ZA200308783B - Quinoline derivatives as ligands for the neuropeptide Y receptor. - Google Patents
Quinoline derivatives as ligands for the neuropeptide Y receptor. Download PDFInfo
- Publication number
- ZA200308783B ZA200308783B ZA200308783A ZA200308783A ZA200308783B ZA 200308783 B ZA200308783 B ZA 200308783B ZA 200308783 A ZA200308783 A ZA 200308783A ZA 200308783 A ZA200308783 A ZA 200308783A ZA 200308783 B ZA200308783 B ZA 200308783B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- pyrrolidin
- alkyl
- quinolin
- hydrogen
- Prior art date
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 6
- 239000003446 ligand Substances 0.000 title description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 108050002826 Neuropeptide Y Receptor Proteins 0.000 title 1
- 102000012301 Neuropeptide Y receptor Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 89
- -1 aryl-SO2-O-alkyl Chemical group 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 208000008589 Obesity Diseases 0.000 claims description 13
- 125000006193 alkinyl group Chemical group 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 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 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229960001243 orlistat Drugs 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 5
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 2
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- 235000011087 fumaric acid Nutrition 0.000 description 1
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- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 239000011976 maleic acid Substances 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
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- 235000012054 meals Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
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- JJIBACXWJHRORI-UHFFFAOYSA-N n,n,2,2-tetramethyl-3-(2-methyl-4-pyrrolidin-1-ylquinolin-7-yl)oxypropan-1-amine Chemical compound C=1C(C)=NC2=CC(OCC(C)(C)CN(C)C)=CC=C2C=1N1CCCC1 JJIBACXWJHRORI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000000369 oxido group Chemical group [*]=O 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 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
- 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
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 150000003141 primary amines Chemical class 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-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
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
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- 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000035924 thermogenesis Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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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
-
- 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
-
- 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
-
- 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
- C07D401/14—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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01112370 | 2001-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308783B true ZA200308783B (en) | 2005-02-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308783A ZA200308783B (en) | 2001-05-21 | 2003-11-11 | Quinoline derivatives as ligands for the neuropeptide Y receptor. |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6818767B2 (ko) |
| EP (1) | EP1395564B1 (ko) |
| JP (1) | JP3715280B2 (ko) |
| KR (1) | KR100621287B1 (ko) |
| CN (1) | CN100376557C (ko) |
| AR (1) | AR035979A1 (ko) |
| AT (1) | ATE387428T1 (ko) |
| AU (1) | AU2002338896B2 (ko) |
| BR (1) | BR0209957A (ko) |
| CA (1) | CA2446324A1 (ko) |
| DE (1) | DE60225274T2 (ko) |
| ES (1) | ES2300478T3 (ko) |
| GT (1) | GT200200090A (ko) |
| MX (1) | MXPA03010565A (ko) |
| PA (1) | PA8545301A1 (ko) |
| PE (1) | PE20021155A1 (ko) |
| UY (1) | UY27300A1 (ko) |
| WO (1) | WO2002094789A1 (ko) |
| ZA (1) | ZA200308783B (ko) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6900226B2 (en) * | 2000-09-06 | 2005-05-31 | Hoffman-La Roche Inc. | Neuropeptide Y antagonists |
| CA2468015A1 (en) * | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 2-aminoquinoline compounds |
| MXPA04007502A (es) | 2002-02-04 | 2004-11-10 | Hoffmann La Roche | Derivados de quinolina como antagonistas de neuropeptido y (npy). |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| CN1665791A (zh) | 2002-07-05 | 2005-09-07 | 霍夫曼-拉罗奇有限公司 | 喹唑啉衍生物 |
| AU2003253364B2 (en) | 2002-08-07 | 2007-06-07 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| MXPA05009722A (es) * | 2003-03-10 | 2006-03-09 | Schering Corp | Inhibidores heterociclicos de cinasa: metodos de uso y sintesis. |
| AU2004274309B2 (en) | 2003-09-22 | 2010-04-08 | Msd K.K. | Novel piperidine derivative |
| AU2004289303A1 (en) | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Fused heterocyclic compounds |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| US20060183763A1 (en) * | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
| CA2618112A1 (en) | 2005-08-10 | 2007-02-15 | Banyu Pharmaceutical Co., Ltd. | Pyridone compound |
| CA2619770A1 (en) | 2005-08-24 | 2007-03-01 | Banyu Pharmaceutical Co., Ltd. | Phenylpyridone derivative |
| AU2006288153A1 (en) | 2005-09-07 | 2007-03-15 | Msd K.K. | Bicyclic aromatic substituted pyridone derivative |
| CA2627139A1 (en) | 2005-10-27 | 2007-05-03 | Banyu Pharmaceutical Co., Ltd. | Novel benzoxathiin derivative |
