments desdits produits |
| HU222726B1 (hu) * | 1990-02-06 | 2003-09-29 | Pfizer, Inc., | Piperidinszármazékok, eljárás elżállításukra és az ezeket tartalmazó gyógyszerkészítmények |
| JPH051033A (ja) * | 1991-06-18 | 1993-01-08 | Tanabe Seiyaku Co Ltd | ベンゾシクロヘプテン誘導体及びその製法 |
-
2004
- 2004-10-08 JP JP2006534415A patent/JP2007508314A/ja not_active Withdrawn
- 2004-10-08 AU AU2004280256A patent/AU2004280256A1/en not_active Abandoned
- 2004-10-08 WO PCT/US2004/033349 patent/WO2005034878A2/en not_active Ceased
- 2004-10-08 US US10/575,177 patent/US20080234498A1/en not_active Abandoned
- 2004-10-08 EP EP04809902A patent/EP1670755A4/en not_active Withdrawn
- 2004-10-08 CA CA002542077A patent/CA2542077A1/en not_active Abandoned
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