NZ584692A - Substituted n-phenyl-bipyrrolidine ureas and therapeutic use thereof - Google Patents
Substituted n-phenyl-bipyrrolidine ureas and therapeutic use thereofInfo
- Publication number
- NZ584692A NZ584692A NZ584692A NZ58469208A NZ584692A NZ 584692 A NZ584692 A NZ 584692A NZ 584692 A NZ584692 A NZ 584692A NZ 58469208 A NZ58469208 A NZ 58469208A NZ 584692 A NZ584692 A NZ 584692A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methyl
- phenyl
- bipyrrolidinyl
- carboxylic acid
- amide
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 title abstract description 8
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 158
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 36
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- -1 thiophen-2-ylmethyl Chemical group 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 42
- 239000004202 carbamide 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 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 16
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- 229910001868 water Inorganic materials 0.000 claims description 14
- KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000012360 testing method Methods 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 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- 241000700159 Rattus Species 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
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- DDOWCQQXWQWZQD-UHFFFAOYSA-N 4-acetylpiperazine-1-carboxylic acid Chemical compound CC(=O)N1CCN(C(O)=O)CC1 DDOWCQQXWQWZQD-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 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 5
- 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 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 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 5
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 238000012549 training Methods 0.000 claims description 5
- NXMHCJSGJBPRQM-UHFFFAOYSA-N 4-ethylpiperazine-1-carboxylic acid Chemical compound CCN1CCN(C(O)=O)CC1 NXMHCJSGJBPRQM-UHFFFAOYSA-N 0.000 claims description 4
- 206010041349 Somnolence Diseases 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
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- 150000002367 halogens Chemical class 0.000 claims description 4
- UCSCBDCRYZONHX-UHFFFAOYSA-N 1-(3-cyanophenyl)-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(C=CC=3)C#N)=CC=2)C)CC1 UCSCBDCRYZONHX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003047 N-acetyl group Chemical group 0.000 claims description 3
- 239000000935 antidepressant agent Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 201000003631 narcolepsy Diseases 0.000 claims description 3
- 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 1
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- 238000001819 mass spectrum Methods 0.000 description 54
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
- 238000005859 coupling reaction Methods 0.000 description 30
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 29
- 230000008878 coupling Effects 0.000 description 29
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
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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
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- 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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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98060607P | 2007-10-17 | 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 |
|---|---|
| NZ584692A true NZ584692A (en) | 2011-12-22 |
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| NZ584692A NZ584692A (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) |
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| AT (1) | ATE534625T1 (enExample) |
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| SI (1) | SI2215058T1 (enExample) |
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Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PL2212283T3 (pl) | 2007-10-17 | 2012-01-31 | Sanofi Sa | Podstawione karboksyamidy N-fenylobipirolidyny i ich zastosowanie terapeutyczne |
| CN101903339B (zh) * | 2007-10-17 | 2012-06-27 | 赛诺菲-安万特 | 取代的n-苯基-联吡咯烷羧酰胺及其治疗用途 |
| MX2010004003A (es) | 2007-10-17 | 2010-04-30 | Sanofi Aventis | N-fenil-pirrolidinilmetlipirrolidin amidas sustituidas y uso terapeutico de las mismas. |
| KR20090129927A (ko) | 2008-06-13 | 2009-12-17 | 주식회사 엘지화학 | 발열체 및 이의 제조방법 |
| US9611171B2 (en) | 2008-06-13 | 2017-04-04 | Lg Chem, Ltd. | Heating element and manufacturing method thereof |
| US10412788B2 (en) | 2008-06-13 | 2019-09-10 | Lg Chem, Ltd. | Heating element and manufacturing method thereof |
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| 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 |
| WO2011143162A1 (en) * | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
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| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| WO2004037257A1 (en) * | 2002-10-23 | 2004-05-06 | Janssen Pharmaceutica, N.V. | Phenylpiperidines and phenylpyrrolidines as histamine h3 receptor modulators |
| 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 |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP5052497B2 (ja) | 2005-03-17 | 2012-10-17 | イーライ リリー アンド カンパニー | ヒスタミンｈ３受容体アンタゴニストとしてのピロリジン誘導体 |
| BRPI0608653A2 (pt) * | 2005-04-01 | 2010-11-30 | Lilly Co Eli | composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso de um composto ou um sal do mesmo |
| ES2370518T3 (es) * | 2005-07-01 | 2011-12-19 | Eli Lilly And Company | Agentes receptores h3 de histamina, preparación y usos terapéuticos. |
| US7943605B2 (en) * | 2005-10-27 | 2011-05-17 | Ucb Pharma S.A. | Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses |
| CN101903339B (zh) | 2007-10-17 | 2012-06-27 | 赛诺菲-安万特 | 取代的n-苯基-联吡咯烷羧酰胺及其治疗用途 |
| PL2212283T3 (pl) | 2007-10-17 | 2012-01-31 | Sanofi Sa | Podstawione karboksyamidy N-fenylobipirolidyny i ich zastosowanie terapeutyczne |
| MX2010004003A (es) | 2007-10-17 | 2010-04-30 | Sanofi Aventis | N-fenil-pirrolidinilmetlipirrolidin amidas sustituidas y uso terapeutico de las mismas. |
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Also Published As
| Publication number | Publication date |
|---|---|
| MY148807A (en) | 2013-05-31 |
| RU2010119554A (ru) | 2011-11-27 |
| HK1146056A1 (en) | 2011-05-13 |
| EP2215058A1 (en) | 2010-08-11 |
| KR20100082349A (ko) | 2010-07-16 |
| AU2008312641A1 (en) | 2009-04-23 |
| CA2702933A1 (en) | 2009-04-23 |
| RU2478094C2 (ru) | 2013-03-27 |
| CN101903341A (zh) | 2010-12-01 |
| EP2215058B1 (en) | 2011-11-23 |
| ES2378011T3 (es) | 2012-04-04 |
| JP5380455B2 (ja) | 2014-01-08 |
| DK2215058T3 (da) | 2012-03-12 |
| IL205002A0 (en) | 2010-11-30 |
| CA2702933C (en) | 2012-12-18 |
| ATE534625T1 (de) | 2011-12-15 |
| MX2010003948A (es) | 2010-04-30 |
| MA31889B1 (fr) | 2010-12-01 |
| US8222290B2 (en) | 2012-07-17 |
| CN101903341B (zh) | 2012-10-03 |
| PT2215058E (pt) | 2012-03-06 |
| ZA201002114B (en) | 2010-12-29 |
| WO2009052068A1 (en) | 2009-04-23 |
| HRP20120166T1 (hr) | 2012-03-31 |
| CY1112391T1 (el) | 2015-12-09 |
| SI2215058T1 (sl) | 2012-03-30 |
| JP2011500697A (ja) | 2011-01-06 |
| RS52221B (sr) | 2012-10-31 |
| US20100173908A1 (en) | 2010-07-08 |
| PL2215058T3 (pl) | 2012-04-30 |
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