JP2005527492A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005527492A5 JP2005527492A5 JP2003561604A JP2003561604A JP2005527492A5 JP 2005527492 A5 JP2005527492 A5 JP 2005527492A5 JP 2003561604 A JP2003561604 A JP 2003561604A JP 2003561604 A JP2003561604 A JP 2003561604A JP 2005527492 A5 JP2005527492 A5 JP 2005527492A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- phenyl
- aryl
- hydrogen
- 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.)
- Pending
Links
- NQKOOIJJWDMYSO-UHFFFAOYSA-N n-[3-(4-chlorophenyl)-1-[4-[1-(diethylaminomethyl)cyclopentyl]piperazin-1-yl]-1-oxopropan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C1CN(C(=O)C(CC=2C=CC(Cl)=CC=2)NC(=O)C2NCC3=CC=CC=C3C2)CCN1C1(CN(CC)CC)CCCC1 NQKOOIJJWDMYSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 99
- 150000001875 compounds Chemical class 0.000 claims 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 70
- 125000003118 aryl group Chemical group 0.000 claims 53
- 229910052739 hydrogen Inorganic materials 0.000 claims 53
- 239000001257 hydrogen Substances 0.000 claims 53
- 125000000753 cycloalkyl group Chemical group 0.000 claims 52
- 125000001072 heteroaryl group Chemical group 0.000 claims 37
- 125000005843 halogen group Chemical group 0.000 claims 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 33
- 150000002431 hydrogen Chemical class 0.000 claims 29
- 229910052799 carbon Inorganic materials 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- -1 perfluoro Chemical group 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000005842 heteroatom Chemical group 0.000 claims 17
- 125000004043 oxo group Chemical group O=* 0.000 claims 14
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 12
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 11
- 150000001721 carbon Chemical group 0.000 claims 11
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 2
- 206010057672 Male sexual dysfunction Diseases 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 238000006845 Michael addition reaction Methods 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical group FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- 229940122355 Insulin sensitizer Drugs 0.000 claims 1
- 101710151321 Melanostatin Proteins 0.000 claims 1
- 102400000064 Neuropeptide Y Human genes 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 239000000674 adrenergic antagonist Substances 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 claims 1
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000003529 anticholesteremic agent Substances 0.000 claims 1
- 229940127226 anticholesterol agent Drugs 0.000 claims 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims 1
- 102000016959 beta-3 Adrenergic Receptors Human genes 0.000 claims 1
- 108010014502 beta-3 Adrenergic Receptors Proteins 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 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 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000006392 deoxygenation reaction Methods 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229940125396 insulin Drugs 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
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims 1
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 150000004713 phosphodiesters Chemical class 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 C*(C*(C)NC1)CC2=C1C=CC=C*2* Chemical compound C*(C*(C)NC1)CC2=C1C=CC=C*2* 0.000 description 26
