DE60115092T2 - Spiro[isobenzofuran-1,4'-piperidin]-3-one und 3h-spiroisobenzofuran-1,4'-piperidine - Google Patents
Spiro[isobenzofuran-1,4'-piperidin]-3-one und 3h-spiroisobenzofuran-1,4'-piperidine Download PDFInfo
- Publication number
- DE60115092T2 DE60115092T2 DE60115092T DE60115092T DE60115092T2 DE 60115092 T2 DE60115092 T2 DE 60115092T2 DE 60115092 T DE60115092 T DE 60115092T DE 60115092 T DE60115092 T DE 60115092T DE 60115092 T2 DE60115092 T2 DE 60115092T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- halo
- isobenzofuran
- spiro
- piperidin
- 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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- RNMPNVBLQHYANU-UHFFFAOYSA-N spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC21CCNCC2 RNMPNVBLQHYANU-UHFFFAOYSA-N 0.000 title abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 173
- 102000028582 Neuropeptide Y5 receptor Human genes 0.000 claims abstract description 126
- 108010046593 Neuropeptide Y5 receptor Proteins 0.000 claims abstract description 126
- 230000027455 binding Effects 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 238000000338 in vitro Methods 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 10
- 208000030814 Eating disease Diseases 0.000 claims abstract description 10
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 10
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 10
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
- -1 hydroxy, amino Chemical group 0.000 claims description 79
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 73
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 68
- 101710151321 Melanostatin Proteins 0.000 claims description 64
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000000651 prodrug Substances 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- 230000004913 activation Effects 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000001514 detection method Methods 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 238000000670 ligand binding assay Methods 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 229910052721 tungsten Inorganic materials 0.000 claims description 7
- 229910052727 yttrium Inorganic materials 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- CLDMDFGJPGYXPI-UHFFFAOYSA-N 1'-(6-acetyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C(=O)C)=CC=C2N1 CLDMDFGJPGYXPI-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 229940075993 receptor modulator Drugs 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 5
- LPOLBQTZZHSRGO-UHFFFAOYSA-N 1'-(6-propylsulfonyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(S(=O)(=O)CCC)=CC=C2N1 LPOLBQTZZHSRGO-UHFFFAOYSA-N 0.000 claims description 5
- JIVDRBRZFUEQBM-UHFFFAOYSA-N 1'-(6-pyridin-3-yl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=CC=2)=NC1=CC=2C1=CC=CN=C1 JIVDRBRZFUEQBM-UHFFFAOYSA-N 0.000 claims description 5
- XWCWKHBTXAFSRD-UHFFFAOYSA-N 2-(3-oxospiro[2-benzofuran-1,4'-piperidine]-1'-yl)-3h-benzimidazole-5-carbonitrile Chemical compound C12=CC=CC=C2C(=O)OC11CCN(C=2NC3=CC=C(C=C3N=2)C#N)CC1 XWCWKHBTXAFSRD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- ZETIZXFYVDSTGO-UHFFFAOYSA-N 1'-(5-phenyl-3h-imidazo[4,5-b]pyrazin-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=NC=2)=NC1=NC=2C1=CC=CC=C1 ZETIZXFYVDSTGO-UHFFFAOYSA-N 0.000 claims description 4
- IRDOMFKPNLFWGW-UHFFFAOYSA-N 1'-(6-methyl-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C)=CC=C2N1 IRDOMFKPNLFWGW-UHFFFAOYSA-N 0.000 claims description 4
