CN100383124C - 作为npy拮抗剂的喹啉衍生物 - Google Patents
作为npy拮抗剂的喹啉衍生物 Download PDFInfo
- Publication number
- CN100383124C CN100383124C CNB038032805A CN03803280A CN100383124C CN 100383124 C CN100383124 C CN 100383124C CN B038032805 A CNB038032805 A CN B038032805A CN 03803280 A CN03803280 A CN 03803280A CN 100383124 C CN100383124 C CN 100383124C
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- CN
- China
- Prior art keywords
- methyl
- tetramethyleneimine
- quinoline
- alkyl
- compound
- 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.)
- Expired - Fee Related
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 5
- 239000005557 antagonist Substances 0.000 title description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 208000008589 Obesity Diseases 0.000 claims abstract description 16
- 235000020824 obesity Nutrition 0.000 claims abstract description 16
- 208000030814 Eating disease Diseases 0.000 claims abstract description 15
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 15
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 15
- 230000002265 prevention Effects 0.000 claims abstract description 15
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 13
- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 13
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 13
- 201000006370 kidney failure Diseases 0.000 claims abstract description 13
- 206010003246 arthritis Diseases 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- -1 benzylcarbonyl Chemical group 0.000 claims description 63
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 17
- 229960001243 orlistat Drugs 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000006307 alkoxy benzyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- QWLSZMHCDHNODH-UHFFFAOYSA-N 2,2-dimethyl-n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)propanamide Chemical compound C=12C=CC(NC(=O)C(C)(C)C)=CC2=NC(C)=CC=1N1CCCC1 QWLSZMHCDHNODH-UHFFFAOYSA-N 0.000 claims 1
- BLIFSQROOJKZEL-UHFFFAOYSA-N 2-methyl-4-pyrrolidin-1-yl-n-(thiophen-2-ylmethyl)quinolin-7-amine Chemical compound C=12C=CC(NCC=3SC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 BLIFSQROOJKZEL-UHFFFAOYSA-N 0.000 claims 1
- HUDWZKOJYXHMGZ-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)-4-pyrrolidin-1-ylquinolin-7-amine Chemical compound C=1C(C)=NC2=CC(NCC(C)C)=CC=C2C=1N1CCCC1 HUDWZKOJYXHMGZ-UHFFFAOYSA-N 0.000 claims 1
- PGBJQQCVESMMIM-UHFFFAOYSA-N 3-methyl-n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)butanamide Chemical compound C=1C(C)=NC2=CC(NC(=O)CC(C)C)=CC=C2C=1N1CCCC1 PGBJQQCVESMMIM-UHFFFAOYSA-N 0.000 claims 1
- YIAYAZXGXKSBRM-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)amino]benzonitrile Chemical compound C=12C=CC(NC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 YIAYAZXGXKSBRM-UHFFFAOYSA-N 0.000 claims 1
- MVJVQMRGBDNHOW-SFHVURJKSA-N 4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methyl-n-pyridin-3-ylquinolin-7-amine Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(NC=3C=NC=CC=3)=CC=C12 MVJVQMRGBDNHOW-SFHVURJKSA-N 0.000 claims 1
- HAYLQPXSZLDLQK-KRWDZBQOSA-N 4-[(3s)-3-methoxypyrrolidin-1-yl]-2-methyl-n-pyridin-3-ylquinolin-7-amine Chemical compound C1[C@@H](OC)CCN1C1=CC(C)=NC2=CC(NC=3C=NC=CC=3)=CC=C12 HAYLQPXSZLDLQK-KRWDZBQOSA-N 0.000 claims 1
- SRNUHYAZNVNSKZ-HXUWFJFHSA-N 4-[[4-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]amino]benzonitrile Chemical compound COC[C@H]1CCCN1C1=CC(C)=NC2=CC(NC=3C=CC(=CC=3)C#N)=CC=C12 SRNUHYAZNVNSKZ-HXUWFJFHSA-N 0.000 claims 1
- YAVPLAQEQDEVLN-IBGZPJMESA-N 4-[[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]amino]benzonitrile Chemical compound C=12C=CC(NC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCC[C@H]1CO YAVPLAQEQDEVLN-IBGZPJMESA-N 0.000 claims 1
