NO995065L - Indole derivatives with combined 5HT1A, 5HT1B and 5HT1D receptor antagonist activity - Google Patents
Indole derivatives with combined 5HT1A, 5HT1B and 5HT1D receptor antagonist activityInfo
- Publication number
- NO995065L NO995065L NO995065A NO995065A NO995065L NO 995065 L NO995065 L NO 995065L NO 995065 A NO995065 A NO 995065A NO 995065 A NO995065 A NO 995065A NO 995065 L NO995065 L NO 995065L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- nitrogen
- oxygen
- sulfur
- hydrogen
- Prior art date
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 239000003727 serotonin 1A antagonist Substances 0.000 title 1
- 239000004000 serotonin 1B antagonist Substances 0.000 title 1
- 239000004001 serotonin 1D antagonist Substances 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 14
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052757 nitrogen Inorganic materials 0.000 abstract 8
- 229910052760 oxygen Inorganic materials 0.000 abstract 8
- 239000001301 oxygen Substances 0.000 abstract 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 7
- 229910052717 sulfur Chemical group 0.000 abstract 7
- 239000011593 sulfur Chemical group 0.000 abstract 7
- 125000005842 heteroatom Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 101000869592 Daucus carota Major allergen Dau c 1 Chemical group 0.000 abstract 2
- 101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Chemical group 0.000 abstract 2
- 102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 101000710899 Homo sapiens Cannabinoid receptor 1 Proteins 0.000 abstract 1
- 101001116937 Homo sapiens Protocadherin alpha-4 Proteins 0.000 abstract 1
- 102100024261 Protocadherin alpha-4 Human genes 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D401/10—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 carbon chain containing aromatic rings
-
- 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
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Forbindelser med formel(l), fremgangsmåter for deres fremstilling og anvendelse av dem som CNS-midler er beskrevet: hvor Ra er en gruppe med formel (i) hvor P1 er fenyl, bicyklisk aryl, en 5- til 7-leddet heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen og svovel eller en bicyklisk, heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen og svovel; R1 er hydrogen, halogen, C-j^alkyl. Cs.øcykloalkyl, COCi^alkyl, C-i.galkoksy, hydroksy, hydroksyCi.ealkyl, hydroksyC-i-ealkoksy, Ci_6alkoksyCi_6alkoksy, C-|_6alkanoyl, nitro, trifluormetyl, cyano, SR9, SOR9, SO2R9. SO2NR10R11, CO2R10, CONR1°R11, C02NR10R11, (CH2)cNR10R11. (CH2)CCONR1°R11, 6alkyl, CO2(CH2)COR10, NR10R11, NR1°CO2R11, NR10CONR10R11, CR1°=NOR11, NR10COOR11, CNR1°=NOR11. hvor R10 og R11 uavhengig er hydrogen eller C-j.salkyl og c er 1 til 4 R2 er hydrogen, halogen, C^alkyl, Cs.ecykloalkyl, Cs.gcykloalkenyl, C-i.galkoksy, acyl, aryl, acyloksy, hydroksy, nitro, trinuormetyl, cyano, CO2R10PCONR1 OR! 1, NR1°R11 hvor R10 og R11 er som definert for R1; aerl, 2 eller 3; eller Ra er en gruppe med formel (ii) (ii) hvor P2 og P3 uavhengig er fenyl, bicyklisk aryl, en 5- til 7- leddet heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen og svovel eller en bicyklisk heterocyklisk gruppe inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen eller svovel; A er en binding eller oksygen, S (O)m hvor m er O til 2, karbonyl, CH2 eller NR4 hvor R4 er hydrogen eller C-i-øalkyl; R1 er som definert ovenfor for formel (l) eller R"! er en eventuelt substituert 5- til 7-leddet heterocyklisk ring inneholdende 1 til 3 heteroatomer valgt fra oksygen, nitrogen eller svovel; R2 og R3 er uavhengig hydrogen, halogen, C-i-salkyl, Cs.