- RQMKJTJDJCTLMI-UHFFFAOYSA-N 1'-[6-(1,3-oxazol-2-yl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound C12=CC=CC=C2C(=O)OC1(CC1)CCN1C(NC1=CC=2)=NC1=CC=2C1=NC=CO1 RQMKJTJDJCTLMI-UHFFFAOYSA-N 0.000 claims description 4
- PUGBOUNLKDOYBK-UHFFFAOYSA-N 1'-[6-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound CC1=NOC(C)=C1C1=CC=C(NC(=N2)N3CCC4(CC3)C3=CC=CC=C3C(=O)O4)C2=C1 PUGBOUNLKDOYBK-UHFFFAOYSA-N 0.000 claims description 4
- GOSQWFMKXKORBV-UHFFFAOYSA-N 1'-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(C(F)(F)F)=CC=C2N1 GOSQWFMKXKORBV-UHFFFAOYSA-N 0.000 claims description 4
- FGCDLQZYHPYSSV-UHFFFAOYSA-N 1'-[6-(trifluoromethylsulfonyl)-1h-benzimidazol-2-yl]spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC2=CC(S(=O)(=O)C(F)(F)F)=CC=C2N1 FGCDLQZYHPYSSV-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 3
- QGOAHRMVFCYWPZ-UHFFFAOYSA-N 1'-(5,6-difluoro-1h-benzimidazol-2-yl)spiro[2-benzofuran-3,4'-piperidine]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C1(CC1)CCN1C1=NC(C=C(C(=C2)F)F)=C2N1 QGOAHRMVFCYWPZ-UHFFFAOYSA-N 0.000 claims description 3
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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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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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25499000P | 2000-12-12 | 2000-12-12 | |
| US254990P | 2000-12-12 | ||
| PCT/US2001/047863 WO2002048152A2 (en) | 2000-12-12 | 2001-12-11 | Spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3h-spiroisobenzofuran-1,4'-piperidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60115092D1 DE60115092D1 (de) | 2005-12-22 |
| DE60115092T2 true DE60115092T2 (de) | 2006-03-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60115092T Expired - Fee Related DE60115092T2 (de) | 2000-12-12 | 2001-12-11 | Spiro[isobenzofuran-1,4'-piperidin]-3-one und 3h-spiroisobenzofuran-1,4'-piperidine |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US20050033048A1 (enExample) |
| EP (1) | EP1347982B1 (enExample) |
| JP (1) | JP2004520299A (enExample) |
| AT (1) | ATE310004T1 (enExample) |
| AU (1) | AU2002220276A1 (enExample) |
| BR (1) | BR0116113A (enExample) |
| DE (1) | DE60115092T2 (enExample) |
| ES (1) | ES2249384T3 (enExample) |
| MX (1) | MXPA03004245A (enExample) |
| WO (1) | WO2002048152A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| EP3558298A4 (en) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
| CN116462666B (zh) * | 2017-01-10 | 2025-07-15 | 瑞士苏黎世联邦理工学院 | 细胞保护性化合物及其用途 |
| SG11201912403SA (en) | 2017-06-22 | 2020-01-30 | Celgene Corp | Treatment of hepatocellular carcinoma characterized by hepatitis b virus infection |
| WO2019131794A1 (ja) * | 2017-12-27 | 2019-07-04 | 公益財団法人がん研究会 | 抗がん剤 |
| WO2020004594A1 (ja) * | 2018-06-27 | 2020-01-02 | 株式会社リボルナバイオサイエンス | 脊髄性筋萎縮症の予防または治療剤 |
| CA3119509A1 (en) | 2018-11-20 | 2020-05-28 | Tes Pharma S.R.L | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxxylase |
| WO2020163689A1 (en) | 2019-02-08 | 2020-08-13 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | 20-hete formation inhibitors |
| WO2020167701A1 (en) | 2019-02-13 | 2020-08-20 | Merck Sharp & Dohme Corp. | Pyrrolidine orexin receptor agonists |
| WO2020167706A1 (en) | 2019-02-13 | 2020-08-20 | Merck Sharp & Dohme Corp. | 5-alkyl pyrrolidine orexin receptor agonists |
| WO2021026047A1 (en) | 2019-08-08 | 2021-02-11 | Merck Sharp & Dohme Corp. | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
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| PE20231384A1 (es) | 2020-08-18 | 2023-09-12 | Merck Sharp And Dohme Llc | Agonistas de bicicloheptano pirrolidina de los receptores de orexina |
