ZA200402359B - Quinoline derivatives as neuropeptide Y antagonists. - Google Patents

Quinoline derivatives as neuropeptide Y antagonists. Download PDF

Info

Publication number: ZA200402359B
Authority: ZA; South Africa
Prior art keywords: pyrrolidin; quinolin; methyl; alkyl; benzonitrile
Prior art date: 2001-09-28

Application number

ZA200402359A

Other languages

English (en)

Inventor

Michael G Klug

Werner Mueller

Matthias Heinrich Nettekoven

Jean-Marc Plancher

Patrizio Mattei

Werner Neidhart

Philippe Pflieger

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

2001-09-28

Filing date

2004-03-25

Publication date

2005-05-03

2004-03-25 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2005-05-03 Publication of ZA200402359B publication Critical patent/ZA200402359B/en

Links

125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 10
101710151321 Melanostatin Proteins 0.000 title claims description 7
102400000064 Neuropeptide Y Human genes 0.000 title description 5
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 title description 5
239000005557 antagonist Substances 0.000 title description 3
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 96
125000000217 alkyl group Chemical group 0.000 claims description 75
-1 amino, acetylamino Chemical group 0.000 claims description 47
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 32
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
229940086609 Lipase inhibitor Drugs 0.000 claims description 18
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 15
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 14
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 14
208000008589 Obesity Diseases 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
235000020824 obesity Nutrition 0.000 claims description 13
229960001243 orlistat Drugs 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Chemical group 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
229910052717 sulfur Chemical group 0.000 claims description 11
239000011593 sulfur Chemical group 0.000 claims description 11
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
150000001412 amines Chemical class 0.000 claims description 9
238000011321 prophylaxis Methods 0.000 claims description 9
208000024172 Cardiovascular disease Diseases 0.000 claims description 7
208000030814 Eating disease Diseases 0.000 claims description 7
208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
208000001647 Renal Insufficiency Diseases 0.000 claims description 7
206010003246 arthritis Diseases 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
206010012601 diabetes mellitus Diseases 0.000 claims description 7
235000014632 disordered eating Nutrition 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
201000006370 kidney failure Diseases 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
238000002560 therapeutic procedure Methods 0.000 claims description 4
CHRSSSYOZYZOFK-UHFFFAOYSA-N 2-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methoxy]benzonitrile Chemical compound C=12C=CC(COC=3C(=CC=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 CHRSSSYOZYZOFK-UHFFFAOYSA-N 0.000 claims description 3
XATCREPNDSEOGK-UHFFFAOYSA-N 2-chloro-4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methoxy]benzonitrile Chemical compound C=12C=CC(COC=3C=C(Cl)C(C#N)=CC=3)=CC2=NC(C)=CC=1N1CCCC1 XATCREPNDSEOGK-UHFFFAOYSA-N 0.000 claims description 3
SNRXFJAQZXURJY-UHFFFAOYSA-N 2-methyl-7-(pyridin-4-yloxymethyl)-4-pyrrolidin-1-ylquinoline Chemical compound C=12C=CC(COC=3C=CN=CC=3)=CC2=NC(C)=CC=1N1CCCC1 SNRXFJAQZXURJY-UHFFFAOYSA-N 0.000 claims description 3
OSHRLFZAABJWIA-UHFFFAOYSA-N 4-[(2,6-dimethyl-4-pyrrolidin-1-ylquinolin-7-yl)methoxy]benzonitrile Chemical compound C=12C=C(C)C(COC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 OSHRLFZAABJWIA-UHFFFAOYSA-N 0.000 claims description 3
FBJUQLXTVWMSMQ-UHFFFAOYSA-N 4-[(2,6-dimethyl-4-pyrrolidin-1-ylquinolin-7-yl)methylamino]benzonitrile Chemical compound C=12C=C(C)C(CNC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 FBJUQLXTVWMSMQ-UHFFFAOYSA-N 0.000 claims description 3
FQMBNIOZTFMQEB-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methoxy]-2-(trifluoromethyl)benzonitrile Chemical compound C=12C=CC(COC=3C=C(C(C#N)=CC=3)C(F)(F)F)=CC2=NC(C)=CC=1N1CCCC1 FQMBNIOZTFMQEB-UHFFFAOYSA-N 0.000 claims description 3
VORUYQGEUJBGHH-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methoxy]benzene-1,2-dicarbonitrile Chemical compound C=12C=CC(COC=3C=C(C(C#N)=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 VORUYQGEUJBGHH-UHFFFAOYSA-N 0.000 claims description 3
YRGQRXMURUGZDN-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methoxy]benzonitrile Chemical compound C=12C=CC(COC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 YRGQRXMURUGZDN-UHFFFAOYSA-N 0.000 claims description 3
ZETVYJWZAJSNLN-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methylamino]-2-(trifluoromethyl)benzonitrile Chemical compound C=12C=CC(CNC=3C=C(C(C#N)=CC=3)C(F)(F)F)=CC2=NC(C)=CC=1N1CCCC1 ZETVYJWZAJSNLN-UHFFFAOYSA-N 0.000 claims description 3
