AU2008312641A1 - Substituted N-phenyl-bipyrrolidine ureas and therapeutic use thereof - Google Patents
Substituted N-phenyl-bipyrrolidine ureas and therapeutic use thereof Download PDFInfo
- Publication number
- AU2008312641A1 AU2008312641A1 AU2008312641A AU2008312641A AU2008312641A1 AU 2008312641 A1 AU2008312641 A1 AU 2008312641A1 AU 2008312641 A AU2008312641 A AU 2008312641A AU 2008312641 A AU2008312641 A AU 2008312641A AU 2008312641 A1 AU2008312641 A1 AU 2008312641A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- phenyl
- bipyrrolidinyl
- amide
- carboxylic acid
- 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
- 235000013877 carbamide Nutrition 0.000 title abstract description 15
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 201000010099 disease Diseases 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 239000004202 carbamide Substances 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- -1 thiophen-2-ylmethyl Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- ZPPXWZDJDIOJFP-UHFFFAOYSA-N 1,3-dihydroisoindole-2-carboxylic acid Chemical compound C1=CC=C2CN(C(=O)O)CC2=C1 ZPPXWZDJDIOJFP-UHFFFAOYSA-N 0.000 claims description 22
- KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
- NEJWFHUMCLLVCF-UHFFFAOYSA-N 3-[acetyl(methyl)amino]pyrrolidine-1-carboxylic acid Chemical compound CC(=O)N(C)C1CCN(C(O)=O)C1 NEJWFHUMCLLVCF-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
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- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 8
- NXMHCJSGJBPRQM-UHFFFAOYSA-N 4-ethylpiperazine-1-carboxylic acid Chemical compound CCN1CCN(C(O)=O)CC1 NXMHCJSGJBPRQM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- TXYHNJMNQMYNTO-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[2-methyl-4-[3-(2-methylpyrrolidin-1-yl)pyrrolidin-1-yl]phenyl]urea Chemical compound CC1CCCN1C1CN(C=2C=C(C)C(NC(=O)NC=3C=C(Cl)C=C(Cl)C=3)=CC=2)CC1 TXYHNJMNQMYNTO-UHFFFAOYSA-N 0.000 claims description 7
- RHEVIGLLTLURAQ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[3-methyl-4-[3-(2-methylpyrrolidin-1-yl)pyrrolidin-1-yl]phenyl]urea Chemical compound CC1CCCN1C1CN(C=2C(=CC(NC(=O)NC=3C=C(Cl)C=C(Cl)C=3)=CC=2)C)CC1 RHEVIGLLTLURAQ-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- PYUCVLVRHYGSER-UHFFFAOYSA-N n-[4-[3-(2-methylpyrrolidin-1-yl)pyrrolidin-1-yl]phenyl]piperidine-1-carboxamide Chemical compound CC1CCCN1C1CN(C=2C=CC(NC(=O)N3CCCCC3)=CC=2)CC1 PYUCVLVRHYGSER-UHFFFAOYSA-N 0.000 claims description 7
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- KBIMBEHOSLKBMG-UHFFFAOYSA-N 1-[(3,5-dichlorophenyl)methyl]-3-[3-methyl-4-[3-(2-methylpyrrolidin-1-yl)pyrrolidin-1-yl]phenyl]urea Chemical compound CC1CCCN1C1CN(C=2C(=CC(NC(=O)NCC=3C=C(Cl)C=C(Cl)C=3)=CC=2)C)CC1 KBIMBEHOSLKBMG-UHFFFAOYSA-N 0.000 claims description 6
- BCCVUKGKQRRJOM-UHFFFAOYSA-N 4-acetyl-n-[4-[3-(2-methylpyrrolidin-1-yl)pyrrolidin-1-yl]phenyl]piperazine-1-carboxamide Chemical compound CC1CCCN1C1CN(C=2C=CC(NC(=O)N3CCN(CC3)C(C)=O)=CC=2)CC1 BCCVUKGKQRRJOM-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- AEDANDOCUNOLBS-UHFFFAOYSA-N 4-phenylpiperazine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCN1C1=CC=CC=C1 AEDANDOCUNOLBS-UHFFFAOYSA-N 0.000 claims 5
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Classifications
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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- Chemical Kinetics & Catalysis (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98060607P | 2007-10-17 | 2007-10-17 | |
| US60/980,606 | 2007-10-17 | ||
| PCT/US2008/079763 WO2009052068A1 (en) | 2007-10-17 | 2008-10-14 | Substituted n-phenyl-bipyrrolidine ureas and therapeutic use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008312641A1 true AU2008312641A1 (en) | 2009-04-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008312641A Abandoned AU2008312641A1 (en) | 2007-10-17 | 2008-10-14 | Substituted N-phenyl-bipyrrolidine ureas and therapeutic use thereof |
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| EP (1) | EP2215058B1 (enExample) |
| JP (1) | JP5380455B2 (enExample) |
| KR (1) | KR20100082349A (enExample) |
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| AU (1) | AU2008312641A1 (enExample) |
| CA (1) | CA2702933C (enExample) |
| CY (1) | CY1112391T1 (enExample) |
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| ES (1) | ES2378011T3 (enExample) |
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| IL (1) | IL205002A0 (enExample) |
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| MY (1) | MY148807A (enExample) |
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| ES2372332T3 (es) | 2007-10-17 | 2012-01-18 | Sanofi | N-fenil-bipirrolidina carboxamidas sustituidas y su uso terapéutico. |