- VDQKHTJHDWFTLL-FQEVSTJZSA-N 4-[[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]amino]benzonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(NC=3C=CC(=CC=3)C#N)=CC=C12 VDQKHTJHDWFTLL-FQEVSTJZSA-N 0.000 claims 1
- CLTYJMAMVSIRCT-UHFFFAOYSA-N 4-cyano-n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)benzamide Chemical compound C=12C=CC(NC(=O)C=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 CLTYJMAMVSIRCT-UHFFFAOYSA-N 0.000 claims 1
- DRZKMEMZVIYCJK-UHFFFAOYSA-N 4-fluoro-n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)benzamide Chemical compound C=12C=CC(NC(=O)C=3C=CC(F)=CC=3)=CC2=NC(C)=CC=1N1CCCC1 DRZKMEMZVIYCJK-UHFFFAOYSA-N 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- QFTGJUGWYARDAE-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-2-methyl-4-pyrrolidin-1-ylquinolin-7-amine Chemical compound C=12C=CC(NCC(C)(C)C)=CC2=NC(C)=CC=1N1CCCC1 QFTGJUGWYARDAE-UHFFFAOYSA-N 0.000 claims 1
- LTWIZCJNLPPYKO-UHFFFAOYSA-N n-(2,6-dimethyl-4-pyrrolidin-1-ylquinolin-7-yl)furan-2-carboxamide Chemical compound C=12C=C(C)C(NC(=O)C=3OC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 LTWIZCJNLPPYKO-UHFFFAOYSA-N 0.000 claims 1
- WDHFAKVAPOJMFZ-UHFFFAOYSA-N n-(2,6-dimethyl-4-pyrrolidin-1-ylquinolin-7-yl)propanamide Chemical compound C=12C=C(C)C(NC(=O)CC)=CC2=NC(C)=CC=1N1CCCC1 WDHFAKVAPOJMFZ-UHFFFAOYSA-N 0.000 claims 1
- BLPGQNHKFXUPKN-UHFFFAOYSA-N n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)cyclopropanecarboxamide Chemical compound C=12C=CC(NC(=O)C3CC3)=CC2=NC(C)=CC=1N1CCCC1 BLPGQNHKFXUPKN-UHFFFAOYSA-N 0.000 claims 1
- HUACSPMJAPGPNA-UHFFFAOYSA-N n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methanesulfonamide Chemical compound C=12C=CC(NS(C)(=O)=O)=CC2=NC(C)=CC=1N1CCCC1 HUACSPMJAPGPNA-UHFFFAOYSA-N 0.000 claims 1
- UPTVWHNDQOIPGI-UHFFFAOYSA-N n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)pyridine-3-carboxamide Chemical compound C=12C=CC(NC(=O)C=3C=NC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 UPTVWHNDQOIPGI-UHFFFAOYSA-N 0.000 claims 1
- SCJXKKGZNILJAE-UHFFFAOYSA-N n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)pyridine-3-sulfonamide Chemical compound C=12C=CC(NS(=O)(=O)C=3C=NC=CC=3)=CC2=NC(C)=CC=1N1CCCC1 SCJXKKGZNILJAE-UHFFFAOYSA-N 0.000 claims 1
- PMJPHEAEMAOVPH-UHFFFAOYSA-N n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)pyridine-4-carboxamide Chemical compound C=12C=CC(NC(=O)C=3C=CN=CC=3)=CC2=NC(C)=CC=1N1CCCC1 PMJPHEAEMAOVPH-UHFFFAOYSA-N 0.000 claims 1
- OEXALPOPMDOTQQ-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]-2-methyl-4-pyrrolidin-1-ylquinolin-7-amine Chemical compound COC1=CC=CC=C1CNC1=CC=C(C(=CC(C)=N2)N3CCCC3)C2=C1 OEXALPOPMDOTQQ-UHFFFAOYSA-N 0.000 claims 1
- MOCIVXBVXMYZJB-HNNXBMFYSA-N n-[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]furan-2-carboxamide Chemical compound C=12C=CC(NC(=O)C=3OC=CC=3)=CC2=NC(C)=CC=1N1CCC[C@H]1CO MOCIVXBVXMYZJB-HNNXBMFYSA-N 0.000 claims 1
- CGXHQPCFJBXZHQ-KRWDZBQOSA-N n-[4-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]pyridine-3-carboxamide Chemical compound C=12C=CC(NC(=O)C=3C=NC=CC=3)=CC2=NC(C)=CC=1N1CCC[C@H]1CO CGXHQPCFJBXZHQ-KRWDZBQOSA-N 0.000 claims 1
- NSMBHSBPIXQKEZ-INIZCTEOSA-N n-[4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-2-methylquinolin-7-yl]cyclopropanecarboxamide Chemical compound COC[C@@H]1CCCN1C1=CC(C)=NC2=CC(NC(=O)C3CC3)=CC=C12 NSMBHSBPIXQKEZ-INIZCTEOSA-N 0.000 claims 1
- RVXIRRIRHVHATB-INIZCTEOSA-N n-[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]cyclopropanecarboxamide Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(NC(=O)C3CC3)=CC=C12 RVXIRRIRHVHATB-INIZCTEOSA-N 0.000 claims 1