- DOWKXUBAZLPNCR-YAPMYUJQSA-N CC(C)CC1(CN(C)CCC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC1(CN(C)CCC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O DOWKXUBAZLPNCR-YAPMYUJQSA-N 0.000 description 2
- UDANECZMJKIQTJ-UHFFFAOYSA-N CC(C)CC1NCc2c1cccc2 Chemical compound CC(C)CC1NCc2c1cccc2 UDANECZMJKIQTJ-UHFFFAOYSA-N 0.000 description 2
- AMJQHOGLKIZODY-UHFFFAOYSA-N CC(C)CC(C1)NCc2c1cccc2 Chemical compound CC(C)CC(C1)NCc2c1cccc2 AMJQHOGLKIZODY-UHFFFAOYSA-N 0.000 description 1
- ZNWANTUKXKBZLP-NLIBRCFJSA-N CC(C)CC(CC1)(CCN1C(C)=O)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC(CC1)(CCN1C(C)=O)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O ZNWANTUKXKBZLP-NLIBRCFJSA-N 0.000 description 1
- GSXDYZPMLCQEKT-IADGFXSZSA-N CC(C)CC(CC1)(CCN1C(C)C)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC(CC1)(CCN1C(C)C)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O GSXDYZPMLCQEKT-IADGFXSZSA-N 0.000 description 1
- DZCIIANMVNXADX-BDCODIICSA-N CC(C)CC(CC1)(CCN1S(C)(=O)=O)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC(CC1)(CCN1S(C)(=O)=O)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O DZCIIANMVNXADX-BDCODIICSA-N 0.000 description 1
- OKDLDIPTQLRFQX-YPJJGMIRSA-N CC(C)CC(CC1)(CCS1(=O)=O)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC(CC1)(CCS1(=O)=O)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O OKDLDIPTQLRFQX-YPJJGMIRSA-N 0.000 description 1
- WNMZATNMIABFKL-YPJJGMIRSA-N CC(C)CC1(CCCC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC1(CCCC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O WNMZATNMIABFKL-YPJJGMIRSA-N 0.000 description 1
- LWBXLZBGWUEHNG-BDCODIICSA-N CC(C)CC1(CCN(C)CC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CC(C)CC1(CCN(C)CC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O LWBXLZBGWUEHNG-BDCODIICSA-N 0.000 description 1
- GGUJTJQWIKRQER-UHFFFAOYSA-N CC(C)CC1(CCOCC1)N(CC1)CCN1C(C(Cc(cc1)ccc1Cl)NC(CC1NCc2ccccc12)=O)=O Chemical compound CC(C)CC1(CCOCC1)N(CC1)CCN1C(C(Cc(cc1)ccc1Cl)NC(CC1NCc2ccccc12)=O)=O GGUJTJQWIKRQER-UHFFFAOYSA-N 0.000 description 1
- UKQFTLKHLRAOAG-UHFFFAOYSA-N CC(C1=CC=CC(C)(C)C=C1C1)(NC=C)NC1C(C)=O Chemical compound CC(C1=CC=CC(C)(C)C=C1C1)(NC=C)NC1C(C)=O UKQFTLKHLRAOAG-UHFFFAOYSA-N 0.000 description 1
- ZBUVKSGDTHZTBY-NLIBRCFJSA-N CCN(CC1)CCC1(CC(C)C)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CCN(CC1)CCC1(CC(C)C)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O ZBUVKSGDTHZTBY-NLIBRCFJSA-N 0.000 description 1
- NMKAUOMKZJYMKD-ZHZZGXISSA-N CN(CC1)CCC1(CC1CCCCC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CN(CC1)CCC1(CC1CCCCC1)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O NMKAUOMKZJYMKD-ZHZZGXISSA-N 0.000 description 1
- URZOMUOVTVPPBR-ZHZZGXISSA-N CN(CC1)CCC1(Cc(cccc1)c1F)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O Chemical compound CN(CC1)CCC1(Cc(cccc1)c1F)N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)NC(CC1NCc2c1cccc2)=O)=O URZOMUOVTVPPBR-ZHZZGXISSA-N 0.000 description 1
- DMGMOBQHTSJVTI-PKEIRNPWSA-N C[C@H](C1)N(C2)C1Cc1c2cccc1 Chemical compound C[C@H](C1)N(C2)C1Cc1c2cccc1 DMGMOBQHTSJVTI-PKEIRNPWSA-N 0.000 description 1
- DMGMOBQHTSJVTI-BXKDBHETSA-N C[C@H](C1)N(C2)[C@H]1Cc1c2cccc1 Chemical compound C[C@H](C1)N(C2)[C@H]1Cc1c2cccc1 DMGMOBQHTSJVTI-BXKDBHETSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35120002P | 2002-01-23 | 2002-01-23 | |
| PCT/US2003/000033 WO2003061660A1 (en) | 2002-01-23 | 2003-01-21 | Melanocortin receptor agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005527492A JP2005527492A (ja) | 2005-09-15 |