øcykloalkyl, C3_6cykloalkenyl, C^alkoksy, acyl, aryl, acyloksy, hydroksy, nitro, trifluormetyl, cyano, CO2R10, CONR10R11, NR10R11 hvor R10 og R11 er som definert for R1; og a og b er uavhengig 1, 2 eller 3; Y er - NH -, NR$ hvor R5 er C-|_6alkyl eller Y er - CH2 - eller - O -; V er oksygen eller svovel; D er nitrogen, karbon eller en CH gruppe; Wer (CR16R17)t hvor t er 2, 3 eller 4 og R16 og R17 er uavhengig hydrogen eller Ci^alkyl eller Wer (CR16R17)U-J hvor u er O, 1, 2 eller 3 og J er oksygen, svovel, CR16=CR17, CR16=N, =CR16Q, =CR16S eller =CR16-NR17; X er nitrogen eller karbon; Rb er hydrogen, halogen, hydroksy, Ci-galkyl, trifluormetyl, C-^alkoksy, C2- salkenyl, Cs.ycykloalkyl eventuelt substituert med C^alkyl eller aryl; Rc er hydrogen eller Ci_salkyl; og ¿ er en enkeltbinding når X er nitrogen eller en enkelt- eller dobbeltbinding når X er karbon.Compounds of formula (I), processes for their preparation and use of them as CNS agents are described: wherein Ra is a group of formula (i) wherein P1 is phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur or a bicyclic heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur; R 1 is hydrogen, halogen, C 1-6 alkyl. C 1-6 cycloalkyl, CO C 1-6 alkyl, C 1-6 alkoxy, hydroxy, hydroxyC 1-6 alkyl, hydroxyC 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkoxy, C 1-6 alkanoyl, nitro, trifluoromethyl, cyano, SR9, SOR9, SO2R9. SO2NR10R11, CO2R10, CONR1 ° R11, CO2NR10R11, (CH2) cNR10R11. (CH2) CCONR1 ° R11, 6alkyl, CO2 (CH2) COR10, NR10R11, NR1 ° CO2R11, NR10CONR10R11, CR1 ° = NOR11, NR10COOR11, CNR1 ° = NOR11. wherein R 10 and R 11 are independently hydrogen or C 1-6 alkyl and c is 1 to 4 R2 is hydrogen, halogen, C 1-6 alkyl, C 6 -cycloalkyl, C 6 , cyano, CO2R10PCONR1 OR! 1, NR1 ° R11 wherein R10 and R11 are as defined for R1; aerl, 2 or 3; or Ra is a group of formula (ii) (ii) wherein P2 and P3 are independently phenyl, bicyclic aryl, a 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur or a bicyclic heterocyclic group containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur; A is a bond or oxygen, S (O) m where m is 0 to 2, carbonyl, CH 2 or NR 4 where R 4 is hydrogen or C 1-6 alkyl; R 1 is as defined above for formula (I) or R 1 is an optionally substituted 5- to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulfur; R 2 and R 3 are independently hydrogen, halogen, C alkyl, C 6 cycloalkyl, C 3-6 cycloalkenyl, C 1-4 alkoxy, acyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, CO2R10, CONR10R11, NR10R11 where R10 and R11 are as defined for R1 and a and b are independently 1 or 3; Y is - NH -, NR $ where R 5 is C 1-6 alkyl or Y is - CH 2 - or - O -; V is oxygen or sulfur; D is nitrogen, carbon or a CH group; Wer (CR16R17) t where t is 2, 3 or 4 and R16 and R17 are independently hydrogen or C1-4 alkyl or Wer (CR16R17) UJ where u is O, 1, 2 or 3 and J is oxygen, sulfur, CR16 = CR17, CR16 = N, = CR16Q, = CR16S or = CR16-NR17; X is nitrogen or carbon; Rb is hydrogen, halogen, hydroxy, C1-6 alkyl, trifluoromethyl, C1-6 alkoxy, C2-salkenyl, C1- cycloalkyl optionally substituted with C1-6 alkyl or aryl; Rc is hydrogen or C1-6 alkyl; and ¿is a single bond when X is nitrogen or a single or double bond when X is carbon.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9707829.9A GB9707829D0 (en) | 1997-04-18 | 1997-04-18 | Novel compounds |