| JP4371164B2 (ja) | 2005-11-10 | 2009-11-25 | 萬有製薬株式会社 | アザ置換スピロ誘導体 |
| WO2008020302A2 (en) * | 2006-08-17 | 2008-02-21 | Pfizer Products Inc. | Heteroaromatic quinoline-based compounds as phosphodiesterase (pde) inhibitors |
| JPWO2008038692A1 (ja) | 2006-09-28 | 2010-01-28 | 萬有製薬株式会社 | ジアリールケチミン誘導体 |
| CA2682727C (en) | 2007-04-02 | 2016-03-22 | Banyu Pharmaceutical Co., Ltd. | Indoledione derivative |
| WO2008141077A1 (en) * | 2007-05-10 | 2008-11-20 | Janssen Pharmaceutica N.V. | Process for the preparation of tetrahydroquinolinyl, benzoxazine and benzothiazine derivatives |
| WO2008142384A1 (en) | 2007-05-17 | 2008-11-27 | Helperby Therapeutics Limited | Use of 4-(pyrrolidin-1-yl)quinoline compounds to kill clinically latent microorganisms |
| US20080303428A1 (en) * | 2007-06-01 | 2008-12-11 | Vsevolod Rostovtsev | Chrysenes for green luminescent applications |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| CA3089569C (en) | 2007-06-04 | 2023-12-05 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| CA2705318C (en) | 2007-11-15 | 2013-12-31 | Boehringer Ingelheim International Gmbh | Inhibitors of human immunodeficiency virus replication |
| JP5285709B2 (ja) | 2007-11-16 | 2013-09-11 | ギリアード サイエンシス インコーポレーテッド | ヒト免疫不全ウイルスの複製阻害薬 |
| US20110015181A1 (en) | 2008-03-06 | 2011-01-20 | Makoto Ando | Alkylaminopyridine derivative |
| US20110015198A1 (en) | 2008-03-28 | 2011-01-20 | Banyu Pharmaceutical Co., Inc. | Diarylmethylamide derivative having melanin-concentrating hormone receptor antagonism |
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| LU43730A1 (ko) * | 1962-06-14 | 1963-07-13 | ||
| US3272824A (en) * | 1962-12-06 | 1966-09-13 | Norwich Pharma Co | 4-amino-6, 7-di(lower) alkoxyquinolines |
| US3812127A (en) * | 1966-10-31 | 1974-05-21 | Pfizer | 4-(quinolin-4-yl)piperazine-1-carboxylic acid esters |
| US4035367A (en) * | 1974-09-09 | 1977-07-12 | Sandoz, Inc. | Hydroxyalkyl-substituted-amino-quinolines |
| CA1247547A (en) | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
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| CA1328881C (en) | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
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| 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 |
| NZ330571A (en) * | 1996-10-01 | 1999-10-28 | Kyowa Hakko Kogyo Kk | Nitrogenous heterocyclic compounds that may contain sulphur or oxygen |
| US6004996A (en) | 1997-02-05 | 1999-12-21 | Hoffman-La Roche Inc. | Tetrahydrolipstatin containing compositions |
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| WO2001034764A2 (en) * | 1999-11-08 | 2001-05-17 | Cytion S.A. | Apparatus and methods for positioning and analyzing biological membranous objects |
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-
2002
- 2002-05-08 EP EP02771639A patent/EP1395564B1/en not_active Expired - Lifetime
- 2002-05-08 JP JP2002591462A patent/JP3715280B2/ja not_active Expired - Fee Related
- 2002-05-08 DE DE60225274T patent/DE60225274T2/de not_active Expired - Fee Related
- 2002-05-08 CN CNB028104013A patent/CN100376557C/zh not_active Expired - Fee Related
- 2002-05-08 AU AU2002338896A patent/AU2002338896B2/en not_active Ceased
- 2002-05-08 ES ES02771639T patent/ES2300478T3/es not_active Expired - Lifetime
- 2002-05-08 MX MXPA03010565A patent/MXPA03010565A/es active IP Right Grant
- 2002-05-08 CA CA002446324A patent/CA2446324A1/en not_active Abandoned
- 2002-05-08 WO PCT/EP2002/005120 patent/WO2002094789A1/en active IP Right Grant
- 2002-05-08 AT AT02771639T patent/ATE387428T1/de not_active IP Right Cessation
- 2002-05-08 KR KR1020037015121A patent/KR100621287B1/ko not_active IP Right Cessation
- 2002-05-08 BR BR0209957-8A patent/BR0209957A/pt not_active IP Right Cessation
- 2002-05-16 PA PA20028545301A patent/PA8545301A1/es unknown
- 2002-05-17 PE PE2002000425A patent/PE20021155A1/es not_active Application Discontinuation
- 2002-05-17 AR ARP020101836A patent/AR035979A1/es not_active Application Discontinuation
- 2002-05-20 GT GT200200090A patent/GT200200090A/es unknown
- 2002-05-20 US US10/151,505 patent/US6818767B2/en not_active Expired - Fee Related
- 2002-05-21 UY UY27300A patent/UY27300A1/es not_active Application Discontinuation
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2003
- 2003-11-11 ZA ZA200308783A patent/ZA200308783B/en unknown
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2004
- 2004-05-24 US US10/852,509 patent/US20050049413A1/en not_active Abandoned
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| Publication number | Publication date |
|---|---|
| CN1522249A (zh) | 2004-08-18 |
| KR20030096416A (ko) | 2003-12-24 |
| CA2446324A1 (en) | 2002-11-28 |
| EP1395564B1 (en) | 2008-02-27 |
| JP2004536066A (ja) | 2004-12-02 |
| GT200200090A (es) | 2003-06-19 |
| BR0209957A (pt) | 2004-03-30 |
| MXPA03010565A (es) | 2004-03-02 |
| CN100376557C (zh) | 2008-03-26 |
| US20050049413A1 (en) | 2005-03-03 |
| ATE387428T1 (de) | 2008-03-15 |
| DE60225274D1 (de) | 2008-04-10 |
| DE60225274T2 (de) | 2009-03-26 |
| WO2002094789A1 (en) | 2002-11-28 |
| PE20021155A1 (es) | 2002-12-17 |
| US20020198194A1 (en) | 2002-12-26 |
| KR100621287B1 (ko) | 2006-09-13 |
| AU2002338896B2 (en) | 2006-04-27 |
| ES2300478T3 (es) | 2008-06-16 |
| PA8545301A1 (es) | 2003-01-24 |
| EP1395564A1 (en) | 2004-03-10 |
| US6818767B2 (en) | 2004-11-16 |
| JP3715280B2 (ja) | 2005-11-09 |
| UY27300A1 (es) | 2002-11-29 |
| AR035979A1 (es) | 2004-07-28 |
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