RVEDDNXDVZBQNM-UHFFFAOYSA-N 4-[[4-(azepan-1-yl)-2-methylquinolin-7-yl]methoxy]benzonitrile Chemical compound C=12C=CC(COC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCCCC1 RVEDDNXDVZBQNM-UHFFFAOYSA-N 0.000 claims description 3
UXMOAHLHPOHSPS-QFIPXVFZSA-N 4-[[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2,6-dimethylquinolin-7-yl]methoxy]benzonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(COC=3C=CC(=CC=3)C#N)=C(C)C=C12 UXMOAHLHPOHSPS-QFIPXVFZSA-N 0.000 claims description 3
SELLRXHGEKIKKL-UHFFFAOYSA-N [4-(azepan-1-yl)-2-methylquinolin-7-yl]methanol Chemical compound C=12C=CC(CO)=CC2=NC(C)=CC=1N1CCCCCC1 SELLRXHGEKIKKL-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
150000004678 hydrides Chemical class 0.000 claims description 3
BHJULLBAVAZKLV-UHFFFAOYSA-N n-butyl-2-methyl-4-pyrrolidin-1-ylquinoline-7-carboxamide Chemical compound C=1C(C)=NC2=CC(C(=O)NCCCC)=CC=C2C=1N1CCCC1 BHJULLBAVAZKLV-UHFFFAOYSA-N 0.000 claims description 3
OFCMJTXCXQZZHQ-UHFFFAOYSA-N (2,6-dimethyl-4-pyrrolidin-1-ylquinolin-7-yl)methanol Chemical compound C=12C=C(C)C(CO)=CC2=NC(C)=CC=1N1CCCC1 OFCMJTXCXQZZHQ-UHFFFAOYSA-N 0.000 claims description 2
DGEQVTJQZRYCHX-QFIPXVFZSA-N 4-[[4-[(3s)-3-ethoxypyrrolidin-1-yl]-2,6-dimethylquinolin-7-yl]methylamino]benzonitrile Chemical compound C1[C@@H](OCC)CCN1C1=CC(C)=NC2=CC(CNC=3C=CC(=CC=3)C#N)=C(C)C=C12 DGEQVTJQZRYCHX-QFIPXVFZSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
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BZCCJWGPBJXSFD-UHFFFAOYSA-N 4-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methylamino]benzonitrile Chemical compound C=12C=CC(CNC=3C=CC(=CC=3)C#N)=CC2=NC(C)=CC=1N1CCCC1 BZCCJWGPBJXSFD-UHFFFAOYSA-N 0.000 claims 1
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
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CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
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102100029549 Neuropeptide Y receptor type 5 Human genes 0.000 description 3
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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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 3
239000011737 fluorine Substances 0.000 description 3
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BPGXUIVWLQTVLZ-OFGSCBOVSA-N neuropeptide y(npy) 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](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCN=C(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](CCCN=C(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 BPGXUIVWLQTVLZ-OFGSCBOVSA-N 0.000 description 3
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DXHPEXGXMQTFLJ-UHFFFAOYSA-N n-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methyl]-3-(trifluoromethyl)aniline Chemical compound C=12C=CC(CNC=3C=C(C=CC=3)C(F)(F)F)=CC2=NC(C)=CC=1N1CCCC1 DXHPEXGXMQTFLJ-UHFFFAOYSA-N 0.000 description 1
IBQQZUFOYSTLFX-UHFFFAOYSA-N n-[(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)methyl]butan-1-amine Chemical compound C=1C(C)=NC2=CC(CNCCCC)=CC=C2C=1N1CCCC1 IBQQZUFOYSTLFX-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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230000003204 osmotic effect Effects 0.000 description 1
125000000369 oxido group Chemical group [*]=O 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
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229920000053 polysorbate 80 Polymers 0.000 description 1
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
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003140 primary amides Chemical class 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical class C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000035924 thermogenesis Effects 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000004360 trifluorophenyl group Chemical group 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
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
- 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
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Ceramic Engineering (AREA)
Manufacturing & Machinery (AREA)
Hematology (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Physical Education & Sports Medicine (AREA)
Structural Engineering (AREA)
Materials Engineering (AREA)
Cardiology (AREA)
Inorganic Chemistry (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Nutrition Science (AREA)
Immunology (AREA)
Vascular Medicine (AREA)
Endocrinology (AREA)
Rheumatology (AREA)
Child & Adolescent Psychology (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

ZA200402359A 2001-09-28 2004-03-25 Quinoline derivatives as neuropeptide Y antagonists. ZA200402359B (en)

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EP01123496		2001-09-28

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ZA200402359A ZA200402359B (en)	2001-09-28	2004-03-25	Quinoline derivatives as neuropeptide Y antagonists.

