DE60205465T2 - Piperazinderivate als agonisten des melanocortin-rezeptors - Google Patents
Piperazinderivate als agonisten des melanocortin-rezeptors Download PDFInfo
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- DE60205465T2 DE60205465T2 DE60205465T DE60205465T DE60205465T2 DE 60205465 T2 DE60205465 T2 DE 60205465T2 DE 60205465 T DE60205465 T DE 60205465T DE 60205465 T DE60205465 T DE 60205465T DE 60205465 T2 DE60205465 T2 DE 60205465T2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title description 91
- 239000000556 agonist Substances 0.000 title description 15
- 108090000950 Melanocortin Receptors Proteins 0.000 title description 9
- 102000004378 Melanocortin Receptors Human genes 0.000 title description 9
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 5
- 208000008589 Obesity Diseases 0.000 claims abstract description 11
- 235000020824 obesity Nutrition 0.000 claims abstract description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
- 206010057671 Female sexual dysfunction Diseases 0.000 claims abstract description 6
- 206010057672 Male sexual dysfunction Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 425
- 238000002360 preparation method Methods 0.000 claims description 315
- 239000000460 chlorine Substances 0.000 claims description 113
- 238000006243 chemical reaction Methods 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 83
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 76
- 238000010168 coupling process Methods 0.000 claims description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 45
- 238000005859 coupling reaction Methods 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 230000008878 coupling Effects 0.000 claims description 35
- 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 description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 230000015572 biosynthetic process Effects 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
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- 150000001412 amines Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
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- 102000004877 Insulin Human genes 0.000 claims description 17
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- 229940125396 insulin Drugs 0.000 claims description 17
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 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 description 14
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- 241000124008 Mammalia Species 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
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- 201000001881 impotence Diseases 0.000 claims description 9
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- 238000006845 Michael addition reaction Methods 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
- 229940122355 Insulin sensitizer Drugs 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 229940125898 compound 5 Drugs 0.000 claims description 4
- 238000006392 deoxygenation reaction Methods 0.000 claims description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 150000004713 phosphodiesters Chemical class 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 3
- 229940100389 Sulfonylurea Drugs 0.000 claims description 3
- 239000000674 adrenergic antagonist Substances 0.000 claims description 3
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 3
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 claims description 3
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 claims description 3
- 239000003529 anticholesteremic agent Substances 0.000 claims description 3
- 229940127226 anticholesterol agent Drugs 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims description 2
- 239000002660 neuropeptide Y receptor antagonist Substances 0.000 claims description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
- 229940126158 β3 adrenergic receptor agonist Drugs 0.000 claims description 2
- 239000000336 melanocortin receptor agonist Substances 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 475
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- 239000000243 solution Substances 0.000 description 253
- 239000000203 mixture Substances 0.000 description 213
- 235000019439 ethyl acetate Nutrition 0.000 description 199
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 196
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 131
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 85
- 239000012267 brine Substances 0.000 description 84
- 239000011734 sodium Substances 0.000 description 79
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 63
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 58
