ZA200502944B - 2-Alkyl-(2-ammino-3-aryl-propionyl)-piperazine derivatives and related compounds as melanocortin receptor ligands for the treatment of obesity. - Google Patents
2-Alkyl-(2-ammino-3-aryl-propionyl)-piperazine derivatives and related compounds as melanocortin receptor ligands for the treatment of obesity. Download PDFInfo
- Publication number
- ZA200502944B ZA200502944B ZA200502944A ZA200502944A ZA200502944B ZA 200502944 B ZA200502944 B ZA 200502944B ZA 200502944 A ZA200502944 A ZA 200502944A ZA 200502944 A ZA200502944 A ZA 200502944A ZA 200502944 B ZA200502944 B ZA 200502944B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazin
- ethyl
- oxo
- methyl
- substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 48
- 239000003446 ligand Substances 0.000 title claims description 26
- 208000008589 Obesity Diseases 0.000 title claims description 4
- 235000020824 obesity Nutrition 0.000 title claims description 4
- 108090000950 Melanocortin Receptors Proteins 0.000 title description 11
- 102000004378 Melanocortin Receptors Human genes 0.000 title description 11
- -1 4-flucrophenyl Chemical group 0.000 claims description 188
- 239000000203 mixture Substances 0.000 claims description 186
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 239000001257 hydrogen Substances 0.000 claims description 117
- 229940080818 propionamide Drugs 0.000 claims description 96
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 78
- 125000000623 heterocyclic group Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 51
- 239000000460 chlorine Substances 0.000 claims description 49
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 42
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004429 atom Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
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- 125000002837 carbocyclic group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
- 125000006416 CBr Chemical group BrC* 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
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- 230000006399 behavior Effects 0.000 claims description 6
- 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 116
- BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 claims 26
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims 20
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 8
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 7
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- ZCLBLSZZIRMCLZ-UHFFFAOYSA-N 1-(methylamino)cyclopropane-1-carboxylic acid Chemical compound CNC1(C(O)=O)CC1 ZCLBLSZZIRMCLZ-UHFFFAOYSA-N 0.000 claims 5
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- 235000019789 appetite Nutrition 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
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- ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 claims 3
- 125000004477 1-amino-cycloprop-1-yl group Chemical group NC1(CC1)* 0.000 claims 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
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- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- IADUEWIQBXOCDZ-UHFFFAOYSA-N azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims 2
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- VHJNUODKRYWBAU-UHFFFAOYSA-N 1-amino-n-[1-[4-[3-(3,4-dichlorophenyl)-1-(methylamino)-1-oxopropan-2-yl]-2-ethylpiperazin-1-yl]-3-(4-fluorophenyl)-1-oxopropan-2-yl]cyclopropane-1-carboxamide Chemical compound CCC1CN(C(CC=2C=C(Cl)C(Cl)=CC=2)C(=O)NC)CCN1C(=O)C(NC(=O)C1(N)CC1)CC1=CC=C(F)C=C1 VHJNUODKRYWBAU-UHFFFAOYSA-N 0.000 claims 1
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
Applications Claiming Priority (1)
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| US42057802P | 2002-10-23 | 2002-10-23 |
Publications (1)
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| US8163779B2 (en) | 2006-12-20 | 2012-04-24 | Takeda San Diego, Inc. | Glucokinase activators |
