AP757A - Tetracyclic spiro piperidine compounds, a process for their preparation and their use as 5HT1D receptor antagonists in the treatment of CNS disorders. - Google Patents
Tetracyclic spiro piperidine compounds, a process for their preparation and their use as 5HT1D receptor antagonists in the treatment of CNS disorders. Download PDFInfo
- Publication number
- AP757A AP757A APAP/P/1997/001006A AP9701006A AP757A AP 757 A AP757 A AP 757A AP 9701006 A AP9701006 A AP 9701006A AP 757 A AP757 A AP 757A
- Authority
- AP
- ARIPO
- Prior art keywords
- methyl
- furo
- piperidine
- indole
- carbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 95
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000011282 treatment Methods 0.000 title abstract description 12
- 208000015114 central nervous system disease Diseases 0.000 title abstract description 5
- 239000002464 receptor antagonist Substances 0.000 title description 3
- 229940044551 receptor antagonist Drugs 0.000 title description 3
- JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical class C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 title description 2
- 101710138068 5-hydroxytryptamine receptor 1D Proteins 0.000 title description 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 235
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000003003 spiro group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
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- 239000001301 oxygen Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
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- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 8
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
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- 239000000935 antidepressant agent Substances 0.000 description 1
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- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
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- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
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- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
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- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
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- 239000008157 edible vegetable oil Substances 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- MASRAGFWFYHMFI-UHFFFAOYSA-N methyl 3-bromo-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(Br)=C1 MASRAGFWFYHMFI-UHFFFAOYSA-N 0.000 description 1
- JEMYOAWPNLLGAM-UHFFFAOYSA-N methyl 4-[4-(acetamidomethyl)-2-methylphenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(CNC(C)=O)C=C1C JEMYOAWPNLLGAM-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- FTRNROIIXSLFLH-UHFFFAOYSA-N n'-acetyl-4-bromo-3-methylbenzohydrazide Chemical compound CC(=O)NNC(=O)C1=CC=C(Br)C(C)=C1 FTRNROIIXSLFLH-UHFFFAOYSA-N 0.000 description 1
- TYXPYEUTRWRSBP-UHFFFAOYSA-N n,n-dimethyl-4-phenylbenzenesulfonamide Chemical group C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=CC=C1 TYXPYEUTRWRSBP-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical compound OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9426029.6A GB9426029D0 (en) | 1994-12-22 | 1994-12-22 | Novel compounds |
| GBGB9512920.1A GB9512920D0 (en) | 1995-06-24 | 1995-06-24 | Novel compounds |
| PCT/EP1995/004889 WO1996019477A1 (en) | 1994-12-22 | 1995-12-06 | Tetracyclic spiro compounds, process for their preparation and their use as 5ht1d receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9701006A0 AP9701006A0 (en) | 1997-07-31 |
| AP757A true AP757A (en) | 1999-09-06 |
Family
ID=26306239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/001006A AP757A (en) | 1994-12-22 | 1995-12-06 | Tetracyclic spiro piperidine compounds, a process for their preparation and their use as 5HT1D receptor antagonists in the treatment of CNS disorders. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5972951A (de) |
| EP (1) | EP0799226B1 (de) |
| JP (1) | JPH10510821A (de) |
| CN (1) | CN1175256A (de) |
| AP (1) | AP757A (de) |
| AR (1) | AR002011A1 (de) |
| AT (1) | ATE199085T1 (de) |