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 48
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- ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
- 229920006395 saturated elastomer Polymers 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
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- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 33
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- 239000008346 aqueous phase Substances 0.000 description 29
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 27
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- LNDQGWAWYKFYAO-UHFFFAOYSA-N tert-butyl 4-(2-aminophenyl)piperazine-1-carboxylate Chemical class C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC=C1N LNDQGWAWYKFYAO-UHFFFAOYSA-N 0.000 description 15
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 13
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Classifications
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P3/04—Anorexiants; Antiobesity agents
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D409/02—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Medicinal Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
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- Gynecology & Obstetrics (AREA)
- Child & Adolescent Psychology (AREA)
- Pregnancy & Childbirth (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26347101P | 2001-01-23 | 2001-01-23 | |
| US263471P | 2001-01-23 | ||
| PCT/US2002/000517 WO2002059108A1 (en) | 2001-01-23 | 2002-01-23 | Melanocortin receptor agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60205465D1 DE60205465D1 (de) | 2005-09-15 |
| DE60205465T2 true DE60205465T2 (de) | 2006-04-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60205465T Expired - Fee Related DE60205465T2 (de) | 2001-01-23 | 2002-01-23 | Piperazinderivate als agonisten des melanocortin-rezeptors |
| DE60205727T Expired - Fee Related DE60205727T2 (de) | 2001-01-23 | 2002-01-23 | Piperazin- und piperidinderivate als agonisten des melanocortin-rezeptors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60205727T Expired - Fee Related DE60205727T2 (de) | 2001-01-23 | 2002-01-23 | Piperazin- und piperidinderivate als agonisten des melanocortin-rezeptors |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7291619B2 (enExample) |
| EP (2) | EP1370558B1 (enExample) |
| JP (2) | JP2004523530A (enExample) |
| AT (2) | ATE302773T1 (enExample) |
| CA (2) | CA2432985A1 (enExample) |
| DE (2) | DE60205465T2 (enExample) |
| ES (2) | ES2246390T3 (enExample) |
| WO (2) | WO2002059108A1 (enExample) |
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| USRE46117E1 (en) | 1999-12-22 | 2016-08-23 | Teva Pharmaceuticals International Gmbh | Modulators of dopamine neurotransmission |
| SE9904723D0 (sv) | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
| SE9904724D0 (sv) | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission I |
| 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 |
| WO2002059108A1 (en) | 2001-01-23 | 2002-08-01 | Eli Lilly And Company | Melanocortin receptor agonists |
| CA2437594A1 (en) | 2001-03-02 | 2002-09-12 | Graham S. Poindexter | Compounds useful as modulators of melanocortin receptors and pharmaceutical compositions comprising same |
| US6911447B2 (en) | 2001-04-25 | 2005-06-28 | The Procter & Gamble Company | Melanocortin receptor ligands |
| 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 |
| 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 |
| 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 |
| UA81749C2 (uk) | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| EP1469851B1 (en) | 2002-01-23 | 2006-10-11 | Eli Lilly And Company | Melanocortin receptor agonists |
| US7026335B2 (en) | 2002-04-30 | 2006-04-11 | The Procter & Gamble Co. | Melanocortin receptor ligands |
| EP1503761A1 (en) * | 2002-05-10 | 2005-02-09 | Neurocrine Biosciences, Inc. | Substituted piperazines as melanocortin receptor ligands |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| CA2498272A1 (en) | 2002-09-11 | 2004-03-25 | Merck & Co., Inc. | Piperazine urea derivatives as melanocortin-4 receptor agonists |
| TW200504033A (en) | 2002-10-23 | 2005-02-01 | Procter & Gamble | Melanocortin receptor ligands |
| WO2004081643A1 (en) * | 2002-12-20 | 2004-09-23 | Kaiser Aerospace & Electronics Corp. | Lenslet array with polarization conversion |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| AR043434A1 (es) | 2003-03-03 | 2005-07-27 | Merck & Co Inc | Derivados de piperizacina acilados como agonistas del receptor de melanocortina-4. composiciones farmaceuticas y usos |