- QYBCQTIWTCSCPL-HNNXBMFYSA-N n-[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2-methylquinolin-7-yl]propanamide Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(NC(=O)CC)=CC=C12 QYBCQTIWTCSCPL-HNNXBMFYSA-N 0.000 claims 1
- RGEWMROOVIYXOZ-UHFFFAOYSA-N n-methyl-n-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)pyridine-3-carboxamide Chemical compound C=1C=C2C(N3CCCC3)=CC(C)=NC2=CC=1N(C)C(=O)C1=CC=CN=C1 RGEWMROOVIYXOZ-UHFFFAOYSA-N 0.000 claims 1
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- 238000001819 mass spectrum Methods 0.000 description 130
- 239000007787 solid Substances 0.000 description 107
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 45
- 239000002585 base Substances 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- 102400000064 Neuropeptide Y Human genes 0.000 description 14
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- 239000002904 solvent Substances 0.000 description 13
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 12
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
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- 239000002671 adjuvant Substances 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 239000007789 gas Substances 0.000 description 6
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 6
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
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- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 235000002374 tyrosine Nutrition 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
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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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
-
- 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
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US6900226B2 (en) * | 2000-09-06 | 2005-05-31 | Hoffman-La Roche Inc. | Neuropeptide Y antagonists |
| JP2004110367A (ja) * | 2002-09-18 | 2004-04-08 | Hitachi Ltd | 記憶装置システムの制御方法、記憶制御装置、および記憶装置システム |
| WO2005030754A1 (en) * | 2003-09-24 | 2005-04-07 | Janssen Pharmaceutica, N.V. | Indole or quinoline derivatives as non-pepticid npy y2 receptor inhibitors useful for the treatment of anxiolytic and depressive disorders and obesity |
| JP4768628B2 (ja) | 2003-11-19 | 2011-09-07 | アレイ バイオファーマ、インコーポレイテッド | Ｍｅｋの二環系阻害剤及びその使用方法 |
| EP2305352A1 (en) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | 5-alpha-reductase inhibitors for use in the treatment of men with metabolic and anthropometric disorders |
| AU2006299671A1 (en) * | 2005-10-05 | 2007-04-12 | Merck Frosst Canada Ltd | Substituted quinolines as inhibitors of leukotriene biosynthesis |
| RU2314295C2 (ru) * | 2006-03-01 | 2008-01-10 | Федеральное Государственное Образовательное Учреждение Высшего Профессионального Образования "Южный Федеральный Университет" | 2-гетарилзамещенные 1,3-трополона, способ их получения (варианты) и фармацевтическая композиция антимикробного действия |
| WO2008141077A1 (en) * | 2007-05-10 | 2008-11-20 | Janssen Pharmaceutica N.V. | Process for the preparation of tetrahydroquinolinyl, benzoxazine and benzothiazine derivatives |
| EP2182950B8 (en) * | 2007-05-17 | 2017-08-23 | Helperby Therapeutics Limited | Use of 4-(pyrrolidin-1-yl)quinoline compounds to kill clinically latent microorganisms |
| WO2010056865A1 (en) * | 2008-11-14 | 2010-05-20 | Gilead Palo Alto, Inc. | Quinoline derivatives as ion channel modulators |
| AR077292A1 (es) * | 2009-06-29 | 2011-08-17 | Agios Pharmaceuticals Inc | Derivados de piperazin - quinolin sulfonamidas y composiciones farmaceuticas |