| AU (1) | AU697361B2 (de) |
| BG (1) | BG61977B1 (de) |
| BR (1) | BR9510419A (de) |
| CA (1) | CA2208244A1 (de) |
| CZ (1) | CZ192397A3 (de) |
| DE (1) | DE69520075T2 (de) |
| DZ (1) | DZ1957A1 (de) |
| ES (1) | ES2153907T3 (de) |
| FI (1) | FI972583L (de) |
| HU (1) | HUT77650A (de) |
| IL (1) | IL116486A0 (de) |
| MA (1) | MA23753A1 (de) |
| MX (1) | MX9704777A (de) |
| NO (1) | NO972910L (de) |
| NZ (1) | NZ298036A (de) |
| OA (1) | OA10610A (de) |
| PL (1) | PL321048A1 (de) |
| SK (1) | SK80297A3 (de) |
| TR (1) | TR199501597A2 (de) |
| WO (1) | WO1996019477A1 (de) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9519033D0 (en) * | 1995-09-18 | 1995-11-15 | Smithkline Beecham Plc | Treatment |
| GB9522845D0 (en) * | 1995-11-08 | 1996-01-10 | Smithkline Beecham Plc | Novel compounds |
| WO1997017351A1 (en) * | 1995-11-08 | 1997-05-15 | Smithkline Beecham Plc | Spiro piperidine derivatives as 5mt receptor antagonists |
| WO1997019070A1 (en) * | 1995-11-22 | 1997-05-29 | Smithkline Beecham Plc | Tricyclic spiro compounds as 5ht1d receptor antagonists |
| GB9605883D0 (en) * | 1996-03-20 | 1996-05-22 | Smithkline Beecham Plc | Novel compounds |
| GB9606396D0 (en) * | 1996-03-27 | 1996-06-05 | Smithkline Beecham Plc | Novel compounds |
| US6156783A (en) * | 1996-04-30 | 2000-12-05 | Smithkline Beecham P.L.C. | Spiroazabicyclic compounds, processes for their preparation, and their pharmaceutical use |
| FR2761069A1 (fr) * | 1997-03-20 | 1998-09-25 | Pf Medicament | Spiroamines derivees de dihydrobenzofuranes, leur preparation et leur application comme medicaments |
| EP1122252A4 (de) * | 1998-10-16 | 2002-06-26 | Takeda Chemical Industries Ltd | Stickstoffhaltige annelierte heterocyclen, verfahren zu ihrer herstellung und agentien, die diese enthalten |
| DE10051981A1 (de) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituierte Phenyluracile |
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7279576B2 (en) | 2002-12-31 | 2007-10-09 | Deciphera Pharmaceuticals, Llc | Anti-cancer medicaments |
| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| PT1656370E (pt) * | 2003-06-03 | 2012-11-29 | Rib X Pharmaceuticals Inc | Compostos biaril-heterocíclicos e métodos de os produzir e de os utilizar |
| US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
| CN101346336B (zh) | 2005-12-26 | 2013-02-27 | 日产化学工业株式会社 | 1,3-二(取代苯基)-3-取代-2-丙烯-1-酮化合物和其盐 |
| AU2008242720A1 (en) | 2007-04-20 | 2008-10-30 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| EP2520561B1 (de) | 2007-06-08 | 2016-02-10 | MannKind Corporation | IRE-1a-Inhibitoren |
| US8952175B2 (en) | 2007-06-27 | 2015-02-10 | Nissan Chemical Industries, Ltd. | Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound |
| WO2010045251A2 (en) | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals, Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| AU2010306768B2 (en) | 2009-10-14 | 2016-08-04 | Xenon Pharmaceuticals Inc. | Synthetic methods for spiro-oxindole compounds |
| MY165117A (en) | 2010-02-26 | 2018-02-28 | Xenon Pharmaceuticals Inc | Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| AR103636A1 (es) | 2015-02-05 | 2017-05-24 | Teva Pharmaceuticals Int Gmbh | Métodos de tratamiento de neuralgia postherpética con una formulación tópica de un compuesto de espiro-oxindol |
| US11498903B2 (en) | 2017-08-17 | 2022-11-15 | Bristol-Myers Squibb Company | 2-(1,1′-biphenyl)-1H-benzodimidazole derivatives and related compounds as apelin and APJ agonists for treating cardiovascular diseases |
| SG11202007198WA (en) | 2018-01-31 | 2020-08-28 | Deciphera Pharmaceuticals Llc | Combination therapy for the treatment of gastrointestinal stromal tumors |
| EA202091763A1 (ru) | 2018-01-31 | 2020-12-14 | ДЕСИФЕРА ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Комбинированная терапия для лечения мастоцитоза |
| EP3938363A1 (de) | 2019-03-11 | 2022-01-19 | Teva Pharmaceuticals International GmbH | Festkörperformen von ripretinib |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
| WO2021030405A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
| JP7818502B2 (ja) | 2019-08-12 | 2026-02-20 | デシフェラ・ファーマシューティカルズ，エルエルシー | 胃腸間質腫瘍を治療するためのリプレチニブ |