| SI2212282T1 (sl) * | 2007-10-17 | 2012-01-31 | Sanofi Sa | Substituirani n-fenil-bipirolidin karboksamidi in njihova terapevtska uporaba |
| WO2009052063A1 (en) | 2007-10-17 | 2009-04-23 | Sanofi-Aventis | Substituted n-phenyl-pyrrolidinylmethylpyrrolidine amides and therapeutic use thereof as histamine h3 receptor modulators |
| KR20090129927A (ko) | 2008-06-13 | 2009-12-17 | 주식회사 엘지화학 | 발열체 및 이의 제조방법 |
| US10412788B2 (en) | 2008-06-13 | 2019-09-10 | Lg Chem, Ltd. | Heating element and manufacturing method thereof |
| US9611171B2 (en) | 2008-06-13 | 2017-04-04 | Lg Chem, Ltd. | Heating element and manufacturing method thereof |
| WO2011143155A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| JP5968307B2 (ja) | 2010-05-11 | 2016-08-10 | サノフイ | 置換フェニルシクロアルキルピロリジン（ピペリジン）スピロラクタム類及びアミド類、それらの製造及び治療的使用 |
| EP2569294B1 (en) * | 2010-05-11 | 2015-03-11 | Sanofi | Substituted n-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| AR081382A1 (es) | 2010-05-11 | 2012-08-29 | Sanofi Aventis | Derivados de n-heterocicloalquil bipirrolidinilfenil amida sustituidos, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades del sistema nervioso central. |
| JP2013526530A (ja) * | 2010-05-11 | 2013-06-24 | サノフイ | 置換されたｎ−フェニルスピロラクタムビピロリジン、その製造及び治療上の使用 |
| TW201202251A (en) | 2010-05-11 | 2012-01-16 | Sanofi Aventis | Substituted N-heteroaryl spirolactam bipyrrolidines, preparation and therapeutic use thereof |
| WO2011143145A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-alkyl and n-acyl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| SG10201602857UA (en) * | 2010-11-15 | 2016-05-30 | Abbvie Inc | NAMPT And Rock Inhibitors |
| EP2694492B1 (en) * | 2011-02-23 | 2015-07-29 | Suven Life Sciences Limited | Novel compounds as histamine h3 receptor ligands |
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| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| US7279491B2 (en) * | 2002-10-23 | 2007-10-09 | Janssen Pharmaceutica N.V. | Phenylpiperidines and phenylpyrrolidines |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7223788B2 (en) * | 2003-02-14 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Substituted N-aryl heterocycles, process for their preparation and their use as medicaments |
| DE602006010833D1 (de) | 2005-03-17 | 2010-01-14 | Lilly Co Eli | Pyrrolidinderivate als histamin-h3-rezeptorantagonisten |
| AU2006232871B9 (en) * | 2005-04-01 | 2011-11-24 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| WO2007005503A1 (en) * | 2005-07-01 | 2007-01-11 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| TW200804274A (en) * | 2005-10-27 | 2008-01-16 | Ucb Sa | Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses |
| WO2009052063A1 (en) | 2007-10-17 | 2009-04-23 | Sanofi-Aventis | Substituted n-phenyl-pyrrolidinylmethylpyrrolidine amides and therapeutic use thereof as histamine h3 receptor modulators |
| SI2212282T1 (sl) | 2007-10-17 | 2012-01-31 | Sanofi Sa | Substituirani n-fenil-bipirolidin karboksamidi in njihova terapevtska uporaba |
| ES2372332T3 (es) | 2007-10-17 | 2012-01-18 | Sanofi | N-fenil-bipirrolidina carboxamidas sustituidas y su uso terapéutico. |
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- 2008-10-14 WO PCT/US2008/079763 patent/WO2009052068A1/en not_active Ceased
- 2008-10-14 PT PT08838702T patent/PT2215058E/pt unknown
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- 2008-10-14 DK DK08838702.2T patent/DK2215058T3/da active
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- 2008-10-14 AU AU2008312641A patent/AU2008312641A1/en not_active Abandoned
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| Publication number | Publication date |
|---|---|
| IL205002A0 (en) | 2010-11-30 |
| RU2010119554A (ru) | 2011-11-27 |
| CA2702933C (en) | 2012-12-18 |
| RS52221B (sr) | 2012-10-31 |
| CY1112391T1 (el) | 2015-12-09 |
| RU2478094C2 (ru) | 2013-03-27 |
| CN101903341A (zh) | 2010-12-01 |
| US20100173908A1 (en) | 2010-07-08 |
| ATE534625T1 (de) | 2011-12-15 |
| MX2010003948A (es) | 2010-04-30 |
| JP2011500697A (ja) | 2011-01-06 |
| PT2215058E (pt) | 2012-03-06 |
| JP5380455B2 (ja) | 2014-01-08 |
| DK2215058T3 (da) | 2012-03-12 |
| NZ584692A (en) | 2011-12-22 |
| HK1146056A1 (en) | 2011-05-13 |
| CA2702933A1 (en) | 2009-04-23 |
| PL2215058T3 (pl) | 2012-04-30 |
| CN101903341B (zh) | 2012-10-03 |
| WO2009052068A1 (en) | 2009-04-23 |
| ES2378011T3 (es) | 2012-04-04 |
| KR20100082349A (ko) | 2010-07-16 |
| EP2215058B1 (en) | 2011-11-23 |
| US8222290B2 (en) | 2012-07-17 |
| HRP20120166T1 (hr) | 2012-03-31 |
| SI2215058T1 (sl) | 2012-03-30 |
| EP2215058A1 (en) | 2010-08-11 |
| MY148807A (en) | 2013-05-31 |
| ZA201002114B (en) | 2010-12-29 |
| MA31889B1 (fr) | 2010-12-01 |
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