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US (4)	US6787558B2 (xx)
EP (1)	EP1432421A1 (xx)
JP (1)	JP4187652B2 (xx)
KR (1)	KR100605765B1 (xx)
CN (1)	CN1289087C (xx)
AR (1)	AR040626A1 (xx)
AU (1)	AU2002342735B2 (xx)
BR (1)	BR0212929A (xx)
CA (1)	CA2460865C (xx)
GT (1)	GT200200197A (xx)
HR (1)	HRP20040272A2 (xx)
HU (1)	HUP0401481A2 (xx)
IL (1)	IL160750A0 (xx)
MX (1)	MXPA04002825A (xx)
NO (1)	NO20041235L (xx)
NZ (1)	NZ531517A (xx)
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PL (1)	PL370414A1 (xx)
RU (1)	RU2300531C2 (xx)
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US6900226B2 (en)	2000-09-06	2005-05-31	Hoffman-La Roche Inc.	Neuropeptide Y antagonists

2002
- 2002-09-19 US US10/247,009 patent/US6787558B2/en not_active Expired - Fee Related
- 2002-09-20 CN CNB028191919A patent/CN1289087C/zh not_active Expired - Fee Related
- 2002-09-20 RU RU2004113207/04A patent/RU2300531C2/ru not_active IP Right Cessation
- 2002-09-20 KR KR1020047004591A patent/KR100605765B1/ko not_active Expired - Fee Related
- 2002-09-20 IL IL16075002A patent/IL160750A0/xx unknown
- 2002-09-20 CA CA002460865A patent/CA2460865C/en not_active Expired - Fee Related
- 2002-09-20 NZ NZ531517A patent/NZ531517A/en unknown
- 2002-09-20 MX MXPA04002825A patent/MXPA04002825A/es active IP Right Grant
- 2002-09-20 HU HU0401481A patent/HUP0401481A2/hu unknown
- 2002-09-20 WO PCT/EP2002/010618 patent/WO2003028726A1/en active IP Right Grant
- 2002-09-20 EP EP02779399A patent/EP1432421A1/en not_active Withdrawn
- 2002-09-20 JP JP2003532058A patent/JP4187652B2/ja not_active Expired - Fee Related
- 2002-09-20 AU AU2002342735A patent/AU2002342735B2/en not_active Ceased
- 2002-09-20 BR BR0212929-9A patent/BR0212929A/pt not_active IP Right Cessation
- 2002-09-20 HR HR20040272A patent/HRP20040272A2/hr not_active Application Discontinuation
- 2002-09-20 PL PL02370414A patent/PL370414A1/xx not_active Application Discontinuation
- 2002-09-25 PA PA20028555401A patent/PA8555401A1/es unknown
- 2002-09-26 PE PE2002000952A patent/PE20030603A1/es not_active Application Discontinuation
- 2002-09-27 AR AR20020103663A patent/AR040626A1/es not_active Application Discontinuation
- 2002-09-27 GT GT200200197A patent/GT200200197A/es unknown
- 2002-09-27 UY UY27462A patent/UY27462A1/es not_active Application Discontinuation
2004
- 2004-03-24 NO NO20041235A patent/NO20041235L/no not_active Application Discontinuation
- 2004-03-25 ZA ZA200402359A patent/ZA200402359B/en unknown
- 2004-07-22 US US10/896,445 patent/US7012073B2/en not_active Expired - Fee Related
2005
- 2005-11-10 US US11/272,207 patent/US7064134B2/en not_active Expired - Fee Related
2006
- 2006-03-16 US US11/376,976 patent/US7166589B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP2005508923A (ja)	2005-04-07
PA8555401A1 (es)	2003-07-28
US7166589B2 (en)	2007-01-23
GT200200197A (es)	2003-06-19
BR0212929A (pt)	2004-10-13
JP4187652B2 (ja)	2008-11-26
US6787558B2 (en)	2004-09-07
UY27462A1 (es)	2003-04-30
IL160750A0 (en)	2004-08-31
US20040259858A1 (en)	2004-12-23
US7064134B2 (en)	2006-06-20
RU2004113207A (ru)	2005-05-27
KR20040039442A (ko)	2004-05-10
US7012073B2 (en)	2006-03-14
HK1074176A1 (en)	2005-11-04
CA2460865A1 (en)	2003-04-10
CN1607951A (zh)	2005-04-20
NO20041235L (no)	2004-03-24
AU2002342735B2 (en)	2005-09-22
WO2003028726A1 (en)	2003-04-10
CA2460865C (en)	2008-09-09
NZ531517A (en)	2005-11-25
PL370414A1 (en)	2005-05-30
RU2300531C2 (ru)	2007-06-10
HRP20040272A2 (en)	2004-08-31
CN1289087C (zh)	2006-12-13
AR040626A1 (es)	2005-04-13
US20030158179A1 (en)	2003-08-21
US20060148794A1 (en)	2006-07-06
EP1432421A1 (en)	2004-06-30
US20060063758A1 (en)	2006-03-23
KR100605765B1 (ko)	2006-07-31
HUP0401481A2 (hu)	2004-12-28
MXPA04002825A (es)	2004-07-02
PE20030603A1 (es)	2003-07-12

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