| GBGB9801882.3A GB9801882D0 (en) | 1998-01-29 | 1998-01-29 | Novel compounds |
| PCT/EP1998/002262 WO1998050358A1 (en) | 1997-04-18 | 1998-04-14 | Indole derivatives having combined 5ht1a, 5ht1b and 5ht1d receptor antagonist activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO995065L true NO995065L (en) | 1999-10-15 |
| NO995065D0 NO995065D0 (en) | 1999-10-15 |
Family
ID=26311401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO995065A NO995065D0 (en) | 1997-04-18 | 1999-10-15 | Indole derivatives with combined 5HT1A, 5HT1B and 5HT1D receptor antagonist activity |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0975593A1 (en) |
| JP (1) | JP2001524116A (en) |
| KR (1) | KR20010006487A (en) |
| CN (1) | CN1260781A (en) |
| AR (1) | AR013076A1 (en) |
| AU (1) | AU732863B2 (en) |
| BR (1) | BR9809092A (en) |
| CA (1) | CA2288662A1 (en) |
| CO (1) | CO4950608A1 (en) |
| HU (1) | HUP0001123A3 (en) |
| IL (1) | IL132409A0 (en) |
| NO (1) | NO995065D0 (en) |
| NZ (1) | NZ500252A (en) |
| PL (1) | PL336317A1 (en) |
| TR (1) | TR199902590T2 (en) |
| TW (1) | TW509687B (en) |
| WO (1) | WO1998050358A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9725931D0 (en) * | 1997-12-05 | 1998-02-04 | Smithkline Beecham Plc | Novel compounds |
| AU753360B2 (en) | 1998-07-31 | 2002-10-17 | Nippon Soda Co., Ltd. | Phenylazole compounds, process for producing the same and drugs for hyperlipemia |
| GB9827882D0 (en) * | 1998-12-17 | 1999-02-10 | Smithkline Beecham Plc | Novel compounds |
| UA62015C2 (en) * | 1998-12-28 | 2003-12-15 | Pfizer Prod Inc | Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants) |
| GB9912417D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| GB9912413D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| JP2003505369A (en) * | 1999-07-15 | 2003-02-12 | エヌピーエス アレリックス コーポレーション | Heterocyclic compounds for treating migraine |
| IL148818A0 (en) | 1999-09-25 | 2002-09-12 | Smithkline Beecham Plc | Piperazine derivatives as 5-ht1b |
| DE60017446T2 (en) * | 1999-11-05 | 2006-03-02 | Smithkline Beecham P.L.C., Brentford | Isoquinoline and quinazoline derivatives with combined 5-HT1A, 5-HT1B and 5-HT1D receptor affinity |
| GB9926303D0 (en) * | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
| DE10051981A1 (en) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituted phenyluracile |
| GB0106419D0 (en) | 2001-03-15 | 2001-05-02 | Smithkline Beecham Plc | Novel compounds |
| GB0106586D0 (en) * | 2001-03-16 | 2001-05-09 | Smithkline Beecham Plc | Novel compounds |
| DE60218037T2 (en) * | 2001-06-07 | 2007-08-23 | F. Hoffmann-La Roche Ag | NEW INDOIND DERIVATIVES WITH AFFINITY TO THE 5-HT6 RECEPTOR |
| ATE416168T1 (en) * | 2002-02-15 | 2008-12-15 | Glaxo Group Ltd | MODULATORS OF THE VANILLOID RECEPTOR |
| KR100636475B1 (en) | 2002-05-13 | 2006-10-18 | 에프. 호프만-라 로슈 아게 | Benzoxazine Derivatives and Uses thereof as 5-HT6 Modulators |
| JP4527730B2 (en) | 2003-12-09 | 2010-08-18 | エフ．ホフマン−ラ ロシュ アーゲー | Benzoxazine derivatives and uses thereof |
| MX2010006046A (en) * | 2007-12-13 | 2010-06-23 | Amgen Inc | Gamma secretase modulators. |
| US8598156B2 (en) | 2010-03-25 | 2013-12-03 | Glaxosmithkline Llc | Chemical compounds |
| GB201106817D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compound |
| CN102924330A (en) * | 2012-09-03 | 2013-02-13 | 华东理工大学 | Method for large-scale preparation of 5-amino-1-naphthyl nitrile |