| JP2005527492A5 true JP2005527492A5 (enExample) | 2006-02-02 |
Family
ID=27613471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003561604A Pending JP2005527492A (ja) | 2002-01-23 | 2003-01-21 | メラノコルチン受容体アゴニスト |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7314879B2 (enExample) |
| EP (1) | EP1469851B1 (enExample) |
| JP (1) | JP2005527492A (enExample) |
| AT (1) | ATE342057T1 (enExample) |
| CA (1) | CA2473036A1 (enExample) |
| DE (1) | DE60308996T2 (enExample) |
| ES (1) | ES2274201T3 (enExample) |
| WO (1) | WO2003061660A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235625B2 (en) | 1999-06-29 | 2007-06-26 | Palatin Technologies, Inc. | Multiple agent therapy for sexual dysfunction |
| US7115607B2 (en) | 2001-07-25 | 2006-10-03 | Amgen Inc. | Substituted piperazinyl amides and methods of use |
| US6977264B2 (en) | 2001-07-25 | 2005-12-20 | Amgen Inc. | Substituted piperidines and methods of use |
| JP2005504043A (ja) | 2001-08-10 | 2005-02-10 | パラチン テクノロジーズ インク． | 生物学的に活性な金属ペプチド類のペプチド模倣体類 |
| US7456184B2 (en) | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
| US7354923B2 (en) | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
| TW200504033A (en) | 2002-10-23 | 2005-02-01 | Procter & Gamble | Melanocortin receptor ligands |
| US7550602B1 (en) | 2004-01-14 | 2009-06-23 | Palatin Technologies, Inc. | Small molecule compositions for sexual dysfunction |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| FR2873693B1 (fr) | 2004-07-29 | 2006-09-15 | Sanofi Synthelabo | Derives d'amino-tropane, leur preparation et leur application en therapeutique |
| US20070021433A1 (en) | 2005-06-03 | 2007-01-25 | Jian-Qiang Fan | Pharmacological chaperones for treating obesity |
| BRPI0616463A2 (pt) | 2005-09-29 | 2011-06-21 | Merck & Co Inc | composto, composição farmacêutica, e, uso de um composto |
| US7652024B2 (en) | 2005-10-18 | 2010-01-26 | Merck Sharp & Dohme Corp. | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
| GB0624987D0 (en) | 2006-12-14 | 2007-01-24 | Acure Pharma Ab | Novel aminoguanidines as melanocortin receptor ligands |
| EP2300036B1 (en) * | 2008-06-09 | 2017-04-05 | Palatin Technologies, Inc. | Melanocortin receptor-specific peptides for treatment of sexual dysfunction |
| US8227628B2 (en) | 2008-07-09 | 2012-07-24 | Northwestern University | Method of synthesizing acetonide-protected catechol-containing compounds and intermediates produced therein |
| JP5514831B2 (ja) | 2008-11-17 | 2014-06-04 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病の治療のための置換二環式アミン |
| EP2413701A4 (en) * | 2009-03-31 | 2012-10-03 | Univ Vanderbilt | SULFONYL-AZETIDIN-3-YL-METHYLAMINE AMIDE ANALOGUES AS GLYT1 INHIBITORS, METHODS OF MAKING THEM AND USE THEREOF IN THE TREATMENT OF PSYCHIATRIC DISORDERS |
| WO2011011506A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Spirocyclic oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| US20120220567A1 (en) | 2009-07-23 | 2012-08-30 | Shipps Jr Gerald W | Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
| WO2011137024A1 (en) | 2010-04-26 | 2011-11-03 | Merck Sharp & Dohme Corp. | Novel spiropiperidine prolylcarboxypeptidase inhibitors |
| EP2568812B1 (en) | 2010-05-11 | 2016-10-26 | Merck Sharp & Dohme Corp. | Novel prolylcarboxypeptidase inhibitors |
| SG186885A1 (en) | 2010-06-04 | 2013-02-28 | Albany Molecular Res Inc | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| EP2579873A4 (en) | 2010-06-11 | 2013-11-27 | Merck Sharp & Dohme | NOVEL PROLYLCARBOXYPEPTIDASE HEMMER |