| US20120142944A1 (en) * | 2010-12-03 | 2012-06-07 | Dow Agrosciences Llc | Processes for the preparation of enamines |
| EP2675787B1 (en) | 2011-02-18 | 2018-03-28 | Endo Pharmaceuticals Inc. | Aminoindane compounds and use thereof in treating pain |
| CA2839703A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| PE20140868A1 (es) | 2011-06-24 | 2014-07-18 | Amgen Inc | Antagonistas trpm8 y su uso en tratamientos |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| WO2014028675A1 (en) | 2012-08-15 | 2014-02-20 | Endo Pharmaceuticals Inc. | Use of aminoindane compounds in treating overactive bladder and interstitial cystitis |
| RS59007B1 (sr) | 2014-02-03 | 2019-08-30 | Vitae Pharmaceuticals Llc | Dihidropirolopiridinski inhibitori ror-gama |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| WO2017024018A1 (en) | 2015-08-05 | 2017-02-09 | Vitae Pharmaceuticals, Inc. | Modulators of ror-gamma |
| KR20180086221A (ko) * | 2015-11-20 | 2018-07-30 | 비타이 파마슈티컬즈, 인코포레이티드 | Ror-감마의 조절물질 |
| TW202220968A (zh) | 2016-01-29 | 2022-06-01 | 美商維它藥物有限責任公司 | ＲＯＲ－γ調節劑 |
| RS63776B1 (sr) * | 2016-07-14 | 2022-12-30 | Crinetics Pharmaceuticals Inc | Modulatori somatostatina i njihove upotrebe |
| TWI774767B (zh) * | 2017-05-12 | 2022-08-21 | 瑞士商多蒂孔股份有限公司 | 茚烷衍生物及其在有機電子產品的用途 |
| MA49685A (fr) | 2017-07-24 | 2021-04-14 | Vitae Pharmaceuticals Llc | INHIBITEURS DE ROR gamma |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| WO2019023278A1 (en) | 2017-07-25 | 2019-01-31 | Crinetics Pharmaceuticals, Inc. | MODULATORS OF SOMATOSTATIN AND USES THEREOF |
| CA3073051A1 (en) * | 2017-08-17 | 2019-02-21 | Ikena Oncology, Inc. | Ahr inhibitors and uses thereof |
| ES2923529T3 (es) | 2018-01-17 | 2022-09-28 | Crinetics Pharmaceuticals Inc | Proceso para fabricar moduladores de somatostatina |
| RU2702648C1 (ru) * | 2019-07-11 | 2019-10-09 | федеральное государственное автономное образовательное учреждение высшего образования «Южный федеральный университет» | 5,7-Ди(трет-бутил)-2-(4,7-дихлор-8-метил-5-нитрохинолин-2-ил)-4-нитро-1,3-трополон, обладающий цитотоксической активностью |
| CA3191084A1 (en) | 2020-09-09 | 2022-03-17 | Gerald Burke | Formulations of a somatostatin modulator |
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| US4035367A (en) * | 1974-09-09 | 1977-07-12 | Sandoz, Inc. | Hydroxyalkyl-substituted-amino-quinolines |
| WO1996037474A1 (en) * | 1995-05-26 | 1996-11-28 | Warner-Lambert Company | Sulfonylquinolines as neuropeptide y1 antagonists |
| CN1245168A (zh) * | 1993-10-28 | 2000-02-23 | 霍夫曼-拉罗奇有限公司 | 氨基喹啉衍生物 |
| WO2002020488A2 (en) * | 2000-09-06 | 2002-03-14 | F. Hoffmann-La Roche Ag | Quinoline and quinazoline derivatives as ligands for the neuropeptide y receptor |
| WO2002094789A1 (en) * | 2001-05-21 | 2002-11-28 | F. Hoffmann-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide y receptor |
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| CA1247547A (en) * | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
| CA1328881C (en) | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
| CA1270837A (en) | 1984-12-21 | 1990-06-26 | Hoffmann-La Roche Limited | Oxetanones |
| CA2035972C (en) | 1990-02-23 | 2006-07-11 | Martin Karpf | Process for the preparation of oxetanones |
| US5274143A (en) | 1991-07-23 | 1993-12-28 | Hoffmann-La Roche Inc. | Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione |
| RU2161967C2 (ru) * | 1994-08-18 | 2001-01-20 | Дзе Проктер Энд Гэмбл Компани | Соединения 7-(2-имидазолиниламино) хинолина, пригодные в качестве агонистов альфа-2-адренорецептора |
| US6004996A (en) * | 1997-02-05 | 1999-12-21 | Hoffman-La Roche Inc. | Tetrahydrolipstatin containing compositions |