| GB201218862D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218864D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| US9980973B2 (en) | 2012-10-19 | 2018-05-29 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218850D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| CN103467374A (en) * | 2013-08-30 | 2013-12-25 | 江苏弘和药物研发有限公司 | Synthesis method of 8-bromine-4-carboxyl quinoline |
| PL3083616T3 (en) | 2013-12-20 | 2021-12-06 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
| JP6693107B2 (en) * | 2015-12-04 | 2020-05-13 | 東ソー株式会社 | Method for purifying lutidine compound |
| CN115197099A (en) * | 2022-05-30 | 2022-10-18 | 安徽昊帆生物有限公司 | Preparation method of N-Boc-1,4-phenylenediamine |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9119920D0 (en) * | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
| GB9119932D0 (en) * | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
| PT533268E (en) * | 1991-09-18 | 2002-02-28 | Glaxo Group Ltd | BENZANILIDA DERIVATIVES AS 5-HT1D ANTAGONISTS |
| JPH09501171A (en) * | 1993-08-06 | 1997-02-04 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | Amide derivatives as 5HT1D receptor antagonists |
| JPH09504004A (en) * | 1993-08-20 | 1997-04-22 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | Amide and urea derivatives for 5HT1D receptor antagonists |
| DE69417427T2 (en) * | 1993-09-03 | 1999-11-25 | Smithkline Beecham P.L.C., Brentford | INDOL AND INDOLIN DERIVATIVES AS 5HT1D RECEPTOR ANTAGONISTS |
-
1998
- 1998-04-14 PL PL98336317A patent/PL336317A1/en unknown
- 1998-04-14 JP JP54766098A patent/JP2001524116A/en active Pending
- 1998-04-14 BR BR9809092-5A patent/BR9809092A/en not_active IP Right Cessation
- 1998-04-14 IL IL13240998A patent/IL132409A0/en unknown
- 1998-04-14 CN CN98806185A patent/CN1260781A/en active Pending
- 1998-04-14 AU AU74310/98A patent/AU732863B2/en not_active Ceased
- 1998-04-14 EP EP98921462A patent/EP0975593A1/en not_active Withdrawn
- 1998-04-14 TR TR1999/02590T patent/TR199902590T2/en unknown
- 1998-04-14 NZ NZ500252A patent/NZ500252A/en unknown
- 1998-04-14 WO PCT/EP1998/002262 patent/WO1998050358A1/en not_active Ceased
- 1998-04-14 HU HU0001123A patent/HUP0001123A3/en unknown
- 1998-04-14 CA CA002288662A patent/CA2288662A1/en not_active Abandoned
- 1998-04-14 KR KR1019997009577A patent/KR20010006487A/en not_active Withdrawn
- 1998-04-16 AR ARP980101760A patent/AR013076A1/en not_active Application Discontinuation
- 1998-04-17 CO CO98021149A patent/CO4950608A1/en unknown
- 1998-04-17 TW TW087105843A patent/TW509687B/en active
-
1999
- 1999-10-15 NO NO995065A patent/NO995065D0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998050358A1 (en) | 1998-11-12 |
| CO4950608A1 (en) | 2000-09-01 |
| EP0975593A1 (en) | 2000-02-02 |
| AU7431098A (en) | 1998-11-27 |
| AR013076A1 (en) | 2000-12-13 |
| KR20010006487A (en) | 2001-01-26 |
| CN1260781A (en) | 2000-07-19 |
| NO995065D0 (en) | 1999-10-15 |
| BR9809092A (en) | 2002-01-22 |
| TW509687B (en) | 2002-11-11 |
| HUP0001123A2 (en) | 2001-04-28 |
| IL132409A0 (en) | 2001-03-19 |
| AU732863B2 (en) | 2001-05-03 |
| PL336317A1 (en) | 2000-06-19 |
| CA2288662A1 (en) | 1998-11-12 |
| HUP0001123A3 (en) | 2002-04-29 |
| TR199902590T2 (en) | 2000-06-21 |
| JP2001524116A (en) | 2001-11-27 |
| NZ500252A (en) | 2001-07-27 |
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| FC2A | Withdrawal, rejection or dismissal of laid open patent application |