| US8916563B2 (en) | 2010-07-16 | 2014-12-23 | The Trustees Of Columbia University In The City Of New York | Aldose reductase inhibitors and uses thereof |
| HUE047346T2 (hu) | 2010-07-16 | 2020-04-28 | Univ Columbia | Aldóz reduktáz inhibitorok és alkalmazásuk |
| EP2632464B1 (en) * | 2010-10-29 | 2015-04-29 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2012100342A1 (en) | 2011-01-27 | 2012-08-02 | Université de Montréal | Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators |
| ES2847934T3 (es) | 2013-06-05 | 2021-08-04 | Shanghai Lumosa Therapeutics Co Ltd | Nuevos compuestos que tienen actividades triples de trombólisis, antitrombóticos y captadores de radicales, y síntesis, nanoestructura y uso de los mismos |
| EP3333165B1 (en) * | 2015-08-04 | 2019-09-18 | Astellas Pharma Inc. | Piperazine derivative |
| AR105654A1 (es) * | 2015-08-24 | 2017-10-25 | Lilly Co Eli | Anticuerpos pd-l1 (ligando 1 de muerte celular programada) |
| PT3352754T (pt) | 2016-06-21 | 2020-12-07 | Univ Columbia | Inibidores da aldose redutase e métodos de seu uso |
| PT3489231T (pt) | 2016-07-19 | 2021-07-14 | Astellas Pharma Inc | Derivado de piperazina |
| IL272246B1 (en) | 2017-07-28 | 2025-09-01 | Applied Therapeutics Inc | Derivatives of 2-(4-oxo/thioketone/azo-3-((substituted)benzo[d]thiazol-2-yl)methyl)- 3,4-dihydrothieno[3,4-d]pyridazin-1-yl)acetic acid for use as aldose reductase inhibitors in treating galactosemia or preventing complications associated with galactosemia |
| EP3966320A4 (en) | 2019-05-07 | 2023-10-25 | University of Miami | TREATMENT AND DETECTION OF HEREDITARY NEUROPATHIES AND ASSOCIATED DISORDERS |
| US11590209B2 (en) | 2020-01-21 | 2023-02-28 | Palatin Technologies, Inc. | Use of bremelanotide in patients with controlled hypertension |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT72076A (en) | 1992-12-11 | 1996-03-28 | Merck & Co Inc | Process for preparing spiro piperidines and homologs which promote release of growth hormone and pharmaceutical compositions containing them |
| US6127381A (en) | 1998-04-28 | 2000-10-03 | Basu; Amaresh | Isoquinoline compound melanocortin receptor ligands and methods of using same |
| AU742425B2 (en) * | 1998-06-11 | 2002-01-03 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| US6294534B1 (en) * | 1998-06-11 | 2001-09-25 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| CA2377369A1 (en) | 1999-06-04 | 2000-12-14 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
| JP2003528088A (ja) | 2000-03-23 | 2003-09-24 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作働薬としての置換ピペリジン類 |
| WO2001070337A1 (en) | 2000-03-23 | 2001-09-27 | Merck & Co., Inc. | Spiropiperidine derivatives as melanocortin receptor agonists |
| JP2004506687A (ja) | 2000-08-23 | 2004-03-04 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作働薬としての置換ピペリジン類 |
| WO2002059108A1 (en) | 2001-01-23 | 2002-08-01 | Eli Lilly And Company | Melanocortin receptor agonists |
| CA2433025A1 (en) | 2001-01-23 | 2002-08-01 | Chaoyu Xie | Substituted piperidines/piperazines as melanocortin receptor agonists |
| JP2004524297A (ja) | 2001-01-23 | 2004-08-12 | イーライ・リリー・アンド・カンパニー | メラノコルチン受容体アゴニスト |
| CA2437594A1 (en) | 2001-03-02 | 2002-09-12 | Graham S. Poindexter | Compounds useful as modulators of melanocortin receptors and pharmaceutical compositions comprising same |