| US8173645B2 (en) * | 2007-03-21 | 2012-05-08 | Takeda San Diego, Inc. | Glucokinase activators |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| KR101478253B1 (ko) * | 2007-09-17 | 2014-12-31 | 국민대학교산학협력단 | 아룸 팔래스티눔(Ａｒｕｍ ｐａｌａｅｓｔｉｎｕｎＢｏｉｓｓ) 유래 항암용 피페라지움 화합물 |
| EP2310372B1 (en) | 2008-07-09 | 2012-05-23 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010056717A1 (en) | 2008-11-17 | 2010-05-20 | Merck Sharp & Dohme Corp. | Substituted bicyclic amines for the treatment of diabetes |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| CA2768577A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| WO2011011506A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Spirocyclic oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| AR077688A1 (es) | 2009-08-04 | 2011-09-14 | Takeda Pharmaceutical | Compuestos heterociclicos, utiles en el tratamiento de cancer |
| EP2470552B1 (en) | 2009-08-26 | 2013-11-13 | Sanofi | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
| EP2563764B1 (en) | 2010-04-26 | 2015-02-25 | Merck Sharp & Dohme Corp. | Novel spiropiperidine prolylcarboxypeptidase inhibitors |
| WO2011143057A1 (en) | 2010-05-11 | 2011-11-17 | Merck Sharp & Dohme Corp. | Novel prolylcarboxypeptidase inhibitors |
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| US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| KR20180032585A (ko) * | 2015-08-04 | 2018-03-30 | 아스테라스 세이야쿠 가부시키가이샤 | 피페라진 유도체 |
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-
2003
- 2003-10-20 TW TW092129035A patent/TW200504033A/zh unknown
- 2003-10-20 US US10/689,022 patent/US7132539B2/en not_active Expired - Fee Related
- 2003-10-22 PL PL376702A patent/PL376702A1/pl not_active Application Discontinuation
- 2003-10-22 CN CNA2003801009342A patent/CN1703221A/zh active Pending
- 2003-10-22 CA CA002501231A patent/CA2501231A1/en not_active Abandoned
- 2003-10-22 BR BR0315614-1A patent/BR0315614A/pt not_active IP Right Cessation
- 2003-10-22 WO PCT/US2003/033402 patent/WO2004037797A2/en active Application Filing
- 2003-10-22 KR KR1020057006836A patent/KR20050072445A/ko not_active Application Discontinuation
- 2003-10-22 JP JP2004546990A patent/JP2006506384A/ja active Pending
- 2003-10-22 PE PE2003001070A patent/PE20040778A1/es not_active Application Discontinuation
- 2003-10-22 MX MXPA05004378A patent/MXPA05004378A/es unknown
- 2003-10-22 AR ARP030103859A patent/AR043054A1/es not_active Application Discontinuation
- 2003-10-22 EP EP03777759A patent/EP1556361A2/en not_active Withdrawn
- 2003-10-22 RU RU2005111967/04A patent/RU2005111967A/ru not_active Application Discontinuation
- 2003-10-22 AU AU2003286557A patent/AU2003286557A1/en not_active Abandoned
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2005
- 2005-04-12 ZA ZA200502944A patent/ZA200502944B/en unknown
- 2005-04-25 MA MA28235A patent/MA27478A1/fr unknown
- 2005-05-23 NO NO20052476A patent/NO20052476L/no not_active Application Discontinuation
-
2006
- 2006-06-23 US US11/473,972 patent/US20060247224A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PL376702A1 (pl) | 2006-01-09 |
| JP2006506384A (ja) | 2006-02-23 |
| AU2003286557A1 (en) | 2004-05-13 |
| US20050010031A1 (en) | 2005-01-13 |
| MA27478A1 (fr) | 2005-08-01 |
| BR0315614A (pt) | 2005-08-30 |
| MXPA05004378A (es) | 2005-07-05 |
| TW200504033A (en) | 2005-02-01 |
| EP1556361A2 (en) | 2005-07-27 |
| NO20052476D0 (no) | 2005-05-23 |
| CN1703221A (zh) | 2005-11-30 |
| RU2005111967A (ru) | 2006-01-20 |
| CA2501231A1 (en) | 2004-05-06 |
| US7132539B2 (en) | 2006-11-07 |
| PE20040778A1 (es) | 2004-12-21 |
| NO20052476L (no) | 2005-05-23 |
| WO2004037797A3 (en) | 2004-11-04 |
| KR20050072445A (ko) | 2005-07-11 |
| WO2004037797A2 (en) | 2004-05-06 |
| AR043054A1 (es) | 2005-07-13 |
| US20060247224A1 (en) | 2006-11-02 |
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