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| JPS55143980A (en) * | 1979-04-27 | 1980-11-10 | Dai Ichi Seiyaku Co Ltd | Anti-allergic preparation |
| WO1995028389A1 (en) * | 1994-04-15 | 1995-10-26 | Yamanouchi Pharmaceutical Co., Ltd. | Spiro compound and medicinal composition thereof |
| US5602024A (en) | 1994-12-02 | 1997-02-11 | Synaptic Pharmaceutical Corporation | DNA encoding a hypothalamic atypical neuropeptide Y/peptide YY receptor (Y5) and uses thereof |
| ID29137A (id) * | 1998-07-27 | 2001-08-02 | Schering Corp | Ligan-ligan afinitas tinggi untuk reseptor nosiseptin orl-1 |
| ES2255330T3 (es) | 1998-11-10 | 2006-06-16 | MERCK & CO., INC. | Espiroindolinas como antagonistas del receptor y5. |
| TWI279402B (en) * | 1999-08-20 | 2007-04-21 | Banyu Pharma Co Ltd | Spiro compounds having NPY antagonistic activities and agents containing the same |
| PL354675A1 (en) | 1999-09-30 | 2004-02-09 | Neurogen Corporation | Certain alkylene diamine-substituted pyrazolo[1,5,-a]-1,5-pyrimidines and pyrazolo[1,5-a]-1,3,5-triazines |
| AU7738000A (en) | 1999-09-30 | 2001-04-30 | Neurogen Corporation | Certain alkylene diamine-substituted heterocycles |
| EP1263768A4 (en) | 2000-01-28 | 2004-05-12 | Neurogen Corp | CHIMEAN NEUROPEPTID Y RECEPTORS |
| AU2001264376A1 (en) | 2000-06-15 | 2001-12-24 | Chaconne Nsi Co., Ltd. | Urea derivative useful as an anti-cancer agent and process for preparing same |
| WO2002048152A2 (en) * | 2000-12-12 | 2002-06-20 | Neurogen Corporation | Spiro[isobenzofuran-1,4'-piperidin]-3-ones and 3h-spiroisobenzofuran-1,4'-piperidines |
| CA2403307A1 (en) | 2001-10-23 | 2003-04-23 | Neurogen Corporation | Substituted 2-cyclohexyl-4-phenyl-1h-imidazole derivatives |
-
2001
- 2001-12-11 WO PCT/US2001/047863 patent/WO2002048152A2/en not_active Ceased
- 2001-12-11 ES ES01270536T patent/ES2249384T3/es not_active Expired - Lifetime
- 2001-12-11 US US10/415,457 patent/US20050033048A1/en not_active Abandoned
- 2001-12-11 EP EP01270536A patent/EP1347982B1/en not_active Expired - Lifetime
- 2001-12-11 US US10/013,846 patent/US6566367B2/en not_active Expired - Fee Related
- 2001-12-11 AU AU2002220276A patent/AU2002220276A1/en not_active Abandoned
- 2001-12-11 AT AT01270536T patent/ATE310004T1/de not_active IP Right Cessation
- 2001-12-11 JP JP2002549683A patent/JP2004520299A/ja active Pending
- 2001-12-11 MX MXPA03004245A patent/MXPA03004245A/es active IP Right Grant
- 2001-12-11 DE DE60115092T patent/DE60115092T2/de not_active Expired - Fee Related
- 2001-12-11 BR BR0116113-0A patent/BR0116113A/pt not_active IP Right Cessation
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2003
- 2003-04-09 US US10/410,648 patent/US6943199B2/en not_active Expired - Fee Related
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2005
- 2005-07-18 US US11/183,615 patent/US20060040964A1/en not_active Abandoned
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| Publication number | Publication date |
|---|---|
| US20060040964A1 (en) | 2006-02-23 |
| JP2004520299A (ja) | 2004-07-08 |
| US6566367B2 (en) | 2003-05-20 |
| WO2002048152A2 (en) | 2002-06-20 |
| DE60115092D1 (de) | 2005-12-22 |
| US20030036652A1 (en) | 2003-02-20 |
| US20050033048A1 (en) | 2005-02-10 |
| BR0116113A (pt) | 2004-08-03 |
| ATE310004T1 (de) | 2005-12-15 |
| ES2249384T3 (es) | 2006-04-01 |
| MXPA03004245A (es) | 2003-09-22 |
| US6943199B2 (en) | 2005-09-13 |
| EP1347982B1 (en) | 2005-11-16 |
| WO2002048152A3 (en) | 2003-05-08 |
| US20040072847A1 (en) | 2004-04-15 |
| EP1347982A2 (en) | 2003-10-01 |
| AU2002220276A1 (en) | 2002-06-24 |
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