| EP1465867A1 (en) * | 2001-10-09 | 2004-10-13 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
-
2003
- 2003-01-21 EP EP03701964A patent/EP1469851B1/en not_active Expired - Lifetime
- 2003-01-21 US US10/500,476 patent/US7314879B2/en not_active Expired - Fee Related
- 2003-01-21 CA CA002473036A patent/CA2473036A1/en not_active Abandoned
- 2003-01-21 AT AT03701964T patent/ATE342057T1/de not_active IP Right Cessation
- 2003-01-21 JP JP2003561604A patent/JP2005527492A/ja active Pending
- 2003-01-21 DE DE60308996T patent/DE60308996T2/de not_active Expired - Fee Related
- 2003-01-21 ES ES03701964T patent/ES2274201T3/es not_active Expired - Lifetime
- 2003-01-21 WO PCT/US2003/000033 patent/WO2003061660A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005527492A5 (enExample) | ||
| JP2004521117A5 (enExample) | ||
| RU2005118409A (ru) | Новые гидроксииндолы, их применение в качестве ингибиторов фосфодиэстеразы 4 и способ их получения | |
| RU2388750C2 (ru) | Ингибиторы фосфодиэстеразы 4, включая аналоги n-замещенного диариламина | |
| Naylor et al. | A potent new class of. kappa.-receptor agonist: 4-substituted 1-(arylacetyl)-2-[(dialkylamino) methyl] piperazines | |
| ES2524916T3 (es) | Compuestos heterocíclicos de ácido borónico | |
| ES2549087T3 (es) | Derivados de aminodihidrotiazina como inhibidores de BACE para el tratamiento de la enfermedad de Alzheimer | |
| FI106200B (fi) | Menetelmä terapeuttisesti käyttökelpoisten piperatsiinijohdannaisten valmistamiseksi | |
| US6777437B2 (en) | Cyclopropylindole derivatives as selective serotonin reuptake inhibitors | |
| US20040082661A1 (en) | Urea derivatives having vanilloid receptor (vr1) antagonist activity | |
| ES2199433T5 (es) | 3,3-diarilpropilaminas, su uso y preparacion. | |
| ZA200603941B (en) | Derivatives of N-[heteroaryl(piperidine-2-yl)methyl]benzamide, preparation method thereof and application of same in therapeutics | |
| JP2008013556A (ja) | 新規ナフタレン化合物、その製造法、およびそれを含有する薬学的組成物 | |
| RU2002101935A (ru) | Аминовые и амидные производные как лиганды для рецептора Y5 нейропептида Y, используемые для лечения ожирения и других расстройств | |
| PL202473B1 (pl) | Związki stanowiące 1,3-dwupodstawione pochodne pirolidyny, sposoby otrzymywania takich związków, kompozycje zawierające takie związki oraz ich zastosowanie | |
| ZA200603942B (en) | Derivatives of N-[phenyl(alkylpiperidine-2-yl)methyl]benzamide, preparation method thereof and application of same in therapeutics | |
| NL1025933C2 (nl) | 4-Fenyl-piperidineverbindingen en de toepassing ervan als modulatoren van opioïde receptoren. | |
| CA2369103A1 (en) | Nitrogen-containing heterocyclic compounds and benamide compounds and drugs containing the same | |
| CA2718959A1 (en) | Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain | |
| KR100258657B1 (ko) | 피롤리딘일 하이드록삼산 화합물 및 그의 제조 방법 | |
| RU2010113358A (ru) | Гуанидинсодержащие соединения, применимые в качестве антагонистов мускариновых рецепторов | |
| Van Emelen et al. | Synthesis of cis-fused hexahydro-4aH-indeno [1, 2-b] pyridines via intramolecular Ritter reaction and their conversion into tricyclic analogues of NK-1 and dopamine receptor ligands | |
| CA2694313A1 (fr) | Derives de 1-oxo-1,2-dihydroisoquinoleine-5-carboxamides et de 4-oxo-3,4-dihydroquinazoline-8-carboxamides, leur preparation et leur application en therapeutique | |
| KR101176675B1 (ko) | 테트라히드로이소퀴놀린 술폰아미드 유도체, 이의 제조, 및치료에서의 이의 용도 | |
| JP7185633B2 (ja) | ７員アザ複素環を含有するデルタ－オピオイド受容体調節化合物、その使用方法及び製造方法 |