| WO2004081005A1 (en) * | 2003-03-07 | 2004-09-23 | Neurocrine Biosciences, Inc. | Melanin-concentrating hormone receptor antagonists and compositions and methods related thereto |
| US8013156B2 (en) | 2003-03-19 | 2011-09-06 | Exelixis, Inc. | Tie-2 modulators and methods of use |
| EP1468999A1 (en) * | 2003-03-20 | 2004-10-20 | MyoContract Ltd. | Substituted piperidine and piperazine derivatives as melanocortin-4 receptor modulators |
| EP1460069A1 (en) * | 2003-03-20 | 2004-09-22 | MyoContract Ltd. | Substituted cyclohexyl and piperidinyl derivatives as melanocortin-4 receptor modulators |
| JP2006521359A (ja) | 2003-03-26 | 2006-09-21 | 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−4受容体作働薬としての二環式ピペリジン誘導体 |
| AU2004265243A1 (en) * | 2003-06-20 | 2005-02-24 | Arena Pharmaceuticals, Inc. | N-phenyl-piperazine derivatives and methods of prophylaxis or treatment of 5HT2c receptor associated diseases |
| JP4765627B2 (ja) | 2003-09-22 | 2011-09-07 | Msd株式会社 | 新規ピペリジン誘導体 |
| US20050119252A1 (en) * | 2003-10-22 | 2005-06-02 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
| US20050192286A1 (en) * | 2003-10-22 | 2005-09-01 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
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| US7410971B2 (en) | 2003-12-26 | 2008-08-12 | Eisai R&D Management Co., Ltd. | 1,2-di(cyclic)substituted benzene compounds |
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| RU2366654C2 (ru) * | 2004-06-08 | 2009-09-10 | ЭнЭсЭйБи, ФИЛИАЛ АФ НЕУРОСЕРЧ СВИДЕН АБ, СВЕРИЙЕ | Новые дизамещенные фенилпиперидины/пиперазины в качестве модуляторов допаминовой нейротрансмиссии |
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| TW200633721A (en) * | 2004-12-14 | 2006-10-01 | Shionogi & Co | A pharmaceutical composition for treating constipation |
| WO2006068058A1 (ja) * | 2004-12-20 | 2006-06-29 | Eisai R & D Management Co., Ltd. | 1-シクロプロピルメチル-4-[2-(3,3,5,5-テトラメチルシクロヘキシル)フェニル]ピペラジンの塩および結晶 |
| RU2417985C2 (ru) | 2005-05-30 | 2011-05-10 | Баниу Фармасьютикал Ко., Лтд. | Новые производные пиперидина |
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| BRPI0616463A2 (pt) | 2005-09-29 | 2011-06-21 | Merck & Co Inc | composto, composição farmacêutica, e, uso de um composto |
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| EP1944301A4 (en) | 2005-10-27 | 2012-01-04 | Msd Kk | NEW BENZOXATHIIN DERIVATIVES |
| US8158791B2 (en) | 2005-11-10 | 2012-04-17 | Msd K.K. | Aza-substituted spiro derivatives |
| US7601844B2 (en) * | 2006-01-27 | 2009-10-13 | Bristol-Myers Squibb Company | Piperidinyl derivatives as modulators of chemokine receptor activity |
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2002
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- 2002-01-23 AT AT02701922T patent/ATE302773T1/de not_active IP Right Cessation
- 2002-01-23 ES ES02714719T patent/ES2246390T3/es not_active Expired - Lifetime
- 2002-01-23 CA CA002432985A patent/CA2432985A1/en not_active Abandoned
- 2002-01-23 JP JP2002559419A patent/JP2004523530A/ja active Pending
- 2002-01-23 JP JP2002559410A patent/JP2004523529A/ja active Pending
- 2002-01-23 DE DE60205465T patent/DE60205465T2/de not_active Expired - Fee Related
- 2002-01-23 ES ES02701922T patent/ES2247298T3/es not_active Expired - Lifetime
- 2002-01-23 CA CA002431996A patent/CA2431996A1/en not_active Abandoned
- 2002-01-23 US US10/466,121 patent/US7291619B2/en not_active Expired - Fee Related
- 2002-01-23 DE DE60205727T patent/DE60205727T2/de not_active Expired - Fee Related
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- 2002-01-23 EP EP02714719A patent/EP1368340B1/en not_active Expired - Lifetime
- 2002-01-23 WO PCT/US2002/000515 patent/WO2002059117A1/en not_active Ceased
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| EP1368340A1 (en) | 2003-12-10 |
| CA2431996A1 (en) | 2002-08-01 |
| WO2002059117A1 (en) | 2002-08-01 |
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| US7291619B2 (en) | 2007-11-06 |
| DE60205727T2 (de) | 2006-06-29 |
| EP1368340B1 (en) | 2005-08-10 |
| WO2002059117A8 (en) | 2003-11-06 |
| US20040092507A1 (en) | 2004-05-13 |
| EP1370558B1 (en) | 2005-08-24 |
| ES2246390T3 (es) | 2006-02-16 |
| ES2247298T3 (es) | 2006-03-01 |
| DE60205465D1 (de) | 2005-09-15 |
| US20040082590A1 (en) | 2004-04-29 |
| ATE301652T1 (de) | 2005-08-15 |
| US7186715B2 (en) | 2007-03-06 |
| JP2004523530A (ja) | 2004-08-05 |
| JP2004523529A (ja) | 2004-08-05 |
| CA2432985A1 (en) | 2002-08-01 |
| EP1370558A1 (en) | 2003-12-17 |
| WO2002059108A1 (en) | 2002-08-01 |
| DE60205727D1 (de) | 2005-09-29 |
| ATE302773T1 (de) | 2005-09-15 |
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