| US6267952B1 (en) | 1998-01-09 | 2001-07-31 | Geltex Pharmaceuticals, Inc. | Lipase inhibiting polymers |
| EP1105123B1 (en) | 1998-08-14 | 2004-04-07 | F.Hoffmann-La Roche Ag | Pharmaceutical compositions containing lipase inhibitors and chitosan |
| PT1105122E (pt) | 1998-08-14 | 2005-08-31 | Hoffmann La Roche | Composicoes farmaceuticas que contem inibidores de lipase |
| DE10064105A1 (de) * | 2000-12-21 | 2002-06-27 | Bayer Ag | Neue Substituierte Imidazotriazinone |
-
2003
- 2003-01-27 ES ES03702533T patent/ES2304498T3/es not_active Expired - Lifetime
- 2003-01-27 AU AU2003205679A patent/AU2003205679B2/en not_active Ceased
- 2003-01-27 JP JP2003565479A patent/JP4216196B2/ja not_active Expired - Fee Related
- 2003-01-27 CN CNB038032805A patent/CN100383124C/zh not_active Expired - Fee Related
- 2003-01-27 RU RU2004126936/04A patent/RU2298002C2/ru not_active IP Right Cessation
- 2003-01-27 MX MXPA04007502A patent/MXPA04007502A/es active IP Right Grant
- 2003-01-27 BR BR0307441-2A patent/BR0307441A/pt not_active IP Right Cessation
- 2003-01-27 AT AT03702533T patent/ATE392897T1/de not_active IP Right Cessation
- 2003-01-27 PL PL03372295A patent/PL372295A1/xx not_active Application Discontinuation
- 2003-01-27 KR KR1020047012036A patent/KR100659428B1/ko not_active Expired - Fee Related
- 2003-01-27 CA CA002473181A patent/CA2473181A1/en not_active Abandoned
- 2003-01-27 WO PCT/EP2003/000777 patent/WO2003066055A1/en not_active Ceased
- 2003-01-27 DE DE60320529T patent/DE60320529T2/de not_active Expired - Fee Related
- 2003-01-27 EP EP03702533A patent/EP1474145B1/en not_active Expired - Lifetime
- 2003-01-30 TW TW092102218A patent/TW200400032A/zh unknown
- 2003-01-31 PE PE2003000111A patent/PE20040120A1/es not_active Application Discontinuation
- 2003-01-31 AR ARP030100304A patent/AR038249A1/es not_active Application Discontinuation
- 2003-02-03 UY UY27646A patent/UY27646A1/es not_active Application Discontinuation
- 2003-02-04 US US10/358,006 patent/US6696467B2/en not_active Expired - Fee Related
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| US4035367A (en) * | 1974-09-09 | 1977-07-12 | Sandoz, Inc. | Hydroxyalkyl-substituted-amino-quinolines |
| CN1245168A (zh) * | 1993-10-28 | 2000-02-23 | 霍夫曼-拉罗奇有限公司 | 氨基喹啉衍生物 |
| WO1996037474A1 (en) * | 1995-05-26 | 1996-11-28 | Warner-Lambert Company | Sulfonylquinolines as neuropeptide y1 antagonists |
| WO2002020488A2 (en) * | 2000-09-06 | 2002-03-14 | F. Hoffmann-La Roche Ag | Quinoline and quinazoline derivatives as ligands for the neuropeptide y receptor |
| WO2002094789A1 (en) * | 2001-05-21 | 2002-11-28 | F. Hoffmann-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide y receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003066055A1 (en) | 2003-08-14 |
| CN1627945A (zh) | 2005-06-15 |
| UY27646A1 (es) | 2003-08-29 |
| PE20040120A1 (es) | 2004-03-06 |
| US6696467B2 (en) | 2004-02-24 |
| AR038249A1 (es) | 2005-01-05 |
| CA2473181A1 (en) | 2003-08-14 |
| US20030153553A1 (en) | 2003-08-14 |
| JP2005523901A (ja) | 2005-08-11 |
| PL372295A1 (en) | 2005-07-11 |
| JP4216196B2 (ja) | 2009-01-28 |
| ES2304498T3 (es) | 2008-10-16 |
| AU2003205679B2 (en) | 2006-06-29 |
| ATE392897T1 (de) | 2008-05-15 |
| TW200400032A (en) | 2004-01-01 |
| MXPA04007502A (es) | 2004-11-10 |
| DE60320529D1 (de) | 2008-06-05 |
| RU2298002C2 (ru) | 2007-04-27 |
| EP1474145B1 (en) | 2008-04-23 |
| RU2004126936A (ru) | 2005-10-10 |
| KR100659428B1 (ko) | 2006-12-19 |
| AU2003205679A1 (en) | 2003-09-02 |
| EP1474145A1 (en) | 2004-11-10 |
| BR0307441A (pt) | 2005-01-04 |
| DE60320529T2 (de) | 2009-06-10 |
| KR20040081484A (ko) | 2004-09-21 |
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