| AU2020417282B2 (en) | 2019-12-30 | 2023-08-31 | Deciphera Pharmaceuticals, Llc | Compositions of 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea |
| SI4084778T1 (sl) | 2019-12-30 | 2024-01-31 | Deciphera Pharmaceuticals, Llc | Formulacije inhibitorja amorfne kinaze in načini njihove uporabe |
| AU2021303146A1 (en) | 2020-06-29 | 2023-02-02 | Bacainn Biotherapeutics, Ltd. | Probenecid compounds for the treatment of inflammasome-mediated lung disease |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2162792T3 (es) | 1991-09-18 | 2002-01-16 | Glaxo Group Ltd | Derivados de benzanilida como antagonistas de 5-ht1d. |
| GB9119932D0 (en) * | 1991-09-18 | 1991-10-30 | Glaxo Group Ltd | Chemical compounds |
-
1995
- 1995-12-06 EP EP95942116A patent/EP0799226B1/de not_active Expired - Lifetime
- 1995-12-06 AT AT95942116T patent/ATE199085T1/de active
- 1995-12-06 JP JP8519477A patent/JPH10510821A/ja active Pending
- 1995-12-06 PL PL95321048A patent/PL321048A1/xx unknown
- 1995-12-06 US US08/849,932 patent/US5972951A/en not_active Expired - Fee Related
- 1995-12-06 FI FI972583A patent/FI972583L/fi unknown
- 1995-12-06 WO PCT/EP1995/004889 patent/WO1996019477A1/en not_active Ceased
- 1995-12-06 CZ CZ971923A patent/CZ192397A3/cs unknown
- 1995-12-06 NZ NZ298036A patent/NZ298036A/en unknown
- 1995-12-06 HU HU9800158A patent/HUT77650A/hu unknown
- 1995-12-06 CN CN95197616A patent/CN1175256A/zh active Pending
- 1995-12-06 MX MX9704777A patent/MX9704777A/es unknown
- 1995-12-06 DE DE69520075T patent/DE69520075T2/de not_active Expired - Fee Related
- 1995-12-06 SK SK802-97A patent/SK80297A3/sk unknown
- 1995-12-06 AP APAP/P/1997/001006A patent/AP757A/en active
- 1995-12-06 ES ES95942116T patent/ES2153907T3/es not_active Expired - Lifetime
- 1995-12-06 AU AU43433/96A patent/AU697361B2/en not_active Ceased
- 1995-12-06 CA CA002208244A patent/CA2208244A1/en not_active Abandoned
- 1995-12-06 BR BR9510419A patent/BR9510419A/pt not_active Application Discontinuation
- 1995-12-19 AR ARP950100629A patent/AR002011A1/es unknown
- 1995-12-19 TR TR95/01597A patent/TR199501597A2/xx unknown
- 1995-12-20 MA MA24106A patent/MA23753A1/fr unknown
- 1995-12-20 DZ DZ950140A patent/DZ1957A1/fr active
- 1995-12-21 IL IL11648695A patent/IL116486A0/xx unknown
-
1997
- 1997-06-20 OA OA70033A patent/OA10610A/en unknown
- 1997-06-20 NO NO972910A patent/NO972910L/no unknown
- 1997-07-01 BG BG101715A patent/BG61977B1/bg unknown
Non-Patent Citations (2)
| Title |
|---|
| JOURNAL OF MEDICINAL CHEMISTRY vol. 23, no. 6, pp. 679-689 (1980) P.A. CROOKS et al. 'Synthesis and analgesic properties of some conformationally restricted analogues of profado' * |
| JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 15, 22 July 1994 WASHINGTON, US pages 2253-2257, J.W. CLITHEROW et al. 'Evolution of a novel series of (N,N-dimethylamino)propyl- and piperazinylbenzanilides as the first selective 5-ht1d-antagonists' * |
Also Published As
| Publication number | Publication date |
|---|---|
| FI972583A0 (fi) | 1997-06-17 |
| NO972910L (no) | 1997-08-14 |
| FI972583A7 (fi) | 1997-08-19 |
| SK80297A3 (en) | 1998-12-02 |
| CA2208244A1 (en) | 1996-06-27 |
| US5972951A (en) | 1999-10-26 |
| BR9510419A (pt) | 1998-05-19 |
| MA23753A1 (fr) | 1996-07-01 |
| EP0799226B1 (de) | 2001-02-07 |
| DE69520075D1 (de) | 2001-03-15 |
| AR002011A1 (es) | 1998-01-07 |
| DE69520075T2 (de) | 2001-08-02 |
| OA10610A (en) | 2002-09-06 |
| AU697361B2 (en) | 1998-10-01 |
| NO972910D0 (no) | 1997-06-20 |
| HUT77650A (hu) | 1998-07-28 |
| AP9701006A0 (en) | 1997-07-31 |
| ES2153907T3 (es) | 2001-03-16 |
| WO1996019477A1 (en) | 1996-06-27 |
| BG61977B1 (bg) | 1998-11-30 |
| ATE199085T1 (de) | 2001-02-15 |
| AU4343396A (en) | 1996-07-10 |
| FI972583L (fi) | 1997-08-19 |
| EP0799226A1 (de) | 1997-10-08 |
| NZ298036A (en) | 1998-11-25 |
| IL116486A0 (en) | 1997-08-14 |
| DZ1957A1 (fr) | 2002-02-17 |
| CN1175256A (zh) | 1998-03-04 |
| JPH10510821A (ja) | 1998-10-20 |
| TR199501597A2 (tr) | 1996-07-21 |
| MX9704777A (es) | 1997-10-31 |
| CZ192397A3 (en) | 1997-09-17 |
| BG101715A (bg) | 1998-02-27 |
| PL321048A1 (en) | 1997-11-24 |
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